The Daily Grind

These day, I am at my desk by 8:00 am and finish around 6pm. Many days, I will have back-to-back 30-min meetings. Sometimes I forget to block time for lunch and end up trying to stuff my face below the zoom camera so no one can see me chewing like a cow. This is due, in part, because I have stepped into a new role at CEO Coaching International and the first 90 days of any job are intense. Part of this is also just how I am wired. I like talking to people. I like trying to solve problems. I like being busy.

A Needed Break

I am heading back from a guys trip to Belize, where the rhythm of the days was completely different. We did ten dives over six days and spent hours transiting to and from the dive sites and sitting on the boat during our “surface intervals.” My friends and I would talk on and off, but mostly we sat and listened to the boat’s engine when we were not diving. I still can hear the ringing in my ears from the engine’s whining

And, to be honest, I was bored a lot of the time.

I wish I could tell you that I had deliberately disconnected, put away my phone, and welcomed the chance to be present. What actually happened was that I realized we were beyond cell coverage after leaving the dock, so I could not stay connected. At some point, I stopped reaching for the phone because there was no point. However, I felt the impulse to want to stay connected like a nervous tick.

There is something embarrassing about traveling to Belize, getting on a dive boat with friends, and discovering that I still wanted to check my phone. But this was the truth and what lead me to this reflection.

An hour without a “task”

I have always struggled with trying to optimize every minute of every day. Even on a Saturday, I will feel guilty if I don’t have an activity planned or a project to work on. I think there is always something I could be doing. I could work on another chapter of my book, read a book, prepare for an upcoming class, or go for a hike or. . . you get the picture. I have lots of interests, and I like being engaged. A free afternoon represents a set of intriguing possibilities.

That makes my restlessness difficult to untangle. Much of what I fill my time with are things I want to do. I don’t want to stop reading, writing, teaching, or spending time outdoors with my wife and friends. But I also recognize how quickly “I could be doing something” becomes “I should be doing something.” And this is my struggle.

On the boat, none of these possibilities were viable. We were heading to a dive site and if it took 2.5 hours to get there, it was going to take 2.5 hours. I have not experienced this same sort of boredom traveling via plane, train, or car. This is probably because I always have a book I could read, a podcast I could listen to, or my computer to work on (like I am doing right now flying from ATL to SLC). I guess I could have brought a book or listened to something on the boat, but I didn’t. I just sat on the bench and looked out at the horizon, listening to the noise of the engine.

At some point, it occurred to me that this was our divemaster, George’s, work world. He did this every day. In fact, during the busy season he had done it 90 days in a row. These hours of nothingness that felt so different from my life were an ordinary part of his.

Of course, we occupied different roles. I could sit there because the Captain was responsible for getting us to the dive site and George was responsible for getting our gear ready and guiding the dives. I knew nothing about whether George felt peaceful, restless, tired, or simply ready to get on with the day. But sitting on the boat next to him made the contrast stark. My life had become so packed that an extended time with nothing to do felt unfamiliar and uncomfortable.

I often tell my wife, Dana—only half jokingly—that I want to be forest ranger or lifeguard at the beach. I am going to add divemaster to that list. I want to sit and watch and think, or so I say.

Looking out the window

Sitting on the boat, I remembered family vacations when I was a child. My sisters and I would sit in the car and stare out the window, when we were not squabbling about something. I was bored then, too, but in my memory I was more willing to accept it. There were long stretches when looking out the window was simply what you did. Obviously, I did not know anything different, and I am probably viewing the past through rose-tinted glasses. However, I don’t remember being restless. I could settle into the moment.

Dana and I have talked about this often. We didn’t let our kids have phones on family road trips. Our boys had coloring books, Legos and other diversions. But, by design, they also spent plenty of time watching the world go by and listening to really good 80’s music ;).

Dana and I wanted them to learn how to be ok with doing nothing and being present to the world around them. Sitting on the boat this week, made me realize how difficult I was finding it for me to find this peace.

On one of the transits, I had another flashback. This time it was to when I was aboard the USS Abraham Lincoln as we spent 30 days transiting from our home port in San Diego to be on station off the coast of Iraq. While we did have days filled with Flight Ops, we also had days of just cruising. During those times, I would often stand on a side deck looking toward the horizon. I used to think about all the sailors of lore who had sailed these seas and looked at this same emptiness. We were on different ships and had different reasons for being at sea, but we had a shared experience.

I don’t imagine their minds were empty. They had hopes, dreams, worries, and families to think about. I imagine the horizon becomes mesmerizing for all of us. And standing there feeling the boat rock back and forth as we sailed the seas could fill hours without me feeling there was something I needed to do.

I recognized something on that dive boat this week that I had experienced before and rarely make room for now.

Stumbling across Seneca

In my last Substack article I posted about how I had given our boys two books on the stoics this summer. One was Letters from A Stoic, a collection of 124 letters Seneca wrote to a friend, Lucilius, about how to lead a wise and virtuous life. I don’t know if my boys will ever read it, but, perhaps, when they are really bored, they will stumble across it and thumb through some of the letters.

I had my copy with me and was perusing it by the pool one day. In Letter #28 he challenges the expectation that travel will cure an unsettled mind, writing “You need a change of soul rather than a change of climate.” Talk about getting hit right between the eyes with truth. Essentially he is saying that you can change your surroundings while leaving the source of your restlessness intact. I.e., your ability to be present to the experience comes down to your ability to quiet your mind.

I hadn’t gone to Belize expecting a lesson in philosophy. I had gone to dive, be with friends and experience a new culture. But his admonition from almost 2000 years ago was spot on. I had changed my setting while retaining a “must be busy all the time every day” orientation.

In On the Shortness of Life, an essay on how people waste time and how to use it well, Seneca describes people who become restless when they stop “working.” They are unable to settle into what we would call retirement today. I know this is I what I was starting to face as I entered this “pre-tirement” phase of life. How do you find purpose? How do you make an impact? How do you define your self when what you have been doing for 30+ years starts to fade away?

To be fair, Seneca, like Plato, Socrates and the other ancient philosophers all considered serious study and partaking in philosophical dialogues with companions virtuous. And, yes, I think this was a bit self-serving. But Seneca’s challenge to being busy for busyness’ sake is a good one for me to meditate on every day.

Yes, I recognize this is yet another “should do” task. And this is where I find myself arguing with him, or perhaps with my own reading of him. Tell me that life is short, and I will add another book to the ever-building stack by my bed. Remind me that time is precious, and I will try to use it more efficiently. I can turn a warning about busyness into a reason to get busier.

I could even justify those boat rides by explaining that boredom supports creativity, that rest makes me more effective, or that wandering thoughts eventually produce useful ideas. But this is my own self-justification. I.e., I was able to use that time to do something afterwards, like writing a SubStack article on the topic.

The judgment I brought with me

Another stoic Epictetus, provides another way to untangle my quandary. He draws a distinction between having an experience and how we judge the experience. For example, for every life moment and every interaction with another human, we filter it through our POV, and make a judgment, usually not a generous one. In modern parlance, we are “meaning making machines.” Epictetus argues that what happens and how we process it are actually two different things, even when when they feel inseparable.

For example, on a Saturday afternoon, the fact could be that I have nothing planned. My judgment is that I ought to have something planned. On the boat, the fact was that there were hours between dives. My starting expectation was that I should find something to do with those hours.

Here is the hard truth. Recognizing that distinction did not make the restlessness disappear. I don’t want to exaggerate what six days in Belize accomplished. I was bored. I still felt the impulse to check my phone. And somewhere along the way, I began thinking about writing this article.

Apparently, I could still find myself a project.

I’m glad those thoughts became something I wanted to write about. Writing has become one of the ways I pay better attention to the world around me. But I can also see how readily I turn experience into material, challenging myself to create something even before I have landed back in Sun Valley. So as I make my way back home I still don’t think I could answer the question: “Can I let an hour pass without needing to justify what I did with it?”

For a few days in Belize, I had the gift of nothingness. I had time. I was in a beautiful setting with good friends and no obligations (I know, it is a first world problem). And yet, I am still learning how to be present. I guess I will need to plan another trip relatively soon to keep practicing. If I do, I will let you know how it goes.

Here is a TikTok kid encountering ideas that are nearly two thousand years old and trying to apply them to his own life. To be fair, neither of them have said anything about Seneca’s Letters From A Stoic, which I also gave them. I can only hope that one day, they will crack that one open.

One of the foundational ideas of Stoicism comes from Epictetus: some things are within our control and others are not. We don’t control what happens to us, what other people think about us, or much of what the world throws our way. What we do control is how we respond. This is simple enough to post on Instagram, but it is much harder to keep top of mind throughout the day. We will see what really lands with him over time.

I have also just wrapped up co-leading a 24-week seminar on James Joyce’s Ulysses. The group worked hard for six months trying to untangle the modern epic, and coming to terms with Stephen Dedalus, Leopold Bloom, and Molly Bloom. Ulysses is often considered one of the great novels of consciousness. Joyce’s great innovation is that he does not just give us insight into how these characters think. He is actually giving us visibility into how thinking actually happens.

His starting point is that we perceive the world through our senses. We then build a POV based on our memories intuitions, prejudices, fantasies and desires. So there is a level of our consciousness tied to our sense making. In the end, we know some things because we see them; we know others because we intuit them and/or make a judgment about them. And, most interestingly, sometimes we know something without really knowing why and/or being willing to admit that we know it.

After six months with Joyce, though, I found myself interested in a slightly different question: “What do you do with what you know?” This is because consciousness and accountability are not the same thing. I think Joyce uses the 3 main characters to offer 3 different perspectives on consciousness.

Stephan Dedalus: Knowing and Avoiding

Stephen Dedalus may be one of the most self-conscious young men in literature. He understands and repeatedly articulates the structures that confine him. For example, his Irish identity, British rule, & Catholicism. And he spends PAGES elaborating on the forces impacting him: i.e., his family, being poor, his father’s failures, his mother’s death and his own guilt around all of the above.

He is clear about the way he is being confined. And his response, mostly, is to refuse to be defined by these structures and identities. Interestingly, at the end of A Portrait of the Artist as a Young Man, he resolves to escape the constraints of nationality, language and religion. He will not accept the identities others have constructed for him, and he will not serve what he no longer believes. In Portrait, Stephen knows what he will say no to. He is less clear about what he will say yes to.

But then, in Ulysses, when we meet Stephen again, he really has not made it that far. He is broke and effectively homeless. He remains haunted by his mother’s death throughout. And while Ulysses is in one way a documentation of his intellectual maturation. He still does not know what he is going to do for a living.

However, he is also not paralyzed like many of the characters Joyce portrays in Dubliners (his earlier work). Stephen rejects being a teacher, a journalist, an Irish Nationalist writer, a lawyer. He has some idea he wants to be an artist, but he is not sure what the means. So Stephen, like most young people, is very good at saying no. The question Joyce leaves unanswered is “what Stephen will do with this realization and the freedom it enables?”

Without trying to make too much of Joyce=Stephen, I think it is fair to say that Stephen is, in many ways, Joyce’s autobiographical alter ego. If we take as a starting point, then Joyce’s own life provides an intriguing answer to the question the novel leaves unresolved. Joyce took the very things Stephen struggles to escape: Dublin, Catholicism, family, Irish history, language, guilt and exile, and then wrote a bunch of stories and books to explore them.

In this case, Joyce did not choose what formed him, but he could choose what to do with it. And this is the core of Agency. Agency is not merely escaping the circumstances that formed us. It is deciding what we will make (create) from them. In Stephen’s case, this could be summarized as: “Knowing and Avoiding.”

Leopold Bloom: Knowing and Accommodating

Leopold Bloom represents a different way of perceiving consciousness and agency. From the beginning of the book, Bloom knows that Molly is going to meet Blazes Boylan at 4pm at their house to have sex! He knows he is going to be cockolded and he does ??? Everything he does during the day and into the night has this reality as the backdrop. So Bloom has knowledge and seems to be avoiding as well. However, I think Joyce is suggesting Bloom represents a different type of reaction to “knowing.”

Bloom is extraordinarily empathetic. He notices people others overlook. He imagines other people’s (and even a cat’s) perspectives. He absorbs insults rather than confronting his tormentors. In many ways, his ability to enter another person’s point of view may be his greatest virtue.

In many ways, this is one of the most frustrating things about Bloom for me. He has so much empathy for the other’s perspective, he shies away from confronting people, specifically Boylan and Molly. Maybe he does not have the courage to confront people, well then, I would have hoped he would leave. Instead he stays. It is not clear, at the end, if he entirely forgives people, but he stays (albeit upside down in the bed with Molly with his head at her feet!!). From this perspective his “acceptance” could look very much like avoidance.

That ambiguity matters because we tend to treat self-awareness as an uncomplicated virtue. We admire people who understand themselves, who can explain what is happening and who can see a problem from multiple perspectives. But this type of knowledge doesn’t help us determine what the right action should be. Yes, of course, sometimes patience is wisdom. However, sometimes patience could be because you fear making a decision or worry about the ramifications of taking an action. Sometimes being able to accept your situation/context is demonstrating maturity. Sometimes acceptance is avoidance. And consciousness alone may not tell us which one we are practicing.

Molly Bloom: Knowing and Affirming

Molly offers a third possibility. In her episode (aka chapter), “Penelope,” the final episode of the book, there is no narrator. This is shocking in of itself because the narrator(s) play such a big role in the other episodes. I think Joyce does this, in part, so that there is no distance between us, as readers, and Molly’s mind. We get it pure and unfiltered and, as such, can see the contradictions in her own narrative. She reflects on her desire, memory, jealousy, resentment, sexuality, tenderness, vanity and affection. They all conjoin into a gordian knot.

What strikes me about Molly, in particular, is how much she externalizes her context. She judges other women harshly. She blames Bloom. She rationalizes being with Boylan. The stories she constructs about herself are no more objectively reliable than the stories that we all tell about ourselves. This is Joyce’s point.

It would be too easy to say that Molly achieves accountability where Stephen and Bloom do not. I think she arrives at something different: Affirmation. If Stephen’s consciousness is all about asserting No to his context/situation and Bloom vacillates between between acceptance and avoidance, then Molly’s consciousness ultimately produces Yes. This is what makes the ending so impactful and hopeful. After all the accounting of her life and experiences and evaluating all of her options, she remembers the moment she chose Bloom: “...and yes I said yes I will Yes.”

I don’t think Joyce is asking us to choose which of these is the right response to “knowing.” Sometimes claiming your agency requires saying no. Often, living with other people requires us accepting what we cannot completely control (just ask my wife). And to live a happy life, I think there are times, where we have to stand up and affirm who we are and what we stand for.

This brings us back to the question: “What do you do with what you know?”

“First, I Got Myself Born”

I was wrestling with this question during our family book club this month when we read Barbara Kingsolver’s Demon Copperhead. The protagonist has one of the best opening sentences ever: “First, I got myself born.”

The irony is immediately clear. Demon most certainly did not choose the circumstances of his birth. He enters a world shaped by poverty, addiction, family and instability. He is subject and confined by economic forces much larger than himself. I would argue that much of what happens to him cannot honestly be understood apart from those circumstances.

During our conversation, I asked the question: “how do we think about personal accountability” given all of this context. I think the group aligned on the fact that it was unrealistic to tell Demon simply to stop blaming other people and take responsibility for his life, which might be the Stoic response.

And yet Kingsolver shows that he is not completely without agency either. “I got myself born.” This is the core tension in the book. I.e. How much of what happens to Demon is the consequence of forces acting upon him? And where does his responsibility begin? That is where the simple version of Stoicism gets difficult.

“Control what you can control” sounds compelling until we confront how radically unequal the range of available choices can be. Some people inherit wealth. Others are victims of generational poverty and addiction. Add to this the fact that greedy corporations were exploiting the poor and uneducated in Appalachia. Circumstance and context matters. At the same time, one’s circumstance cannot be the whole story either. If everything is circumstance, you give up agency.

Listen to the Pronouns

The question then isn’t “whether circumstances matter.” It is more like “given the circumstances I did not choose, who can I become and what can I (do I) do?

I’ve started noticing a version of this question in many different contexts. For example, I sat in a recent board meeting of a company I coach, where we spent forty-five minutes talking about why we missed the quarter. Never a fun conversation. The CEO and executive team explained that the market has slowed down; sales didn’t build enough pipeline; the product shipped late; customers delayed decisions. You get it. And, actually, every statement might be true. Yet at some point I realized that the team had become remarkably good at explaining what happened without deciding what it is going to do differently. This hit home because I have been in that EXACT situation, sitting in that same seat, having the same conversation with my board, using the same justifications. And, most importantly, not being crystal clear about what we were going to do.

This is the hard thing about hard things. Consciousness without agency can turn high-functioning teams into victims. One of the things I’ve learned to listen for in these moments now is surprisingly simple—what pronouns are they using. There are really 4 ways a CEO and executive team can frame the reality they are experiencing.

• “They didn’t execute.”

• “You didn’t give us enough resources.”

• “We missed the assumptions underlying the plan.”

• “I didn’t recognize the problem soon enough.”

The facts haven’t changed. What has changed is where the CEO (or us in our own situations) assign ownership.

“They” places the cause outside us. “You” places responsibility across the table. “We” recognizes that some outcomes are collectively created. “I” asks the hardest question: What part of this is my failure as CEO?

Note: I don’t think aCEO always has to fall on the sword and say “I” am the reason why we did not hit the goal. Leadership is inherently collective. And sometimes “they” is accurate. Other people really do make mistakes. Markets really do change. Systems really can be unfair.

This is reality, and accountability does not require you to pretend otherwise. However, if you are going to be intellectually honest about your own accountability, then you need to distinguish between what happened to us and what can we do about it. This brings me back to the book I gave our boys.

Epictetus begins the Enchiridion by separating the things that are up to us from the things that are not. Two thousand years later, this distinction is enticing as a platitude. However, both Joyce and Kingsolver show us how hard it is live this way. Stephen (and Demon) are subject to forces they did not chose. Stephen responds by rejecting them. Demon responds by trying to assert his agency (getting sober, getting a job, visiting the ocean). Bloom knows and feels real pain and has to decide what he can accept versus what he is going to avoid. Molly rationalizes, remembers, and finally affirms.

None of the characters is able to control the world around them. Neither do we. Maybe that is what I hope my sons eventually discover in those Stoic passages. The point isn’t to pretend circumstances/context don’t matter. It is also not to assume responsibility for everything that happens. The goal is to be super clear about where this boundary is.

• What happened to me?

• What did I contribute?

• What is outside my control?

• What remains mine?

Consciousness allows us to see the distinction. Accountability asks us to own our part in it. Agency begins with what we do next. Perhaps that is the question that has stayed with me after six months exploring the consciousness of Ulysses. We see / perceive something. Then we can know something. Then, perhaps there is an epiphany. Then the most important question is “what can/ should we do?”

As plebes at the US Naval Academy in 1986, we were required to memorize 1000+ facts, quotes, and random crap (aka “Rates”) during our Plebe summer. I still remember one of those quotes, at the time ascribed to John Paul Jones (the father of the US Navy) :

“It is by no means enough that an officer of the Navy should be a capable mariner. He must be that, of course, but also a great deal more.”

The passage went on to describe a naval officer as a person of “liberal education,” capable of distinguishing “error from malice, thoughtlessness from incompetency, and well-meant shortcomings from heedless or stupid blunder.”

I thought that was darn-right enlightened. This is exactly what I hoped to become—a person who learned how to discern right from wrong (i.e., apply judgment) when the answer was not clear.

When Scholarship Confronts and Corrects Tradition

The only problem was that John Paul Jones had not actually written those words. The quote first appeared in a 1900 biography written by Augustus C. Buell. In 1986 (the year my class started at Navy), the Naval historian James C. Bradford exposed Buell as a fabricator who invented multiple letters and statements. However, the Academy did not formally correct Reef Points until 2003! And, classic Navy, rather than discard the passage, the Academy retained it under a corrected heading: “Written by Augustus C. Buell in 1900 to reflect his views of John Paul Jones.” I did not know about this until this week when I was researching this article.

That story captures something essential about military education. Tradition gave the passage authority; however, it is important to give room for scholars to explore what we assume is true. To be clear, the discovery that Jones did not write the words did not make it less inspirational to me and, I imagine, many of my classmates. It did require an institution (i.e., the Naval Academy) to correct a story it had been telling about itself for GENERATIONS! This is exactly what education should do. It should teach us to respect inherited traditions while, at the same time, allowing for self-reflection when a new fact pattern is discovered.

Why This Matters Now?

Why am I making a big deal over a quote from 1900?? Because the DoD is considering a complete restructuring of the way the service academies approach their mission to educate the officers of the future. According to an unreleased draft memorandum obtained by CBS News, the proposal would eliminate civilian tenure at the service academies (and senior war colleges) and subject every course to a “line-by-line” review. The new standard applied to the course would be that they need to advance “tactical, operational or strategic warfighting.” Courses deemed nonessential or “ideologically driven” could be eliminated. (note: as of July 30, the memorandum had not received final approval.)

To be clear, I do think there is some legitimacy to the review. The service academies, by definition, are not ordinary universities. Their stated purpose is to prepare officers to defend the country. Thus, their curricula should be rigorous, relevant, and connected to that mission. And, I think it is totally fair to expect Civilian faculty to be held accountable for the quality of their teaching, scholarship, and contribution to the institution. Moreover, I know from experience that tenure does not guarantee excellence.

Behind The Wizard’s Curtain

I was an English major at the Naval Academy, graduating with a BS in English (yes, I get the irony). Most of my professors in my department were civilians. I then had the good fortune to go back as a “military instructor” in the English department. Thus, I got to see what really happened behind the Wizard’s curtain and also spent time getting to know many of these professors as colleagues and some as friends. In reflection, they were not all great teachers, and most were not all active scholars (to be fair, the Naval Academy was not a “research university,” so the research requirement was pretty light). Thus, tenure did not automatically produce continuing contribution.

Some professors were deeply committed to the mission of developing future officers. Others appeared to be just putting in their time. There were exceptions, of course. I remember one professor, in particular, who challenged the Academy almost weekly. He ruffled lots of feathers. And while I think his arguments were provocative, sometimes they seemed unnecessarily so. At the same time, some of his criticisms were true, and they forced the institution to confront questions it might otherwise have preferred to avoid (ironically, Pres Trump and Sec. Hegseth would have loved this guy’s take on DEI at the Academy)

This experience left me with a mixed POV re: tenure. It can (and does) protect mediocrity. At the same time, it protects the person willing to tell an institution something it does not want to hear.

The World Beyond The Academy

I have been reading Rick Atkinson’s The Long Gray Line, his account of West Point’s Class of 1966. This class of 560ish entered West Point at a time when the Academy inculcated a fixed moral architecture: duty, honor, country. This also included what Sec Hegseth would call the warrior ethos: loyalty to the unit; obedience to lawful authority; & courage in the face of danger.

The book follows this class through Vietnam and then back to the US in the early 70s, which had changed radically from the time they entered West Point in 1962. They became part of what Atkinson describes as the first generation of West Pointers to join a losing Army. To be clear, their struggle was not caused by the absence of principles. It arose because the reality they faced was often confusing, and it was hard to reconcile which principle in their moral architecture should apply. Atkinson shares many stories of these young officers wrestling with hard-to-answer questions such as:

• What did an officer owe his soldiers when the mission appeared strategically incoherent?

• What did loyalty to the chain of command require when senior leaders seemed disconnected from conditions on the ground?

• How should an officer reconcile the urgency of protecting his men with obligations toward civilians?

• When did honor require obedience, and when did it require candor?

• How could an officer distinguish between a lawful order, a wise order, and a moral one?

Each of the men featured in his book comes up with different answers to these questions based on their specific situation and moral compass. Some survived, and many died. Even more were scared (physically, mentally, emotionally) for life based on their experience in Vietnam.

We have seen how this same dynamic play out in more recent conflicts such as Iraq and Afghanistan. Ultimately, the morality of war is gray. The hardest choices are rarely between obvious good and obvious evil. They are between competing duties, incomplete information, and consequences that cannot be fully anticipated.

This is where the distinction between Military “training” and “education” becomes meaningful. Training teaches a person to perform a known task under defined conditions. Education prepares a person to determine what the conditions mean, which principles apply, what consequences may follow, and what to do when the rules seem to be in conflict. Today’s officers need both. They must know how to execute a mission. They must also understand the mission’s relationship to the broader strategic purpose. They need to understand military law, their constitutional obligation, and their moral responsibility. An order can be lawful and still be foolish. A commander can satisfy the immediate demands of the chain of command while failing the soldiers or citizens whose trust gives that command its legitimacy. Thus, I would argue that developing judgment is an essential warfighting capability. But how does one develop judgment?

Good thing we have 1000s of years of thinking on the topic to refer to!

Educating the Guardians

One of the earliest examples we have of how to educate the guardians of a Republic is Plato’s dialogue The Republic, written more than 2000 years ago. In The Republic, Socrates asks what qualities should characterize those entrusted to guard the city (i.e., the military). He shows that courage and martial spirit (i.e., the warrior ethos) are necessary but not sufficient. The Guardian must possess seemingly opposite qualities: he and she (yes, there were female guardians in The Republic) must be both fierce toward the city’s enemies but also gentle toward its citizens.

So how does a Guardian discern who is friend and who is foe? This distinction depends upon recognition and knowledge. The Guardian must be more than strong. He must be capable of determining whom he is obligated to serve. That is why Plato devotes so much of The Republic to the education of those entrusted with power. Plato, Republic, Book II, 375e-376d.

Because he understands how profoundly education shapes the Guardian’s character, Plato also permits the rulers of his imagined city to regulate its stories, poetry, music, and myths. I.e., Plato is suggesting that the rulers use education as a means of limiting what the Guardian is allowed to think. And this insight is at the heart of the tension within military education. The state must educate its Guardians well enough to exercise independent judgment. Yet the state may also be tempted to control that education so tightly that independent judgment becomes impossible. WOWZA!! This seems pretty relevant today.

Constitutional Loyalty Versus Political Compliance

A constitutional republic should expect constitutionally loyal officers. At the same time, it should also not want politically compliant officers. These ideas are not synonymous. Political compliance attaches loyalty to the people temporarily holding power. Constitutional loyalty attaches loyalty to the constitution these officials have sworn to preserve. That distinction requires officers who can reason historically, legally, morally, and strategically. It also requires officers capable of offering civilian leaders candid advice. These civilian leaders should embrace these thought partners, not purge them from the military.

This is why the proposed standard for curriculum review is inadequate. History courses may not appear to contribute “directly” to tactical warfighting until a commander must recognize that battlefield victories are not producing political progress. Reading books may seem peripheral until an officer must be able to empathize with the humanity of the enemy. Studying Philosophy may seem abstract until duty, honor, law, and loyalty each suggest different paths forward when confronted with a moral quagmire. These disciplines do not distract from the formation of warfighters. In fact, properly taught, they help prevent warfighters from becoming mere instruments of force.

The Naval Academy’s own mission recognizes this broader responsibility. I.e., its mission is to develop midshipmen “morally, mentally and physically” and to prepare them for “the highest responsibilities of command, citizenship and government.” It is a mouthful, but certainly broadens the remit of a military education and echoes what Buell said about John Paul Jones 200 years ago.

Another Lens to Use

The proposed review should therefore ask more thoughtful questions than just whether a course has an obvious connection to warfighting. For example, does a course:

• Develop strategic reasoning?

• Deepen historical and cultural understanding?

• Sharpen ethical and constitutional judgment?

• Does it teach officers to connect tactical action to political purpose?

• Expose students to arguments they must be able to understand and answer?

Or to be more precise, for the Naval Academy, you could just ask: “Does it contribute demonstrably to the Academy’s mission?” Ultimately, the standard should be contribution, not conformity.

Accountability without ideological purification

The language of the draft memorandum creates a deeper concern. It reportedly proposes eliminating courses deemed “ideologically driven” without explaining who will make that determination or by what standard. Obviously, every curriculum reflects judgments about which ideas, histories, and capabilities matter. Removing a course can be as ideological as creating one. The question is not whether ideology can be eliminated from education. It is whether students will encounter serious competing arguments and learn to assess them through evidence, reason, and debate.

