I can easily fall in love with the idea of something. Convince myself that this is the answer to all my problems. My problems being: wtf should I do with my life after burning out as a social media manager and struggling as a full-time influencer.

In attempting to learn from my mistakes, I set an intention for October to do little experiments as a way to put less pressure on myself and gather some information.

🧪 Experiment #1: Untangling Sessions

The first experiment I ran was five Untangling Sessions, as I’ve been calling them. I’ve been thinking about becoming a life coach but have been nervous to fully dive in. Is this something I’d even like doing? Or am I just excited about the idea of it and the thought of new possibilities?

So, I decided to test it out and do five free Untangling Sessions. People come with a problem they are untangling, and we spend 30 minutes walking through it and figuring out an action plan.

A low-key, low-pressure way to dip my toes into life coaching and see if I even like it before diving deeper with a certification and such.

The result and what I learned surprised me…

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Jeremy and I are on our way to a wedding outside of the city, so I’m working on this newsletter a bit earlier than usual and the format is going to be a tad different.

After reading this lovely list from Jo Piazza of things that made her life easier it got me thinking about my own version of this. It got me thinking about how sometimes the things making our lives better aren’t massive or overwhelming. The tiny tweaks can make a difference.

And so, I present thee with the 12 simple things that have made my life infinitely better.

12 simple things that have made my life better

1. Getting a Brick. A few months ago I bought a Brick, a device that you set up to block you off of certain apps on your phone. Mine automatically kicks me off of social media from 10PM-9AM and I’ve started “Bricking” my phone when I go out and about so I don’t end up obsessively checking instagram likes and such.
   

2. Using a mesh body exfoliator in the shower instead of a loofah. I use so much less body wash because of it, and it does a good job of sloughing off all the dry skin.
   

3. Saving packing lists I frequently use in my Notes app. I realized I was making the same packing list over and over again. I now have a saved packing list for when I go home to my parents in Westchester, LA trips, and beach-y vacations. It means I’m less likely to forget something important like contact lenses…
   

4. Creating a “Keep going” folder on my phone. This came as a rec from a manager of mine years and years ago. Whenever you get a written compliment in an email, on Slack, or in my case on social media, save it to a folder. I know some people use this wins folder as fodder for a raise. For me it’s a nice pick-me-up if I’m starting to question why I do what I do…
   

5. Fake commuting. If you’re someone that works from home, I absolutely recommend the “Fake Commute.” It’s simply going for a walk when the work day ends and before you launch into evening mode. It’s so helpful for switching gears.
   

6. Printing out a list of all my medications. I did this before my surgery earlier this year. It was SO much easier to just hand someone my list than trying to dictate all the meds and dosages.
   

7. Have a list of go-to outfits. I write this out in my notes app on my phone season by season, noting outfits for casual things like dinner with friends and then slightly nicer outfits for events, etc. You can also take photos and save them to a folder on your phone. Makes getting dressed so much easier.
   

8. Lay out your clothes the night before. This has been a habit of mine since high school when I’d obsessively figure out my outfits. But it’s stuck all these years. I workout first thing in the morning most days and not having to dig for my favorite pair of leggings in a sea of black leggings makes the morning less chaotic.
   

9. Setting up text shortcuts on my phone and computer for your email, emojis, etc. I set up a shortcut on my phone that when I type “@@” my email autopopulates. So much less annoying that writing the whole thing out constantly. I also set this up for emojis I use frequently as it applies to both your iphone and mac.
   
   On an iphone go to: Settings » General » Keyboard » Text replacement to set yours up.
   

10. Going on phone-free walks. Well really, it’s me actively not looking at my phone during these walks. But same idea. I made a rule for myself this summer that I don’t look at my phone walking to the gym in the AM. It’s become habit now and i LOVE it. I feel like my thoughts can breathe again.
    

11. The Quip toothbrush. I’ve been using Quip for years and years now. It’s an electric toothbrush that has a 2 minute timer and pulses every 30 seconds so you switch quadrants of your mouth. I have a subscription set up so I don’t even have to remember to change the head every few months, it just arrives automatically. And anytime I go to the dentist for a cleaning they always say I’m doing a good job!
    

12. Getting a pill organizer. I never have to question if I took my meds. I love this case in particular as I don’t have to worry about it opening up when i’m traveling. I can also bring a few days rather than the whole thing.

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How about you? What’s one tiny thing you’ve bought, started doing, or figured out that’s made your everyday life a little better?

And with that, I’ll see you next week with the November plan 💗

Kayla

💌 Read next…

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• The creator with the $7 million launch.

• The influencer who quit their 9-5 job and now earns more than ever.

• The writer who pays her rent with Substack.

And I love these stories. They remind us what is possible.

But what about the person who took a chance on themselves and it didn’t work out quite like they planned? Or the person who tried something and realized, wait, I don’t even like this!? What about the people who leap publicly and loudly, but the net did not, in fact, appear…

Ummm, hiii, that’s meee.

Last year I quit my full-time job as a social media manager to pursue my own content creation. I had over 200,000 followers, a steady pace of brand partnerships, and a whole lot of chutzpah about what I could do if I wasn’t balancing my own social media with a full-time job.

And then the brand partnerships started to slow down. I found myself trying to figure out how to turn this thing that I’d spent over a decade building into something that could actually support me financially. I tried a little bit of everything. YouTube. Paid Substack subscriptions. A podcast for subscribers.

And more recently, I launched a membership community for women in their 30s who, like me, were in the messy middle and trying to figure out wtf comes next.

More than 400 people joined the waitlist. I was blown away by how excited people were about this idea. I’ve heard over and over that people are craving community and connection, and now more than ever.

When the community doors opened, I hit my launch goal. During the first batch of virtual events, the energy was incredible. Women were really sharing, connecting, and feeling seen. I felt like I was starting to get to know people. The online discussion boards were active.

Then the initial excitement started to wear off…

People canceled their membership. Group engagement and event attendance started to wind down after that initial burst. Converting people from the waitlist into paid members was more challenging than I expected.

The content I shared about it did well—people were definitely interested in it in concept! But it didn’t necessarily turn into people joining.

I found myself constantly coming up with discussion questions to get people talking. I worried there weren’t enough events every week, so I kept adding more more more to provide value. If I’m being honest, I started wishing I was spending those nights on the couch with my partner instead of hosting a Zoom event.

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It all felt oddly familiar. I left my full-time social media job because I was burnt out from constantly needing to create, post, and engage. And here I was, tap dancing as fast as I could again.

I started to realize that I loved the idea of running a community more than I actually loved running one. Which, hey, maybe should’ve been obvious as an introvert, but ya live, and ya learn.

So I stopped. 3 months after the community launched, I shut it down.

If I’m talking about the experience openly and honestly with, let’s say, my husband, I’d tell him I don’t regret it.