Similarly, a “line-by-line” review can be a tool of institutional accountability. However, it can also become an ideological purification campaign, particularly if the reviewers begin with a political conclusion about which questions may be asked. This is where civilian faculty perform a distinct institutional function. Military instructors bring recent operational experience, professional credibility, and the “lived experience” of being in the Fleet. Civilian professors bring disciplinary depth and provide institutional continuity. Because military officers rotate every 2-3 years, civilian professors also preserve knowledge and programs across generations of leadership. This continuity provides perspective over time.

What To Do About The Deadbeats?

I do think there is an opportunity to uplevel the impact and effectiveness of civilian professors (and military instructors). But this is not by eliminating intellectual independence (as protected by tenure). Instead, one way to do this would be to build a stronger system of accountability around it. I.e., tenure should protect rigorous inquiry, not weak performance. Faculty should be evaluated on the quality of their teaching, the seriousness of their scholarship, and their contribution to the Academy’s mission. Existing procedures for addressing nonperformance should be examined and strengthened where necessary. But a professor should not have to worry that a historically grounded point of view or a criticism of institutional policy will be the justification for being fired.

If we don’t protect intellectual independence at the Academies, the midshipmen and cadets will never learn how to reconcile competing ideas. Professors will avoid difficult subjects. Administrators will remove controversial readings. They will be living in Orwell’s 1984. This may produce conformity, but it will not produce judgment.

A capable warfighter, but also a great deal more

As Buell wrote, a naval officer must indeed be a capable mariner, “but also a great deal more.” Yes, technical competence is indispensable. Yes, physical courage is indispensable. At the same time, historical understanding, moral imagination, constitutional loyalty, intellectual humility, and the ability to distinguish error from malice are indispensable. To that point, the West Point Class of 1966 did not enter Vietnam without principles or courage. Their ordeal began when principles came into conflict and courage demanded more than physical bravery.

To be clear, I don’t think any curriculum could provide officers with ready-made answers to every moral or strategic dilemma. These are not “Rates” to be memorized. Instead, a military education should be focused on developing the habits of mind and character necessary to face those dilemmas responsibly. And this is not the same type of education a college kid gets at a civilian school. Nor should it be.

These officers (aka guardians) are trusted with the power of life and death. And, as a republic, we should expect that they know how to fight and win. At the same time, as Plato wrote 2000 years ago, a republic must also educate its guardians to understand why they fight, what limits their power, whom they serve, and how to respond when duty, honor, law, and strategy no longer point in the same direction.

Cyclops

Joyce, via the narrator, characterizes the unnamed “Citizen” as bombastic, sentimental, learned, threatening, and occasionally perceptive. Throughout this episode, the Citizen speaks for an Ireland that has been a British colony for 700 years. During that time, its people were suppressed, its economy exploited, and millions were forced to leave (most recently due to the potato famine). So his grievances are not invented. At the same time, he is frequently shown as being absurd, creating a myth of a pre-British Ireland that is, at best, fanciful. This is what gives the episode its power. Joyce does not make the Citizen a fool for loving Ireland. He makes him dangerous because his love of Ireland is inseparable from his hatred of the British and those he believes do not belong there.

Monticello

I first visited Monticello 45ish years ago with my family. To put this in perspective. At the time, the Jefferson Foundation still rejected the idea that Thomas Jefferson had fathered Sally Hemings’s (one of his slaves) 6 children. I remember, nearly 50 years ago, being impressed by the many books, scientific instruments, and all the cool gadgets he had in the house (e.g., the dumbwaiters). Last Friday (July 3rd), I went with my mother to celebrate the 250th anniversary of the Declaration of Independence. This time, I had a better appreciation for how this house stands as a monument to the Enlightenment ideals that Jefferson and the other founders sought to inculcate in our early national identity.

I was also very clear that this house stood as a monument to contradiction. The man who wrote that “all men are created equal” lived with 400+ enslaved men, women, and children who were essential to the operation and upkeep of Monticello and its 5,000 acres. He only granted a small number (Heming’s children) freedom through direct action and as part of his will. Most remained enslaved at his death, and many were sold as part of the settlement of his estate.

The two experiences raised the same question: Who is included when a nation says “we”?

Make Ireland Great Again (MIGA)

The Citizen believes Ireland was once heroic, culturally coherent, and populated by men of courage and conviction. He argues that its greatness was stolen through foreign conquest, economic exploitation, and cultural contamination. Its ruin was due mostly to evil women influencing their men. For example, he short-hands the story of King Mac Murchada inviting Norman lords to help him reclaim his lands in 1167 by saying “the strangers, says the citizen, Our own fault. We let them come in. We brought them in. The adulteress, and her paramour brought the Saxon robbers here” (lines 12. 1161-1164).

Myths, by definition, are not true; however, they are often rooted in a truth or a perceived truth. This is why myth-making is so powerful when defining a national identity. While the Citizen is right that this incident led to Norman lords coming across to Ireland and, eventually, Henry II arriving in 1171, which then led to 700 years of occupation, the story is much more complicated than how he frames it. He is fostering a myth.

In the Citizen’s worldview, Ireland can only reclaim its greatness by restoring what he thinks was true before—i.e., Make Ireland Great Again. Throughout “Cyclops,” Joyce parodies this vision via a second narrator’s voice, often called the parodist, by transporting the ordinary life of the Dublin pub into what feels like a “King Arthurian” world full of Gaelic kings, warriors, saints, giants, ceremonial processions, heroic contests, and improbable national glory.

The Citizen himself assumes mythological proportions. He is introduced as a massive, almost prehistoric figure, “seated on a large boulder at the foot of a round tower”; he was a “broadshouldered deepchested stronglimbed frankeyed redhaired… (you get the idea) [12.150-167ish]. And he is accompanied by a mangy dog whose lineage is recited like the genealogy of an ancient king in one of the interpolations (note: interpolations are interruptions in the narrative). In fact, Joyce uses 33 different interpolations to inflate the men in the pub and Irish Nationalism into heroes from some lost Irish epic.

The parodies in the interpolations are funny and, at the same time, sharp. Through them, Joyce is showing us what nationalism does to history. The Citizen’s Ireland is ancient, masculine, Catholic, and of one ethnicity. Its people are the heirs of warriors and martyrs. Its decline is due to foreigners (primarily the British occupiers and immigrants) and those Irish who lack the proper degree of loyalty. What his view of Ireland does not include is the failures, contradictions, and evolutions that constitute an actual country. Instead, he—and the other Irish Nationalists like him—harken back to an imaginary nation that existed before outsiders, weak leaders, elites, and traitors corrupted it.

In this episode, the Citizen also transforms this love of Ireland into a kind of loyalty test of who is entitled to be Irish. And this is where Bloom, a modern-day Odysseus, confronts the Citizen in a way that echoes Odysseus’ own confrontation with the Cyclops in Homer’s Odyssey. Bloom was born in Dublin and is an active “citizen.” He works at the local newspaper and knows many other citizens with whom he interacts throughout the day (e.g., he attends Patty Dignam’s funeral with a group of men). Thus, he is part of the city as much as any other citizen. However, he is also Jewish, the son of an immigrant, and is more empathetic than a typical Dublin man at that time.

In the earlier episodes, these differences mark him as an outsider. He makes a faux pas when riding in the carriage and is not familiar with the routine of the mass when he enters the church in the Hades episode. He suffers low-grade antisemitism from the people he works with at the Newspaper office in the Aeolus episode. Moreover, he chooses to operate outside of the accepted social mores. For example, he does not stand a round of drinks when he walks into the pub in Cyclops and chooses not to eat with the other men in the pub in the Lestrygonians episode, instead choosing to eat a cheese sandwich at another restaurant.

Even though Bloom was born in Ireland, to Citizen, he fails the test of national authenticity (or purity). His ancestry is suspect, and his religion places him outside the dominant culture. Most importantly, he refuses to hate Ireland’s designated enemies with sufficient enthusiasm and so fails the “loyalty” test as well. When Bloom argues that persecution cannot be answered by more persecution, the Citizen does not treat him as a fellow Irishman with a different political view. He treats him as an alien whose claim to Ireland is fundamentally fraudulent. This is where patriotism becomes nationalism.

A patriot, by definition, is someone who loves, supports, and is willing to defend their country. Bloom makes clear that he is a patriot. But this is not enough for the Citizen. The Citizen wants to decide which people have the right to love Ireland, and this is always the foundation of nationalism. The Citizen’s nationalism is therefore not simply an expression of national pride. It is a theory of national ownership. Ireland belongs to a particular kind of Irishman, and anyone who does not match that type must continually demonstrate their loyalty. This sounds eerily familiar today.

The Politics of “Again”

At its core, the MAGA movement is also a politics of restoration. It begins with a story of national decline. America was once stronger, safer, more prosperous, more unified, more respected, and more culturally confident. That greatness was then squandered by weak leaders, corrupt elites, immigrants, globalists, and citizens who no longer honor the country’s history or traditions. To that point, in his 2017 inaugural address, President Trump promised to “rebuild our country and restore its promise.” And in his 2025 inaugural address, he described himself as having been saved by God to make America great again and repeatedly promised that the country would become powerful, prosperous, and productive “once again.” His constant use of “again” is actually brilliant. It has enabled millions of people to share a feeling of dispossession without requiring them to agree about precisely what has been lost or when the golden age existed. That ambiguity is politically effective. However, it is also dangerous because we don’t have clarity on what we are working to restore. The questions that it begs include

• When was America great?

• Who was free?

• Who could vote?

• Who could own property, attend a university, enter a profession, serve on a jury, marry freely, or move about freely without fearing the power of the state?

Without clarity on these questions, it is left to the leader, in this case, President Trump, to define.

Our Republic was Limited by Definition

I have been working my way through We The People: A History of the US Constitution by Jill Lepore, and she makes clear that, at first, our Republic was not a fully representative democracy. Voting qualifications varied by state, but political power remained overwhelmingly concentrated among the elites (i.e., mostly white men who met property, tax, religious, or other qualifications). One source states that only about ~6% of the total population was eligible to participate in the nation’s first elections. Women were generally excluded from formal political power. Enslaved people were treated as property, and Native Americans were largely considered outside the constitutional community. Free Black Americans faced severe restrictions, even where they were not formally prohibited from voting.

Thus, the most revolutionary idea of the Declaration of Independence (DoI) was stating the ideal “all men are created equal” within a radically restricted society. Jefferson and the other founders knew that this language was expansive, and they had to wrestle with the contradiction from the beginning. Jefferson’s original draft of the DoI included an attack on the transatlantic slave trade. Congress removed the passage during its revisions, in part because slavery threatened the political unity necessary to declare independence. To be fair, Jefferson’s language placed much of the blame on the British Crown rather than recognizing the colonists’ own participation in and profit from the trade. Jefferson understood the contradiction better than his defenders sometimes admit.

But recognizing a moral contradiction is not the same as escaping it. Jefferson was caught in a moral quagmire, one of his own making. He could see that slavery violated the principles of the Revolution, and he understood that the institution of slavery would only deepen the nation’s political and moral crisis. Thus, he could articulate ideals that would eventually be used to condemn slavery, but he remained personally, economically, socially, and psychologically dependent upon the system he knew to be unjust. This conflict became clear to me as I walked the grounds of Monticello and realized that Jefferson, who had 6 children with his first wife, had 6 children with Sally, made Sally’s 6 children live in the slave quarters (Sally had a special room). He was not the father of 1 “oops” child with the maid; he had 6 children whom he never claimed, who looked like him, and whom he had to see daily. Thus, he was confronted with his own hypocrisy for 50 years after writing the Declaration of Independence.

The DoI does not deserve reverence because its author perfectly embodied its principles. Clearly, he did not. Instead, it matters because its words created a standard by which Jefferson himself, the founding generation, and every subsequent generation could be judged. In his last known letter, written on June 24, 1826 (about 2 weeks before he died on July 4th!!), Jefferson expressed the hope that the document would eventually awaken people everywhere to self-government and human rights. “All eyes,” he wrote, “are opened, or opening, to the rights of man.” Jefferson could see the direction the world needed to travel more clearly than he could live it himself. And, in fact, he was right. 100+ countries have incorporated parts of the US Declaration of Independence in their own declarations. People get the ideal.

Restoration Versus Expansion

This is where the Citizen and the DoI point in opposite directions. The Citizen believes a nation becomes great by recovering a mythic history. He searches the past to find a pure Irish population capable of inheriting Ireland (there is even an invented 12 tribes of Ireland interpolation). By contrast, the DoI suggests that our nation can become even greater by including people it once excluded. In fact, over the past 250 years, we have seen different groups embrace the ideal of “all men are created equal” to create a more expansive definition of citizenship (very much in line with Bloom’s POV). For example, from the day it was published, abolitionists seized the Declaration’s language and applied it to slavery. Frederick Douglass used the nation’s founding principles to expose the hypocrisy of celebrating liberty while millions remained enslaved in a speech on July 4th in 1852, saying:

“The rich inheritance of justice, liberty, prosperity and independence, bequeathed by your fathers, is shared by you, not by me. The sunlight that brought light and healing to you, has brought stripes and death to me. This Fourth July is yours, not mine. You may rejoice, I must mourn.:

Likewise, the women at Seneca Falls adapted the Declaration to demand political and civil equality. The Reconstruction era attempted, however imperfectly, to create an interracial democracy. More recently, the civil rights movement demanded that the country honor promises it had repeatedly deferred. Each generation has widened the meaning of “we.”

MAGA suggests a different path forward. Like the Citizens’ nationalism, MAGA’s leaders, such as JD Vance, ask us explicitly to return to an earlier age, before some combination of immigration, globalization, secularism, feminism, civil rights, demographic change, institutional decay, and elite betrayal altered the country. To be fair, not every concern articulated by MAGA adherents is illegitimate. Many Americans have experienced dispossession & economic insecurity. We have all suffered through the fallout and cost of too many failed wars and military actions since WWII. And today, we are experiencing cultural fragmentation due to increased and seemingly overwhelming immigration. Finally, many feel that the institutions that our government has created are too big, bureaucratic, ineffective, and wasteful. Thus, any path forward that refuses to acknowledge those failures will not defeat restorative nationalism. It will feed it.

Joyce’s warning is not that grievances are imaginary. His warning is that these grievances can become an identity in and of themselves. Once a movement understands itself primarily as the victim of national betrayal, nearly any act can be defended as restoration. Political opponents are enemies who should be harmed. Immigrants are invaders who should be repulsed. Judges become conspirators and journalists become traitors. In this world, elections are only legitimate if they deliver the proper result. Politics is no longer an argument among citizens over the common good. It becomes a struggle over who owns the country. Sound familiar?

The Biscuit Tin

Joyce finally exposes the Citizen’s pretensions through comedy. After speaking in the elevated language of Irish heroism, national destiny, sacrifice, and betrayal, the Citizen pursues the departing Bloom and hurls a biscuit tin after him, echoing the Cyclops throwing the boulder at the fleeing Odysseus in the Odyssey. The gesture is ridiculous, but not harmless. That is Joyce’s point. Nationalism presents itself in epic language. It invokes ancient heroes, sacred soil, betrayed ancestors, and the destiny of a chosen people. But its grandeur often culminates in petty cruelty directed at a real person.

The Citizen imagines himself defending Ireland. He is, in fact, attacking another Irish citizen. He wants to fight the persecution by the British, but then, in turn, he persecutes a Jew. He sees himself as a national hero, but, in effect, he has become a drunken bully throwing a biscuit tin. This is made clear when the narrator, who has been on the Citizen’s side throughout the episode, turns on him at this point and says, “Arrah, sit down on the parliamentary side of your arse for Christ’ sake and don’t be making a public exhibition of yourself” (12.1792-3) through the streets of Dublin.

America at 250

Joyce called the episode “Cyclops” because nationalism epitomized by the nameless Citizen produces a distinctive kind of blindness. The Citizen does not lack sight. Instead, he has a very narrow, monocular vision where he can only see the wounds inflicted upon Ireland as a persecuted people. Ironically, he can’t see or admit to the persecution of Bloom, even when Bloom says he is part of a persecuted race as well, saying “I belong to a race too. . . that is hated and persecuted. Also now. This very moment. This very instant” (12.1467-8). MAGA sees real failures in modern America. However, like the Citizen, MAGA looks at these problems through the single eye of restorative nationalism. As enlightened as Jefferson was, he could also not fully see either, or, to be more precise, could not force himself to confront how the rights he articulated in the Declaration of Independence actually condemned the world he lived in.

On our 250th birthday, the question is not whether we will make the country great again, but how we will make America even greater in the years to come. And this is where we can turn to Bloom (the voice of Joyce) again, who says “A nation is the same people living in the same place” (12.1422). For Bloom, a nation is created by people who contribute to the community. The irony in this Episode is that it is Bloom who is taking care of his fellow citizens. The Citizen’s implicit definition of a nation is ancestral and exclusionary. Bloom can live in Ireland, serve Irish people, and call himself Irish, but the Citizen still sees him as a foreign Jew.

Our choice today is not between patriotism and shame. It is really about two different visions of national greatness. One tells us that greatness lies behind us. We can recover it by restoring the culture, hierarchies, & boundaries of a bygone era. The other suggests we can continue to build on our historical greatness by embracing our history as a nation of immigrants. For sure, we need to be intentional and disciplined about who we continue to welcome to our country and how we provide a path to citizenship. But this assumes that we embrace a look forward versus look back view of what it means to be a people and a nation.

As companies scale, CEOs must delegate more responsibility to Presidents, COOs, CFOs, CROs, and sometimes Executive Chairs. But adding new executives does not change the core reality of corporate leadership: the CEO is ultimately “accountable” for the company’s performance against the plan. This essay explores how and when to introduce new executives and how to set up a system to ensure alignment and accountability as you scale.

Four takeaways:

1. The CEO can delegate responsibility, but not accountability.

2. The President, COO, CFO, CRO, and Executive Chair roles should expand leadership capacity, not create ambiguity about who owns the overall results.

3. The CEO remains accountable for creating and overseeing a system that produces performance. The key roles include developing a compelling vision, being on top of cash AT ALL TIMES, ensuring the right people are in the right seat, establishing and maintaining key relationships inside and outside of the organization.

4. The CEO’s ability to scale with the organization comes down to their ability to learn and adapt quickly.

The Navy Lesson

One of the most useful leadership lessons I learned in the Navy has stayed with me throughout my career: Responsibility can be delegated, but accountability cannot. A commanding officer (CO) of a ship delegates constantly. While they may be on the bridge overseeing the ship’s operations, the core functions such as navigation, engineering, flight operations, logistics, weapons, maintenance, communications, and safety all depend on other officers and enlisted sailors doing their jobs.

No skipper can personally stand every watch, inspect every valve in the engine room, or make every tactical call when engaging the enemy. But if the ship runs aground, the skipper is held accountable. One recent example was the US Williams, which ran aground in Africa in 2024. The captain was relieved of command two months after the grounding "due to a loss of confidence in his ability to command." The helmsman may have actually made the critical mistake. The navigation team may have missed a warning sign. The watch team may have failed to escalate what they were seeing to the Officer of the Deck. In the navy, it is ABUNDANTLY clear that the CO owns the larger system: training, readiness, standards, supervision, judgment, command climate, and operational discipline. And, if a ship runs aground, the system has broken down, and the CO will be held accountable. In the Navy, we call this “the burden of command.”

The same principle applies to a CEO in the corporate sector. A President may own the day to day business results while the CRO may own the booking number. In the back office, a COO may own the systems, teams and tech the produce the data to inform the business and the CFO may own the 13 week cash forecast. However, the CEO owns the command. And, like the skipper of a ship, the CEO is the only executive who cannot say, “That was not my area.”

The Scaling Dilemma

Every growing company eventually runs into the same problem: the CEO becomes the bottleneck. At the beginning, the founder or CEO can stay close to everything Decisions about product roadmap, customers, hiring, capital, culture, pricing, pipeline, delivery, board communication, and strategy all run through the same person or small group. Many founders find this exhilarating. They are in the weeds with regards to every decision because they want to have their fingers on every pulse of the business. When the company is small, these founders are able to make decisions quickly using their ability to sense what needs to happen based on their deep insights into the customer problem set and product capabilities.

However, at some point, the complexity of the business starts to overwhelm most founders, and the company needs to hire executive capacity. This may include hiring a President to run the business, especially if the founder is more of a technical/ engineering type. In finance, companies will often move from an outsourced bookkeeper to hiring a controller and then eventually a CFO, especially if they are planning to raise money from professional investors. Once you take on investors, you will need a board and it is often a good idea to add an experienced Executive Chair who can support governance, board management, and succession planning if you are a first-time founder/CEO.

This is not a failure of leadership. It is a sign that the company is scaling. But there is a risk to be aware of. As you add new roles, people can start to confuse role expansion with accountability transfer. The risk is you hire executives without being explicit about roles and responsibilities and, most important, decision rights. If these expectations are not made clear you, as the CEO, may assume the President owns execution. At the same time, if you have a President and COO, the President may assume that the COO owns the operating cadence. The COO, who is aggregating and reporting results, assumes the functional leaders own the outcomes.

And to be clear: the board ALWAYS assumes the CEO has command of the whole system. This works until the company misses plan. That is when the ambiguity becomes visible with lots of finger pointing in the Executive Meetings.

What Only the CEO Can Own

A.G. Lafley, the former CEO of Procter & Gamble, wrote in Harvard Business Review about “what only the CEO can do.” His core insight was that the CEO has a unique enterprise-level role that cannot be fully replicated by any other executive. The CEO sits at the intersection of the inside and the outside, the present and the future, the organization and the market. McKinsey’s CEO Excellence research reaches a similar conclusion using a broader set of companies. McKinsey identifies six core elements of the CEO role: setting direction, aligning the organization, mobilizing through leaders, engaging the board, connecting with stakeholders, and managing personal effectiveness. McKinsey use different language, but it is highlighting the same pattern: The CEO needs to be the integrator.

When I first read Make Big Happen by Mark Moses, founder of CEO Coaching International, where I am now a partner, I saw a similar framework expressed in more practical CEO language. Specifically, he identifies five domains the CEO can never abdicate. These include:

• Vision

• Cash

• People: right people in right seats

• Key relationships

• Personal Learning

We use this framework with clients to help CEOs examine where they are actually spending their time and energy versus where the role requires them to spend it. For example, while the CEO may not write every part of the strategy, the CEO owns whether the company has a clear direction. Similarly, the CEO is probably not building the financial model. But the CEO owns whether the company has enough cash, credible forecasts, and disciplined capital allocation. As the company scales, the CEO will inevitably have less direct contact with the front lines and middle-management ranks. At the same time, the CEO must ensure there is a talent system in place that hires great people, raises standards, and promotes the best leaders based on exceptional performance. One of the CEO’s key responsibilities is to invest and nurture key relationships across the spectrum of stakeholders (e.g., customers, investors, partners, board members, analysts and influencers). Doing so helps build brand authority in the market and credibility with investors.

Finally, the CEO has to own their own learning agenda. They need be deliberate and intentional about how much time are they spending learning about industry trends, studying competitor moves, listening to customers, and staying current with business innovations. In 2026, this also includes a practical question: is the CEO personally using AI enough to understand how it will change the operating model of the business?

The CEO can and should delegate the work and assign ownership. They can create leverage through a President, COO, CFO, CRO, or Executive Chair. But the CEO cannot delegate accountability for whether the enterprise system is working. That is where the Navy lesson comes back: responsibility can be delegated, but accountability cannot.

Strategy and Execution Cannot Be Separated

One of the more dangerous myths in scaling companies is that the CEO should “set strategy” and then leave execution to others. At the same time, there is some truth in this statement. The CEO should not run every meeting, approve every decision, or become the company’s chief problem solver. A CEO who stays too deep in the weeds risks becoming a super-COO rather than a true enterprise leader. But the opposite failure mode is just as dangerous. If the CEO only focuses on talking strategy with the board, entertaining the most important clients and delegates execution to the team, they will lose touch with the truth of the business.

In its research, Bain has argued that the best CEOs do not treat execution as someone else’s job. They may not do the work themselves, but they stay close enough to understand whether the priorities they are communicating are actually being funded, staffed, measured, and executed. As Sun Tzu is often quoted as saying “Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.”

Bain suggests that the bridge between the two is the operating model (or system). And they define an operating model as the way the company organizes resources, assigns accountabilities, makes decisions, governs tradeoffs, measures progress, and coordinates work. The CEO does not need to personally run the operating model. But the CEO is accountable for whether the operating model fits the strategy.

What do I mean?

• If the strategy depends on enterprise customers, but the company still operates like a velocity SMB machine, that is a CEO issue.

• If the plan depends on expansion revenue, but customer success has no commercial accountability or product influence, that is a CEO issue.

• If the company needs to solve for profitability, but the executives incentives still reward growth at any cost, that is a CEO issue.

• If every executive believes someone else owns cross-functional execution, that is a CEO issue.

This is where defining the other key executive roles, their scope and responsibilities to include the decisions they own, becomes critical to scaling successfully.

The Roles Around the CEO

The President, COO, CFO, CRO, and Executive Chair are all roles that can create leverage for the CEO, but only if each role has a clear purpose and charter.

The President is often the most flexible and therefore the most confusing role. In one company, the President owns day-to-day business performance. In another, the President owns a business unit, geography, customer segment, or commercial engine. In a founder-led company, the President may be the internal operator who complements a visionary CEO. In a professionalized company, the President may carry broad P&L accountability while the CEO focuses more on strategy, capital, board, executive team, and major external relationships. There is no single correct model. However, to make this role successful, the CEO and President need to answer one question: “What business result does the President own that the CEO should no longer personally manage day to day?”

If there is no clear answer, then the President role needs to be better defined.

The COO role often has a similar challenge. Harvard Business Review called the COO the “misunderstood” second-in-command because the role is so dependent on the CEO, the strategy, and the company’s stage. A COO may be an executor, change agent, mentor, partner, complement, or successor. In my experience, the role is not defined by the title. It is defined by the problems the individual takes on. In a scaling company, the best COO is not merely a process person or meeting runner. At Maxio, we introduced a COO role to help build the operating system that would make the company more predictable, more scalable, and more accountable. This person included the data, tech, systems and people to help us understand what was going on across our 2000 customers and many products. The question for the COO is: “What execution problem disappears because this role exists?”

The CFO and CRO have clearer functional anchors, but the same principle applies. The CFO may own the financial model, closing the books, forecasting, capital structure, and reporting on operating metrics (if there is not a COO). The CRO usually owns bookings, pipeline, retention, and revenue execution. But neither role owns the ultimate results. They own essential components of the plan.

The Executive Chair is different. This role can be powerful when it provides governance, stewardship, CEO support, succession discipline, and long-horizon judgment, especially when there is a new CEO in role. I had a great Executive Chairman, Monte Zweban, at RocketFuel when I took over as CEO. We talked almost daily for the first 6 months. During this time, Monte would make clear that he was providing ideas and suggestions but that the decision was my call. Or, to be precise, he would help me understand what were board-level decisions versus management decisions. This mentoring was incredibly valuable and it continued even after he moved from Executive Chair to Chairman. At the same time, I have seen other relationships between Exec Chairs and CEOs become toxic. This is especially true when the Exec Chair becomes effectively a second center of command. Spencer Stuart’s work on Executive Chairs reinforces the importance of trust, division of labor, and clarity between the Executive Chair, CEO, and board.

Net/net: As a business scales, it is important to onboard experienced executives (and advisors). It is absolutely critical to delegate work and responsibility to get as much done as quickly as possible. But there can only be one CEO.

The Missed-Plan Test

There is an old adage about “how growth hides many sins.” Essentially, when a company is growing, role ambiguity, weak decision rights, fragile forecasts, and execution debt can all remain below the waterline. But when growth slows or the company misses plan, those hidden weaknesses surface quickly. We saw this pattern play out in the dot.com bust of the 2000s and more recently with the SaaSpocalypse of the last couple of years.

When performance is strong, you can hide structural issues. and, honestly, the board will usually give the CEO and ELT more room to try things. Growing companies celebrate quarterly results, as they should. However, many avoid the harder question of whether the system is actually well designed. As Ric Elias, CEO of Red Ventures, in an open letter once wrote: “growth hides many sins and we must not get complacent about our culture or our performance.” When a company starts to miss its plan quarter after quarter, the temperature in the board meetings starts to get turned up. If things are starting to slip, then the CEO and the Executive Team need to proactively start to do some soul searching. Specifically, they need to get clear on what went wrong. E.g.,

• Was the strategy wrong?

• Was the forecast too optimistic?

• Was the market softer than expected?

• Did pipeline quality deteriorate?

• Did churn surprise the team?

• Did product delivery slip?

• Did implementation capacity constrain growth?

• Did the company hire too fast ahead of revenue to address capacity constraints?

• Did the executive team fail to confront reality early enough?

And the hardest question of all: “At what point does the board lose confidence in the explanation, the team, or the CEO’s ability to change the trajectory?”

Answering these questions requires the entire executive team to engage honestly. But eventually, the board comes back to the CEO. This is not because the CEO was personally responsible for every miss. Nor is it because they expect the CEO to solve every problem. They look to the CEO because the CEO is the captain of the ship. The CEO put the plan forward, built or evolved the leadership system, allocated the resources (people and $$s), and, as such, is accountable for why the enterprise system did not produce the expected result.

To be fair, boards usually do not replace CEOs for a single miss. They replace CEOs when they lose confidence in the CEO’s judgment, the team’s ability to execute, or the system’s capacity to produce different results. What shakes the board’s confidence? It happens when the CEO cannot explain reality clearly, diagnose the root cause, make the hard people or resource calls, adjust the operating model, or restore belief that the company can get back on track.

That is why CEO accountability is different from a functional leader’s responsibility. A CRO may miss the sales number for 2-3 quarters. A CFO may miss the forecast. A COO may struggle with operating bottlenecks or reporting discipline. Even a President may get time to correct course. But if the miss is material and sustained, the board will lose confidence and the CEO will pay the price.

The Real Job of Delegation

None of this is an argument against delegation. It is the opposite. The CEO who refuses to delegate becomes the constraint. The company cannot scale beyond the CEO’s personal span of control. Every decision slows down. Every executive waits for permission. Every problem comes back to the CEO to solve. That is not accountability. That is bottleneck leadership, which we see many first-time founders suffer from.

The goal is to delegate responsibility without losing visibility, control points, or accountability for the system. The best CEOs build an operating architecture where the following are explicit:

• Who owns the result?

• Who makes the decision?

• Who has input?

• Who has veto rights?

• Who performs the work?

• Who escalates risk?

• Who is accountable if the result is missed?

Some companies use frameworks such as OARP (Owner, Approver, Reviewer, Participant) or RAPID (Recommend, Agree, Perform, Input, Decide) to help make decision roles more clear and bring to light key decisions that need to be made. The key takeaway is not the acronym. The key is companies move faster when decision rights are explicit. Contrary to what many people think, role clarity is not bureaucracy. It actually accelerates momentum. Similarly, for early stage start ups, ambiguity feels flexible, fun and fluid. It is until the stakes rise. Then it becomes drag.

What This Means for CEOs

For CEOs scaling SaaS companies quickly, there are a few practical implications.

The first is not to confuse delegation with distance. You do not need to run every function. In fact, if you are still running every function, you have become the constraint. But you do need mechanisms that tell you whether the business is performing, where the system is breaking, and whether your leaders are facing reality.

The second is to make role boundaries explicit before the company starts to miss the plan. If the President owns the operating plan, define what that means. If the COO owns execution cadence, define what authority comes with it. If the CFO owns forecasting, define who owns forecast quality versus forecast inputs. If the CRO owns revenue, define how product, marketing, customer success, pricing, and sales capacity connect to that number.

Along those lines, most executive-role confusion is not caused by bad intent. It is caused by unspoken assumptions about accountability, ownership, execution, and governance. Accountability is who is ultimately answerable for the outcome. Ownership is who manages the result day to day. Execution is who runs the mechanisms that produce the result. Governance is who oversees, challenges, and protects the long-term interests of the company.

Other leaders may own, execute, and govern pieces of the system, but the CEO always remains accountable for whether the system works. That is why the CEO has to inspect the operating model, not just the dashboard. Dashboards tell you what happened. The operating model tells you why it happened and whether it is likely to happen again.

Finally, it is critical to remember that the board is always watching both. I.e., It is evaluating the results, but it is also evaluating the CEO’s command of the system. Does the CEO understand what is happening? Is the CEO acting early enough? Is the CEO making the right tradeoffs? Does the CEO have the right people in the right seats? Is the company learning faster than the problem is compounding? Can the board still trust the CEO’s judgment?

That is the CEO test. Like the skipper of the ship owning the command, a CEO owns the enterprise. This means owning the strategy, the people, the cash, the operating model, the board relationship, the key external relationships, and the learning system that allows the company to adapt when reality changes. CEOs who do this well will usually avoid running aground. And, then, again, sometimes there is a perfect storm and you run aground. This is what makes the CEO role so exhilarating and terrifying at the same time.

Source note: This essay draws on A.G. Lafley’s Harvard Business Review article “What Only the CEO Can Do,” McKinsey’s CEO Excellence research, Mark Moses’s Make Big Happen, Bain’s work on operating models and decision rights, HBR’s work on the COO role, and Spencer Stuart’s research on Executive Chairs

• A.G. Lafley, “What Only the CEO Can Do,” Harvard Business Review, May 2009
  https://hbr.org/2009/05/what-only-the-ceo-can-do

• Carolyn Dewar, Scott Keller, Vikram Malhotra, “The Mindsets and Practices of Excellent CEOs,” McKinsey & Company, October 2019
  https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/the-mindsets-and-practices-of-excellent-ceos

• Carolyn Dewar, Scott Keller, Vikram Malhotra, CEO Excellence: The Six Mindsets That Distinguish the Best Leaders from the Rest
  https://www.simonandschuster.com/books/CEO-Excellence/Carolyn-Dewar/9781982179670

• Mark Moses, Make Big Happen
  https://books.forbes.com/books/make-big-happen/

• James Allen, “How the Best CEOs Get the Important Work Done,” Harvard Business Review / Bain & Company, September 2016
  https://www.bain.com/insights/how-best-ceos-get-important-work-done-hbr/

• Eric Garton, “Is Your Company Actually Set Up to Support Your Strategy?” Harvard Business Review / Bain & Company, November 2017
  https://www.bain.com/insights/is-your-company-actually-set-up-to-support-your-strategy-hbr/

• Marcia Blenko, Eric Garton, Ludovica Mottura, “Winning Operating Models That Convert Strategy to Results,” Bain & Company
  https://www.bain.com/insights/winning-operating-models-that-convert-strategy-to-results/

• Nate Bennett and Stephen A. Miles, “Second in Command: The Misunderstood Role of the Chief Operating Officer,” Harvard Business Review, May 2006
  https://hbr.org/2006/05/second-in-command-the-misunderstood-role-of-the-chief-operating-officer

• Spencer Stuart, “When an Executive Chair Helps or Hinders Company Performance”
  https://www.spencerstuart.com/research-and-insight/when-an-executive-chair-helps-or-hinders-company-performance

I was talking with a friend’s son the other day, who was working on an essay about the future of space power. His argument was that control of space will increasingly shape military strategy and geopolitical influence. We ended up discussing how great powers use new technologies to project force, secure commercial interests, and expand their spheres of influence in different domains (land, sea, and air) and how this pattern might play out in space. Our conversation reminded me of the first time I learned about “force projection” at the Naval Academy.

When I joined the Navy in 1986, during the Cold War, we were talking about power projection, carrier battle groups, and the need for a 600-ship Navy. The ability to respond to crises anywhere in the world was part of what made the US a global commercial power after World War II. The new international order depended on cargo ships moving freely across the seas, and that meant naval power was not merely a military asset. It was one of the underlying foundations of global trade and geopolitical stability.

To that point, at the Naval Academy, we studied Admiral Alfred Mahan’s The Influence of Sea Power Upon History, published in 1890. Mahan argued that maritime strength had a determining influence on the rise and fall of countries and empires. Commerce, ports, fleets, geography, and national policy formed an integrated system. When he was writing, Britain had already demonstrated the point. Its navy did not simply defend an empire. It helped build one by working alongside commercial entities such as the East India Company to protect trade routes and ensure that resources flowed back to the motherland.

After WWII, the US adapted this logic to a different kind of world order. Rather than constructing a formal empire, we built forward bases and deep alliances (e.g., NATO) to secure an open-market system undergirded by global sea lanes. This system was broader than the British imperial system, and we benefited immensely as a country, both economically and politically. One of the core principles of our global power was that, while we did not own the seas, we assumed primary responsibility for keeping them open.

Our Admirals Know the Lesson

Nearly forty years later, some of my classmates are now leading our modern Navy as two and three-star Admirals. In fact, some are responsible for the theaters (the Gulf and the China Sea) where we are now seeing an ancient power struggle play out. I am certain that these admirals, and the rest of our Naval leadership, understand sea control, sea denial, power projection, and the risks that choke points pose. So the issue is not whether America’s admirals understand history. The issue is whether our political leadership understands the system that those admirals are being asked to defend. A recent New York Times opinion essay on Iran, Hormuz, the Navy, and the South China Sea raises this very question: “What happens when a regional power can use geography to challenge a global naval power?” What interests me is that Herodotus addressed this question and documented this pattern in The Histories, which he wrote 2400 years ago.

What Salamis Teaches Us About Choke Points

In 480 B.C., Xerxes (of Persia) invaded Greece to extend his empire (I wrote why great powers go to war here). At that time, Persia was becoming the most important empire in the world. It had immense wealth, a huge army, and the biggest navy in that theater. During the war, Xerxes marched his army across Greece and conquered Athens. The Athenians had to retreat to another island to establish a stronger defensive position. Herodotus tells us that the Greek fleet also gathered at Salamis in part because the Athenians had the largest number of ships in the fleet during the war. They had already provided the largest contingent at Artemisium and, again, provided the most ships at Salamis.

Themistocles, one of the Athenian generals (who oversaw the fleet), recognized that they would not be able to win against the Persian fleet in open water since they were significantly outnumbered. However, he realized he could use geography to his advantage, specifically the narrow channel near Salamis. In the straits, the large number of Persian ships would become a liability. In this case, scale became a disadvantage.

This is the 2,400-year lesson. Naval power is never just measured by the size of a fleet. In open water, scale may dominate; however, in narrow channels, scale can be a disadvantage. And, as such, Salamis has stood as a warning for generations of naval leaders. If you really want to own the seas, then geography becomes strategy.

Hormuz and the Return of the Choke Point

We are seeing this lesson play out in the Strait of Hormuz. Iran does not need a blue-water fleet to challenge the US on the open seas. As it is proving, it only needs to make the Strait of Hormuz dangerous enough that insurers won’t insure commercial shipping. As many reporters have already documented, a significant share (25% or so) of the world’s oil and liquefied natural gas passes through the strait. We are now seeing, in real time, the downstream impact of controlling this choke point in the energy markets, including a significant rise in oil and gas prices. The biggest issue is that there is no easy way out of this quandary of our own making. We either have to escalate or accommodate.

The kicker is that we have been talking about the risk in this specific strait for decades. We were talking about it when I was at the Naval Academy 40 years ago. And since then, it has been the subject of countless policy papers and role-played endlessly in war games. And the current situation is proving the strategic point that a regional power can destabilize global commerce without conquering territory or defeating a great-power navy. As we have seen, Iran does not even have to fire on every ship that enters the strait. It just has to make the perceived risk credible. And this changes how we should think about global commerce, military investment, deterrence, and the relationship between regional power and the global order.

Sea Denial as Maritime Guerrilla Warfare

We often think of naval power in terms of decisive battles, where large platforms (battleships and/or aircraft carriers) fight massive engagements. But the reality of the choke point is that we cannot counter Iran’s “maritime guerrilla” warfare tactics. Drones, mines, fast attack boats, anti-ship missiles, unmanned underwater vehicles, cyber disruption, and shore-based sensors do not need to defeat the US Navy. They just need to make the Navy’s mission harder, slower, and more expensive. Ultimately, time is on Iran’s side as the political resolve (and ability to pay for this war) in the US continues to erode.

This is the lesson of land-based guerrilla warfare applied to the high seas. The weaker actor avoids the stronger actor’s preferred battlefield. It uses terrain and disperses risk. It creates uncertainty and then turns tactical disruption into political leverage. On land, we saw versions of this strategy play out in Vietnam, Iraq, Afghanistan, and others. We spent millions of dollars and too many of our young men and women’s lives fighting in these conflicts, and, at best, we were able to create stalemates (e.g., in Korea). Too often, we retreated, and the regime we left behind crumbled. We are seeing this same principle of denial, in this case, “sea” denial, play out in the Strait of Hormuz. And Iran, as a Regional Power, is impacting almost every other country at this point.

Global Power and Regional Leverage

At the heart of this conflict is the distinction between Global Power and Regional Leverage. Global powers require mobility. Their military strength, alliance commitments, commercial interests, and political credibility all depend on force projection at a distance. Regional powers require leverage. They do not need to project everywhere. They just need to exploit the geography nearest to them. This is the lesson of Salamis. It is also the logic of Hormuz, Bab el-Mandeb, the Suez Canal, the Strait of Malacca, and the maritime approaches to Taiwan and the South China Sea. While the specific political contexts differ, the strategic reality is the same. Wherever global commerce must transit a narrow passage, regional actors can gain asymmetric power.

And the rapid advance of technological innovation is only making this asymmetric power more asymmetric. Much like how the battlefield in Ukraine is being transformed by drone warfare, the way that Iran is using technology to fight this conflict will inform future “choke point” confrontations. And guess what. All of our potential enemies are watching very closely. Drones, missiles, mines, unmanned, AI-powered systems, and surveillance networks are transforming how we need to think about building the armies and navies of the future.

What the United States Must Rethink

The United States now has to rethink its approach to building and using naval power without abandoning what has made it so effective over the past 40 years. The answer is not to choose between big ships and small systems. It needs both, and Admiral Mahan’s insights are still very relevant. Aircraft carriers, submarines, destroyers, logistics ships, and forward bases still matter because global power requires reach. The only difference is the need to integrate the lessons of Salamis more fully. Ultimately, we need to find a way to preserve freedom of the seas without being forced into a maximal war, with the threat of using nuclear weapons, every time a regional actor threatens a choke point. Thus, the future of naval power will require a fuller theory of control. It must combine the ability to project overwhelming force with the ability to defeat distributed disruption. And we must do this with allies.

Allies Matter More Now Than Ever

This is where the political question becomes more urgent. Our Navy can clear mines, escort ships, hunt submarines, and deploy unmanned systems. But the US cannot, by itself, rebuild the credibility needed to encourage other countries to participate and to make potential adversaries think twice. As we have seen since WWII, global maritime order is not built transaction by transaction. It depends on credibility, coalition trust, shared burden, and predictable commitments. The open sea-lane system has taken 8 decades to build. If allies start to doubt that it works and adversaries begin to challenge it, we will see it unravel.

There is a deeper irony here. The United States built the postwar maritime order in part because it understood that commerce, alliances, and deterrence were inseparable. The ability of a ship to sail safely through the Gulf or the Suez Canal was largely due to our NATO partners and other countries trusting that we would honor our commitments. By undermining that system politically, the military challenge grows harder. We will never be able to build enough ships, drones, and missiles to compensate for the loss of this credibility, and it will take a generation (s) to rebuild the trust.

My conversation with my friend’s son began with space power, with the next domain of global competition and the next generation’s understanding of power projection. Space will shape the future of warfare and commerce in ways we are only beginning to grasp. But recent events in the Strait of Hormuz remind us that some of the oldest lessons remain relevant.

Executive Summary

This essay is the first of a two-part reflection on Joyce’s use of the hero’s journey in Ulysses. Part One follows the novel through Episode 6, “Hades,” as this is where the slow-read seminar I am co-leading has reached. I will publish Part Two after we complete the book. At that time, I plan to return to the questions of transformation, homecoming, and whether Leopold Bloom is ultimately a modern hero or something else.

The heroic journey is one of the West’s most enduring narrative patterns. It usually involves a young man (though it could be a woman) leaving home and then encountering and overcoming significant trials. It often entails the hero confronting death (either physical or spiritual). And it resolves with the hero returning changed/transformed. In The Odyssey, Odysseus is the primary embodiment of this journey. At the same time, we have another protagonist, Achilles, who epitomizes what a Greek hero should be in The Iliad and what his post-death realization is in The Odyssey. Joyce ingests this structure in Ulysses and begins to remake it through Bloom.

By the end of “Hades,” the transformation is already visible. In The Odyssey, Odysseus is directed by Circe to venture to the underworld to find the way home. By contrast, in Ulysses, Bloom enters a Dublin cemetery and receives neither a prophecy nor insight from the dead. Instead, he reflects on the rituals of death and funerals. He also spends time meditating on the fact that death is one of the few shared human experiences.

This difference, and what Joyce is up to, is the focus of this essay. I don’t think Joyce is mocking the heroic journey. Instead, he begins to humanize it. By Episode 6 in Ulysses, we see that Joyce is evolving the meaning of heroism away from what the Greeks valued (glory, conquest, and legacy) toward a new set of values and virtues (e.g., attention, sympathy, and the capacity to remain fully human). Joyce suggests that the modern hero may not be the man who rises above ordinary life, but more like an Everyman who moves through life without surrendering his humanity.

Part One: From Glory to Sympathy

As a young man, I yearned to be a hero in something like the Greek sense. I went to the Naval Academy when the Cold War was still very real. If you had asked me then why I chose that path, I would have spoken about duty, country, leadership, and service. All of that was true, but beneath this lofty aspiration was also a longing to test myself. I wanted to fly planes. I wanted to be on the front lines if war broke out with the Russians. I wanted to leave behind some evidence that I had done my part, even if that meant, paraphrasing Neil Young, “burning out” rather than “fading away.” Yes, I was young and naive.

But this longing was not just naive ambition. It was rooted in one of the foundational narratives of the Western imagination: the hero’s journey. Joseph Campbell named this narrative structure in his seminal work The Hero with a Thousand Faces. He was describing a structure that had already shaped many of the stories and culture experience I (and my generation) grew up with. Most action films (e.g., the Marvel films, James Bond), war stories (e.g., Hacksaw ridge), fantasy epics (e.g., Lord of the Rings), and coming-of-age novels (e.g., All the Pretty Horse) that I voraciously consumed all draw from some version of it. For example, George Lucas has been explicit about Campbell’s influence on Star Wars. Frank Herbert’s Dune, written before Campbell’s book, reveals the darker possibilities of the same heroic arc. The appeal of this narrative structure is enduring because the pattern rests on two deeply human premises:

• We all face ordeals

• We find meaning in life partly through how we meet, respond, and are defined/changed by these ordeals

That is one of the most interesting Homeric transformations Joyce undertakes in Ulysses, and it points to a central question for the novel: what happens when one of the oldest heroic patterns in Western literature is set within the ordinary movements of a single Dublin morning?

The Heroic Ideal We Inherit

For Homer, the hero stands apart. He usually is exceptional in some way. For example, he could have unusual strength, courage, cunning, endurance, or force of will. He is clear that the way to win honor is through action (usually in battle) and that his legacy will be determined by how he conducts himself. But, at the end of the day, his life matters because it is not ordinary: he is extraordinary.

Achilles is the purest embodiment of that ideal. In The Iliad, he has the opportunity to choose his path: He can either live a long, obscure life or die young and win glory forever. He chooses glory because Achilles is the hero who will not settle for an ordinary life. He wants greatness, and he is willing to pay for it with his life. This aspiration has been enormously important for generations and explains why Achilles has remained so compelling for nearly three thousand years. The young are often drawn to him because he lives intensely. He doesn’t want to be a baker, marry a nice girl, and crank out some kids. He wants his life to matter on the largest possible scale.

And this is the appeal.

I recognized some version of that aspiration in myself. I wanted to serve, but I also wanted my service to matter. I wanted to believe that if I demonstrated courage, was willing to sacrifice, and seek excellence, I would live a life worth living. I.e., there would be some external validation. The heroic journey narrative shows the way. It encourages us to leave home, face the world, and confront death so that we can return with a deeper sense of our identity. At the same time, it helps to make suffering more meaningful. We want to know whether difficulty can transform us. We want to know whether life can be more than just making it through.

Odysseus and the Heroic Journey of Return

One of the best parts of reading The Odyssey right after The Iliad is seeing how Homer evolves and expands the heroic ideal. Achilles represents one form of Greek greatness: glory won through courage, force, and the willingness to risk everything for honor. Odysseus represents another set of qualities: intelligence, endurance, cunning, and the capacity to survive and return home. The Greeks value both. Achilles is the hero of war. Odysseus is the hero of resourceful endurance.

Odysseus is not merely trying to survive the aftermath of Troy. He is trying to come home, defined broadly. I.e., he is not just returning to Ithaka. His return also includes him reestablishing his identity after being gone for 20 years. Before he left, he was a husband to Penelope, a father to Telemachus, and a son to Laertes. He was also the king of Ithaca and clearly the master of his household. In essence, he was a “known” man for all the right reasons.

That is what makes The Odyssey such a profound account of heroism. Sometimes the greatest danger is not death, but losing an understanding of who you are and the desire to return. Again and again, Odysseus encounters temptations that could prevent him from returning home. The Lotus-Eaters offer forgetfulness. Circe offers pleasure and delay. Calypso offers immortality. The Sirens offer knowledge severed from obligation. Each temptation asks, in a different form, whether home is still worth wanting. Odysseus’ heroism lies in his continued desire to return home and reestablish his identity. He does not simply endure danger. He remembers who he is by remembering where he belongs, and that makes the journey and travails worth it.

That is why the descent to Hades in Book 11 of The Odyssey matters so much. The hero can’t return home; he first moves through death. Odysseus has crossed seas, survived monsters, and endured Poseidon’s wrath. But he still lacks the knowledge required to return fully, not just the directions to sail to Ithaka. Circe tells him that he must go to the land of the dead and consult Tiresias, the blind prophet.

What the Dead Teach Odysseus

Odysseus’ visit to Hades is not merely an eerie interlude. It is an essential moment in The Odyssey and stands as one of the most important lessons for Homer’s audience throughout the ages. Before the dead can speak, Odysseus must perform the proper rites. He digs a trench, pours libations, sacrifices animals, and holds the shades back until Tiresias arrives. The underworld may be terrifying, but it is not meaningless. It has order, and there is a right way to conduct the ritual.

Tiresias then tells Odysseus what lies ahead. Poseidon remains angry. The island of the Sun will become a decisive test. If Odysseus’ crew leaves the cattle of Helios untouched, they will survive. If they kill the cattle, destruction will follow. Tiresias tells him that he will eventually reach Ithaca alone, on another man’s ship, and that he will find suitors consuming his house and courting his wife. He tells Odysseus that he must defeat them. He even tells him that after the restoration of his household, another journey remains: he must carry an oar inland until he reaches people who do not know the sea. For a world where everyone seeks oracles for guidance, this guidance is particularly specific. The future is knowable. Odysseus cannot control it, but he can be told its outline. Fate does not remove agency; however, this insight gives Odysseus guidance (similar to Achilles’ knowing his fate).

His mother, Anticleia, gives him another kind of knowledge. Odysseus did not know she had died. Seeing her among the dead is one of the episode’s great shocks. From her, he learns what has happened in Ithaca during his absence. Penelope remains faithful and sorrowful. Telemachus lives, but Laertes has withdrawn into grief. His mother herself has died not by disease or violence, but from longing for him. Talk about mother guilt!! (side note: Stephen D in Ulysses has some of this going on big time). This changes the meaning of return. Odysseus’ absence has not merely endangered his estate. It has wounded those who love him. Home is not sitting untouched, waiting for his arrival. Home has suffered because he has been gone.

Then come Achilles and Agamemnon, each offering a different correction to the heroic imagination. Odysseus praises Achilles as fortunate, honored in life, and powerful among the dead. Achilles rejects the consolation. He would rather be a hired laborer among the living than king over all the dead. The greatest hero of The Iliad now tells us that glory does not transcend death. HEAVY!

That moment does not erase Achilles’ heroism, but it complicates it. The man who chose fame over life now speaks from the far side of death and tells Odysseus that life itself is more precious than heroic memory. Odysseus, who has always wanted to get home alive, receives confirmation that his desire is not merely cautious. It is deeply human.

Agamemnon offers a darker lesson. He survived Troy only to be murdered at home by Clytemnestra and Aegisthus. His story warns Odysseus that the very act of returning can be dangerous. A man does not simply arrive home and resume his place. He must assess the house he is re-entering. He must conceal himself, test loyalties, and recognize that intimacy can be treacherous.

And this sets up the rest of the story. So Hades gives Odysseus more than prophecy. It gives him a moral map of return. He learns what is happening at home, what death reveals about heroic glory, and why homecoming must be approached with caution. The dead teach him how to live.

Joyce Brings Bloom to Hades

Joyce gives Bloom his own Hades in Episode 6 of Ulysses, but the experience is radically altered. Bloom does not cross the River Ocean. He rides through Dublin in a funeral carriage that crosses over the Grand Canal. He does not descend into a shadowy realm populated by legendary dead. He attends the burial of Paddy Dignam at Glasnevin Cemetery. There is no Tiresias waiting. His dead mother does not step forward to speak. Bloom receives no map for the future. He gets no prophecy about Molly, Boylan, or the course of his own day.

Yet, Joyce clearly wants us to see the parallel. Bloom has left home. At this point in the novel, he has passed through appetite, concealment, religious ritual, and private desire—the trials of everyday life. Now he enters the realm of death. Joyce is still using the hero’s journey arc, but the terms have changed. If Odysseus’ Hades is a place where death speaks and provides insight, then Bloom’s Hades is a place where death provokes thought.

In the previous episode, “Lotus Eaters,” Bloom enters a Catholic church and watches the Mass. He is curious and receptive to the beauty of ritual. But he also experiences it from the outside. He recognizes that the ritual depends upon genuine belief, saying, “Thing is if you really believe in it.” He has the same sense for the ritual of the funeral. Bloom hears the language of salvation and what it means to have a soul, but he does not really process it. What I find especially interesting in this episode is that his thoughts and imagination do not ponder heaven or eternal reward. Instead, he ponders coffins, corpses, worms, decay, burial practices, premature burial, cremation, widows, children, and the practical realities after someone dies. Contrast this with Stephen Dedalus’ musings in Episode 3 on Aristotle, Aquinas, etc.

This is important. Bloom is not simply irreligious. He is an outsider moving through a religious culture whose symbols he can recognize but not fully possess. He sees the consolation ritual offers. The funeral does not disclose the meaning of death to him. It gives him occasions to think about death from multiple angles: physical, social, domestic, and emotional. In Homer, the dead explain themselves. In Joyce, the living must ponder what death means in the presence of the dead.

From Heroic Death to Ordinary Mortality

There is another important difference in the representation of the underworld. Homer’s underworld contains many souls, but the episode focuses on extraordinary figures (e.g., Tiresias, Anticleia, Achilles, Agamemnon, and Ajax) who offer insight and advice. Death becomes an opportunity for Odysseus to deepen his understanding of the ideas of honor, fame, household, and betrayal. Most importantly, he confronts the limits of heroic achievement through his conversation with Achilles, and, I think, this is the key moment of his transformation. “Dead” Achilles would trade all of his honor and glory to be alive again, even if it meant he was only an ordinary day laborer. After this conversation, Odysseus recognizes the value of being able to return home and “fade away” versus “burn out.”

By contrast, Joyce democratizes the underworld. Paddy Dignam is not Achilles. He is not a king, warrior, prophet, or founder. He is an ordinary man from Dublin. He leaves behind a widow, children, debts, and acquaintances. As Joyce makes clear through the other characters, even though many people knew Dignam, their memories are already beginning to blur or become confused by the time of his funeral. His funeral is meaningful, but it is really just one death among many. In fact, there are two more funerals teed up for the next day.

Bloom’s inner monologue shows that he sees the cemetery as a landscape crowded with ordinary people. All these people, once alive, are now buried in the same place regardless of title or social status. The question is not only what Dignam’s life meant. It is what any life means once the person is gone and the world keeps moving.

This gives Bloom a kind of moral sensitivity that is very different from Homeric heroism. He is not measuring the dead by the lives they lived or by whether they had glory or fame (i.e., external validation of honor or glory). While the other men in the carriage participate in the funeral as a public ritual by talking, recalling, speculating, joking, and observing the social conventions of mourning, Bloom goes beyond the surface. He thinks about the widow and children. He thinks about the body in the grave. He thinks about the awkwardness of resurrection when bodies have decayed. This is not heroic in the Homeric sense. But Joyce seems to ask whether it might be heroic in a modern one.