I’m so glad I tried!

I didn’t lose money, so that’s one thing!

It connected me with some really cool people, both members and people that came in to lead workshops!

And in many ways, it was what I needed for my sanity at the time, as I was recovering from surgery in the dead of New York winter.

Ending it gave me this huge sigh of relief. But there was also a tinge of something else mixed in there…

Embarrassment.

Not because I regret trying or even ending it.

No, I felt embarrassed because I shared about this thing that only ended up lasting for 3 months so publicly. I talked about it. I shared about it. I posted content about it. I was shamelessly loud, as you tend to be when you are promoting something.

It’s hard not to wonder what people think. I’m only human. And it’s especially hard to keep your blinders on when you’ve opened yourself up to literally thousands of people.

Sharing your life online can be weird. You invite people into your world, and suddenly they have opinions about your decisions, your career, your partner, what you should be doing… and what you definitely shouldn’t be doing.

Sometimes these opinions do get in my head.

I have this very specific fear that I’m becoming the millennial content creator version of a suburban MLM mom who’s always announcing her next exciting business opportunity. omg hey girl!!!

Do people just think I’m… flailing? That I’m jumping from one thing to the next. That I don’t know how to stick with something long enough to make it work? These are the things I ask myself at 4:00AM when I can’t sleep. And sometimes, when I venture into the deep, dark corners of the internet, I find strangers saying similar things about me. These strangers can poke at my bruises so accurately.

The part I don’t love admitting? Sometimes I worry they’re right. That I am the cautionary tale of a girl with privilege, and here I am… flailing.

I'm shifting how I think about this…

What if it’s not flailing, but experimenting?

To me, flailing lacks direction and awareness. Quite literally, a wacky inflatable arm flailing tube man, moving in the breeze.

Experimenting? That’s different. It’s testing something, seeing if it works. Seeing if what you suspect is true. And then collecting data from there. Attempting to run a community taught me a lot about how I don’t want to operate. I’m not built for high-energy hosting… no matter how many times I try to convince myself otherwise. Just because I can turn it on as a performer and former camp counselor doesn’t mean I should. My strength lies elsewhere, and that’s very much okay!

I still feel weird about being seen in the messy middle. Sharing so openly about figuring it out. But in sharing, I’ve realized more than anything that I’m not alone. I’ve gotten more comments on this note about trying and failing than anything else I’ve shared on Substack. It sparked the idea to write this larger essay.

People were sharing all sorts of experiences. Grad school programs they dropped out of because they weren’t the right fit. Businesses they launched and eventually closed. Years spent building something that never quite panned out.

How are we supposed to figure out what we want without trying things? How are we supposed to try things when we’re so afraid of looking foolish (or ending up with a Reddit thread) if they don’t work out?

I’m still very much a work in progress when it comes to caring less about how I’m perceived.

And even so, I’d rather be seen trying (and maybe being a little cringe) than let the fear of embarrassment keep me from finding out what I actually want.

So, tell me: What’s something you tried that didn’t work out the way you imagined?

Leave a comment

I think we need to hear more of those stories, too 💗

The vibes were immaculate—appropriately witchy for the end of October, complete with a cauldron and tarot cards. I pulled the Ace of Pentacles, a card that represents a new beginning in the material, financial, or physical realm. And according to the Google search I just did, it’s one of the most auspicious yes cards in the deck.

It’s taken me a while to get here, and by here I mean owning that what I’m building is, in fact, a portfolio career, or one where you have a few different income streams rather than one full-time gig. I am hesitant to say it’s what I’m doing with my full chest. Declaring things like I’ll never go back to a 9-5 job! or I’m going to be a full-time content creator!! has backfired on me before…

But this is where I’ve landed, or at least for right now. Building a multi-passionate career with a few part-time jobs. Assistant to an author. Front desk at a Pilates studio. Content creator. And maybe throwing in coaching pretty soon, but more on that another day.

Walking into this room, a networking dinner party for women with portfolio careers, I felt like a bit of a fraud. My version of a portfolio career feels unimpressive compared to those with consulting accolades and fractional roles at fancy companies. I’m a 36-year-old who burned out as a social media manager and now wipes down Pilates reformers between classes.

Networking events aren’t my strong suit. The second I’m thrown into a space like that, where you’re holding a cocktail and mingling over carrots and hummus, I instantly become the most awkward version of myself. It’s like I suddenly don’t know how to be a functioning social human being. My ability to hold a conversation floats away.

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We sat down for dinner. I’m relieved to find that there are assigned seats. I don’t have to awkwardly figure out where to sit in a room full of strangers. Luckily, I like to think I am much better at sitting down and making conversation with those around me than at the usual pre-dinner hover.

It comes time for introductions around the table. What we’re excited about. And what we’re struggling with as we navigate our portfolio careers. Hearing the women share their stories—maybe not the same as mine, but with flavors of burnout and disappointment in corporate, and trying to figure out what comes next—I find myself nodding along, knowing the feeling well. Here I am, at a table of women exploring, trying, and putting themselves out there. Suddenly, this unconventional path of uncertainty feels a little less scary. A little less lonely.

I won’t pretend I suddenly became a social butterfly. I left the party at 10 PM, ready to sit in silence with my husband, a book in my hand. But I’m still proud of myself. For putting myself out there. For putting myself in a space with these women. For even saying in a room, "Yes, this is what I’m building toward."

I don’t know what will come from this evening. Will it lead to anything more than a tasty dinner and feeling seen in my own journey? Who knows.

This morning I propped the Ace of Pentacles card up on my desk. I like to think it’s a reminder that yes, I’m on the right path.

A shameless ask…

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Thank you for being here and part of this community. Your support truly means so much to me 💗

On a different note…

I’ve been on the hunt for fall wedding guest dresses

And I think I found two really good options!

[the top dress + the bottom dress, which can be worn a few different ways]

I’m still TBD on which I’ll wear for a wedding we have next weekend, but phewww is it a relief to have options!

I’ve been LOVING the book The Burning Side by Sarah Damoff. It’s a family drama told through multiple timelines and different family members' perspectives. This book had been pretty hyped up for me (as is her previous novel, The Bright Years), and so far it’s delivering.

I also finished Go Gentle by Maria Semple. She wrote Where’d You Go, Bernadette and a personal fave of mine, This One Is Mine.

In the end, I thought this book was meh. It had a lot of promise in the beginning; the main character was fun, if a bit quirky, and I loved that she was building her own “coven” on the Upper West Side, recruiting single women in their 50s and beyond to live on her floor so they could all split things like groceries. Then it took some sharp turns and just became something very different.

I’ve been listening to this thing called Activations. They're almost like bite-sized meditations, but with more of a pep-talk vibe.

I’ve been listening to them throughout my day, including on the way home from last night’s dinner, to unwind before bed.

Use this link for 25% off your membership.

And with that, it’s time to log off. Hope you have a lovely weekend 💗

Kayla

Liked this post? Be sure to hit the “like” button. It really helps more people see my content. And if you really really loved it, feel free to share my Substack with a friend.

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Top of mind today?

• the shift I’ve been feeling lately

• an endometriosis + GLP1 update

• honeymoon planning (!!)

Let’s get into it…

So, I think I got my sparkle back!?

I was talking with a good friend the other day and giving her an update on how things are going in the various corners of my life. She commented on how different I sounded compared to 6 months ago, how suddenly there’s been an undeniable shift in both my energy and the opportunities coming my way.

And it’s true.

I think I got my sparkle back after it was nowhere to be found for a while.

I’ve shared bits and pieces about this over the last. couple of months — the new jobs, the experimenting, and the cautious optimism. But lately I’m noticing how different I actually feel.

Of course, I’ve been trying to reverse-engineer what exactly caused this shift. What is my magic answer for getting your sparkle back!?

And while I don’t think it’s any one thing, or a step-by-step plan I can prescribe, there are a few things that made this shift possible…

Read more

Something I’ve struggled with over the last year is this feeling of, okay, I’ve done the 9-5 thing. I tried the full-time influencer thing. But neither has felt quite right [or sustainable!]

So… is the problem me?

That’s a big part of why I wanted to talk to Janel Abrahami.

Janel’s career started with a very clear plan: graduate from NYU, work in HR, climb the corporate ladder. When that stopped feeling right, she built a career coaching business. And when that stopped feeling right, even though it was growing and helping people, she found herself asking the same question.

What’s wrong with me?

Her writing about portfolio careers has helped me see a version of work beyond the two options I kept trying to squeeze myself into. And something she said in our conversation really stuck with me: she still enjoys coaching. She just enjoys it more when it doesn’t have to be her entire livelihood.

We talked about the difference between doing work you love and building a business around it, why slowing down can feel so frustrating when you're lost, and how a reliable income stream can give your other ideas room to breathe.

Here’s our conversation, edited and condensed for clarity.

Let’s start at the beginning. What did you think your career was going to look like?

Janel: Twelve years ago, when I graduated college, I was on a very linear plan. I’d studied organizational psychology, HR, and adult learning, and I started at NBCUniversal, managing the East Coast internship programs.

I graduated from NYU at Radio City Music Hall on a Sunday and started that job on Monday. The next day.

It was like, Whoa, I am on track. Checking all those boxes and following all the rules really worked out for me.

Oh, my sweet summer child, 22-year-old self was like, “Great! I found my thing. I’m good at this. I enjoy it. I admire the executives on this team, and I can clearly see myself following in their footsteps.”

About two years later, I got into a dream grad program in London. I deferred my admission to save money and get more experience, then moved there. NBC had a UK office, so I thought, “Obviously, after graduation, I’ll go straight into that office. My life is set up perfectly.”

And then, shockingly, once I moved to a brand-new country and met hundreds of cool people, I realized there was a big world outside the one company I’d ever worked for.

Pretends to be shocked. But I was shocked!

I ended up studying learning and development at growth-stage startups and speaking to people working at those companies in San Francisco. After graduation, I moved there instead of going back to New York.

I spent three years in the tech startup space, holding different roles within HR. I thought I was really diversifying myself.

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When did you start realizing that path wasn’t what you wanted anymore?

Janel: I left a company during the pandemic. It wasn’t a good situation. I panicked, searched for months, and found another job.

Once I got into that role, I was like, “Whew. I’m safe. I can afford my life.”

But that process also made me realize: I don’t want this forever.

That was ground-shifting for someone who’d been so particular about putting all the chess pieces into place. This was supposed to be perfect. But it wasn’t giving me what I thought it would.

I started asking, “What would I do if it wasn’t this?” It became clearer that I wanted to build something of my own.

Up until then, I’d been such a picture-perfect company girl. I was known for doing good work, knowing my shit, and being passionate… but only within the companies I worked for.

I started seeing people I knew getting really cool opportunities through Instagram and LinkedIn. Things I would have loved to do and thought I’d be great at. But I couldn’t see a path to anyone inviting me to do them.

How do I become known as just Janel, instead of Janel on the learning and development team at that company?

The online coaching world was popping off, and I thought, “I could be a career coach.” I’d worked at NYU’s career center in college, and coaching had always been part of my HR roles.

So I built a career coaching business alongside my full-time job. Eventually, I decided to go all in.

Goodbye, corporate.

But then you built the business, and that didn’t feel right either.

Janel: I grew that business for two years. I created a framework called Pivot with Purpose, helping people move from one corporate job to another. I still use those concepts today.

But about two years in, I realized: Wait. I don’t actually want to be the CEO of a career coaching company.

The business was growing. People needed the solution. It was working for everyone but me.

I’d followed the directions to a T, and this still didn’t feel good. What was wrong with me?

I made it mean something about myself: you’re too flighty, too indecisive, you can’t commit. You built something great. People want what you have. Why don’t you want it? Why are you throwing it away?

I could see the path ahead. To keep scaling, I’d need to hire and manage a team of career coaches. And I didn’t want to do that.

But if it wasn’t this, I didn’t know what else it was.

I needed to make money. I’d used all my savings to invest in the business, and I didn’t have anything to fall back on. So I did another months-long job search and got another corporate job.

I thought, “Okay, I guess I’m just not cut out for it.”

And I really fell into a depression. I’d experienced depression before, but after the adrenaline of conquering the job search wore off, I was like, “I hate this. Why is nothing feeling right?”

About eight months in, I took a medical leave. I got outpatient support and changed my medication. I truly felt like my brain was breaking down.

I came back from that leave, and two weeks later, I was let go.

Kayla: God. What timing.

Janel: Really fun times for everyone. That was February 2024.

At that point, I was like, “I’ve failed at corporate. I tried to be an entrepreneur, and I failed at that too. There’s really nothing left for me.”

What helped you start coming out of that?

Janel: I really attribute the shift that happened that year to the mental health support I put in place.

I got locked in with a fantastic therapist I’d been using more as a spot treatment before. Now it was like, “No, we’ve gotta lock in, hun. We’re in this together.”

I changed my medication. I asked my closest friends for support. I told them very transparently, “I’m really struggling, and I need you right now. Can we have a weekly dinner?” I needed things to look forward to.

It wasn’t a switch flipping. It was very much brick by brick, clawing out of that.

Eventually, I realized I hadn’t failed at those things. I was trying to force myself into one lane when I was interested in multiple things.

Toward the end of 2024, a company I’d applied to in 2023 reached out. I hadn’t gotten that job, but I’d made it pretty far in the process. Now they were hiring for fractional, part-time roles.