The Everyman Hero, So Far

By Episode 6, Joyce has not yet completed Bloom’s journey. We do not yet know whether Bloom makes it home, and if he does, whether he is transformed. This is what I will explore in Part 2. But, at this point, we can already see that Joyce is remaking the old heroic pattern.

• Odysseus leaves home and enters a world of mythic danger <>Bloom leaves home and enters a world of estrangement.

• Odysseus descends to Hades to receive knowledge from the dead<>Bloom enters the cemetery and receives no revelation. He only becomes more aware of death’s presence in common life.

• Odysseus learns how to navigate fate<> Bloom moves through a world where fate no longer seems to be at play.

The evolution challenges our expectations of a hero. The Homeric hero is, by definition, exceptional. He is stronger, more cunning, more enduring, more favored or harried by the gods than other men. He stands apart.

By contrast, Bloom is remarkable precisely because he does not stand apart in that way. He is ordinary, vulnerable, socially awkward, physically embodied, and only partially at home in the world through which he moves. At the same time, Bloom notices things others don’t. He is able to sympathize/empathize with others. Finally, he refuses, at least so far, to harden himself against the awkwardness and sorrow of other human beings, even when he, himself, is being discriminated against.

Through “Hades,” Bloom has not become a hero in any final sense. Joyce has not yet told us what his journey will mean. But he has already begun to ask whether the Everyman who moves through death, ritual, uncertainty, and the uncelebrated losses of ordinary people with his humanity intact may deserve a place beside the older heroes after all.

The Chain of Consent

If you have been following the news, it seems the idea of what constitutes a “free and fair election” has been popping up almost daily. Last week, the Supreme Court issued its decision to revise the Voting Rights Act. Yesterday, a judge said that the FBI did not have to return the records it had confiscated. And today, another judge blocked the redistricting in VA. All of this means that we are focused on the process of voting versus being focused on the candidates and the issues, which seems kind of bizarro.

What is happening?

Everyone says they support free and fair elections. That is part of the problem. The phrase has become so universally affirmed that we have lost track of the 2nd order questions that ensure we actually have free and fair elections. For example:

• Free from what?

• Fair according to whom?

• Protected by which laws?

• Administered by whom?

Part of the issue, I think, is that we tend to think about elections as moments. We all submit our ballots (either in person or via mail) on election day, and then we watch to see who wins on TV. But an election is less a moment than a chain of activities. At the simplest level, elections are a pretty straightforward process. First, citizens register; then they vote. After the election, officials count the votes, and Election Boards certify the results. When required, courts resolve lawful disputes. When there is faith in the process, losers accept defeat, and winners can get on with the business of governing. If there are process breakdowns in this process, then we are undermining one of the core principles of our republic. Specifically, elections represent the people giving “consent” to be governed by legitimate power. It calls into question the very idea of self-government. . . and that is a BIG DEAL!

What we are seeing now is that the threat to free and fair elections is not confined to Election Day. It is a full-system attack on this “chain of consent.” Before the vote, rules can be written to make participation harder or representation less meaningful. During the vote, election workers can be intimidated, exposed, or driven out. After the vote, losing factions can contest, delay, refuse, or delegitimize lawful outcomes.

The Founders anticipated this problem at the structural level. For example, Hamilton saw the same problem in the machinery of elections. In Federalist No. 59, defending Congress’s constitutional backstop over federal election rules, he wrote that “every government ought to contain in itself the means of its own preservation.” That is why Article I, Section 4 in the Constitution gives states (not the federal government) authority over the “Times, Places and Manner” of congressional elections. At the same time, this section gives Congress the power to “make or alter such Regulations.” I.e., the founders were trying to build in checks and balances. As Madison put it in Federalist No. 51, “ambition must be made to counteract ambition.” The Constitution was designed around the assumption that power would always seek advantage, and that ambition would have to be checked by institutions, law, and civic restraint.

Hamilton made the institutional point in Federalist No. 59. For him, election rules were not clerical details: they were constitutional infrastructure. If one political actor could control the rules for choosing representatives, that actor could endanger the representative system itself. That is why the Constitution creates a balance of power between the states and Congress. The Founders were treating election administration as a vulnerability that had to be checked. And we are now seeing this vulnerability being exploited.

To address this vulnerability, it helps to revert to the 4P framework (principle, policy, process, and practice) that I introduced a year ago. In this context,

• The principle is consent. Our government derives its legitimacy from the governed.

• The policy is the legal architecture that protects both secure elections and meaningful access.

• The process is the machinery that turns votes into certified outcomes.

• The practice is how citizens, candidates, parties, courts, and officials act when power and the perceived threat to power are at stake.

When one level breaks, the others are stressed. When all four are attacked at once, the republic enters dangerous territory.

Before the vote: Who actually is voting?

The first link in the chain is participation. And there has been an ongoing debate for many years on this topic. But the volume on this specific issue has gone to 11 in the past year. The key questions to consider are:

• Who gets to vote?

• Under what rules?

• With what burdens?

These point to the larger question of how we, as citizens, can trust that the system treats all eligible citizens as legitimate participants in self-government.

No serious person can argue that election security does not matter. Of course, citizenship matters. It is also critical to ensure we have accurate voter rolls and that ballots remain secure. We need to monitor the process closely to detect fraud at each stage. And the evidence shows that voter fraud is NOT a myth. Doing a cursory search today shows that fraud exists, but it is rare, usually local, and often detectable. It manifests in abuses such as absentee-ballot fraud, voter registration fraud, duplicate voting, or misconduct by campaign operatives. However, the most documented vulnerabilities are not the ones most often invoked to justify broad restrictions on voters. For example, in-person voter impersonation is nearly nonexistent. News21’s review of alleged election-fraud cases from 2000 to 2012 found that absentee-ballot fraud and registration fraud were the two largest categories, while in-person voter impersonation accounted for only 10 alleged cases. The AP’s review of the six 2020 battleground states disputed by Trump found fewer than 475 potential fraud cases out of 25.5 million presidential ballots cast, far too few to affect the outcome.

To be clear, noncitizen voting occurs, but the documented cases are isolated. The 2018 North Carolina 9th District case shows that election fraud can be serious enough to force a new election, but it also shows the real pattern: organized misconduct around absentee ballots, not millions of illegal voters.

Net/net: a republic should take fraud seriously. But taking fraud seriously means matching the remedy to the evidence, and not using rare misconduct as a pretext to burden lawful voters, intimidate election workers, or delegitimize every outcome one faction dislikes.

Does The Remedy Reflect Proportional Response

Perhaps more important is the need to evaluate whether a particular rule solves a real problem without creating unnecessary burdens for eligible citizens. A law can use the language of election integrity while actually weakening lawful voters’ ability to participate. That is the debate around the SAVE America Act. This bill would require proof of citizenship for voter registration and impose new federal requirements around voting eligibility. Supporters presented it as a safeguard against noncitizen voting. Critics argue that it risks disenfranchising eligible voters who lack ready access to the required documents or whose documents do not match their current names, such as married women, older voters, lower-income citizens, and people with complicated records. Reuters recently reported that the bill had passed the House but faced a Senate filibuster threshold, making passage difficult.

Again, I am not arguing whether noncitizens should vote. They should not. The issue at stake here is whether the proposed remedy is proportionate to the demonstrated problem and does not place an undue burden on eligible citizens. If the practical effect of a security rule is to make lawful participation more difficult, then the policy may preserve the appearance of integrity while weakening representation.

The same problem appears in the evolving Voting Rights Act (VRA) landscape. The 15th Amendment states that the right to vote cannot be denied or abridged on account of race, color, or previous condition of servitude. The VRA of 1965 was intended to close the gap between what was articulate as a “right” and actual political access on the streets of America. The Court has not erased the Voting Rights Act in one stroke. But over the past several years, the practical direction has been toward narrowing the scope of federal voting-rights protections, especially regarding redistricting and race-conscious remedies. In April 2026, the Court struck down a majority-Black congressional district in Louisiana, a ruling AP described as weakening a landmark Civil Rights-era law and opening the door to more redistricting fights across the country.

This is the policy-level danger. A right that exists only in theory is not yet self-government. The vote must be legally protected, practically accessible, and politically meaningful. If laws or court decisions narrow participation or representation while claiming neutrality, the “chain of consent” becomes less trusted before Election Day even arrives.

During the vote: the people who ensure the votes are counted

The second link in the chain is administration. Elections are run by clerks, registrars, poll workers, observers, county officials, state boards, judges, volunteers, and ordinary citizens who agree to do unglamorous work under pressure. It just amazes me that this is what happens around the country for every election. The election worker is the infrastructure. That is why the recent federal intervention in Fulton County, Georgia, matters. The issue is not only that the Justice Department has confiscated materials from the 2020 election. It is that the investigation has moved toward the people who administered the election. According to AP, the DOJ sought the names and personal contact details for people involved in Fulton County’s 2020 election. Fulton County moved to quash the subpoena, arguing that it was overly broad, lacked a legitimate prosecutorial purpose, and risked intimidating or harassing election workers.

That is a serious escalation. A subpoena for records is one thing. A demand for workers’ and volunteers’ personal information is another. It undermines the human infrastructure of elections. Remember, Fulton County is the same place where election workers Ruby Freeman and Shaye Moss became targets of false fraud claims after the 2020 election. Their lives were upended by false accusations. They later won a major defamation judgment against Rudy Giuliani, but no court judgment can fully restore a community’s confidence in the process when ordinary election workers are turned into political targets.

That is the point at which “election integrity” can become a form of intimidation. A republic needs lawful mechanisms to investigate real misconduct. But when the power of federal investigation is directed at election workers amid repeatedly debunked fraud narratives, citizens are right to ask whether the system is protecting elections. Ultimately, our ability to hold “free and fair elections” depends on this civic workforce willing to count the vote. If these workers are harassed, exposed, threatened, or driven out, the system is undermined before any ballot is cast.

After the vote: when losing becomes delegitimizing

The third link in the chain is acceptance of lawful outcomes. An election is not fully complete when voters vote. As we have witnessed over the past several election cycles, the votes must be counted. And then the election needs to be certified at several levels. Unfortunately, we have had to rely on the courts to adjudicate in recent elections due to a perceived breakdown at this stage. This is where the Trump era introduced something especially corrosive. This pattern did not begin in 2020; it actually began in 2016, after Trump won the Electoral College but lost the national popular vote. Rather than simply accepting the constitutional victory, he claimed without evidence that he would have won the popular vote if millions of illegal votes had not been cast. FactCheck.org described the claim as bogus and unsupported.

That matters because the claim was not necessary to challenge the result. Trump had won. The claim served another purpose. It turned victory into a grievance. It taught supporters that an unfavorable democratic signal (i.e., Trump not winning the popular vote), even when there was a successful constitutional outcome, could be explained away as fraud. This pattern metastasized after 2020. And my home state of Georgia became one of the central battlegrounds. It was not just because of the small win that Kamala eked out. More concerning was that Federal investigators seized more than 600 boxes of 2020 election materials from Fulton County. This meant that a state election process was being interfered with by a federal body—a dangerous re-balancing of the constitutional powers. Reuters reported that the investigation is tied to Trump’s unfounded claims of widespread voter fraud in Georgia, and a federal judge recently allowed the DOJ to keep the materials. It will be interesting to see how this plays out.

At the same time, Georgia’s election oversight system became a separate issue after 2020. The Georgia State Election Board, which has the authority to set election rules and investigate election administration, has become increasingly contested over the past 6 years. The board adopted controversial rules before the 2024 election, and Trump publicly supported/ endorsed some of these board members. The Georgia Supreme Court later invalidated four of seven rules passed by the board, including measures critics argued could have delayed certification or required hand counts after polls closed.

This is where the issue becomes bigger than one candidate, one state, or one case. We have seen that our republic can survive recounts and hard-fought disputes over election rules. What it cannot survive is a permanent politics of delegitimization, where every loss is fraud, every administrator is suspect, every certification is conditional, and every institution is legitimate only when it produces the desired outcome. Lawful challenge is part of democracy: Permanent delegitimization is not.

What we can do about it

The answer cannot be only outrage. If the threat is a full-system attack on the chain of consent, the response must operate at every level: principle, policy, process, and practice.

• Principle. We need to restore the basic standard that a free and fair election is possible, even if “my” side does not win. Instead, a free and fair election is one in which eligible citizens can vote, lawful votes are counted, disputes are resolved through evidence and law, and the outcome is accepted as legitimate even by those who lose. That standard has to be stated clearly because it is no longer universally practiced.

• Policy. We should defend secure access. The choice is not between election security and voting rights. A serious republic needs both. Citizenship verification, accurate voter rolls, ballot security, and fraud prevention matter. But it also needs to support reasonable access, equal representation, and enforceable remedies when states or parties make participation harder for lawful voters. The question for any newly proposed election law should be direct: Does this rule or policy protect the vote, or does it protect power?

• Process. If our election workers (clerks, registrars, poll workers, observers, county officials, state boards, judges, and volunteers) are intimidated, exposed, harassed, or replaced by factional actors, then our system is weakened before a single ballot is cast. We need citizens to volunteer, and we need local leaders to monitor board appointments and rule changes. Both business and civic leaders should be vocal in support of election workers.

• Practice. We need to restore the discipline of evidence-based investigations and the idea that losing an election is part of the process. Obviously, we should be vigilant and investigate real fraud. But we should not tolerate fraud claims as political theater. If someone says an election was stolen, they should prove it in court by producing evidence. Otherwise, we will continue to erode public trust. Finally, when a lawful election is lost, the answer should not be to attack the system. Instead, the answer should be to re-group, re-organize, and get ready for the next election.

This may be the hardest part. A constitutional republic depends not only on winners who govern lawfully, but on losers who accept legitimate defeat. That is not a weakness. It is the discipline that makes self-government possible. To that point, the Founders built institutions to guard against our worst tendencies in elections. However, these institutions depend on a set of common values and accepted behaviors, such as restraint, evidence, lawful challenge, peaceful transfer, and the willingness to accept that the people may choose someone else. Free and fair elections do not just happen. They exist only when citizens defend the principle, protect the policy, monitor the process, and practice the restraint that republican government requires.

That is the work in front of us for the next 6 months.

My starting point: I do not have a PhD in classics, literature, philosophy, or theology. While I did study “English” in college, taught literature for a brief 3 years, and took an MALA in the “Great Books” at St John’s College, this was many years ago. I have continued to read lots of books over the past 30 years, but I have spent most of these years in the corporate world. It is only recently that I have returned to the Great Books with the Slow Read Symposium. I began as a participant and am now facilitating some seminars. Last quarter, I led a seminar on Rumi, the 13th-century Persian poet. This quarter, I am co-leading a seminar on Joyce’s Ulysses.

One of the benefits of tackling a “Great Book” in a seminar is realizing that everyone else struggles with these texts. The other thing that strikes me this time around with these books is that I will never know it all. There is always more context, more history, more translation nuance, and more debate to be had when re-reading these books. This is in large part what makes them “Great.” A new insight for me is how many of these books require you to learn how to read again.

What do I mean?

Most of us assume reading is something we already know how to do. We can follow a plot, identify themes, and summarize arguments. Ultimately, we make a judgment about what we like or not like about a book/text. But the Great Books demand something more. They ask us to slow down, to notice structure, to sit with confusion, to let repetition become meaningful, and to resist the temptation to translate everything too quickly into our own modern categories.

This was most evident in a seminar I did on Plato’s Republic last year, which I wrote about in an earlier essay. I am now experiencing this sensation even more explicitly in a seminar on “Reading the Great Books through Plato’s Meno,” in which we are using Klein’s commentary alongside the Meno. Finally, in the Ulysses seminar, Joyce’s call to rethink how we “read” a text could not be clearer. He elevates style over plot and character, deliberately challenging ALL the assumptions we have as readers.

Ultimately, the value of reading these types of text is not about mastering a text. Heck, I don’t think it is possible to really master one of these texts completely. The value is recognizing that you are actually being changed by the effort to understand it.

But the effort, especially with a text like Ulysses, can feel overwhelming. Thus, I want to provide some principles for readers who may be new to reading the Great Books to consider. These principles have emerged for me from reading Plato, Herodotus, Homer, Shakespeare, Adams, Joyce, and others over the past two years, in conversation with others.

A slow-read symposium seminar is not a lecture. It is a structured conversation where the book remains the center of gravity, and the group slowly learns to see more than any one reader could see alone. I would like to thank all my fellow seminar participants for helping me become a better reader.

Try to identify the “governing” question

Great books rarely announce their intent (aka thesis) at the beginning. They often start by introducing a challenging idea or concept. For example, in the Meno, Plato does not simply tell us what virtue is. He lets Meno display a kind of confidence about virtue that Plato then slowly dismantles through dialectic. Herodotus does describe his theory of empire-building. Instead, he shares stories, speeches (that he could not have heard!!), customs, warnings, reversals, and competing explanations until we begin to see how hubris, fear, and ignorance lead to the rise and fall of empires. I have just started Henry VI, Part 1 for the first time and am reminded that, in many of his plays, Shakespeare begins by depicting political disorder and then helps us understand the deeper moral disorder beneath it as the play unfolds.

So while it is, of course, important to ask questions about plot and characters to better understand the context, the key question to start with is: “What question is this text asking us to consider?” This shift matters. It helps us move from answer-hunting to observing what is happening in the text and paying attention to what is happening in us as we engage with the text and the conversation. This core, “governing” question is something you will continue to ask throughout the text. And your answer will usually evolve and deepen. Often, your answer will change. It’s a good exercise to start and end your reading of a text with this question.

Treat the structure/style as a critical part of the experience

Often, modern readers feel that a Great Book’s style or structure is too hard or too foreign. Thus, one of the most important paradigm shifts is to recognize that “how” an argument is presented is as important as “what” the argument is. So, as you read, you want to think at least two levels and ask questions such as: “Why does this scene follow that one?” For example, in Adams’ Mont Saint Michel to Chartres, why does he move from a description of architecture in chapter 1 to a description of a song in chapter 2? He is doing it deliberately, and unlike Joyce, he provides some clues in the text. Another example would be in almost any of Plato’s dialogues. He often interrupts a discussion to go on a seemingly random tangent. For example, in the Meno, he interrupts a discussion of virtue to inquire into shape and color. The question to sit with is “why?” What insight, new perspective, or new line of inquiry does this interruption help unlock in our understanding of “virtue”? A final example would be Joyce, who changes his style from chapter to chapter and sometimes employs multiple styles/structures in a single episode. This is not just Joyce showing off, although I do think there is a lot of that going on. Joyce is challenging us to consider the style as part of the overall experience.

To be clear, I am not arguing that every great book is perfectly constructed. Many are ragged, or seem stitched together, or just plain indecipherable (Kant, anyone?). However, I would argue that when we approach a text that has stood the test of time, we should always ask how the author uses structure by asking: “Why here?” “Why now?” “Why in this form?”

Those questions are especially important because many great books do their deepest work indirectly. The plot may move only slightly, while the moral or philosophical import increases dramatically. In Plato, the action is often nothing more than a conversation. In Adams’ Mont St Michel to Chartres, the movement is through architecture, theology, history, and imagination. In Joyce’s work, the plot centers on 2 men spending 1 day in Dublin. But then Joyce this “typical day” of an everyman to create an epic of consciousness.

Embrace the suck

In the military, there is a saying: “Embrace the suck.” The idea is that you’ll have many days that suck. Your opportunity is to lean into it and get the most out of the experience. In reading Great Books, the suck = confusion. Most modern readers read texts, instructions, etc., hoping to eradicate confusion, bring clarity, and or answer a question. However, with Great Books, feeling confusion is often a signal that something important is happening.

When Socrates changes the terms of the conversation, when Herodotus offers multiple explanations for the same event, when Shakespeare’s characters seem morally unstable, or when Joyce makes ordinary thought feel fragmented, we should resist the instinct to skip ahead or simplify it. Instead, we should pause and ask: “What kind of confusion is this?” Specifically, is it:

• Intellectual?

• Moral?

• Political?

• Theological?

• Linguistic?

• Narrative?

A great book often teaches by challenging our confidence in an idea or set of assumptions. That is why we need to read sympathetically. This means trying to live in the author’s argument before we dismiss it. This matters especially with ancient texts. For example, Plato forces us, throughout all his dialogues, to check and recheck our assumptions. And when we approach medieval texts, it is important to understand that their assumptions about honor, piety, hierarchy, gender, the soul, fate, nature, and political order may differ markedly from ours. If we immediately translate them into modern categories, we lose the encounter. For example, this is EXACTLY what Henry Adams invites us to do in Mont St Michel to Chartres.

Part of the value of these books is that they make our own assumptions visible. They remind us that our modern distinctions and paradigms are neither universal nor timeless. That is one of the great benefits of slow reading. It does not just help us understand old books. It helps us see the limits of our own age. Thus, the most helpful way to approach these texts is to:

1. Try to understand the world of the text

2. Then test the assumptions or arguments

3. Then decide what still speaks to us today by asking: “What can we learn by viewing our world through this lens?”

Pay attention to repetition and character evolution

Great books often build meaning through repetition. An author will use a word or a symbol multiple times. Or, they may start with an image, and then mutate it throughout the text. Or maybe you notice a character repeats a gesture under different circumstances. Or, in the case of Joyce in particular, different characters react to the same event from different perspectives (what is called parallax).

In Plato, words such as virtue, knowledge, recollection, opinion, and soul evolve as the dialogue unfolds. And this can feel frustrating. Just when you thought you had a grasp on his definition of “justice,” he literally says he was wrong or kidding and starts over. In Herodotus, freedom, custom, vengeance, divine warning, and overreach recur across different peoples and regimes. In Joyce, words like agenbite, yes, home, father, body, and soul create hidden connective tissue. In Shakespeare, legitimacy, blood, ceremony, nature, and disorder are often the point more than the plot itself. Thus, a useful tool is to keep a running vocabulary list. You want to notice which words, ideas, and symbols keep returning. Then ask how their meaning or treatment is changing?

This is also how we begin to read characters more deeply. In a great book, a character is rarely just a personality. A character often embodies a way of seeing the world. Meno is not only a young man asking about virtue. He represents a certain aristocratic confidence, a desire for answers without discipline. Mr. Deasy in Ulysses is not merely an old crank. He carries inherited history, prejudice, imperial memory, and a limited moral imagination. In the Iliad, Achilles is not merely angry. He represents the heroic code pushed to its limit. In Shakespeare, Falstaff is not merely funny. He is appetite, wit, anti-heroism, and a critique of honor all at once. So we can start by asking at different points in the novel: “Do we like the character or not, and why or why not?” But the real insight comes when we ask:

• What way of life does this character represent?

• What is attractive about it?

• What is incomplete or dangerous in it?

Let the books, the critics, and the companion texts argue with themselves

The Great Books rarely have only one way to read them. They contain tension, reversals, counterarguments, and unresolved contradictions. Plato often lets a bad argument reveal a real problem. Herodotus preserves multiple accounts and lets the reader judge. Shakespeare gives morally serious lines to compromised characters. Joyce lets styles interrogate one another. Adams can sound nostalgic, ironic, reverent, and skeptical within the same chapter. That means the question is not always, “What does the author believe or mean?” Sometimes the better question is: “What conflict (or tension) is the book circling around and/or evolving versus resolving cleanly?”

This is where historical context helps, but only if we use it properly. It certainly helps if we know something about Athens, the Persian Wars, medieval France, Tudor succession politics, Catholic ritual, Irish nationalism, or modernist experimentation when we engage these texts. In this way, context can help illuminate a text, but we should make sure that we don’t let it overshadow the centrality of the text itself. In the world of literary theory, this approach to reading, called New Criticism, and is my preferred. Otherwise, I find conversations can tend to run down rabbit holes. For example, we could spend most of the time talking about the Hundred Years’ War instead of exploring the dynamic between the different house in Henry VI, or we could spend hours debating Greek democracy instead of asking why Socrates conducts the inquiry into the “city of speech” the way he does. To net it out: context can help explain what the text is assuming; however, the real value comes from a close reading of the text.

There are, of course, a couple of exceptions where the author presupposes the reader has access to and knowledge of many other books and texts. Dante’s Divine Comedy and Joyce’s Ulysses are two that come to mind. You can read both as standalone texts. But to really unlock the greatness of the books, you have to rely on other sources. But, in my opinion, these are the exceptions.

Read at three levels: sentence, scene, & whole

One of the challenges of reading a Great Book is maintaining a bifurcated perspective while you read. You need to understand what the words mean and what is happening in the sentence, and at the same time, observe how a sentence, section, or scene helps our understanding of the full text. Questions that can help with getting the balance right include:

• At the sentence level. “Why this word, this metaphor, this turn of phrase?”

• At the scene or chapter level. “What is happening structurally, morally, or psychologically?”

• At the whole-book level. “How does this section alter the larger question?

Doing this prevents two common problems that can appear during a conversation. First, is getting buried in line-by-line detail without seeing the larger movement. The second is floating above the text, in generalities, without anchoring to the actual words on the page.

The final question and recommendation

In summary, when reading a Great Book (or any challenging tex), the opportunity is to move from asking only, “What does this book mean?” to “What kind of reader does this book require me to become?” Some books ask us to judge. Some ask us to remember what we think was common knowledge. Some challenge us to see events or inherited history differently.

This is the hidden value of the slow-read modality. It teaches us not only how to interpret a book, but how to sit with difficulty (“embrace the suck”) long enough for it to change the quality of our attention. And this requires humility. It requires a willingness to be wrong. It requires returning to the text. It requires respecting partial insight. It also requires a tolerance for unresolved questions. This is why my final “tip” is to use the question above to build a rolling summary of four categories of inquiry:

• The central (governing) question of the work

• The evolving moral or philosophical issues

• The key symbols and structural patterns

• The major interpretive questions still open.

This way, each week will build on the previous. Over the course of the seminar, the group will begin to develop–together–a broader understanding of what the text is about and what it asks of us.

You do not really read Ulysses once

I have just started co-leading a seminar on Ulysses with a good friend as part of the Great Books Symposium. There are 10 participants with varying levels of exposure to Ulysses. For some, this is the first time. For others, it is their 6th or 7th. So it promises to be an interesting conversation for the next 24 weeks. I have just finished rereading it myself, and I am struck by the fact that Joyce seems to presuppose that you have already read it once.

When talking to people about their first attempt, you often hear them talk about how they endured it rather than how they understood it. I think it really is only on the 2nd, maybe 3rd time, that the patterns become clearer. You get a sense not just for what is happening (honestly, not that much in terms of plot) but also for what Joyce is doing, and how this is different/radical compared to what we expect a novel to be.

I remember when I was trying to jam-read Ulysses in 2 weeks during college, I felt overwhelmed and often unsure whether I was failing to read the book properly or Joyce was deliberately being difficult. Years later, after several more readings, exploring companion books, chasing down allusions and references in annotated versions, and listening to podcasts and lectures, I have a greater appreciation for what Joyce was doing. Joyce is not simply telling a difficult story: he is inviting us to read differently. This is not an entirely new idea. Heck, when you look back at Plato’s Republic or the Phaedrus dialogue, this is EXACTLY what he was doing as well, i.e., asking us as readers to read differently (alas, that is a topic for another essay).

The modernist conceit

I remember in college wanting to explore modernism because I thought it was the ultimate “intellectual” achievement to master the modernists. I wanted to be hanging out with Hemingway, Pound, and Stein in some Parisian salon debating the nuances of form, substance, authorial intent, etc. Or, at the very least, to try to impress the coeds at local colleges. Many would agree that Joyce’s Ulysses is one of, if not the, most important “high modernist” novels. And at that time, I was going to take it on and try to master it. But as I worked my way through it and other modernist novels, I became aware of an underlying conceit of the modernist movement as a whole. Modernist authors and artists often don’t think that their art needs to meet the reader halfway. They produce art for art’s sake, and the reader (or the viewer) must learn the work’s terms. At some level, this is just arrogant. But it also helps explain the book’s enduring power: Ulysses is not merely telling a story. It is trying to redefine how we read stories.

Writing at the turn of the century, Joyce is—in large part—reacting to the conventions of the “realist” novel that were in place before him. The Victorian writers taught readers to expect a stable world, intelligible characters, a linear plot (for the most part), and a narrative that moved forward clearly enough to guide interpretation through exposition. Even in the late 19th century, when writers like Henry James began to turn more inward and explore consciousness, the novel remained largely coherent. Joyce changes that contract with his readers.