I interviewed and got one. That gave me structure and flexibility at the same time. I could ask, “What do I want to fill in the gaps with?”

What does your portfolio career look like now?

Janel: There’s that fractional client, a venture capital fund, where I program manage and facilitate webinars, educational programs, and community for the executives in their portfolio. That draws directly on my HR experience.

There’s content creation, where I get to be creative and seen as just Janel. And there’s one-on-one career coaching. I still do that, but because it’s not the one and only thing I do, I enjoy it so much more.

I got to have more fun with content. Again, shocking information: when you have fun with your content, it performs better. It was an “Oh, duh, Janel” moment. But you have to experience it to really get it.

I’m getting the kinds of opportunities in my inbox I used to be jealous of. Sometimes it’s overwhelming, but I’m like, “Wait, this career is so fun. I’m succeeding.”

And there’s nothing wrong with me. It was the structure that was wrong for me.

We have such different career histories, but that “What’s wrong with me?” feeling is so familiar.

If someone is in that phase right now, what’s the first thing they can do?

Janel: My response is going to be very frustrating. But if I could talk to myself when I was in that space, the number one thing I’d say is: you need to slow down.

2024 Janel would have been like, “Shut up. Don’t tell me to slow down. This is an emergency.”

Kayla: Slow down??? What do you mean? 🙃

Janel: Exactly. I know it’s counterintuitive. But doing everything from a sense of panic or urgency clouds your connection with what you know is right for you.

I go back to the support I worked so hard to put in place. And it doesn’t have to be a life-changing practice or a retreat. Breathe for five minutes. Give yourself ten minutes to feel safe.

Then you can start making the next decision, and the next decision, one at a time.

So: slow down, unfortunately.

Kayla: God, that is not what I did either. I wanted to take action, and I knew I was good at taking action. What can I do next? How can I muscle and force my way to the revelation?

I’ve also been thinking about not making decisions from a heightened state. Sometimes I get more excited about the yes than the actual thing.

Janel: The reverse happens to me too. Pretty much like clockwork, there’s a week every month when I’m like, “I’m quitting everything. This is too much. Absolutely not.”

Then three days later, I’m like, “Oh, I’ve decided I’m okay now.”

Kayla: The number of times I’ve been up at 4 AM like, “I’m going to burn it all down. Archive everything. Start a new account.” Then two days later, when I’m well rested and have had some coffee, I’m like, “Oh my god, I love doing this.”

Janel: I can handle this. Completely.

I want to come back to something you said: you enjoy coaching more now that it doesn’t have to be your entire livelihood. What changed?

Janel: When I was figuring out my exit from corporate, coaching seemed like the perfect answer. I loved the calls. I understood the people I was working with, and I could see the transformation.

I was like, “Did I just stumble upon my calling? Amazing. That was easy.”

But doing the work and building the business are different things.

When something becomes your livelihood, there’s pressure. Suddenly you’re over your phone calculator: “If I want to make X this year, and I charge this much per person, I need this many clients per month.”

Kayla: Yep. I do that.

Janel: All the time. “What if I increased every session by fifty bucks? What would that do?”

It started feeling like pass/fail. You either pass at building a business or you fail. And failure, to me, meant not hitting a specific revenue goal.

After a while, I felt separated from the work. I want to be respectful of my clients, because I did connect with them. But it became easy to lose sight of the fact that these were humans. This is people-to-people work. I’m not Jeff Bezos, figuring out how many widgets a factory can produce.

I could have a fantastic breakthrough session with a client, then immediately think, “How do I turn this into a lesson for content?”

It took me out of the part I enjoyed.

Now, it’s no longer, “If I don’t book X clients this month, I’m fucked.” I’m okay. It feels more organic.

Kayla: That’s such an interesting aha. It’s not the actual work you dislike, but the gunk around it.

For someone curious about a portfolio career, where do they start? And what are the pitfalls?

Janel: A sustainable portfolio career is an art, not a science. You can put together a beautiful strategy on paper, but living it is different.

There’s a tension: you need to experiment to find out, “Do I like this? Is there a need? Will people pay for it? Can I find the work?” But if you’re trying to build too many revenue streams at once, you won’t succeed at any of them.

The way I see it, you need a low-stakes experimentation phase while you still have income and stability elsewhere. Pinpoint two things, maximum, and push those a little further. Then choose one and get it to a stable, predictable place.

That’s often an anchor client: recurring consulting, advisory, or freelance work. Somewhat predictable monthly revenue gives you the foundation to add something else, experiment, and let it fail in the beginning without acting from that desperate, panicky place.

Kayla: Man, where was this a year ago for me?

Janel: Truly. For myself too.

Kayla: There’s something to be said for the potentially boring, not-sexy stability thing. Framing it as this allows me to do the other stuff makes me appreciate it more.

I’m working front desk at a fitness studio, a job I’ve done at 22, at 29, and now at 36. At 29, I resented needing it to make my full income as a fitness instructor.

Now I see it as something that allows me to do the other things I like, experiment, and feel less anxious if they’re not producing the way I want them to yet.

Janel: Yeah. And I’m still figuring that out. I’m very much in flux.

How do you balance having a big vision with being open to things changing?

Janel: For better or worse, I’m a big-picture, long-term thinker. I always needed the five-year plan. That gave me so much drive in corporate: “Great, I see exactly where I’m going. Now we just have to reverse engineer it.”

That’s still true in my portfolio career. But it can be anxiety-inducing, because all I focus on is the huge gap between where I am now and the potential I can see.

The work I’m still doing is balancing that long-term vision with the present: Do I actually like this? Is it worth it? Is it what I thought it would be?

Or an unexpected opportunity lands in my life. Should I get on the ride I’m being given a ticket for, or stick to the path I thought I was going down?

I’ve learned to take the ticket and take the ride.

I recently shared a post about my ultimate goal for one part of my business. Going Places, my Substack and the brand I’m building, could become something like Hello Sunshine: different types of media telling the stories of people reimagining their careers, work, and purpose.

Right now, it’s my Substack, my short-form content, and an event series. And the event series came to me.

A couple of years ago, I wanted to put on dinners, but I didn’t have the budget. Later, someone approached me: “We have this space, and we love your content. Do you want to experiment with an event series?”

I was like, “I don’t have an event series. What do you mean?” But the container opened, and I could fill it.

Kayla: There’s something to be said for shamelessly saying what you want. If people don’t know what you’re looking for, how can they help you find it?

What are you soft launching right now? The thing you’re experimenting with or still figuring out?

Janel: I’m medium, semi-soft launching—because it’s already launched—my monthly event series, the Future Self series. The events are about helping you actually become your future self instead of just dreaming about it. They happen in New York City.

[Kayla note: if you’re in NYC, the next event is 10/20!]

This was on my ten-year plan. Now that I’m actually in it, I have to live it, iron out the kinks, see what I like and don’t like, and let it evolve.

It’s exciting and a little anxiety-inducing. I want people to have a great time and exceed their expectations, while having realistic expectations for myself.

Visibility was a key component in getting here. But so were curiosity, building relationships, asking questions, and asking for help.

It wasn’t just building a nice billboard and waiting for people to offer me things. I tried a lot of things, pursued different avenues, and collected that data. Then, when the conditions were conducive, the opportunity arose.

Kayla: It’s that reminder to slow down and take the little steps, instead of thinking, “I must have this all figured out and conquer my five-year plan tomorrow.”

Janel: I feel like I’m just talking to myself. I need to hear this.

✨Connect with Janel✨

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More Change of Plans conversations:

If this conversation resonated, hit the like button or share it with a friend who’s also figuring out what comes next 💗

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💭 On my mind…

Is anyone else kind of a jerk to themselves? I’ve been thinking a lot about this, and how easily I extend kindness to those around me… but I don’t offer it to myself.

Example: I was talking with Kayli, whom I adore, for my new series, Change of Plans. As she told me about her career journey, the twists and turns it’s taken, I thought how freaking cool it is that she’s had these different experiences. She’s followed these itches and twinges she’s felt over the years. Incredible! Love!

Yet when I think of my own career story — also twisty and turny — I am always so… embarrassed.

Kayla went to college and then changed her mind about being an actor, accidentally ended up in marketing when she couldn’t get a job as a fitness instructor, eventually became an instructor, went back to 9–5 life during the pandemic, and then burnt out. My god, woman, why can’t you just pick one lane? Stop hopping around!!!!!!!

I told my therapist about this, the stark contrast between how I viewed Kayli’s journey and how I viewed my own with loathing and judgment. She challenged me to reframe my career story and write it through a new lens. How can I turn this flaw, so to speak, into a superpower?

Kayla Kleinman is a multi-passionate person with broad career experience, giving her unique insight into the intersection of creativity, identity, and storytelling, with expertise in social media.

Same story, different telling.

I had a similar moment yesterday while interviewing Janel, another person I adore. She talked about realizing her career didn’t feel like the right fit for her. It was like she was forcing herself into a space that didn’t make sense. The story felt oh so familiar to me, trying to make yourself fit into a certain career box, but as you squeeze yourself in, it doesn’t feel right.

My heart went out to her as she shared her story. And I felt proud of her for listening to what she needed and not accepting that this is just how it is.

Meanwhile, I wonder if I could have stuck it out longer at my own 9-5 job. Sucked it up. I’ll tell myself now that it wasn’t that bad… even though I was looking forward to a colonoscopy because it meant sleeping and not being attached to my phone for an hour.

Maybe some of this comes from always performing. I’ve literally always been a performer. In front of the camera. On a stage. Being critiqued. Whether I was an actor, fitness instructor, social media manager, or creator.

I can get caught up in how a decision will be perceived before I ask whether it makes sense for me.

I want to keep practicing my therapist's suggestion. Take the part of my story I’m embarrassed by and write it as if it belonged to a woman I adore.

What would I notice? What would make sense once I understood what she was going through?

What happens when we’re less of a jerk to ourselves? When we look at our story through a lens of empathy and curiosity, like we would for someone else.

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What I’m Reading…

I finished reading The Thoroughbreds by Elin Hilderbrand and Shelby Cunningham. The book is the second in a duology set at an elite New England boarding school. It felt a bit long at times, but I still enjoyed seeing where the characters ended up and seeing all the drama that went down at the school.

I started reading Go Gentle by Maria Semple. She’s best known for Where’d You Go Bernadette, but I first discovered her through This is Mine, which I remember LOVING.

I’m about halfway through the book and have NO clue where it’s going—we start in current NYC and flash back to the 90s in LA. What I do know is the main character is a philosopher; she’s forming what she calls a coven in her apartment building, where single women in their 50s and beyond can live on the same floor and care for each other. It’s a bit quirky for my taste, but I’m still enjoying it.

A few things I’m loving…

• I visited The Rabbit, a new bookstore + bar in the East Village. It’s so stinking cuuuuute! I could picture myself sitting there and reading a whole book while I drink a latte.

• a new sushi handroll spot, Sushinoon, opened up in the Village. I got a salmon + avocado handroll as a mid-afternoon snack and it was perfect.

• also on the sushi front… I’ve been loving Sendo. I’ve only had their to-go, but the fish is always incredibly fresh and tasty.

And with that, time to log off 💗

Love, Kayla

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Growing up, I was an avid journaller.

Every night, before watching an episode of Roseanne or Scrubs, I’d lie in bed and write about my day in elaborate detail in a marble notebook. Granted, those details were mostly recapping the interactions I had with my crush-of-the-moment that day…

Writing my life down in these marble notebooks was how I processed the rollercoaster of emotions, hopes, dreams, and, unfortunately, disappointments that occurred between the ages of 13 and 18.

Journaling looks different for me now, at 36. I don’t recap the day’s minutiae with the same intensity as a 13-year-old with an aching crush. But I still turn to writing to process, understand, reflect, and make sense of things.

When I’m feeling anxious or like my thoughts are overflowing, I put pen to paper. In my brain, it’s jumbled and messy. It’s scary. It’s hard to sort through the thoughts. But once they’re on paper, I no longer feel so weighed down by it all.

One of the things I love about journaling is that there are so many different ways to go about it. I see my journaling habit as a toolbox. I don’t use all of them all the time, but I like having them on hand when it feels appropriate.

Note: you don’t need to do all of these, either. If you’re getting started, pick one that feels useful and easy enough to try.

The different ways I use journaling in my life these days…

Every night: One Line a Day

Every night before I go to bed, I write a quick recap of my day in my ONE LINE A DAY journal. It’s usually 1–2 sentences about what I did. Sometimes I talk about how I’m feeling, too.

It takes about 2 minutes, tops.

Besides loving the ritual of sitting down for a minute to reflect on the day, I love that each date has its own page, with space for 5 years’ worth of entries. I’ve been doing this since 2022, and it’s SO interesting to look back on where I was on any given day over the years.

Some of it is fun memories. I bring the journal with me when I travel, so it makes me smile when I come across entries from trips to Montauk, Cape Cod, Turks and Caicos, London, etc.

But it also reminds me how far I’ve come. I look back on entries from the year when I had really bad anxiety, when nausea and fear plagued me every day. It felt like that would be my life forever… but now it’s a distant memory.

Also of note… I think some people feel they HAVE to start this journal on January 1, or it’s ruined. I started doing this on a random night in July of 2022!

Some mornings: My version of Morning Pages

The idea of Morning Pages comes from Julia Cameron’s The Artist’s Way. Her practice is three pages of handwritten, stream-of-consciousness writing first thing in the morning.