What makes Ulysses a great book that continues to entice and frustrate readers today, 110 years after its publication, is that the paradigm Joyce challenged in 1917 remains the one most modern readers use when approaching a novel. Most readers today come to fiction expecting developed characters, a linear plot, continuity, and narrative guidance as needed. From the beginning of Ulysses, Joyce makes clear he is not interested in playing that game.

The four expectations we bring to a novel

The simplest answer to why reading Ulysses still feels hard is that Joyce undermines the reader’s ordinary expectations across four dimensions that most of us bring, consciously or not, to almost every novel we open: character, plot, perspective, and style.

• Character. We expect character to be made legible. Someone walks onto the page, and the novel provides enough description, action, and social context to begin to understand who this person is.

• Plot: We expect the plot to provide orientation. Things happen in a more or less coherent sequence, and that sequence tells us what matters.

• Perspective. We expect the author’s use of perspective to help flesh out and make sense of the experience. Whether the novel is first person, third person, or something in between, we usually know who is seeing, who is knowing, and where we stand in relation to the consciousness on the page.

• Style. Style is the way that the author brings the words (and the story) to life. Most readers expect style to carry meaning without drawing too much attention to itself. The prose may be plain or elaborate, lyrical or ironic, but it usually serves the larger work of making character, plot, and perspective intelligible.

Joyce does not eliminate any of those things: Ulysses has characters, a plot, perspective, and style in abundance. But he rearranges their relationship. Characters are no longer brought to life through robust description. Plot does not drive the story forward in the same way as the Victorian novel. Perspective is shifting all the time, and it is often hard to figure out who is saying what and who is thinking what. And style, rather than serving the other elements, moves to the foreground. It becomes an active force in how character is disclosed, how plot is interrupted, how perspective shifts, and how meaning itself is made.

Episode 1 is about educating the reader’s education

That is why the first episode matters so much. “Telemachus” is not simply the beginning of the story. It is the beginning of the reader’s education. At first, the opening appears manageable enough. The setting is a tower that you can still see in pictures today. It is morning, and 3 men are starting their day with the normal rhythms. There is shaving, cooking, and an interaction with the milkmaid. There is friendly banter, and some conflict starts to emerge. On one level, this feels familiar. It resembles the opening of a recognizable social novel. But from the very beginning, Joyce challenges how we learn about the characters, the conflict, and the underlying themes.

“Stately, plump” Buck Mulligan does not simply enter the scene. He arrives performing an irreverent version of the mass. “Introibo ad altare Dei” turns an ordinary morning routine into a mock liturgy. On one level, it is funny. On another, it is theatrical. On another still, it frames the entire social and spiritual atmosphere of the episode. Mulligan is not just shaving. He is claiming the stage, profaning inherited ritual, and placing Stephen inside a world where language is never merely functional.

That first example touches all four dimensions at once. Buck’s character is not introduced through neutral description alone, but also through performance. The plot gets interrupted even before we get going. Buck’s ritual parody takes over the scene, and we are left wondering what is going on. Perspective is already becoming unstable because we are not simply watching events unfold from a fixed external vantage point. Multiple perspectives begin to compete with one another as Joyce slips from inner monologue to external description. Finally, Joyce is deliberating using style to challenge our assumptions about how we build meaning in real life.

The power of interruption.

Stephen, one of our protagonists, seems almost like a minor character given Buck Mulligan’s grand entrance. There is no long description. Instead, Joyce has him emerge through different interactions and reflections. It is as if he is painting him more slowly than we are used to in a typical novel. One of Joyce’s most powerful techniques to do this is the “interruption.” Jocian scholars describe these mini-episodes as interpolations, and they become much more obvious in episodes like “The Wandering Rocks” (episode 8). However, at this point Joyce uses interruption in an unsettling way. For example, when Stephen says, “I am the boy / That can enjoy / Invisibility, ” it seems to come out of left field. In a more conventional novel, a memory like that might be explained in more detail or seem to flow more naturally from the context. Joyce, however, is asking us to think more about how consciousness actually works. In this case, this fragment simply arrives. It appears in the scene without context.

The point is not just to puzzle the reader. The point is to force the reader to recognize that meaning in Ulysses is often built associatively rather than sequentially. Character is being disclosed, but not by summary. The plot unfolds, but not in a straight line. The perspective shifts inward, and style is the medium by which we feel that shift happen. Style, in some ways, trumps everything else. . . and this, for me, is the epitome of modernist conceit.

This is where inner monologue becomes so important. It is one of Joyce’s central tools for destabilizing the ordinary reading experience. The surface world of the tower remains present, but it is repeatedly interrupted by Stephen’s inward life: memory, grief, association, resentment, and recoil. We are no longer simply watching a scene from the outside. We are being asked to move between outer reality and inner consciousness, often without warning. It requires one to slow down, re-read a passage, and reorient oneself to what is going on and what the deeper meaning could be.

When grief breaks the scene

A powerful example of this in Episode 1 is the return of Stephen’s mother through the Latin prayer, “Liliata rutilantium...,” and Stephen’s cry, “No, mother! Let me be and let me live.” This is not information delivered for the reader’s benefit. It is an interruption. The scene is punctured by grief, guilt, religion, and unfinished psychic conflict. Joyce does not first explain Stephen’s burden and then show its consequences. He lets the pressure of Stephen’s grief break through (ala “Hamlet”, which becomes more relevant in later chapters). In this way, a character is no longer something simply described. Character is something the reader experiences through ruptures in the scene. Plot is no longer merely what happens next. It is the conflation of memory, inward life and whatever else Joyce throws into the mix. Perspective becomes unstable because the scene is now being lived from inside trauma as well as outside action.

This is all possible because of the style that Joyce deploys. The narrative is moving along, and then another Joyce introduces another element, for example, a ritual, a song, a memory, inward speech, a parody, or grief. At first, these can feel like obstacles. But as one learns to read Joyce, they begin to feel less like breaks in meaning and more like an opportunity to explore further.

A reading method for Ulysses

By the end of the first episode, Joyce has already begun teaching the reader a new discipline. When the narrative is interrupted, the point is not to panic or simply push through. The point is to ask better questions.

• Who is speaking or thinking?

• What was the catalyst for the interruption?

• What is the interruption doing?

• How does it connect to what has come before or, when rereading, how does it connect to what is coming?

• As we move back to the core story, what has changed in our understanding of the character, the context, or the conflict?

Read that way, the difficulty of Ulysses becomes less a wall than a method. Joyce is training the reader to stop assuming that the novel’s job is to make experience immediately legible. Instead, he asks us to move through language the way consciousness itself moves: by association, return, interruption, pressure, and layered awareness.

Why Ulysses still feels hard, and why it still matters

At times, Ulysses can feel like a dare, almost like a puzzle. But the book lasts because it is not only a puzzle. At some level, I don’t think Ulysses can ever really be solved. On every reading, I learn something new, but I still find passages that are completely incomprehensible. Perhaps, in this way, it is more like poetry. As much as academics have made their careers chasing down all the references and Joyce takes pride in how erudite he was, I don’t think the real value in reading and re-reading Ulysses is chasing down all the references and allusions. I think the real value is that it encourages us (like Plato before him) to learn a new mode of attention.

That may be why no one really forgets a first reading of Ulysses. One survives it, perhaps half-disoriented and half-exhilarated, and then returns to discover that Joyce was never simply withholding the story to be difficult. He was teaching us to look for the story in places conventional fiction does not teach us to look. A scene is never only a scene. The voice is never only one voice. The story is never only a sequence of events. That is why Ulysses still feels hard today. It is also why it still matters. Joyce does not just ask us to read a difficult book. He asks us to become a different kind of reader.

This week, my son came home from college for Spring Break with his girlfriend, who is delightful. They are in that early stage of young love, where everything is new and all-consuming. They are inseparable, I mean, like Siamese twins, inseparable. It is clear that they love each other, and this makes my wife and me happy. At the same time, it is obvious that this relationship now occupies most of their time outside of classes. For now, their world is each other.

This week I also happened to listen to an episode of The Daily Podcast on “looksmaxxing”: “Injections, Bone Hammering and the Pursuit of Peak Male Beauty.” The theme was familiar. Many young men are struggling to find direction, structure, and a sense of identity, and some are taking that search to an extreme. Some might argue they are suffering from the Adonis Complex. What is true for this type of subculture is that the relationships they are establishing with other men are anchored in external validation, how they look, how they rank, and how they are perceived by others. They are not anchored in becoming good men. They argue that doing things such as injections, supplements, and bone hammering (seriously, this is a thing) are justified because looks determine power. (Yes, I can sense all the women who read this rolling their eyes at this point)

Both of these relationships illustrate young men trying to figure out who they are and where they belong. In one case, identity is being shaped almost entirely through a romantic relationship. In the other, it is being shaped through status and validation among other men. Neither is inherently wrong, but both feel incomplete. Seeing those two patterns back-to-back made me reflect on what it means to have healthy male relationships at different stages of life. More specifically, it reinforced something I have come to understand over time but did not appreciate when I was younger. The relationships that shape you early in life do not sustain themselves. At some point, they depend on what you choose to maintain. What looks like connection at this stage does not always translate into something that endures.

In the U.S., most boys really start to individuate when they leave home, whether that is for college, the military, or something else. At that point, they step out of the web of relationships that supported them through their first 18 years, whether they fully recognized it or not. Family, coaches, other parents, older siblings, and the broader community were all, in different ways, invested in helping them transition from boyhood to manhood (I wrote about the stages of a man’s life in this article).

None of those relationships disappears, but their bonds begin to loosen. As a college-bound kid, you move from a world where relationships are largely a function of your environment and your family’s priorities, e.g., church, school, sports, Boy Scouts, into a world where the relationships become mostly self-directed. And this is NOTHING that you, as a parent, can do to influence those choices.

I remember that shift vividly. In college, pursuing romantic relationships became my primary motivation outside the Naval Academy, sometimes at the expense of building male friendships. After that, as I launched my career & got married, I formed relationships around life stage, career path, interests, and proximity. Each stage came with its own set of connections, but very few male relationships carried forward automatically. That is the part I did not fully appreciate at the time. Your home web never disappears, but nothing naturally replaces it. And without deliberate effort, relationships with other men often fade first.

How Men Often Build Trust

In my experience, men build friendships through activities. My best friends are the ones I ride bikes, train, and travel with. We spend time doing things where conversation is not the point. In this modality, you build trust through repetition and shared experience. The emotional layer is there, but it is usually accessed later and sometimes only during a crisis (e.g., divorce, death of a parent, major injury). I find that, when there is a shared time of vulnerability and emotional connection, there is a directness to it. There is a willingness to challenge, to say things without filtering for how they will land. It is less about processing and more about calibration. Love and affection are often demonstrated by making fun of the other person, which drives my wife nuts. This kind of relationship is easy to take for granted because it does not demand your attention in the same way others do. It does not insist on itself. But it will fade away unless you make a deliberate effort to invest.

Looking back, I had these types of male relationships in abundance at the Naval Academy. We trained together, competed together, and spent most of our time in close proximity. There were also older men who served as mentors (officers, coaches, sponsors). The good ones modeled what it meant to be a professional officer and helped us define the type of men we wanted to be. Thus, college acted like another web of support. None of it required much effort to maintain because it was built into the environment. At the time, I did not think about it as something I would need to sustain later. Like a lot of things that are given to you early in life, I assumed it would always be there in roughly the same form.

What the Classics Reveal About Male Friendship

There is a moment in the Iliad where Achilles loses Patroclus. Their relationship was built through shared experience and fighting side by side. Homer does not fully articulate the depth of that bond until it is gone. Achilles’ dramatic grief reveals what had been there all along. That pattern feels familiar. The depth is real, but it is often expressed indirectly, and sometimes only becomes visible in its absence. It is one of the reasons male friendship is easy to misunderstand from the outside. What matters is often embedded in shared history, not always in shared language.

A similar idea shows up in Ulysses by James Joyce. Written more than two thousand years later, it explores a different dimension of male relationships. Stephen Dedalus has a father, but he is also testing other figures, observing, selecting, deciding who to learn from. He rejects some, tries to impress others, and works through what it means to find intellectual and moral grounding. It is not just inheritance. It is a choice. This dynamic never goes away. However, over time it becomes less structured and harder to navigate. The expectation that you will find and maintain the right relationships shifts almost entirely to the individual.

These two examples point to two dimensions of male friendship. There is a horizontal dimension, the peers who know you through shared experience and activity. And there is a vertical dimension, the relationships built across generations with mentors and, over time, the role of becoming one yourself. Books like Iron John and King, Warrior, Magician, Lover point toward the same gap in modern life. There are fewer structured ways for men to move through the necessary stages of maturity. We have less shared understanding of what those transitions require. We have fewer rituals to recognize moments of transition. We have less clarity about how to honor our maleness without impinging on a woman’s ability to be all that she can be. The problem is that when we are not focusing energy and effort on building healthy male relationships, something else fills the gap, and it is not always constructive.—like looksmaxxing.

When the Web Begins to Thin

Strong relationships do not fail all at once. Whether they hold depends on what you do during the years when it is easiest to let them fade. If you do not invest time and energy, the connection becomes a thin strand. You end up trying to catch up on 40 years in 5 minutes at your next high school reunion, which I will do in April. I know this from personal experience. As I moved through life, my own web started thin. It was gradual, driven by the fact that I moved around a lot for various jobs and was consumed with raising a family. I had fewer shared experiences with men who knew me outside of the role I was playing at that stage of life.

Some people do the opposite. They continue to invest, and those relationships deepen over time. These lifelong friends knew you before your current role, and they can see you across stages. There is real value in being known by people who have seen you at different points in your life, not just who you are now, but who you were becoming. That is part of what I was trying to get at in Seasons of a Man’s Life. Who you are evolves over time, naturally and necessarily. The ultimate value of healthy male relationships is that they do two things at once. (1) They can keep you grounded in your core values and (2) they help shape who you are in the next stage. Thus, they give you both continuity and development. They remind you where you came from; they challenge you and the choices you make; and they help call you forward to be the best you can be. At the risk of another classical allusion, this is one of the key drivers of Socrates engaging Glaucon and others The Republic. He is trying to help them realize what it means to live a “just” life focused on “the good.”

Built-In Bonds and Deliberate Investment

Over the past month, Dana and I have had a number of people visit us in Sun Valley. Some were couples we are close with, and I enjoy spending time with both the women and the men. These weekends follow a common pattern. We do things together, meals, activities, and have conversations that include everyone. I am grateful for these “couple” friendships. The relationships are meaningful, and these friends have been part of our lives for many years. But they are different than my male friendships.

By that point, a group of my closest male friends (plus 1 woman who can kick all our asses) came to visit the other week. These are people I have known for decades. In our early years in Seattle, we did everything together. We rode bikes; we did adventure races; we skied; we spent long days exploring the Pacific Northwest. For many years, we also worked together. It was intense and constant, requiring little thought to maintain. Then life shifted. I moved to Oakland, and we became focused on our careers. Staying connected required more effort. Over the years, we would meet in places like Hawaii, Napa, or Santa Barbara to ride bikes. These trips were always anchored in a shared activity, but it was no longer automatic.

A third group of men, who have come to Sun Valley and will come again this year, are my guy friends from the Naval Academy. Our shared experience was a different kind of intensity. Four years of trying to survive at a formative stage, followed by early separation, and then reconnection later in life. Early in our Navy careers, we would connect at reunions and periodically on social media. The connection was still there, but it was thin. What brought it back was a shared recognition that (1) these types of relationships mattered, (2) it was good for the soul to spend time together again, and (3) if we wanted those relationships to continue, we had to invest in them deliberately.

Looking at all of these relationships together, the pattern becomes clear. Your support web does not disappear; it just stops holding on its own. Career, family, geography, and the natural progression of life all loosen the connective tissue. That loosening is inevitable. What is not inevitable is whether the relationship survives it.

And, Not Either/Or

Watching my son, I can see the beginning of the same transition. He is building something new, and that matters. I would not want to interrupt that. But at some point, the web around him will loosen in the same way it did for me. The question is not whether he will care about male relationships in his life. The question is whether he will learn early enough that relationships only endure if you keep choosing to invest in them. It does not have to be an either/or choice. I.e., it is not a question of choosing between a relationship with a partner or relationships with other men. The challenge is learning how to build both and to invest enough time over the next 3 years so that his male relationships survive the stages of life that will pull them apart.

To be fair, not every friendship needs to last for life (I wrote about this dynamic in an article about friendships for a season, a reason, or a lifetime). Some should fade. Some belong to a specific stage. But there is real value in carrying a few of them forward, especially the ones built on trust, shared history, and mutual respect. These friendships become a source of perspective, grounding, and renewal. Most of us do not think about that early enough. I certainly did not. But looking back and seeing where I am now, I can see that male friendship is not a luxury in a healthy life. It is part of how a man stays connected to who he has been, and part of how he grows into who he still needs to become. I am extremely grateful for the ones that have persisted.

A Moment That Didn’t Quite Make Sense

I’ve spent the last 24 weeks working through Herodotus’s Histories with the Symposium Institute, which offers quarterly seminars on the great books. One of my biggest takeaways from this text is how often the motivations and justifications of leaders from 2400 years ago feel so contemporary. I was reminded of this again when President Trump called on our allies to help secure the Strait of Hormuz this week, and they said “No.” There was no ambiguity and, perhaps more interestingly, their responses were not coordinated. Some questioned our objectives; others pointed to the lack of consultation before the attacks; and several declined outright without giving a reason. At first glance, this could be written off as a familiar debate about burden sharing, who does more, who pays more, and who needs to show up when. However, I would suggest this was a signal that alignment with our allies can no longer be assumed, and that something more structural is shifting in how the world works today.

To be clear, this was not a failure of capacity or capability. Our NATO allies have the ability to act, and they have done so in the past. What was missing in this case was agreement on the purpose, potential risk, and likely outcome. Trump, with Prime Minister Netanyahu of Israel, decided to invade Iran based on intelligence and timing. They saw their opportunity and took it. Some argue that Israel was going to attack Iran regardless, and Trump did not want to be left behind. We will probably never know the full truth on that front. However, we do know that these two leaders moved forward without bringing other allies along. The implication is that the mechanism that once reinforced cooperation among allies may be weakening, and this is where Herodotus becomes relevant.

What Herodotus Actually Shows About Alignment

In Book 9 of The Histories, as King Xerxes of Persia begins to withdraw, he leaves his general Mardonius behind to take a final stand. In this phase, Mardonius marshals a force of 300,000 Persians and allied troops and must determine whom he can rely on. He seeks visible demonstrations of loyalty, not passive support. This is most evident with the Thebans, a Greek city-state that has already “medized” (aligned with Persia). At this point, Thebes has expressed support for the campaign, but Mardonius pushes them to prove that loyalty by attacking other Greeks. Thebes draws a line and refuses to attack fellow Greeks, choosing instead to operate in a more measured and conditional manner. The result is participation that satisfies Mardonius’ demand for alignment without fully embracing its implications.

The deeper insight is that loyalty tests often do not strengthen relationships or trust. Instead, they reveal the limits of the alliance. Loyalty that must be demonstrated on demand is already under strain, and testing it exposes that strain rather than resolving it. When the war turns, and the Greeks prevail, Thebes is judged and punished as an opportunist whose commitment was always partial. That outcome is not simply about choosing the wrong side, it is also about the nature of the alignment itself. Herodotus shows that power can produce compliance but not conviction, and that distinction becomes decisive when outcomes are uncertain and risks are high. The Theban example demonstrates that “compelled alignment” produces risk-averse behavior. Actors comply just enough to avoid punishment but not enough to share the strategic burden. Thus, Persia has a HUGE coalition on paper, but its medized allies mostly act cautiously, which is exactly the condition that undermines coordination in decisive moments. This pattern repeats throughout the ages.

From Alignment to Compellence

The pattern that emerges is not unique to Persia, nor does it depend on ancient conditions. As I wrote in this article, many countries throughout history have justified invading others on the basis of perceived threats or fear of invasion. Over time, some of these countries secured regional hegemony and, like ancient Persia, Athens, Rome, and France under Napoleon, sometimes became empires. In the 19th century, we saw another evolution in power through the “spheres of influence” strategy. As this process unfolds, alignment shifts from being negotiated with allies to being expected from those who are subjugated. Eventually, expectation turns into entitlement. The challenge is that when alliances begin to fray under those conditions, the instinct is to apply pressure rather than rebuild agreement. The result is a transition from persuasion to compellence, which changes the nature of the broader political system.

The reason this transition matters is that it alters the quality of participation. Leverage can compel action, but it cannot create alignment. Systems built on alignment begin to degrade under pressure. The implication is not that power disappears, but how it is used must change, especially in situations that require coordination rather than unilateral action. That distinction matters because alliances are not simply collections of capabilities; they are systems of shared risk, and shared risk depends on voluntary commitment. Alliances are also built among people with egos, and when those relationships are devalued or ignored, trust erodes and commitment becomes conditional.

The Return of Gunboat Diplomacy

The New York Times has run several articles alluding to “Gunboat Diplomacy” over the past couple of months. Gunboat Diplomacy refers to European powers’ use of naval forces in the 19th century not only to fight wars but also to secure access to trade routes, resources, and strategic positions. The approach was effective at producing immediate compliance but rarely produced durable partnerships because the underlying alignment was never established. A more recent example would be Venezuela, where the US has been using economic pressure for years and then, in January, used military force to secure resources (oil) and assert regional power more directly. In the end, Gunboat diplomacy is not just about force. It is about sequencing. Action comes first, and alignment is sought afterward. That sequence works against weaker states. However, it fails with allies because it bypasses the very process that creates legitimacy.

This metaphor helps contextualize a series of military actions that might otherwise seem unrelated. Venezuela, Greenland, the first attack on Iran, and now the standoff in the Strait of Hormuz differ in context, but they share a common structure in how power is applied. In each case, the US is using leverage rather than legitimacy to secure security, resources, or a strategic position. With the most recent escalation, we see the Trump administration attempting to apply these tools to both allies and adversaries. The implication is that the boundary between coercive and alignment-based power is blurring.

Allies, Adversaries, and the Misapplication of Power

The post-WWII global order depended on maintaining a clear distinction between how power was used against adversaries and how it was used with allies. The United States did not build its post-war power base by conquering its allies, as ancient Persia and other empires did. Instead, it helped former enemies such as Germany, Italy, and Japan rebuild their economies and political systems, and over time, some of these former adversaries became some of its most reliable partners. The reason is that the US was deliberate in how it organized the postwar system. It worked with like-minded countries (largely democracies or social democracies that embraced capitalism and the rule of law) through global and regional institutions designed to reduce the risk of another world war. The assumption was that shared interests and shared values would make participation both rational and legitimate, producing durable alignment rather than coerced compliance. As Sting once sang, “I hope the Russians love their children too.”

Obviously, that system has not been perfect, and debates about burden sharing, particularly within NATO, have persisted for decades. The challenge was never the absence of disagreement, but how those disagreements were resolved. These institutions functioned because alignment was grounded in consent rather than extraction, and because consultation reinforced legitimacy even when outcomes were uneven. When alignment was strong, the separate countries were able to coordinate action and response, even in complex and high-risk situations. The First Gulf War under President George H. W. Bush is a clear example in which the United States built a broad coalition with defined objectives, international backing, and shared ownership of both risks and outcomes. By contrast, the 2003 invasion of Iraq under President George W. Bush revealed what happens when alignment is weaker. As the coalition narrowed and legitimacy was questioned, participation became more conditional. That distinction matters because the effectiveness of power is not simply a function of capability, but of whether it is exercised in a way that sustains alignment or erodes it.

What appears to be changing today is not simply the level of contribution, but the method used to secure it. When tools associated with coercion are used in relationships that depend on alignment, the nature of those relationships changes. Hard power tactics such as the use of military force before consultation, tariffs, sanctions, and trade restrictions are examples. These tools may be effective when dealing with adversaries, where compellence is the objective. By contrast, alliances have historically relied on different tools, including legitimacy built through consultation, participation in shared institutions such as NATO, and economic integration through financial systems. This connective tissue builds mutual obligation over time. You cannot compel allies the way you confront enemies, and you are not going to conquer them, so applying pressure in these contexts often produces hesitation rather than commitment. The result is participation that is narrower, slower, and more conditional. That change is subtle at first, but it accumulates over time and becomes visible in moments like Hormuz, where coordination fails because of the weakness of the relationship, not the strength of the military.

The deeper logic of this type of system was actually articulated by Alexander Hamilton in Federalist No. 11. In this essay, he argues that commercial relationships create alignment in ways that coercion cannot. Thus, trade, interdependence, and shared prosperity bind nations together because they make cooperation mutually beneficial rather than externally imposed. The implication is that influence built through economic integration is more durable than influence imposed through force. That distinction became the foundation of the postwar order, even if it was not always articulated that way.

Why This Moment Matters

Thus, the Strait of Hormuz is not just a policy dispute; it is a signal about how the global world order is changing. When allies decline to participate, the issue is not simply compliance; it is the condition of the relationship that would have produced participation in the first place. The real question we face now is whether our relationships (alliances) are at a point where alignment must be re-negotiated each time rather than assumed.

That shift has implications that extend beyond any single conflict or country, because it affects how quickly and effectively countries can coordinate when interests overlap. Canadian Prime Minister Mark Carney warned in his remarks at the recent Davos Conference that the assumptions underlying the postwar economic and political order are beginning to break down, particularly the expectation that major powers will operate within a shared framework of rules and coordination. The implication is that we are not simply observing isolated policy disagreements, but entering a world in which each country must rethink how it relates to others. The result is a system in which alliances become more conditional, cooperation becomes more transactional, and the ability to organize collective action becomes less reliable. This is not uniquely American, and it is increasingly reflected in how leaders across the global system describe the current moment. The postwar order was built on assumptions about legitimacy, shared interest, and coordination, and those assumptions are now being tested in visible and cumulative ways. The implication is not immediate collapse, but gradual fragmentation, in which the system continues to exist but functions with less cohesion and predictability.

The Leadership Challenge

The challenge we face today is structural and sits at the intersection of power, legitimacy, and alignment. In an earlier essay, I argued that leaders of republics must be clear about the moral and political objectives when they use force, because ambiguity leads to strategic drift. That remains true, but it is no longer sufficient. Leaders must also understand the type of power they use and whether it aligns with the relationships and alliances they seek to sustain.

Herodotus shows that this dynamic is not new, and it emerges when systems transition from one mode of organization to another. The deeper question is whether we can recognize that transition early enough to adjust how we operate within it. Because once alignment weakens to the point where it must be compelled, the system is already breaking, even if its structures remain intact. Power does not fail immediately when coercion replaces legitimacy. It simply stops working when it matters most.

The question, then, is not whether today’s global order is under strain: It is. The question is “do we understand the source of that strain clearly enough to respond to it?” If alignment with our allies must be rebuilt each time, then we are already operating in a different kind of system, one where cooperation is negotiated rather than assumed. That shift does not eliminate power, but it changes how power works. Leverage can compel action, but when it replaces legitimacy, it does not sustain the system. It begins to undermine it.

A Typical Strategic Planning Meeting… At First

A few weeks ago, I was sitting in on a strategic planning session with one of our clients at CEO Coaching International. Strategic planning is one of the key ways we work with CEOs and their Exec teams, and the process follows a fairly structured rhythm. The leadership team completes pre-work that documents the previous quarter’s (or year’s) performance, identifies what worked, calls out the misses, and captures what lessons were learned. The Coach aggregates those inputs and works with the CEO to shape the agenda for the planning offsite.

Most strategy sessions follow a familiar sequence that balances reflection, goal-setting, and strategic debate. The team begins by reviewing financial performance and operational metrics from the previous period, focusing on the drivers that explain the company’s results. From there, the conversation shifts toward defining the next set of quarterly (or annual) goals and the input metrics that will signal whether the company is making progress. The leadership team then turns to broader strategic questions, such as:

• Where should the company focus its energy?

• How fast should it grow?

• How should we allocate capital and headcount?

Eventually, teams get to the most difficult part of planning: determining which initiatives to fund and which to pause or kill. That is where the run really begins!

A new player at the table

I have participated in or led sessions like this for the past 15 years as an executive, CEO, or Board Member, so the rhythm is very familiar. But this meeting had a new player at the table. In this case, the CEO Coach helped the leadership team build what they called a “Strategic Partner” GPT that (who?) was effectively sitting alongside the executives during the conversation. The team had trained it on their operating plan, recent board decks, financial models, and internal operating metrics. In other words, the GPT had access to the same information the leadership team normally relies on to prepare for planning discussions.