I’ve adapted this practice in a few ways…

This summer, I did a version where I’d write for 10 minutes in bed first thing every day. I take a workout class first thing most mornings and didn’t want to be late because I was trying to hit my 3 pages. Setting a timer let me plan accordingly.

Sometimes, I’ll do this post-workout once I’ve gotten ready and I’m sitting down at my desk to work.

For me, this acts as a brain dump. Usually, I use it to think through my day: what I’m expecting from it, what I’m stressed about, or what I feel will be an annoying part of it. I also inevitably end up making a to-do list of things I want to remember.

I think of it as a kind of brain cleansing. I get the gunk out, and then I can move on without that clogging my brain feed.

When I’m anxious: A brain dump or worry journaling

If I’m feeling extra anxious before going to sleep, I’ll set a timer for 10 minutes to brain dump everything swirling in my head. Usually, it’s career anxiety or ideas I’m trying to figure out for future content.

I don’t use a prompt; I just write down everything I’m thinking (and inevitably overthinking). I don’t worry about it being coherent. Sometimes it’s complete sentences; other times, it’s bullet points. It’s messy. It’s not meant for anyone else. It’s just about getting the things out of my brain.

Instead of spiraling about them over and over in my head, I find this helps me fall asleep on those more anxious nights.

If I’m having a Bad Anxiety Day, I’ll do a similar practice that I think of as “Worry Journaling.” I set a timer and go ham writing down what I’m anxious about and what I’m feeling. When the timer goes off, I stop writing… and also tell myself it’s time to stop worrying.

I can get really anxious before travel or big events and have found this practice helpful.

When I want to go deep: Prompts

Sometimes, I use a journal prompt to get me started or think about something specific.

This summer, every night I’d answer the question

• Today I felt most like myself when…

Another one that I come back to a lot is

• What’s been bringing me energy lately + what’s been draining me?

I shared a bunch of prompts in this post

Also, a shameless plug: a few years back, I published a whole book of journal prompts for every day of the year. You can check it out here!

At the end of every month: Monthly check-ins

I answer the same prompts:

• One-sentence recap of the month

• What brought me joy?

• What drained me?

• What did I learn about myself?

• What do I want to carry forward?

• What do I want to leave behind?

I like repeating the same questions every month; it gives me a way to compare and notice patterns that keep coming up. Like, if I say the same thing drained me 3 months in a row? Cough cough, going to events… Maybe a sign to make some changes…

At the end of every year: My own journaling challenge

As many of you know, I host a [free!] journaling challenge at the end of every year. It’s one prompt a day for the month of December, focused on reflecting on the year and then looking to the year ahead.

Every year, I answer these questions myself. I’ve started keeping them in the same place so I can compare year over year, which makes it really interesting to see how things evolve.

I’ll be sharing more on this at the end of November 💗 Make sure to subscribe to this here Substack for all the info:

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And when I’m feeling chaotic… my Notes app or a random doc.

In college, I got into the habit of writing down what I was thinking, feeling, and noticing in a random Word doc. It wasn’t meant to be anything, and most of it is really mortifying to read back now, but hey, it was a form of journaling for me!

In recent years, that habit has morphed into more of a Notes app thing. And yes, this very much counts as journaling!

I clearly process my thoughts by writing them down. I don’t even know what I’m actually thinking until I put pen to paper—or really, finger to iPhone in this case.

For whatever reason, I do this on walks fairly often. I’ll have an idea pop into my brain, or something I’m turning over and over. I’ll put it in my notes app.

It’s messy. It’s incomplete. But it can be some of the most powerful journaling I end up doing. It’s where I have the big a-has.

Handwriting vs. digital

Okay, I do notice a slight difference between typing and writing. Sometimes the physical act of writing by hand is what I need — it slows me down! BUT some of my juiciest journaling moments have happened in my Notes App on a walk, so I’m definitely not a handwriting purist.

Play around with what works best for YOU. You don’t have to pick one method and stick to it forever.

How to make a journaling habit actually stick

For me, the biggest thing is making it easy. My One Line a Day journal lives next to my bed with a pen ready to go. I write in it before I crawl into bed to read, so it’s become part of my wind-down routine. I don’t have to remember to do it, because it’s just what happens before bed.

And no, I’m not perfect about it. Some nights, I’m exhausted and skip it. When that happens, I make a little dot on that date when I fill in the recap later. Missing a night doesn’t ruin anything. You just pick back up.

I also think it’s okay for journaling to ebb and flow. Some seasons, certain practices really serve me; other seasons, they’re not a focus. That’s using the tool when you need it.

If something isn’t sticking, it might be worth asking where the resistance is coming from.

If you keep forgetting, tie it to something you already do and keep your journal where you’ll see it. If you sit down and clam up, try a prompt or set a timer and write whatever comes. And if you just don’t enjoy it? Maybe it’s not the right type of journaling for you, and it’s worth trying something different.

“But I’m bad at journaling”

I don’t think there’s such a thing as being good or bad at journaling. It’s not a skill you’re graded on. It’s simply a practice, and hopefully something you find useful.

It doesn’t need to be pretty.

It doesn’t need to be organized.

It doesn’t need to be for anyone else.

Play around. Figure out what works for you.

What do I write when I sit down, and my mind just goes blank?

I think this comes down to what kind of blank you’re dealing with. Sometimes you sit down and genuinely have nothing to say. That’s when a prompt helps.

Other times, the “blank” is actually the opposite. There are 900 thoughts in your head, and you don’t know where to start. When that happens, I set a timer and brain dump. No structure, no full sentences required, just get it out.

Tonight, pick one prompt or write two sentences about your day.

See how you feel afterward.

From my friends!

I asked a couple of friends how journaling shows up in their lives, because I love seeing how differently it looks for everyone.

Kelsey Donlon (Substack | Instagram)

How do you use journaling in your life?

I started journaling after I had my son in September 2024. I was dealing with postpartum anxiety and some depression, and I’d started seeing a therapist to work through the mental load, my new body, and my identity around work and my business. The hardest part was that I couldn’t say out loud how I felt. The brain fog and exhaustion were too much.

I use a small spiral notebook or my Notes app, usually the app since my brain moves faster than my hands. It’s mostly a brain dump of whatever’s overwhelming me.

It began as a way to manage the negative spiral, and now it’s how I figure out what I actually think about everything, from motherhood to client work to business strategy to my marriage.

Any advice for people wanting to get started?

If you’re struggling to start, use prompts. Just don’t treat it like you’re being graded on the answers. Write until you can’t write anymore, then step away and come back to it.

Nnenna (Substack | Instagram)

How do you use journaling in your life?

My junk journal is a creative outlet where I like to visually document things that happen in my life. I use my reading journal to jot down notes and thoughts about each of the books I read. And then my 5-year diary is for daily journal entries where I’ll write about whatever comes to mind in that moment.

Any advice for people wanting to get started?

The best way to figure out your journaling style is to start and try different things. You might find that you prefer a certain journal size over another, or a certain type of journaling vs. another. Start small and expand from there. And remember, you have complete control of what your journaling practice looks like.

Now I want to hear from you: What does journaling look like for you? What’s actually stuck? Are you handwriting, using your Notes app, recording voice memos, something else entirely? Tell me in the comments 💗

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💭 On my mind… surviving the October Slide

Apparently, I am experiencing the phenomenon known in the chronic illness world as the October Slide. A [lovely] period of time when symptoms tend to worsen because of the change in season.

I was not warned about this, which also makes me think they should really hand out a “So You're Chronically Ill!” handbook when you get diagnosed with something funky. Luckily, my beloved pelvic floor PT mentioned this when I brought up that I was feeling off again — I’ve been struggling more with exhaustion in the last few weeks, and my stomach is doing its angry thing where it puffs out, making most clothes uncomfortable and my back pissy.

I learned the October Slide is something my PT sees a lot in her chronically ill patients, and learning about it has been oddly illuminating. All my weird symptoms that eventually led to getting diagnosed with endometriosis first popped up 2 years ago this week. It always seemed so sudden: one day I was fine, the next day I looked pregnant, but it turns out it wasn’t totally random. Who knew!

Anyway… here’s what I’ve been doing to survive this weird little time…

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How I’m Surviving the October Slide

Wearing my favorite cozy clothes that don’t feel tight on my stomach. These pants are always my go-to. I am also eyeing these from Lululemon as something to try on soon.

Drinking digestion tea at night. I’m not a mint tea person, or really even a tea person, but this tea + a splash of dairy-free creamer + honey is my favorite thing when I’m not feeling great.

Being realistic about capacity. And realizing there is a difference between things I must do because if I don’t, I won’t get paid, or I’ll lose one of my jobs… and things I should do but it’s okay if they slide for a week.

I slept in instead of working out. Honestly, you know I’m not feeling great when I don’t want to work out. I have to listen to what my body is telling me, and this weekend my body was telling me to sleep.

Going less hard in my workouts. I still did end up working out later this week, but I was very cognizant of not pushing myself. I definitely didn’t go all out with any cardio. I also modified any core stuff that I know makes my stomach feel worse.

Trying to be kinder to myself 💗 Easier said than done… Navigating this has been so… weird. And honestly, sharing about it makes me self-conscious, not because I’m embarrassed by any of the actual medical stuff, but because I am so afraid of being perceived as lazy or not hardworking. It’s a mindfuck to be someone who has always seen themselves as driven and a hard worker who is now living in a body that just… can’t. Also, sharing parts of my life on the internet has opened me up to criticism based on what others perceive. To put it bluntly, it hurts to be seen as not a hard worker or as someone who is coasting on their financial privilege.

In reality, I’m simply doing the best I can right now with what I’m working with… even if that best looks a lot different than it did at other points in my life.

What I’m Reading…

I’m still reading The Thoroughbreds by Elin Hilderbrand and Shelby Cunningham. It’s a continuation of their book, The Academy, which follows a group of teachers and students at an elite boarding school.

It’s been such a fun world to get lost in; there is something about high school drama and how high the stakes feel at that age, mixed with my curiosities about life at boarding school. As a duology, I also feel like I’m catching up with old friends.

A few things I’m loving…

• Okay, I’ve found my new holy-grail face product. It’s a moisturizer that gives light coverage, and it has SPF. Everything I want in one product. It’s super lightweight… and someone even complimented how good my skin looked on Instagram this week. I’ll take it!

• I’ve been layering the above with this balm foundation (it’s like soothing skincare but also provides some coverage!) alongside this balm in petal as blush + whisper for a little extra glow.

• Drag Race UK, Season 8. I get SO much joy from not only watching a new season of Drag Race, but also listening to a bunch of recap podcast episodes after. I highly recommend getting obsessed a show that has a weekly drop where there’s a ton of fan podcasts to listen to after.
  This crop of UK queens is growing on me, I like that they aren’t all youngins and I find British queens to be excellent performers.

• My best friend was in town last weekend and we went to see the new cast of Rocky Horror on Broadway. Oh my goddd, it was soooo good!

And with that, time to log off 💗

Love, Kayla

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September was all about stabilizing my life.

Getting used to my new work schedule and what that actually looks like in practice. I’m learning how much other work I can get done on the days I also work a 7+ hour shift at the Pilates studio. Figuring out when I’m the most creative for my own stuff. And getting into a good rhythm with the freelance work I’ve been doing, which involves admin, content creation, and social media coaching. I also had some exciting brand partnerships for my own Instagram account.

It’s a lot of different things. But as someone who has a history of getting bored at work, it’s been an oddly good fit. There’s enough variation and new challenges.

This month I wanted to really focus on the things I was already committed to rather than trying to build the next thing and add more to my plate before I’ve figured out how much I can actually handle.

I had so many moments this month where I thought, Wait, I get to do this for work??

I’d be making a slideshow nerding out about social media strategy for the coaching program I’m co-leading, or editing a video for one of the author’s clients, and I’d feel this little pang of, shouldn’t you be doing something else??

Then I’d remember: Nope. This is what I’m getting paid to do. And how amazing is that!?

I’ve also been LOVING doing interviews for my new series, Change of Plans

I get to yap with interesting people, record our conversation, and then make content from it? Love. Years and years ago, I had a short-lived interview podcast (were any of you around for those days?!) where I did something similar. But this has felt different. I think it helps that it isn’t a podcast but rather a conversation I record and then pull stuff from.

I can get so self-conscious of my valley girl accent or saying something dumb while being recorded. Instead, I can focus on being curious and seeing where the conversation naturally goes.

Between steady work and brand partnerships, I've had some breathing room. I’m less afraid about what comes next. Yes, I still need to earn money. But I’m also more open to playing around with things that don’t have an immediate financial payoff. Will Change of Plans ever be this monetized thing? I don’t know, but for now I’m doing it because I’m genuinely enjoying it. I can’t wait to share more of those interviews with you

Side note… my content plan as of right now is once a month, but would you want them more frequently? What do you think?

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As we head into October, I’m feeling excited [and ready!] to enter my next micro era

I’m itching for a little momentum. Because let’s be honest, I can never sit still for very long…

October feels like a good month to experiment. Try something out.

But I also want to lay out a clear idea of what enough looks like so it doesn’t turn into me being my usual chaos goblin of trying to figure out my entire future right this second…

As I did in September, I’m asking myself 5 questions…

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“Don’t make decisions at 4AM”
— An email I obviously sent to myself at 4AM…

More often than I’d like to admit, I find myself awake at 4AM thinking about, well, everything.