The experience reminded me a little of having “Data” from Star Trek sitting in the room, listening to the conversation, and ready to answer questions. Except in this case, the role was not science fiction, and the cost structure was radically different. In many strategic planning sessions, this analytical role is filled by FP&A leaders, strategy teams, or, sometimes, expensive management consultants, with a team of analysts preparing the models behind the scenes. The leadership team debates the question, and then the analysts or consultants run the numbers. The process usually takes hours or days to complete, producing a new deck that requires yet another meeting to discuss. It is the epitome of “soul-sucking time-wasting.”

What was different in this session was that the “analyst” was operating in real time. As the conversation unfolded, the team began using the GPT to summarize historical performance, surface operating trends, and test strategic scenarios DURING the discussion. At one point, the conversation turned to headcount planning, and the CEO asked how three different hiring paths would affect growth, margins, and the company’s Rule of 40 trajectory over the next two years. The GPT produced a clear analysis within seconds, something that normally would have required hours of spreadsheet work, followed by several meetings to review and pressure-test the assumptions.

The realization

What struck me was not simply the speed of the answer, although that was impressive. The deeper realization was that the presence of a “Strategic Partner” GPT at the table begins to change how leadership teams should operate. If an AI system can synthesize operating data instantly, the question becomes how much effort organizations should spend preparing information for leadership meetings in the first place. If strategic scenarios can be modeled during the conversation itself, the implication is that teams should spend far less time producing slides and far more time debating the actual decision. As someone who has spent thousands of hours preparing for these types of planning sessions and asking teams to do the same, I find the potential shift in efficiency, effectiveness, and even job satisfaction difficult to overstate.

The Deeper Question

That experience led me to a deeper question about what AI-powered augmentation might mean for how companies are run. If the cost of analysis is collapsing, CEOs should begin asking how their companies’ operating systems should evolve in response. Traditionally, a company’s operating system governs how information flows, how decisions are made, and how resources are allocated across the organization.

Why does this matter?

Because a wrong decision can impact your growth trajectory and, by extension, your valuation, which in turn affects your ability to secure funding for future growth. For example, research from SaaS Capital shows that the median private SaaS company has been growing roughly 30%/ year. If a company is growing at 30% per year, a single resource-allocation mistake can erase a significant portion of its future growth potential. For example, if you choose to hire too aggressively in sales/marketing, overinvest in an unproven product initiative that does not expand the addressable market, or underfund customer success when retention is the real growth lever, momentum can start to stall. The challenge is not alignment around goals. The challenge is allocating capital and talent in ways that compound growth over time

Why Do We Even Have Operating Systems?

Most CEOs think about operating systems in terms of methodology. The conversation usually focuses on whether the organization should run EOS, OKRs, Make Big Happen, or an internally developed business rhythm (ROB) process. Those choices certainly matter, but over time, I have come to believe that the deeper value of an operating system lies not in the methodology itself. The real value lies in the discipline it creates around tradeoffs and capital allocation. When an operating system works well, it forces leadership teams to decide where resources will be placed and which initiatives will not receive investment.

The challenge becomes clearer as companies scale into the $10M to $200M ARR stage. At that point, most organizations already have alignment on strategy and goals, yet sustaining growth becomes more difficult. The reason is that success at this stage depends less on clarity and more on consistent resource allocation decisions across the organization. Teams propose new initiatives, product roadmaps expand, and hiring plans accelerate across multiple functions. Without a disciplined operating system to force trade-offs, the company slowly drifts toward reactive decision-making rather than deliberate growth.

Four Layers of Operating Systems

In my experience, most leadership operating systems fall into four broad categories, each designed to address a different coordination problem inside a growing company.

The first category: strategic alignment systems ensure that everyone in the organization is literally on the same page regarding company priorities. The original version of this approach was Management by Objectives (aka MBOs), introduced by Peter Drucker. Andy Grove later evolved this construct into the Objectives and Key Results (OKRs) framework, popularized by Google. The key value of alignment systems is that they translate strategy into measurable outcomes that every team can understand. Without this layer, individuals work hard, but it can seem that teams are moving in slightly different directions, or in the worst case, working at odds because teams interpret priorities differently. I wrote an article on how to right-size one of these systems (Salesforce’s V2MOM) for a start-up’s context.

If the first category emphasizes alignment, the second category focuses on operational execution. Systems such as EOS by Gino Wickman and Chief Executive Operating System by Joel Trammell establish a structured cadence of quarterly priorities, weekly leadership meetings, and accountability mechanisms that help organizations translate plans into consistent action. For companies transitioning from the founder-led stage, where the founder can be involved in every decision, to a leadership team model (~$1M-$5M), these systems can feel transformational. The value of execution systems is that they impose discipline on how the organization operates, allowing teams to spend less time reacting to problems and more time executing against clear priorities.

A third category focuses on growth and capital allocation. Frameworks such as Mark Moses’ Make Big Happen System, which we use at CEO Coaching International, force leadership teams to make deliberate investment decisions across people, capital, and strategic initiatives. The central insight behind these systems is that durable growth does not come from pursuing every opportunity but from concentrating resources where the company has the highest probability of compounding advantage. These systems create structured conversations about trade-offs, helping leadership teams decide which initiatives to invest in and which ones to divest or defer.

A fourth category is beginning to emerge as artificial intelligence changes the economics of analysis. As mentioned above, leadership teams have historically relied on FP&A groups, strategy teams, or expensive consulting engagements to synthesize information and test strategic scenarios. That analytical layer sat outside the company’s operating system and typically delivered insights hours or days after a discussion. AI is beginning to collapse the cost of that analytical work, allowing leadership teams to explore scenarios, test assumptions, and synthesize operating data during the conversation itself.

This creates what might be called an intelligence layer inside the leadership operating system. Instead of waiting for analysis to arrive after the meeting, the leadership team can interact with a system that surfaces insights in real time and helps orchestrate the flow of information between humans and machines. The implication is not simply faster decision-making. Over time, it changes how leadership teams structure meetings, evaluate trade-offs, and coordinate strategic decisions. For the past twenty years, most SaaS leadership teams have embraced the first three layers. The fourth layer is just beginning to appear

The Productivity Frontier is Rising

One way to understand the magnitude of this shift is through a simple “growth efficiency” metric: revenue per employee. For most of the SaaS era, the best companies operated within a fairly consistent range. Benchmark studies by SaaS Capital and High Alpha show that typical SaaS companies generate roughly $125,000 to $250,000 in revenue per employee, while strong performers often reach $300,000 to $400,000. A handful of highly efficient public SaaS companies can leverage their scale to achieve $ 500,000+ per employee. Those tiers have traditionally reflected the natural productivity limits of the SaaS operating model (i.e., the “productivity frontier). As I have always said, SaaS is a people business. This is because 70-80% of your costs are people-related. For example, you need engineering teams to build, deploy, and maintain the product; marketing teams to generate demand; sales teams to acquire customers (unless you have a product-led growth [PLG] model); and customer success teams to delight customers, ensure retention, and drive expansion. Thus, even with great execution, the traditional SaaS model requires significant human labor to generate and support revenue.

AI-native start-ups are turning the SaaS operating model on its head, as reflected in their revenue-to-employee efficiency. In fact, some early AI companies are exceeding $1 million in revenue per employee, and a few analyses suggest that top performers may eventually reach $2 million or more as automation expands across product development, customer support, analytics, and go-to-market operations. A couple of examples include:

• Midjourney (~$4.1M revenue per employee)

• Cursor / Anysphere (~$3.3M revenue per employee)

• OpenAI (~$2.8M revenue per employee)

Yes, these are extreme examples, but they are directionally important data points. Over time, these figures will almost certainly normalize as those companies scale and hire more people, but the clear signal is impossible to ignore. If the productive capacity of a software company rises materially, the leadership team must change the operating system that governs how information flows, how resources are allocated, and how decisions are made.

Strategic inflection points

This dynamic illustrates what Andy Grove described as a strategic inflection point. Strategic inflection points occur when the underlying economics of an industry change, and a company must adapt its operating and business models to remain competitive. The classic example was the shift from “on-prem” software deployment to “cloud-delivered” applications in the early 2000s, which ushered in the SaaS revolution. Software companies redesigned their distribution models and, more importantly, their pricing structures to target OPEX rather than CAPEX. The result was a sea change in how the business model and economics worked for vendors and buyers. And there were clear winners and losers from this age.

The recent revolution of generative (and agentic) AI has created another such inflection point. The technology is not simply making companies faster; it is changing expectations for the productivity frontier. What used to be good enough (~$200k/employee) is starting to look downright inefficient, especially as the cost structure is also changing. For example, Sam Jacobs wrote a great article on “agentic math” that captures the new reality of gross margins for AI companies. To net it out: for pure software companies, compute used to be effectively free, and, thus, you would expect a SaaS company’s Gross Margin to be >85%. For AI-native companies, the current reality is GM is 40% because the cost of compute has risen dramatically. The only way to offset this hit to GM is to increase efficiency through leverage, which can be measured by revenue/ employee. Given this new reality, every SaaS CEO must reevaluate how they run their businesses and whether they need to rethink their operating systems to align with the new market’s economic realities.

The CEO’s role in an intelligence-augmented company

The implication for CEOs is that their role needs to shift from managing information to orchestrating intelligence. As companies grow, CEOs naturally spend less time executing work themselves and more time designing the systems through which work happens. Leadership operating systems such as OKRs, EOS, or Make Big Happen were created to address that scaling challenge by helping CEOs align teams, coordinate decisions, and execute consistently as the company grows. These systems assumed that collecting data was difficult, analysis required time, and leadership teams needed significant preparation before strategic discussions could occur. As a result, companies built elaborate processes to gather information from multiple systems, assemble presentations, and distribute analysis through structured meetings.

Artificial intelligence changes the economics of that model by collapsing the cost and time required to synthesize information. CEOs are no longer primarily responsible for ensuring that information flows upward through the organization. Instead, they must design the environment in which human judgment and machine intelligence interact productively in near real time. The upside is that, in this new reality, meetings can evolve from information briefings into decision forums where leaders debate trade-offs rather than review slides. What it means to prepare for a planning session also changes. Now, rather than focusing on assembling reports, leaders can focus on framing the strategic questions that matter most.

In this model, human expertise does not disappear, but its role changes. Analysts and operators remain critical participants in the decision process, yet their contribution increasingly centers on interpretation and judgment rather than data preparation. AI systems surface insights, model scenarios, and synthesize information immediately, while leadership teams focus on evaluating implications and choosing a course of action. The CEO’s role, then, is to orchestrate the interaction among people, data, and intelligent systems (i.e., agents) so that the organization can move faster while maintaining execution discipline aligned with strategic priorities.

From Management Systems to Orchestration Systems

Seen in this light, AI introduces a new layer into the company’s architecture. The operating systems that defined the SaaS era were designed primarily to coordinate human activity. Alignment frameworks ensured that teams pursued common priorities, execution systems imposed operational discipline, and capital allocation frameworks forced leaders to make trade-offs about where to invest resources. These three layers solved the core coordination problems of scaling organizations during a period when analysis was expensive, and information moved slowly through the company.

The emerging AI layer changes how those systems function by embedding intelligence directly into the leadership workflow. Instead of waiting for analysis to arrive after a meeting, leadership teams can now explore scenarios, test assumptions, and synthesize operating data during the conversation itself. Analytical copilots and specialized agents become participants in the decision process, surfacing insights and helping leaders evaluate strategic alternatives in real time. The result is not simply faster decisions but a different operating rhythm in which insight emerges continuously rather than episodically through prepared reports.

Just as cloud infrastructure transformed how software was built and distributed, intelligence systems are beginning to transform how leadership teams process information and coordinate decisions. Companies that recognize this shift will start to redesign their operating systems to deliberately incorporate these capabilities TODAY! Those that do not will gradually accumulate “operations debt” (e.g., more meetings, more reporting, and more coordination overhead in an attempt to manage increasing complexity). Over time, the difference between these approaches will compound. CEOs who learn to orchestrate intelligence allocate capital more effectively, adapt strategy more quickly, and sustain momentum as they scale. And they will leave their competition behind.

A few months ago, I was sitting in a board meeting at a growth-stage SaaS company when one of the directors asked about the company’s AI strategy. . . again. From what other CEOs tell me, this has been the recurring question in nearly every board meeting over the past 18 to 24 months. It is no longer a thought experiment; it is an expectation. Many VCs are shifting their entire investment thesis toward funding AI-first companies. And most are pushing their current “non-AI-first” portfolio companies to become AI-first as quickly as possible

In this case, the CEO answered well. He walked through how the company was using AI to augment people’s capabilities. For example, Engineering was adopting the latest tools to write higher-quality code faster; Customer Success was experimenting with summarization and internal knowledge assistants; and Marketing was leveraging large language models (LLMs) to produce personalized content at scale. At this meeting, I was struck by the fact that all of these activities fall in the realm of “AI augmentation.” I.e., the company was using AI to accelerate existing workflows and improve output quality. But it begs the question: “Is faster output the same thing as an AI-first strategy?”

What no one in that room asked were questions such as:

• “If AI meaningfully reduces the cost of intelligence, should we still be organizing the company around static dashboards and monthly reporting cycles?”

• “Should forecasting still be a quarterly ritual, or should it become a continuous ‘learning system’ that reconciles sales activity, product usage, and billing data in real time?

Fast forward to this past month: Mark Moses, CEO of CEO Coaching International, challenged all partners to be deliberate in helping clients think about their AI strategy. We are now using four questions to frame these conversations:

1. How is AI impacting your industry?

2. How is AI impacting your business?

3. What job can an agentic AI solution reinvent in the next six months?

4. How is AI impacting your job as CEO?

The first two questions are increasingly straightforward, though still important to clarify. McKinsey’s 2025 State of AI report shows that 65% of organizations now report regular use of generative AI in at least one function, nearly double the figure from the year prior. Adoption is broad and accelerating. Yet nearly two-thirds of respondents say their organizations have not begun scaling AI across the enterprise. In other words, experimentation is common; however, companies are still struggling with integration.

The third question, around agentic AI, is generating a lot of interest and, to be honest, a fair amount of confusion today. People are asking questions such as:

• What does agentic even mean?

• What roles can an agent play?

• How do I think about building out functions that have human+agent teammates?

According to McKinsey, roughly 62% of organizations are at least experimenting with AI agents. There is far less clarity around what to redesign and what to leave alone.

The fourth question is the one I find most interesting for CEOs to think about more deeply. At the consumer level, Pew Research reports that roughly half of U.S. adults have used a LLM (e.g., ChatGPT) at least once. But regular, structured use is far lower. Which brings us back to the boardroom. When directors ask about your AI strategy, they are partly asking about product features and cost leverage. But they are also asking something more fundamental: “Have you, as the CEO, changed how you think and behave?”

This essay is about that shift. Because the way you adopt AI as an individual will shape the ceiling of how your company adopts it.

My own journey through augmentation

When ChatGPT came to market, like most people, I started experimenting with it. I used it to draft emails, help with research, and summarize findings for articles. I spent time playing with prompts to make “chats” more efficient. In May of last year, I wrote an essay that summarized where I was at that point. At that time, I was intrigued by the ideas of cognition and authorship. Specifically, how do you know what is “your idea” versus what was “augmented intelligence”?

At Maxio, I was encouraging the organization to rethink workflows. At the same time, we had more than $20 billion in billing and invoicing data across our customer base. The strategic question was not whether AI could write better emails. It was whether that data, properly modeled, could reposition us as an insight engine rather than just a system of record. We wanted to be AI-first, but we also had 2000+ customers we were currently supporting and needed to keep improving the current platform, addressing tech debt, etc.

What I did not fully appreciate at the time was that my own maturity with AI was still largely at the augmentation stage. I was using it to make myself more productive. I was not yet using it to redesign how I thought about systems.

What’s the difference?

Augmentation thinking asks, “How can AI help me do this task faster or better?” Systems thinking asks, “If the cost of intelligence collapses, how should I redesign the workflow entirely?” The first improves efficiency; The second changes architecture. And this “systems thinking” is what I needed to embrace to help lead the company forward. I left Maxio in March 2025, but have continued my own AI journey.

A Personal AI Maturity Table

To make this concrete, I started thinking about AI adoption not just as a company journey, but as a personal one. I believed that, before you can architect AI into an organization, you have to understand how it shows up in your own cognitive workflow (i.e. how you think). That led me to sketch what I am calling a Personal AI Maturity Matrix. There are three primary dimensions that determine where you sit on the Matrix.

• Reach: How consistently are you using AI in your own work? Is it occasional experimentation, or is it part of your daily rhythm?

• Depth: How embedded is AI in your recurring cognitive workflows, such as strategy formulation, hiring decisions, capital allocation, and board preparation? Is it a peripheral tool, or is it shaping how you structure problems?

• Delegation: How much intellectual authority are you granting it? Is it editing your words, stress testing your logic, modeling scenarios, synthesizing data, or shaping first-draft frameworks that you then refine?

When you look at these three dimensions together, patterns start to emerge. I then built out five stages that reflect different ways of thinking and behaving along the AI journey. To ground this in something more than anecdote, I asked ChatGPT to synthesize adoption data from Pew, McKinsey, and the Stanford HAI AI Index to approximate how these levels might distribute across the U.S. population. To be clear, these are directional estimates, not census-level precision, but they align with what public research shows. Currently, there is high awareness, relatively lower integration, & very low systems-level redesign.

Interestingly, if you step back, the pattern roughly maps to Geoff Moore’s technology adoption curve from Crossing the Chasm. Today, most people fall into the late majority or laggard categories in their use of AI. Very few people are operating at the frontier.

Personal AI Maturity Table

• Level 0 | Avoidance
  Estimated U.S. adult population: 40 to 50 percent
  This is where most people still are. They are aware of AI. They have opinions about it. They may even feel threatened by it. But they are not using it in any meaningful way. Reach is effectively zero. Depth and delegation are nonexistent. From Moore’s lens, these are the laggards, i.e., those who do not see a compelling reason to change their behavior because they don’t know how to start, don’t think there is real value, or are just afraid.

• Level 1 | Curiosity
  Estimated population: 20 to 25 percent
  These individuals have experimented with AI, trying ChatGPT or Claude once or twice. They may have asked them to draft a vacation itinerary or summarize an article. But their usage is sporadic. At this level, reach is inconsistent, and depth is shallow. Delegation is limited to simple tasks like drafting or summarizing. This group is interested, but not yet committed. In Moore’s framework, this aligns loosely with the late majority who are observing but not yet rethinking their behavior.

• Level 2 | Utility
  Estimated population: 15 to 20 percent
  At this level, people start to use AI regularly. They use it for drafting emails, preparing outlines, summarizing research, or debugging code. Reach is high at the individual level. Depth, however, remains task-based rather than workflow-based. Delegation extends to research and light analysis, but their thinking about AI and its impact on their daily lives remains largely unchanged. This is where I was in May of last year. I was faster. I was more efficient. But I had not yet redesigned how I approached problems.

• Level 3 | Integrated Workflows
  Estimated population: 5 to 8 percent
  At this level, people are embedding into recurring workflows. It is part of how they prepare for board meetings, how they frame strategic tradeoffs, how they evaluate hiring decisions, or how they structure complex writing. On a personal level, it could include how they think about training and nutrition on a daily basis. Reach is consistent. Depth increases because AI is now shaping recurring processes rather than isolated tasks. Delegation expands to include scenario modeling, counterargument generation, and synthesis across multiple inputs. This is where I believe I sit today.

• Level 4 | Systems Thinker
  Estimated population: 1 to 3 percent
  This is the pivot. At Level 4, AI begins to influence how you design systems, not just how you execute tasks. You start asking: if the “cost” of intelligence has collapsed, what workflows should I redesign? Delegation is bounded but strategic. You define explicit roles for AI in planning, review, and analysis. This is where augmentation turns into architecture. This is where I am intentionally trying to move over the next several months.

• Level 5 | Orchestrator
  Estimated population: <1 percent
  At this level, an individual intentionally designs systems that integrate AI across domains, with governance, metrics, and defined human override. AI is not just a tool; it is an integrated layer in how value is created. Ownership and accountability are explicit. This is rare territory today, but it will not remain so for long.

There are three macro observations from this exercise:

1. If these estimates feel skewed toward the lower levels, that is consistent with the research. McKinsey data shows widespread experimentation, but far fewer organizations report material workflow redesign or measurable business impact. Personal maturity mirrors that pattern.

2. There is no shame in being at Level 1 or Level 2. That is where most people are. This technology cycle is still early, and experimentation is rational.

3. The only way to move up the table is through practice. AI maturity is not theoretical. It is behavioral. You have to use it, reflect on it, and intentionally redesign your own workflows before you can credibly redesign your company’s.

And that last point is where this stops being an intellectual exercise and starts becoming a leadership issue. Because in a growth-stage SaaS company, the CEO’s cognitive ceiling often becomes the company’s strategic ceiling.

The Impact of the CEO’s Personal Adoption of AI

What has become increasingly clear to me is that for CEOs in particular, learning how to use AI well is no longer optional. Not because it is trendy, but because it is becoming foundational to how decisions are made and systems are designed.

If you, as the CEO, are operating primarily at Level 2, your company will likely adopt AI at Level 2. You will encourage productivity gains. You will sponsor pilots. You will celebrate efficiency wins. But you will unconsciously limit the scope of what the company can become, because you are still thinking in terms of augmentation.

If, on the other hand, you are operating at Level 4, you begin asking a different class of questions. Instead of asking, “How can we use AI to do this task better?” you begin asking, “If the cost of intelligence has collapsed, how should we redesign this workflow entirely?” You begin asking architectural questions such as:

• Revenue Model: If AI improves our ability to predict customer behavior, should our pricing, packaging, or expansion model evolve to reflect that new insight advantage?

• Capital Allocation: If intelligence becomes cheaper and faster, how should that change where we deploy human capital versus automation across product, go-to-market, and customer success?

• Org Design: If AI meaningfully reduces the cost of analysis and coordination, which roles in our organization are still designed for information routing rather than decision-making?

That shift in your personal experience allows you to reframe both the threat and the opportunity that AI presents for how your company competes and how you build it.

Where do you sit?

Do I expect CEOs to print out the Personal AI Maturity Table and bring it into their next board meeting? No.

That is not the point. The point of this essay is to encourage folks to ask: “what is my actual relationship to AI?" and “how can I get better?” If you want to diagnose yourself, do not ask how often you use it as “frequency” is not the indicator of success. The real indicator of success is if your thinking has changed. So ask yourself, based on your use of AI today:

• Has your decision-making speed meaningfully improved?

• Are you seeing second-order consequences more clearly because you are modeling scenarios and stress-testing assumptions more rigorously?

• Have you redesigned at least one major leadership workflow because AI changed the economics of intelligence?

• Are you spending more time on architecture and less time producing artifacts?

The answers to these questions can help reveal whether you are still augmenting output or have begun to operate at the systems level. In my own journey over the past ten months, that has been the real inflection. I interact with AI constantly, but the meaningful shift was not volume. It was perspective. I am now using it to structure problems differently, to surface blind spots earlier, and to redesign workflows I once accepted as fixed.

The unusual opportunity in the AI tech revolution wave is that the barrier to raising your own maturity is low. You do not need a transformation budget to evolve from augmentation to systems thinking. You need to be intentional in your practice and disciplined in your reflection. In my own journey over the past ten months, that shift has been the real inflection. As I wrote about in the previous essay, I am talking to some form of AI all day/every day. But now I am using it to literally think differently

So, when the board asks for your AI strategy, they are asking about product and margin. The more important question is whether you have one for yourself.

Introduction

I have been wanting to write a version of this article for several months. In Dec, I wrote an essay titled “Why Herodotus? Why Now?” about the attack on Venezuelan boats in International waters. It seemed to me to be a clear signal of Trump’s imperial ambition and desire to revert to a 19th-century “Sphere of Influence” realpolitik model. His capture of Maduro on Jan 3rd reinforced my belief.

Then I was going to write it when he was threatening to invade Greenland in early Jan, seemingly another “sphere of influence” play. Fast forward to today (Feb 28th), and he has initiated, with Israel, a “major attack” on Iran. The context is different because Iran, obviously, is not in our sphere of influence; however, there are some similarities across these scenarios. And now I need to get this essay out before he decides to “speak loudly and hit with a big stick” again.

To be clear, this essay is not a partisan critique of the attack on Iran. There are a bunch of political pundits arguing both sides of that debate right now. Instead, I want to step back and ask how a Republic should think about war. I draw on Clausewitz and Herodotus to examine how leaders throughout history have constructed their casus belli. My concern is not whether force is ever justified. It is whether we have become less disciplined in distinguishing among the justifications for “major combat operations” and/or declaring war (e.g., for defense, prevention, or influence). More importantly, I would argue that we, as citizens and our representatives in Congress, need to demand more clarity about the moral rationale and political objectives before our leaders—no matter who the leader is—initiate military action against sovereign foreign governments.

The Question We Must Ask

Today, President Trump announced sustained strikes aimed at degrading Iran’s missile and naval infrastructure, framing the action as necessary to eliminate emerging threats to American interests and regional stability. He has been hinting at this for a while, most clearly at the State of the Union Address last week. It is important to note that he has not declared war (Congress still retains that power); however, he has committed an enormous force (with Israel) to attacking Iran on his own. The challenge he must overcome is less about the process: it is, more importantly, a moral and political one. When a Republic initiates large-scale combat operations, its leadership must articulate two things to its citizens:

• The moral rationale and

• The political (strategic) objectives

In the US, we trust that a President (supported by Congress) will clearly articulate the “moral rationale”, i.e., what wrong has been done to the US, and that responding with force is appropriate. The most obvious example of this is the Japanese attack on Pearl Harbor. The moral rationale for our declaring war was crystal clear.

In the last 50 years, I think we have had too few examples of leaders (regardless of political party) who can clearly articulate both the moral rationale and the political objectives (i.e., the end state we seek, and how we will achieve it once the dust settles). An example of where we did this right was General MacArthur’s work in post-war Japan and the Marshall Plan’s impact on Europe after WWII. Unfortunately, what we have seen in more recent conflicts, such as Vietnam, Iraq, Afghanistan, is that if the strategic objectives are not clear or if we have not planned for the post-war nation-building, we get mired in extended and VERY expensive conflicts.

Clausewitz and the Political Objective

I pulled out my copy of On War by Clausewitz to remind myself of his views on the link between war and political objectives. In the very first chapter, he says that war is a continuation of politics by other means. Thus, the political objective governs the military aim. For example, if the political objective is survival, a country’s strategy is constrained and finite. It is a defensive posture. However, if politicians start banging the drum about prevention or influence, the requirements for declaring war change. He warns that the risk of lacking clarity regarding the political objectives is that war becomes untethered from its purpose. In many cases, the initial strike becomes the first step in something larger than originally described and justified. If you look at the last 50 years of our efforts to intervene, most have devolved into long-running foreign entanglements.

When a Moral and Political Objective Align

Hearing the phrase “major combat operations” took me back to 1986, when I joined the Navy during the Cold War. At that time, the Soviet Union was not an abstract concept. It had more than five million active personnel, approximately 2x what we had. At its mid-1980s peak, the Soviet Union possessed ~40k nuclear warheads, again, nearly double the American arsenal. And its intercontinental missiles could strike American cities. In this way, the Soviet Union represented an existential threat to our very existence.

The Reagan administration responded with a substantial defense buildup. I remember there was a goal to build a 600-ship Navy, and military spending increased each year. Joining the military at that time felt like the right thing to do. The moral objective was clear: we needed a strong military to defend against a very real threat. The political objective was survival. This narrative played out broadly in our culture with movies such as Red Dawn, in which the Soviets invaded Colorado, The Hunt for Red October, where we were one turn of a key away from nuclear Armageddon, and Top Gun, which showed that spending lots of $$ on Aircraft Carriers and Naval Aviation would allow us to project our power around the world.

From Deterrence to Preemptive Strikes

Before 1989, when the wall fell, our primary posture on the world stage was one of deterrence. We were clear that going to war with the Soviets would lead to mutual destruction. This led presidents from both parties to pursue influence through proxies and to support small-scale “interventions.” The wall fell in 1989, and our posture changed in 1990, when Iraq invaded Kuwait. In response, President G.H.W. Bush created a “coalition of the willing) to restore Kuwait’s sovereignty. He was able to do this because the moral rationale was clear and the political objective was defined and limited. We were supporting an ally who had been invaded and trying to stabilize a region. (Comparing what we did/did not do in Kuwait to what we are doing/not doing in Ukraine will need to wait for another essay.)

By 2003, the argument had shifted. President G. W. Bush (the son) justified the preemptive invasion of Iraq on the grounds of preventing the potential future use of weapons of mass destruction (WMDs). The burden threshold moved from responding to aggression to predicting a theoretical threat. As we all know now, the intelligence President Bush relied on was faulty; there were no WMDs. And, unfortunately, Iraq became an expensive quagmire for 8 years. According to an article by Rand, The Invasion of Iraq: A Balance Sheet, the war cost between $2 and $3 trillion in direct and long-term costs. Moreover, 4,400 U.S. service members were killed, and more than 32,000 were wounded. That’s a big “whoops.”

Even when confronted with the costs of a preemptive posture, the US has continued to embrace this doctrine, and almost every president since has used force to eliminate potential dangers before they materialized. This is obviously a slippery slope, as we can’t actually know what a regime will do. However, this was a strategic shift in how we justified the use of “military action.”

Herodotus and the Narration of Necessity

Herodotus shows that the problem of justification is ancient. In Book 1 of The Histories, Croesus of Lydia consults the oracle at Delphi before attacking Persia. He is told that if he crosses the river Halys, he will destroy a great empire. He assumes it will be Persia’s. It is his own. The episode is not simply about unreliable prophecy. It is about how leaders interpret ambiguity to align with their ambition. What begins as uncertainty becomes inevitable through narrative manipulation.

Under Darius I, Persian expansion is framed not as conquest but as stabilization. Campaigns against distant peoples are justified as necessary to secure order and prevent future revolt. In this logic, unrest anywhere signals potential instability everywhere. Darius wanted to expand the empire’s perimeter to ensure internal peace. Ironically, what began as defense becomes preemptive consolidation.

This is “defense” logic stretched to its outer boundary. If disorder beyond the frontier is treated as an intolerable threat, then expansion becomes the path to security. The implicit argument is simple: Darius sought to establish a “Pax Persica” by conquering the known world. The danger in this reasoning is not that security is irrelevant. It is that the definition of threat expands with the leader’s (or state’s) ambition. Once instability anywhere is grounds for action everywhere, the justification for war becomes nearly limitless. And this is what we are witnessing today.

The key for me about this episode is that Herodotus tells this history by “preserving” speeches he probably never heard. To his credit, he does offer competing explanations for why things happen. One of the things Herodotus makes clear is that a leader’s narrative creates the sense of necessity for war. In this way, war enters the people’s imagination before a country deploys troops or ships. Leaders shape the future today, just as they did 3,000 years ago. This is a permanent feature of statecraft.

This reality does not make war illegitimate. However, it makes clarity essential. Because once a leader has constructed the narrative of necessity, citizens must decide what kind of necessity it is:

• Are we defending ourselves?

• Honoring an alliance?

• Preventing imminent harm?

• Or projecting influence?

These are not rhetorical distinctions. They define the moral and strategic burden of the conflict.

The Categories of War and Their Burdens

There are only a few reasons states go to war, each of which carries a different burden of justification.

• Defense. Responding to an attack on our country (e.g., Pearl Harbor or 9/11) requires the lowest moral burden. The right of self-defense is foundational. At the same time, the strategic objective is often defined and finite. We are going to strike back to prevent future invasions.

• Honoring an Alliance. This is a VERY interesting one, especially regarding what is playing out in Ukraine. While Ukraine is not a member of NATO, which defines our obligations, it is an ally, and the moral burden rests on commitments. The strategic burden is also relatively clear. The response should be proportional and focus on preserving the coalition’s legitimacy. This is why Article 5 of NATO has been sacrosanct for 60 years.

• Preemption or prevention. When operating in the realm of a “potential" threat, the moral burden is obviously greater. At the very least, the leader needs to provide credible evidence of an imminent or intolerable threat. This was President Bush’s WMD argument. Similarly, the strategic burden requires the leader to be clear about the end state and ensure we avoid open-ended escalation. This is the argument that President Trump ran on during his 2nd campaign—no more wars of foreign entanglement.

• Expansion or influence. As I wrote about in the earlier essay, this reason was used in the 16th-19th centuries to justify many countries’ ambitions to secure resources and/or influence. Today, this casus belli carries both the highest moral and strategic burden. It risks becoming a justification for imperial ambition. And, if pursued, it requires governance capacity, legitimacy, and willingness to own the consequences. Putin has used this justification for his invasion of Ukraine. It will be interesting to see what he and Russia do to the lands they retain when the fighting finally ends.

What about Iran?

The Trump administration is currently framing the attack as “prevention.” The administration argues that degrading missile and nuclear capabilities now reduces future danger. To be clear, Iran is not the Soviet Union of the 1980s. It is a regional power with asymmetric capabilities. It cannot mount a conventional invasion of the American homeland. That distinction matters. If the justification is prevention, the evidentiary standard must be high and the political objective precise. If the objective is influence or regime change, the burden rises even more because, then, the United States becomes responsible not only for attacking weapon sites and infrastructure. It also becomes responsible for shaping and financing what follows. This is going to be REALLY hard without putting troops on the ground.

Our Burden Now

Herodotus shows how states narrate necessity, and Clausewitz reminds us that politics must define the aim. Together, they expose a permanent tension in Republican governments. War can be justified. But its legitimacy depends on clarity before action, not rationalization after the fact. The burden of a Republic is not to avoid force at all costs; it is to be clear about the moral and political objectives for using force. If we are defending ourselves, we should say so plainly and define the limits of that defense. If we are honoring an alliance, we should anchor the action in a treaty and ensure proportionality in our response. If we are acting to prevent future harm, the evidentiary standard must be high and the end state defined precisely. If we are pursuing influence, we should acknowledge the moral and strategic weight of reshaping another nation’s future.

When these distinctions blur, we end up with “forever wars." The cost is not only financial or military, though history shows those costs can be staggering. We have seen this move before in Vietnam, Iraq, and Afghanistan. In each case, the absence of a clearly defined political object made victory elusive and our ability to exit VERY difficult.

The deeper cost is our legitimacy as a Republic. When this happens, citizens lose trust that force is being used appropriately, leading to protests and civil unrest. Abroad, we are already seeing allies question our reliability. To that point, several countries sent troops to Greenland as a counter to Trump’s threat to invade. Eventually, adversaries (e.g., China) will start to test our resolve in their own spheres (e.g., our willingness to defend Taiwan). Ultimately, the global order becomes less predictable, leading to market instability. No one wants this. . .

Our obligation now is not partisan. It is constitutional and civic. Congress must assert its authority. President Trump and his team must define their moral rationale and political objectives with precision. And we, as citizens, must demand clarity about what category of war we are entering, the expected costs, and what the “end state” looks like.

In mid 2024, I was sitting with Brian Austgen, our head of Demand at Maxio, and we were discussing a troubling trend in our pipeline analytics. Paid search was still generating leads at a reasonable cost, but our organic traffic had declined significantly. He concluded that it was due to the rise of AI summaries (what became known as AEO), powered by LLMs. While we had pretty sophisticated attribution models in place, this was a new dynamic, which led to a conversation about shifting spend from demand to brand, and then to a more existential question: what does ‘brand spend’ mean in an AI world?

I was reminded of this conversation while reading the 2026 Brand vs Demand Benchmarks Report from Benchmarkit.ai. This report surveyed 168 CMOs of B2B tech companies and found that, on average, they spend ~70% of their dollars on demand gen and only ~25% on brand building. Yet when asked what the ideal allocation should be, these marketers said it should be ~50% demand and ~40% brand.

Why the disconnect?

You fund what you can defend. 73% of them agreed that brand spend makes demand generation more efficient over time; however, only 28% say they could directly tie brand investment to pipeline. Thus, in a digital-dominant marketing landscape, demand gen has been more defendable, at least until the new world of AI marketing we are all facing today.

The Rise of Measurability

When I joined Avenue A in 2000, digital advertising was still a small fraction of global ad spend. Television was still where most of the dollars went, and, if you can believe it, print still mattered. At that time, internet display advertising was funded from experimental dollars, and people were trying to figure out if it really worked. Online, creativity mattered a lot less than on TV. I remember someone joked that to improve a display ad’s performance, you should “Make it pink and make it blink.” The key was measurability. We could track impressions, clicks, conversions, and cost per acquisition. We believed we had solved the problem that John Wanamaker, the famous department store owner and early marketer, decried in the 19th century: “Half the money I spend on advertising is wasted; the trouble is I don’t know which half.”

Wanamaker was talking about print. He could see his sales increase, but he could not attribute it to specific ads. Digital advertising promised to fix this, and we went on a tear for 26 years. Internet advertising grew from low single digits of global ad spend in the early 2000s to become the dominant channel, eventually surpassing television in most markets. The rise was not just about targeting. It was about accountability.

That shift also changed who won the budget debate. In the television era, the creative director held influence. Think of the show Mad Men, which captures the glory days of TV advertising. Brand campaigns shaped preference and identity. In the digital era, the analyst (aka the performance marketer) became the hero. Clicks, leads, and ROAS drove allocation decisions. Because bottom-of-funnel actions were easier to measure, digital marketers increasingly optimized for them. Everyone still believed that Brand programs mattered. However, they just became harder to defend. And that has been the tension for 20 years+.

Search Engine Land recently reported in Nov 2025 that when Google AI Overviews appear, organic click-through rates (CTR) can fall by more than 60 % and paid CTRs drop as much as 68% for some searches. To be fair, “organic” CTRs declines are most pronounced on informational queries, where AI Overviews appear. The data shows that the impact on “commercial” queries is more mixed. In any case, AI-generated summaries reduce the need to click through to underlying sites. At the same time, multiple industry analyses show the continued rise of zero-click searches, where users find answers without ever visiting a website. To that point, in an Oct 2025 article, “New Front Door to the Internet: Winning in the Age of AI,” McKinsey noted that ~50% of consumers are already using AI-powered search tools as part of their research and decision making process. I am a data point of one, but I now do 90% of my “searching” with Google Answers and ChatGPT. I never click on the paid links. If I want to buy a product, I go directly to Amazon, REI, or another retailer.

This is a fundamental disruption in how CEOs and CMOs need to think about distribution. One way to frame the new way of thinking could be:

• Search Engine Optimization (SEO) is about ranking.

• Answer Engine Optimization (AEO) is about answering.

• Generative Engine Optimization (GEO) is about being included.

Traditionally, for SEO, you optimized your website content to ensure high rankings on Google. This led marketing orgs to invest significant time and money into content production. I have talked to many CMOs who have teams of people focused on writing SEO optimized articles, embedding keywords, and ensuring the HTML code was correct. In the classic “ten blue links” world, visibility meant ensuring you were on page one of the search results. An entire industry of Search Engine Marketing Agencies grew up to help companies optimize their SEM and SEO spend. This took years.

With the rise of AEO, teams needed to start to create content so that AI systems could extract and present it directly as an answer. But this change has happened in less than 3 years, and few people really know how to do this today. Brian would say that the best marketers have figured out that optimizing AEO is similar to SEO in terms of trying to capture “long-tail” demand. The two key differences is that you have a more constrained budget, it is more complicated and Google is not making it easy to understand the rules of the game.

GEO is even harder because now you have multiple engines, each with its own algorithm. The objective for GEO optimization is to be cited or summarized inside an LLM-generated response. The challenge is that these engines are taking in much more input to determine your “authority.” Thus, to be successful, you have to optimize your brand’s presence across:

• Earned media

• Reviews

• Forums

• Wikipedia

• Industry publications

• Analyst reports

In the AI-mediated world, visibility means inclusion in the answer set. Here is a quick check to see if your company is doing this well.

1. Go to ChatGPT and prompt it to evaluate your market, the key competitors, the relevant trends, and how it is evolving.

2. See if your brand and/or products are listed and if your content is cited.

If you aren’t, look at who is. They are doing it right.

The underlying business dynamic is changing.

Discovery is now increasingly mediated by models that synthesize information before a buyer ever reaches your site. Thus, “influence” has moved upstream of the click. As a result, attribution models built for the SEO era are now less reliable because fewer clicks occur.

How should CEOs and CMOs think about this new reality?

In the digital era, you have a lot more direct control over your demand gen spend and results. You would increase paid spend and watch the leads rise. Yes, at some point, you would hit the efficient frontier, but you often had a lot of room to spare before things became inefficient. This is why 55% of marketers in the 2026 Brand versus Demand Benchmark Report said they would protect demand, compared with only 11% who said they would protect their brand spend when faced with cuts.

At the same time, if you continue to optimize solely for last-click performance metrics while organic discovery shifts to AI summaries, you will see traffic decline, panic, and over-rotate toward spending more on paid search. The impact will be rising CAC, slowing pipeline velocity, and eventually pressure on growth multiples because efficiency erodes. I just wrote an article about concerning trends in CAC Payback. This dynamic is one of the causes.

In the AI era, you must treat authority and clarity as strategic assets. Your brand must be structured in a way that models can recognize, trust, and include. This requires even more cross-functional alignment across marketing, product marketing, content, PR, and even product documentation. To that point, user-generated content platforms e.g., Reddit) are increasingly influencing answer sets. How many of you have a Reddit activation/content strategy?

Brand versus Demand in the AI world

The question that will make budget conversations more complex over the next two years is this: when you fund AEO and GEO initiatives, are those brand dollars or demand dollars? If your company appears in an AI-generated shortlist when a buyer asks for the best platforms in your category, you are clearly influencing “in-market” demand. Yet, the reason you appear is the accumulated “authority” you have built over time. This new reality blurs the traditional split. I don’t think this means AI advertising is a new category, as there are still only two core economic objectives behind marketing: (a) increase preference and (b) capture intent.

What is actually happening is a collapsing of the artificial separation between brand and demand we saw in the “Search”-dominant era. In the digital-dominant era of 2020-2026, brand programs largely drove awareness while demand programs captured intent once it appeared. You could treat them as sequential and somewhat distinct. In an AI-mediated environment, that separation weakens. Brands now need to focus on building authority so that you are included in the answer set. Inclusion in the answer set directly shapes in-market demand capture. In other words, brand authority becomes a prerequisite for demand capture. That is the shift.

What Changes is the Mechanism

I would argue that AI optimization is not a new objective; it is a new distribution layer. Just as television, search, and social each reconfigured how preference and intent were connected, AI now sits between buyer and brand as the next distribution layer. The economic objectives remain the same: increase preference and capture intent, but the mechanism that links them has changed in a way that forces CEOs to rethink how the dollars are allocated.

As a CEO or COM, you should not wait until your traffic collapses before adjusting. As I mentioned in the other article, this is where second-order metrics can help, e.g., rising CAC despite stable spend. Other things you could look at include shorter website sessions, as answers are consumed off-site. You could poll your sales teams to see how many people are arriving with a short list of competitors and evaluation criteria, obviously generated by AI tools.

What does not change is the same question that Wanamaker had: “Where do we spend to maximize sales?” The answer has always been some combination of building preference and capturing intent.

The new reality facing today’s CEOs and CMOs is that if AI reduces attributable clicks, then your board is going to pressure you to spend less money on marketing. The CEOs who win this board battle will recognize that the power center has shifted again, from the creative director to the analyst to the agent, and they will have to completely rethink their marketing strategy, team composition (human+agents), and tactics before the agents start deciding which brands matter.

Managing the Cost of Growth While Building the Next Engine

Over the past couple of weeks, I have been thinking about what is required to scale a company from $100M to $500M. One part of the catalyst has been my conversations with CEOs who are operating squarely in this zone in my new role as a CEO coach. But part of the catalyst has been my reflection on my own experience in this zone after writing this article on “Strategic Inflection” points.

When I ran Rocket Fuel, we were a ~$400M public company. The issues we wrestled with were very different from the ones I faced earlier in my career. And when we sold Percolate, then a ~$30M company, to Seismic, I had a front-row seat to how a scaled company thinks about cadence, capital allocation, and managing multiple go-to-market motions at once across products, segments, and regions.

So I have been thinking about what lessons CEOs should learn and apply as they face this inflection point. It is actually hard to define what “best in class” companies and CEOs do at this stage, given the few data points. According to Crunchbase, of the 4600 public software companies, only 46 fall into the $100-$500M range. However, the good folks at Bessemer have done the hard work of looking across private and public companies to develop a set of benchmarks, which they aggregated in their 2024 report: “From Start-up to Centaurs: The Founders’ Roadmap to $100M.”

At first glance, companies between $100M and $500M look relatively healthy. And many of the headline metrics do not change dramatically as companies cross from $50M-$100M into the $100M+ range. Gross margins remain consistent. Net revenue retention tightens slightly but stays strong. One metric, however, changes the CEO’s job: CAC payback. In the $50M–$100M range, the average CAC payback is roughly 21 months. At $100M+, it is closer to 30 months. This is significant.

But what does this mean?

Effectively, it signals that acquiring the next dollar of ARR requires more capital and more time. If margins and retention remain intact while CAC payback extends, the issue is most likely not product-market fit: It is capital efficiency. At this size, capital gets tied up longer, and it is harder to pivot. The business can continue to grow, but growth becomes more expensive to finance. This essay focuses on what CEOs should consider as they face the “Efficient Scale” inflection point.

$100M to $500M | Efficient Scale

The transition from $100M to $500M is not primarily about adding complexity. Most companies have already layered in new products, segments, or regions by this stage. Scaling efficiently means managing the rising cost of growth while deliberately building the next “growth engine.” When CAC payback lengthens, the CEO can’t afford to fund multiple initiatives haphazardly. Capital allocation becomes tighter; decision rights matter more; tradeoffs can no longer be implicit. Perhaps most importantly, the executive team can no longer just solve for their function. At this stage, the CEO’s job shifts from launching more initiatives to underwriting fewer, larger bets with clear ownership and defined outcomes.

What success looks like from $100M to $500M

The research shows that companies that successfully navigate the $100M to $500M transition embrace three best practices.

1. Protect and Extend the Core Before You Invest in Adjacencies

Chris Zook, in his book “Profit from the Core,” states that enduring growth comes from expanding outward from a position of strength (aka “your core”), not from abandoning your core in search of the next cool thing. This is because at at $100M, your core growth engine is working. You most likely have a defined ICP, a repeatable GTM motion, and some form of structural advantage. But because the company feels “established,” there is a temptation to treat the core as solved and shift attention and dollars to the next thing. By contrast, the most successful CEOs at this stage go all-in on their core. They spend the time to define the core explicitly. They quantify their differentiation. And they invest to deepen the core’s advantage by building moats and walls.

At the same time, the most successful CEOs don’t have blinders on. They are deliberate about finding the next $100M business. At this stage, then, the strategic question becomes: “What adjacent potential growth engine leverages our core capabilities and can realistically become $100M on its own?”

This requires a different way of thinking about investment. Specifically, it requires dedicated ownership, milestone-based funding, and explicit “kill” criteria that people will actually use to kill a project if the engine starts to stall.

The pressure on the CEO and executive team intensifies as the risks of making a mistake are high, and you probably can’t make many mistakes and keep your job. The risk then becomes incrementalism. You explore segments, products, and geographies without forcing any of them to graduate into a scaled engine. The organization feels innovative, but you start to see CAC payback stretch. The result is not a collapse. It is drift.

2. Design for Coherence as Complexity Rises

By $200M, the issue is usually one of alignment. One of my favorite books is Patrick Lencioni’s “The 5 Dysfunctions of a Team.” He has lots of useful concepts, but the one that resonates most at this stage is his “first team” concept. In essence, the executive team must operate as leaders of the business and not as a collection of functional leaders. At this scale, it becomes easier to optimize for your specific function’s needs amid so much complexity. For example, sales pushes for more flexibility to close deals so they can hit the number. Product expands its roadmap commitments because it now has to support multiple customer segments across multiple regions. Finance tightens cost controls to improve EBITDA in accordance with investors (most likely PE) and/or public company shareholders’ desire for the company to generate (and distribute) cash. Each executive’s decision is individually rational. Collectively, they can create a coordination tax. And the death knell is leadership meetings that report on activity versus focusing on the single most important objective and working through hard trade-offs to realize the company’s ambition.

I first experienced this when I was at RocketFuel, working with very senior executives. We were executing a major turnaround, and I needed each executive to lean in, figure out what was best for the business, and make appropriate sacrifices. Most importantly, they needed to be able to represent these tradeoffs to their organizations.

This is why, at this stage, the CEO’s job requires them to see organizational design as a strategic lever. What does this mean? A couple of examples include:

• Clarifying decision rights and the decision-making process.

• Making enterprise tradeoffs explicit in the All Hands.

• Aligning incentives around shared outcomes, specifically an executive scorecard.

• Protecting a small number of cross-functional priorities.

If you do not deliberately design for coherence, the organization’s complexity will start to drag down your growth potential. Thus, the cost of growth, as represented by CAC payback, increases not because the market disappeared, but because organizational “friction” is mucking up the system.

3. Make Capital Allocation Explicit and Earn the Right to Invest

Warren Buffett has long argued that capital allocation is the CEO’s most important job. In early-stage SaaS companies, this can feel abstract because if growth is solid, capital should be relatively abundant and investors relatively forgiving. At $100M, the calculus changes. Every dollar invested in a new segment, product, geography, or AI initiative has an opportunity cost.

If your CAC payback is now 30+ months, you are, in effect, underwriting a longer risk window. This is where McKinsey’s Three Horizons framework becomes informative.

Horizon 1 is about protecting and extending the core (point #1 above). For most companies between $100M and $500M, Horizon 1 products account for the bulk of revenue over the next 12 to 24 months. They fund everything else, so you want to make sure youare devoting enough time and energy to these products.

The challenge at this stage is either complacency or starvation. Complacency shows up as incremental roadmap work, while competitors innovate faster than you and start winning more deals on the strength/breadth of their product. Starvation shows up when leadership diverts too much attention and capital into adjacencies, assuming the core is stable enough.

The CEO’s question for Horizon 1 is straightforward: “What are the two biggest threats to our core engine, and are we investing enough to defend and deepen it?” If CAC payback is starting to extend, you cannot afford a weak core. Embracing Horizon 1 discipline earns you the right to invest in the next two horizons.

Horizon 2 is about scaling adjacencies that can become material. As CEO, you need to define a small number of “close” adjacencies that leverage your core strengths. That could be a new product in the same ICP, a new segment with the same capabilities, or a tuck-in acquisition that accelerates something you were already building. The key is to be intentional. As CEO, you are underwriting the possibility that this productor business can become meaningful within 2 to 5 years.

The CEO’s question for Horizon 2 is: “If this works, how big can it be, and what must be true for it to get there?” If you cannot answer that clearly, you are funding activity, not building another real “growth engine.”

The biggest potential mistake a CEO can make when thinking about Horizon 1 versus Horizon 2 is running the whole company like Horizon 1, then telling the board you have a growth strategy because you are “exploring” new markets or “doing AI.” The trick is to invest in Horizon 2 initiatives as if they were real businesses, with ownership, milestones, and kill criteria, while still protecting Horizon 1 discipline.

Horizon 3 is the hardest to protect. This horizon is where you invest to prevent disruption. By definition, Horizon 3 investments have a long-term payback, involve significant uncertainty, and are easy to cut when quarterly pressure rises. To point #2 above, this is where you need the executive team to act like a “first team” and make the necessary trade-offs to fund Horizon 3 investments, even when this may impact their team’s ability to succeed in Horizon 1.

Think about the companies that saw the AI wave forming in 2020 and invested in data infrastructure and product re-architecture before customers demanded it. By 2024, they were positioned to lead. The ones that waited are now reacting from a position of weakness.

The CEO’s question for Horizon 3 is: “ What shift could make our current advantage irrelevant within five years, and are we investing early enough to shape that shift?” When capital discipline is clear, the organization needs to understand why some initiatives scale and others stop. That clarity alone improves coherence and reduces friction, thereby improving CAC payback.

The $100-$500M Failure Mode

In my other article, I talked about “dominant failure modes” as a way to call out the one thing to watch out for at each stage. In the $100-$500M stage, the failure mode is not chaos; It is incrementalism. At this size, the company will usually keep growing, as it is likely a category leader, has an established customer base, and has built out appropriate processes and systems to support “at-scale” operations. But this growth tends to be about layering more on top of the same operating model. For example, you may add a new segment, a new product, or a new region. Maybe you introduce a new partner channel. And, at this size, you probably have bought at least one company to add “inorganic” growth. When you are inside this company, it feels like it is progressing because there is always something happening.

Meanwhile, CAC payback is extending because every new bet adds friction before it generates revenue. The organization compensates by holding more meetings, granting more exceptions, and escalating more to the top. The result is a company that looks active, but the growth is not compounded efficiently. The real impact is that your “next growth engine” never manifests. Over time, you end up optimizing the core until it slows down or you start to lose market share to more nimble/ smaller competitors. It becomes a death spiral because your options start to narrow, and the cost of change rises even higher.

Summary: The Real Shift

As mentioned above, the $100M to $500M transition is not about “handling complexity.” Most companies at this stage are already complex. The shift is economic. Growth costs more, as indicated by an increasing CAC Payback. The CEO’s job changes accordingly. It becomes less about inspiration and more about architecture. I would suggest there are 5 key pivots to embrace at this stage.

• First, your strategy must move from a priority list to a portfolio. At $100M, a company’s strategy can often seem like a list of annual initiatives. At this inflection point, the CEO needs to realize that they are managing a portfolio of bets with different payback windows and risk profiles. If the CEO does not force that discipline, everything will get a little funding, and nothing will get enough.

• Second, capital allocation must become explicit. CAC payback is not just a sales metric. It is a capital efficiency metric. Core expansion, new product, new segment, international, partner leverage, M&A, and AI initiatives all compete for capital. The CEO’s role is to define how those bets are compared and what must be true for them to continue. The shift is from “what feels important” to “what we are underwriting.”

• Third, you need to build a decision-making system that forces tradeoffs. At this scale, companies rarely fail due to a lack of effort. They stall because trade-offs are not clearly resolved. Functional leaders make rational local decisions that create enterprise friction. The CEO must clarify decision ownership, escalation paths, and the few priorities that truly matter across the enterprise.

• Fourth, focus requires subtraction. Between $150M and $250M, there are many viable paths. The key for the CEO is to be clear about what is the appropriate sequencing and timing. Even more important is naming what will not be done. This reassures people that the CEO is willing to make the hard calls and say no.

• Finally, CAC payback should be treated as a constraint, not a lagging metric.
  Top-line growth can mask stress. Second-order metrics do not. CAC payback, retention by segment, and sales efficiency trends often move before the P&L tells you something is wrong. Specifically, when CAC payback starts to extend, it usually signals ICP blur, conversion friction, or weak expansion relative to acquisition cost. Those are fixable problems. But they cannot be outspent indefinitely.

Ultimately, the CEO’s role in the $100- $500M range is not to be everywhere. It is to design a system that makes tradeoffs repeatable, capital allocation disciplined, and Horizon 2 real, while ensuring Horizon 1 remains strong enough to fund the journey. Between $100M and $500M, the companies that win are not the ones that add the most initiatives. They are the ones who manage the cost of growth while deliberately building the next engine.

Civic Complicity

In a recent conversation with friends about the Jeffrey Epstein case, I was reminded of the Ring of Gyges thought experiment in Plato’s Republic. In sum, Glaucon asks Socrates a simple question: if you could act unjustly and never be exposed (because you were wearing a ring that made you invisible), would you? At its core, the ring of Gyges is a thought experiment about justice. Glaucon is asking: “Do we act rightly because we are good, or because we fear shame and punishment?” Socrates dismantles this argument, but before doing so, acknowledges that this is a thoughtful argument. This pause invites the reader to consider the thought experiment more carefully. If you could 100% escape consequences, what would you do?

As Frodo from The Lord of the Rings reminds us, it is tempting. . . .

During the conversation, a friend, Rebecca Weber, steered us in a different direction. She argued that this case is not just about Epstein’s and the other pedophiles’ accountability. It is also about the people around him, his associates and friends, who enabled him. More provocatively, she argued that the case is about those who suspected or knew about Epstein’s crimes and chose to either remain in a relationship with him and/or stay silent. Rebeca’s question has stayed with me for the last couple of weeks.

What is our accountability?

Most of my writing has focused on civic responsibility in the political sphere. How do we hold leaders accountable? How do we preserve a republic against corruption and ambition? The Epstein case is forcing us all to think more deeply about our own accountability in the personal sphere. This essay will address several questions:

1. When does private vice become public harm?

2. How much knowledge creates a moral (if not civic) obligation to act?

3. Does proximity increase our responsibility to act?

4. What type of society are we if our most powerful citizens, in particular, choose not to confront crimes?

What would Plato say?

In the Republic, Plato actually makes a relevant point about justice that addresses the Epstein case. He states that justice depends on structure, not merely personal restraint. A corrupt individual is dangerous, but the real danger is a community that tolerates corruption. The Epstein case brings this scenario to life. Injustice persists not only because of his criminal acts, but also, as Robert Draper, a NYT reporter, wrote recently in this article, because others made the calculation that their comfort, access, or reputation mattered more than confronting and/or reporting him. This raises two questions:

• When does another person’s wrongdoing become my responsibility?

• How do we draw that line without sliding into a culture of suspicion and denunciation?

Athenian Civic Duty

In Athens, citizens were not passive observers of the law. Any citizen could bring a public action against an illegal decree. Known as “graphe paranomon,” the principle was simple: laws do not enforce themselves. Citizens must guard them. In the Athenian Constitution, legal accountability was participatory. But there were also guardrails in place. Accusers faced real risk. Frivolous or malicious claims could result in financial penalties, reputational damage, and public shame. Thus, their system balanced two dangers: apathy that allowed lawlessness to spread and the potential weaponization of accusation that would corrode trust. That tension feels very modern. Today, I think most rational people would state that they want accountability without creating a surveillance culture.

Parrhesia and the Line Between Vice and Harm

The Greeks had several other relevant concepts that can help us parse this moral dilemma. The first, “parrhesia,” is defined as frank and courageous speech in the public sphere, what we might call “speaking truth to power” today. To be clear, for the Greeks, parrhesia was not suspicion, nor was it about surveillance. It was public truth-telling when public harm was evident. And it is important to note the distinction between private “vice” and public “harm.”

Idia versus Koinon

In some ways, a “witnessed” crime happens twice. First, when an individual commits the crime. Second, when others with knowledge decide that personal safety, reputational risk, or privileged access matter more than justice. To be fair, a “free” society can’t demand universal suspicion, monitoring, and reporting. The Greeks drew a distinction that can help us make a meaningful distinction. They separated “idia,” aka “private matters,” from “koinon,” aka matters of the “common good.” And they thought that, in a free society, people should leave idia largely alone. Thus, adults can make choices others dislike, and having a disagreement does not create a civic duty to report. But when conduct crosses into the koinon, the community has a stake, and a citizen needs to act.

Thresholds of Responsibility in a Free Society

And this brings us back to Epstein and the choice his colleagues and friends faced. This case is clear. Epstein was not merely immoral. He was found guilty of criminal exploitation. There is a line here. We, as citizens, are not obligated to police private sin; however, we are obligated to act when we have credible knowledge of serious harm. The challenge for a free society is finding that line and having the courage to stand on it. I would suggest there are 3 thresholds of understanding that require different responses:

1. Difference of opinion/preference

2. Suspicion of wrongdoing

3. Knowledge of criminal activity

First Threshold: Difference of Opinion or Preference

An example of a “difference of opinion” would be associating with someone who does something you might consider a “vice,” but it is legal. One example would be smoking pot or perhaps gambling. In some states, these activities are legal, and, as such, there is no civic duty to intervene. In fact, I would argue that the opposite is true. The virtuous thing to do in this case is to let the other person live their life. You can choose whether or not to be friends with this person, but it is not up to you to pass judgment.

Now, if that person is smoking pot in a state where pot is illegal, it becomes more gray. This is where you need to think about the dimension of harm (covered below). Who is the person harmed by engaging in the illegal activity? If it is just harmful to the individual, I would argue you don’t have a civic responsibility to report them. You may have a moral responsibility to intervene to provide help if they are a friend or family member. But that is judgement call you get to make. . . . and live with.

Second Threshold: Suspicion of Wrongdoing

“Suspicion of wrongdoing” is self-explanatory. In this scenario, you may suspect something deeply immoral or seriously illegal is happening; however, you do not have proof. The Greeks feared two dangers in this case:

1. Cowardice that ignores warning signs

2. Sycophancy that weaponizes accusation

As mentioned above, in Athens, they tried to balance these two by attaching risk to making an accusation. It is important to underscore that the principle was not universal reporting along the lines of what Orwell warned us about in Animal Farm and 1984. Suspicion alone did not mandate denunciation. There are several factors to consider when evaluating the right action to take:

• Knowledge

  • Rumor does not equal responsibility. Credible knowledge changes the calculus.

• Harm

  • Not all illegality is equal. Regulatory violations (e.g., illegal gambling) differ from coercive exploitation (e.g., forced prostitution or sex trafficking). The more severe the harm or asymmetric the power imbalance, the stronger one’s duty is to engage.

• Proximity

  • A casual acquaintance is not the same as a close association with the perpetrator.

• Vulnerability of the victim

  • A society has a heightened duty when the victims cannot protect themselves.

Thus, the deeper your knowledge, the greater the harm, and the closer your proximity, the stronger your obligation. At the very least, if you have a suspicion without evidence that something illegal is happening, then you should end the relationship. I think this is where many of Epstein’s e-mails are starting to expose people’s lack of judgment. Before he was found guilty, it was clear that many people knew something was not right; however, they continued to maintain a relationship because of Epstein’s connections, influence, and access to money. And many are now paying the consequences.

One notable example is Dr. Peter Attia, profiled in a recent Atlantic article. (caveat: I was a huge fan of Dr. Attia; I read and promoted his book, I listened to his podcasts, and I bought his protein bars.) This guy had it made, except for the fact that he maintained a relationship with Epstein and, as the e-mails suggest, knew what Epstein was up to. As Tom Bartlett wrote, “[wellness advisors are] selling wisdom. Follow my advice, they contend, and you’ll live a longer, healthier, more fulfilled life. But a chummy, yearslong association with a convicted child predator is, at the very least, unwise.” Now Dr. Attia’s reputation is in shambles, and his professional career is probably over, which is appropriate

The real issue is that Dr. Attia is just one of a few people now being held accountable in the court of public opinion. I assume there are many more in the 3M pages of documents that have not yet been released, and we will hear more in the years to come.

Third Threshold: Knowledge or Witness of Criminal Activity

If you witness criminal activity, especially exploitation, silence is no longer neutral. And this is where the Athenian model really stands out. In Athens, there was no separate professional prosecutorial class as we understand it today. Investigations of public crimes were often initiated by private citizens. We have a much bigger democracy, so we need codified laws and enforcement agencies (e.g., the police, FBI, etc.) to ensure compliance. But the core idea of what it means to be not just a citizen but a participant in protecting our community remains the same.

To my point above, I am not suggesting we need a community of constant surveillance, ala East Germany or any other authoritarian regime. I am suggesting we DO share responsibility when harm is evident. This obligation is rooted in a set of shared values and a commitment to protecting those who can’t protect themselves. The moment you continue association with a criminal after witnessing harm, you cross from proximity into complicity. Even if you are not legally culpable, you incur moral obligation, and, we would hope, reputational risk for not taking action. And this is probably the most distressing part of this case. We are witnessing an entire class of society, what Robert Draper in his NYT article calls “The Epstein Class” of mostly rich men who acted as if their elite status shielded them from any potential repercussions

Summary

The lessons of Gyges and Epstein force us to confront two different but related questions:

• Gyges tempts the individual. I.e., will you act justly when no one is looking?

• The Epstein case, by contrast, tests the collective. I.e., what are we, as citizens, willing to tolerate?

The Epstein case illustrates what happens when an elite network blurs the line between the two. Continuing association after credible knowledge signals endorsement, even if it is not necessarily legal guilt. In the “Epstein Class,” silence protected access and reputations. Ironically, they acted as if they were each wearing their own ring of Gyges. Clearly, they did not realize that there were 7m records of wrongdoing just waiting to be exposed. Or perhaps they thought there was just no way they would get caught, especially after Epstein committed suicide. In many ways, the conspiracy theorists had it right.

So what is the lesson for the rest of us?

Civic responsibility is not just about what we do in the public sphere. As Rebecca reminded us, it extends to the relationships we maintain and choices we make. The question is not whether we will ever encounter wrongdoing. We will. The question is whether we will calculate our own risk first or the victim’s. When we have a difference of opinion or preference, we should practice tolerance. When confronted with suspicious behavior, we should exercise prudence. However, if we have clear knowledge of wrongdoing, then we must have the courage to act.

Why Strategy Must Change as You Scale

Last year, I wrote an article called Embarking on the CEO’s Odyssey: Mastering the Art of Strategy. In that article, I used sailing as a metaphor. Essentially, if “execution” is about trimming the sails, then “strategy” is about setting the course. At the time, I was focused on helping CEOs answer a foundational question:

“Do you know the game you are playing, and can you win it?”

I introduced the strategic choice framework from Playing to Win that I learned at Salesforce, and which I have used at every company since.

As I have reflected on my own journey and started working with other CEOs of different-sized companies, I have started to think more about how the nature of strategy itself changes as you scale. I dug into this during a recent podcast with CEO Coacing Intenational, where I am now working.

As we talked about strategy, execution, and results, I realized that many of the hardest CEO struggles do not come from a lack of strategic thinking, but from using the wrong kind of strategy for the company’s current scale. What works at $5M can is not sufficient for a company that is $25M. Similarly, what you would do for a $100M company can feel onerous if you are $40M.

The trick is understanding what the core set of questions you need to answer at these inflection points is before you get there. The challenge is that most CEOs are not taught how to recognize these inflection points and lack a framework for how to adjust their strategy in response. Below, I provide a way to think about what you need to do as a CEO as you ramp from $1M to $100M+.

I would argue that there are 4 revenue thresholds that act as proxies for different strategic inflection points. In my experience, it is approximately at these stages that things start to break or the work feels extra hard because there is a mismatch between how the company is being run and what the next stage actually demands. Specifically, at each inflection point, three things shift:

• The underlying business dynamics,

• The role of the CEO, and

• The dominant failure mode

The purpose of the framework below is not to prescribe everything a CEO should do at a given size, but to surface the primary strategic question that must be answered, the role the CEO must play to answer it, and the failure mode that emerges when yesterday’s strategy is applied to tomorrow’s scale.

$1M ARR | Validation

Clarity Is Strategy

For a SaaS company, hitting $1M in ARR is a significant milestone. It is a validation of what calls Problem/Market fit. The two questions to answer are:

• “Do we have a real problem, with a real buyer, who is willing to spend real money?”

• “Is this replicable?” I.e., is there a swath or buyers (matching an ICP) that we can execute a repeatable motion with?

Knowing where to play and how to win matters. But at this scale, the goal with strategy is not a strategic framework. It is really about thinking about how to institute a set of constraints to ensure focus. Thus, the CEO’s job at this stage includes things such as:

• Narrowing the ICP until the signal is unmistakable

• Commiting to a primary use case

• Optimizing for learning velocity over growth rate

• Distinguishing traction from noise

The most common failure mode at this stage is confusing activity with validation. Especially as a first-time founder/CEO, booking real revenue, getting positive customer feedback, and/or having enthusiastic investors can create a false sense of confidence. In response, many CEOs start to add headcount, primarily Sales and Marketing to soon. They may start to broaden the product roadmap before they have truly validated problem/market fit. The result is that the organization scales complexity before it has scaled learning.

The impact?

You end up burning a lot of cash. and may be making “one-way” product decisions too early. This is how Seed or Series A capital gets consumed before the business has demonstrated that it can win in a repeatable way.

$10M ARR | Repeatability

From Individual Wins to Systems That Scale

$10M is the next major milestone that few startups actually achieve. In fact, according to Chart Mogul, only 13% of start-ups reach this milestone even after 10 years. If you are one of the few who make it, the good news is that the company is working. You have real customers who are paying you real money. And hopefully, you have a large # of customers renewing with you. The challenge at this stage is that success is driven mostly by individual heroics, direct founder involvement, or one-off deals.

At this stage, the key strategic question changes from “do we know the problem we are trying to solve” to “why do we win, and can we reproduce it without extraordinary effort?” This is also the stage where many companies plateau. It is not a demand problem. It is a systems challenge. This is where the “where to play, how to win” logic from my earlier article becomes critical. The CEO must now:

• Articulate a clear and consistent win narrative

• Enforce ICP and deal discipline

• Decide what kind of go-to-market company this actually is

• Design systems that make winning repeatable

The failure mode at this stage is the institutionalization of inconsistency. Early success often comes from adaptability, heroics, and deal-by-deal problem solving. For example, every rep sells a deal differently. You see this manifest in non-standard pricing and individual customer promises, which impact the product roadmap or cause major headaches for the implementation and customer success teams. You see this when the CEO or a few trusted leaders have to stay deeply involved to “make it work.” You see this when systems are implemented to manage growth rather than to reinforce strategy.

Some companies at this stage will argue that flexibility is a competitive differentiator. And I don’t disagree. This is how small companies compete with the big ones. However, over time, when this type of inconsistency becomes structural, the company will struggle to scale results, no matter how hard people work. This is what Kieth Pham is pointing to in this article. He says that only .4% of start-ups make it past that point. Yes, you read that right, 99.6% of start-ups are unable to scale beyond the founder.

$50M ARR | Orchestration

When Coordination Becomes the CEO’s Primary Job

If you have reached the $50M revenue threshold, you are in rarefied company. According to SaaStock only .04% of all SaaS companis are able to reach this milestone.

Why?

Because now you are dealing with compounding complexity. You have most likely moved from ICP to multiple ICPs. You probably have multiple products and may be working on selling a platform versus a point solution. You likely have different GTM motions (e.g., Product-led Growth [PLG] and Sales-led Growth [SLG]). You may have introduced partners as another channel, or perhaps you have executed your first M&A deal to get new capabilities or add more customers or segments. None of these initiatives are wrong. But you have to get really clear on the sequencing. At this stage, the strategic question becomes: “How do we align multiple growth vectors into one coherent GTM engine?”

This is why I prefer to describe this stage as “orchestration” rather than “focus” or anything else. The CEO is no longer just choosing a direction. They are integrating leaders, systems, and tradeoffs across product, go-to-market, and capital. His/her job is not about:

• Hiring and then aligning strong leaders who have competing priorities

• Managing tradeoffs explicitly, not implicitly

• Protecting organizational coherence as complexity rises

• Deciding where incremental investment actually produces returns using business cases and ROI analysis

The most common failure mode at this stage is allowing complexity to outrun coordination. As the company adds products, segments, GTM motions, and leadership layers, executives add meetings instead of strengthening business operating rhythms. In your weekly leadership meeting, executives spend time reporting on activity rather than being laser-focused on the metrics that matter and then teeing up the decisions on the highest-priority trade-offs.

Functional leaders optimize their own areas instead of operating as what Patrick Lencioni describes in his book The 5 Dysfunctions of a Team as a “first team” aligned on a small set of shared priorities. The organization stays busy and moves quickly, but it does not move together, and sustained growth becomes harder to achieve.

$100M ARR | Durability

Capital Allocation, Leadership Depth, and the Next Act

At $100M and beyond, the company no longer needs to prove it can grow. Instead, it needs to prove that it can endure. At this stage, the strategic question shifts to: “How do we compound advantage over time?”

Here, strategy becomes inseparable from capital allocation, developing leadership depth, and building credibility with a different set of investors as you prepare for an IPO or strategic exit. The CEO is no longer able to know all the details, nor should they. They need to be really good at asking good questions and then being the final say on tradeoff deadlocks and capital allocation. Their work is mostly about:

• Allocating capital across competing growth initiatives

• Building leadership depth and succession

• Reinforcing the core economic engine

• Ensuring the company delivers on the results for the next 12 months (horizon 1) while also investing in “next act”-type initiatives that pay off in the next 24-36 months (horizon 2 and 3)

The failure mode at this stage is optimizing near-term performance at the expense of long-term strength. CEOs and leadership teams feel the pressure to respond to investor expectations (especially if public), board pressure, or market conditions by prioritizing predictable, short-term results over investments that sustain advantage. They can defer leadership development, underinvest in succession, and starve future investments because that is a “next year” problem. They risk making capital allocation decisions that favor incremental optimization of the current engine rather than deliberate bets on what comes next.

Over time, the company may continue to meet its numbers, but it does so by narrowing its strategic options and weakening its ability to adapt to major market shifts. For example, every SaaS company is now confronting this exact existential challenge the rise of AI. Thus, the company could continue to grow, but its durability erodes. The last few years have produced no shortage of modern examples, from Twilio and DocuSign to Peloton and Zillow, where companies sustained growth by optimizing their existing engines, only to discover too late that they had underinvested in adaptability, leadership depth, and strategic optionality when the environment changed. In many ways, this dynamic lies at the core of what people are now calling the “SaaSpocalypse,” which I touched on in this post.

The Evolution Most CEOs Miss

One thing is true across all of these inflection points: as a company grows, its strategy must evolve. Knowing the game you are playing still matters. But, probably more importantly, is knowing when the rules of the game have changed. One way to see these inflection points before they become crises is to look at second-order metrics, not just top-line growth. In a previous article, I wrote about Net Revenue Retention and ARR per employee as indicators of organizational inflection points. What struck me then, and continues to show up in my coaching work, is that these metrics often start to move before leaders acknowledge that something fundamental has changed.

At $10M, declining NRR often signals that the company has not yet made the leap from individual wins to repeatable systems. Sales may still be closing new deals, but expansion slows because customers experience inconsistency across onboarding, product, and support. At $50M, stagnating or declining ARR per employee often reflects coordination failure. Headcount grows faster than leverage as teams add capacity without aligning around a single growth engine. And at $100M, both metrics can look “fine” in the short term, even as the organization quietly sacrifices adaptability by optimizing for near-term performance. In each case, the data is not just reporting results. It is revealing that the strategy running the company no longer matches its scale.

This is why I believe strategic inflection points are not abstract concepts. They reveal themselves if you have a scorecard in place and are focused on tracking, reviewing, and engaging leading indicators. CEOs who learn to read these types of signals can get ahead of strategy evolution deliberately, rather than being forced to react after options have narrowed.

SaaS (i.e., software) businesses are “people” businesses. They do not face the inventory, manufacturing, or working-capital dynamics of traditional product companies, which means the majority of their cost structure and execution risk are tied to the people. To that point, most SaaS companies spend 70 to 80% of their total costs on people. This is why SaaS CEOs and investors spend so much time talking about efficiency. The issue is that these conversations often collapse two very different ideas into one.

• Cost per employee

• Revenue per employee, typically expressed as ARR per FTE

They are related, but they answer fundamentally different questions. And when leaders conflate them, they end up optimizing the wrong thing at the wrong time.

Cost per Employee Is About Containment

Cost per employee ($/FTE) is usually the first efficiency lens applied, especially by private equity firms and late-stage investors. There is a standard playbook to improve $/FTE:

• Tap offshoring companies or build offshore teams to arbitrage labor costs.

• Hire contractors and fractional talent versus full-time employees to save on additional costs (e.g., benefits) and enable quick ramp-up/ramp-down based on business performance.

• Initiate tool consolidation and process automation to optimize the way work is done.

Over the past 3 years, we have seen significant experimentation with AI augmentation. All of these levers matter since they can materially improve margins and extend the runway. But they all operate on the same axis. They are about pulling cost out of the system. And this axis has a floor, and there is an asymptote to how much you can wring out of the cost structure

There are also risks to the business that are sometimes underappreciated by those running the spreadsheet. For example, code quality can start to slip, and the customer experience can be negatively impacted. Leadership overhead increases as alignment becomes harder to maintain across a thinner, more distributed organization.

AI can help smooth that curve by reducing friction and absorbing work that used to require people. But AI does not remove the underlying constraint. In many ways, cost efficiency is ultimately a defensive discipline. It helps you avoid inefficiency, but it does not, by itself, create scale. That is where the second metric comes in.

ARR per Employee Is About Leverage

ARR per employee (ARR/FTE) tells a very different story than $/FTE. Especially in early and mid-stage SaaS companies, ARR/FTE is less about productivity and more about trajectory. It measures whether the revenue engine is compounding faster than the organization required to support it. In other words, it asks a structural question: is the company getting the maximum leverage from the organization without risking an implosion? This is why investors care so deeply about both the level and the trend.

• When ARR/FTE is rising, something structural is working.

• When it flattens or declines, growth is usually still dependent on linear headcount, heroics, or fragmented coordination.

AI only sharpens this distinction. As Ray Rike, CEO of Benchmarkit, recently highlighted in a post, the gap between traditional SaaS companies and AI-native companies is widening quickly, particularly in ARR/FTE. And this is where many companies get tripped up. They assume that efficiency problems show up only on the cost side. In practice, many companies fail not because they overspend, but because they outgrow the organizational model they are using to scale.

ARR per FTE as a Signal of Organizational Maturity

For years, many SaaS leaders used ~$200K of ARR/FTE as a meaningful milestone. It was never a hard rule. This threshold often represents product-market fit, a repeatable go-to-market motion, and early evidence that systems (and tools) are starting to support the load.

What has changed in the last few years is not the metric’s relevance, but its trajectory. Ray’s Benchmark data shows that ARR/FTE has been improving since 2022, as companies were forced to grow more efficiently and became more disciplined about headcount. AI is now accelerating this trend by compressing coordination costs across engineering, marketing, operations, and customer support. In fact, according to Ray’s data, the median “Implied ARR per FTE” in public SaaS is $401K and a mean of $487K (2x what used to be seen as industry leading).

• AppLovin: $3.6M Implied ARR per FTE

• Palantir: $1.07M Implied ARR per FTE

• DataDog: $545K Implied ARR per FTE

• SnowFlake: $538K Implied ARR per FTE

• HubSpot: $367K Implied ARR per FTE

And there are 50 AI-native companies on track to deliver $1M ARR/ FTE (5x what legacy SaaS is targeting.

This is where I see CEOs sometimes make a subtle but serious mistake. They treat ARR/FTE as a pure productivity metric. It is not. I would suggest that ARR/FTE is best understood as a lagging indicator of organizational design. When this number improves sustainably, it usually reflects deeper shifts that have already taken place:

• Decisions are no longer bottlenecked at the top

• Roles are clearly defined and clearly owned

• Managers act as operators rather than messengers

• Systems carry the load instead of individuals

In other words, the company has crossed an organizational inflection point. That idea may sound modern, but it is not.

Why Rome Matters in a Conversation About Scale

For thousands of years, large institutions have struggled with the same basic constraints modern companies face today.

• Communication does not scale linearly.

• Trust degrades with distance from HQ.

• Coordination costs rise as organizations spread across space and time.

If anything, these challenges are amplified in remote-first and hybrid environments, where shared context erodes even faster. The Roman army is a helpful metaphor because it solved a problem every scaling organization eventually faces. How do you increase output without increasing dependence on individual heroics? Rome’s answer was institutionalizing scale. Specifically

By the time Rome reached its peak, its army was deliberately designed around predictable unit sizes, clear command layers, and replaceable leadership. A Roman legion was not a mob of thousands. It was a carefully nested system of smaller units, each sized so that the army could operate across distance, time, and turnover without losing effectiveness. That is the core insight worth carrying forward.

Size as a Design Constraint

The Roman army implicitly acknowledged something modern leaders still struggle to accept. There are natural limits to how many people one person can effectively lead, how much context can be shared informally, and how far trust can stretch without structure. The Roman army was designed around those limits. Small units were sized for cohesion and visibility. Larger formations existed to coordinate those units, not replace them. Command scaled through layers, each with clear authority and responsibility.

Contubernium

The Contubernium was the smallest living and fighting unit (~8 soldiers) in the Roman Army. This was the basic trust unit. Soldiers trained, marched, and slept together. Accountability was immediate and personal.

• Insight for modern SaaS. This size (2 teams and a pizza) allow for a high-context team where peer pressure and shared work replace process.

Century (Centuria)

A century was sized (~80 soldiers) sized so that a single experienced leader could directly command and enforce discipline.

• Insight for modern SaaS companies: this is where the first true management layer where leadership replaces proximity.

Cohort (Cohors)

The cohort was the primary tactical unit (~500 soldiers [6 centuries]) that could maneuver independently while still operating within a larger system.

Insight for modern SaaS companies. This is where you start to introduce functional team or department teams who have clear ownership and measurable outcomes.

Legion (Legio)

The legion was the core operating unit of Roman power. It combined combat, logistics, engineering, and command into a self-sustaining system and includes ~4,800 to 5,500 soldiers (10 cohorts)

Insight but modern SaaS companies: This is where a CEO needs to think about an integrated system rather than a collection of teams.

The Organizational Implication for CEOs

This is where the metaphor becomes directly relevant. As SaaS companies grow, they hit the same invisible thresholds:

• A CEO can no longer be in every decision

• Informal alignment stops working

• Proximity is replaced by process

• Trust must be reinforced by clarity

When companies ignore these inflection points, they compensate with intensity. More meetings. More heroics. More escalation to the top. Rome avoided this trap by building a leadership system. Individual commanders mattered, but the system mattered more. Units could be recomposed, and leaders could be replaced. But the Roman Legions marched on to conquer the world.

ARR/ FTE is the modern proxy for that same transition. It signals when an organization has stopped relying on intensity and started relying on structure. The next question, of course, is what leaders are supposed to do with that signal.

Mapping ARR per FTE to Org Design Requirements

This is where ARR per FTE becomes operational rather than theoretical. At lower ARR per FTE levels, most companies are still building capacity. Hiring runs ahead of revenue, particularly in sales and marketing. Decision-making is centralized with the CEO. Communication and coordination feel smooth because everyone shares context, often literally in the same room.

As ARR per FTE rises, that model stops working.

Unless the organization evolves, growth slows or breaks.

Conceptually, the inflection points tend to follow a familiar pattern.

Lower ARR per FTE

• Founders make most decisions

• Context is shared informally

• Accountability is loose but effective

• Speed comes from proximity

• A lot gets done quickly

Mid-range ARR per FTE

• The first real management layer appears

• Functional ownership becomes necessary

• Processes begin to form

• The CEO must shift from doing to delegating

Higher ARR per FTE

• Managers manage managers

• Work is automated and codified

• Roles deepen and specialize

• Generalists give way to specialists

• Executives focus on prioritization, capital allocation, and context-setting rather than execution. At this stage, leadership is no longer about doing the work. It is about designing and maintaining the system that does the work.

When ARR per FTE rises faster than organizational maturity, the symptoms are predictable. Decisions slow. Accountability blurs. Culture becomes a values slide instead of a lived experience.

That friction is not a sign of failure. It is a sign that the organization is overdue for redesign.

AI Changes the Economics, Not the Constraints

AI forces leaders to revisit assumptions we have held for centuries about how organizations scale. AI can augment individual output; it can compress coordination costs; and, as many people fear, it can eliminate entire categories of work (i.e., jobs). The first-order impact will be improved cost efficiency per employee. Over time, it shows up as higher ARR per FTE.

Agentic systems push this logic even further. They raise the possibility that workflows, decisions, and execution loops can be partially or fully automated. This has fueled speculation about billion-dollar companies run by a small executive team. Some of that will prove true, and early examples already show extreme ARR per FTE outcomes.

But one constraint remains stubbornly intact. Organizations still hit inflection points driven by:

• Communication

• Coordination

• Clarity

• Leadership legitimacy

AI can amplify people. It cannot eliminate the need to create shared context, align on intent, make decisions, and enforce accountability. Those are human constraints, not technological ones. The mistake is assuming that because AI allows revenue to scale faster, organizational redesign can wait. History suggests the opposite. Rome’s lesson is not about armies. It is about respecting the constraints of human coordination. In fact, the faster output scales, the more deliberate leaders must be about structure.

The Core CEO Question

Which brings us to the real question. It is not how high ARR/FTE can go. It is whether the organization is evolving fast enough to support it. The companies that win will not be the ones that chase efficiency in isolation. They will be the ones who recognize that every efficiency gain creates a new organizational inflection point. That pattern has held for thousands of years. ARR/ FTE may rise dramatically in the AI era, but organizational inflection points do not disappear. They simply arrive sooner and with higher stakes.