What thing should I launch? What content should I create? Is this a good idea for a Substack post? Could this be an Instagram carousel? Should I become a Pilates instructor? Am I overthinking my content strategy? Am I underthinking my content strategy? Should I go back to school? [For the love of god, no, Kayla.] Should I archive everything on this Substack and give myself a fresh start?????

Eventually I’ll get back to sleep, and when I wake up a few hours later, again, I’ll find 5 emails I sent to myself in that stupor at 4AM.

Case in point…

Oh, how I wish my brain was this active at, say… 2:00PM.

It’s always so tempting to make a decision from this place of frenzy in the wee hours of the morning. The city still dark and quiet, my husband inevitably fast asleep in the next room as I usually move to the couch in these moments. Ah yes, what I need is a fresh start on Substack. Archive it all! The a-ha feels so potent.

But then, in the light of day, not so much. Although I think there will still eventually be an essay about little sister energy.

I’m not a very patient person. You might have grasped that about me by now. When I want something, I usually don’t wait and just kind of take action. Sometimes that’s a good thing — I didn’t think too long and hard about launching a blog and just kind of did the thing as a clueless 21-year-old in college. I’m glad I didn’t wait months and months, overthinking it. Who knows if I’d be here, all these years later, oversharing on the internet.

This intensity, this urgency I accidentally create, it can also backfire. I’ll come up with some grand plan from that heightened (and undeniably sleepy) state without really thinking through whether it will still be the right decision during daylight hours…

Like literally a few weeks ago I was convinced I was going to launch a second off-shoot Substack. Kayla, my sweet self, focus on the one you already have.

Last night the spiral was about this newsletter. Should I scrap this whole Logging Off format? [Again.]

[The answer is… no.]

I’ve been challenging myself to slow the eff down and not make decisions from this place. To let things linger a little bit longer.

And honestly this also goes for making decisions when I’m in a bad mood, about to go to sleep, or hungry. How I feel about something when I’m in these states? Not accurate! At all!!!!!!!

One exception to the rule was this decision. It ended up being what this chronically ill bride needed, even if I’m sure people were rolling their eyes at me. That idea still sounded right come morning…

It’s okay to let things marinate.

To let them wait.

And if it is a really really good idea, it’s not going to float away. It will stick around.

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I made my new digital vision board for fall!

Over the last few years, I’ve started making a vision board for my phone. I also love to make a physical one that I hang over my desk, but having one as my phone background as well makes me disproportionately giddy.

Why just make one a year when I can make a few… so I tend to give my vision board a seasonal refresh at the beginning of summer and fall. Can you guess what I’m leaning into this season?

Which brings me to…

✍️ WEEKEND HOMEWORK

Make your fall vision board and set it as your phone background.

Who says you can only vision board in January!? My method is — save a bunch of stuff on Pinterest that represents the vibe I’m going for and what I’m focusing on. I then make the collage in Canva.

I find the whole experience oddly soothing? Which makes me want to make more digital collages for the hell of it. And I also get such a spark of joy seeing my new home screen whenever I look at my phone.

WHAT I’M WEARING…

I’ve been in full cozy fall mode this week. I forgot how much i LOVE this sweater — it’s 100% cotton and I find it’s the perfect weight for being cozy but not too hot for this sweaty girl. I have the two above colors [speckled beige and shell pink] but am considering getting a few more colors…

Are you allowed to wear linen pants in the fall? Well, I am. These have become a fast favorite of mine — the waistband doesn’t bother me even on bad, bloated days.

Also, I think I found my new go-to t-shirt!? It’s got a good weight and structure to it without feeling too heavy [can you tell being sweaty is a number one concern of mine?].

📚 CURRENTLY READING

I finished reading How to Find Love in the Cereal Aisle by Alissa Derogatis and LOVED it. As much as I consider romance my genre of choice, after years of reading romances I’ve started to crave something a bit more from them. I recently heard someone describe their taste as romance grounded in reality, and I think that’s very much what I go for — too saccharine can turn me off.

ANYWAY… this was very much my vibe. I love that, in addition to being a romance, it’s also about a romance author finding herself again after her ego is rocked by a break-up. It pokes fun at trope-y romance, but it's self-aware in a way I appreciated.

I also started The Thoroughbreds by Elin Hilderbrand and her daughter, Shelby Cunningham. It’s the second book in their boarding school duology and exactly what I need as the weather gets chillier here. It picks up at the beginning of the next school year, and something about it feels like reuniting with old friends. I adore Elin Hilderbrand’s Nantucket novels, and gotta say her signature style of soapy meets great writing, and characters is very present here. I’m so excited for a pretty chill weekend ahead, with lots of time to spend with this book.

✨OF POSSIBLE INTEREST

✍️ As someone who has said they want to do the Artist’s Way for… well, decades… I love this approach that’s more realistic to real life.

📚 LOVE this book round-up of campus novels.

✨i really want to do these 20 questions for starting over (and it’s a game!)

🫶🏻 ICYMI…

Some recent shares:

And with that, time to log off 💗

Love, Kayla

Liked this post? Be sure to hit the “like” button. It seriously helps show my content to more people. And if you really, really loved it, feel free to share my Substack with a friend.

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There’s a particular kind of career crisis that I’ve been thinking about a lot lately. That moment when you realize the thing you’ve been doing, the thing you’re technically really good at and getting celebrated for, doesn’t feel like the right fit anymore.

That’s a big part of why I wanted to talk to Kelsey Donlon, founder of Grey Areas, a career coaching business focused on helping women navigate all the complicated, and yes, grey areas of work.

I originally connected with Kelsey through her writing about leaving her social media position at Nasdaq… a career crisis that is all too familiar to me.

We talked about how she accidentally found her way into social media, the dream job she didn’t get that ultimately changed the trajectory of her career, boredom as an overlooked part of burnout, why so many women seem to be questioning traditional work right now, and the surprising amount of permission we need to make changes we already know we want to make.

Here’s our conversation, edited and condensed for clarity.

Let’s start at the beginning. How did you even get into working in social media?

Kelsey: I went to school for journalism because I really wanted to work in a newsroom. My dream job, like most women our age, was to work at Vogue and be some kind of features director.

We were all in our Lauren Conrad/Rory Gilmore era. I was like, No, I’m definitely going to work at Vogue. No one’s going to stop me.

After college, I went to Northeastern for a one-year journalism program and chose the digital track. This was 2012, so Blogspot was a big deal, and I started a lifestyle blog called Tickle Me Pink. I actually made money from it. I joined LTK, went to Fashion Week, and got to do all this really cool stuff.

Originally, I had just created the blog because I needed a portfolio to graduate, but that was when I started realizing the power of social media. I would write five blog posts a week—which now feels insane—and promote everything on Facebook and Twitter. Instagram had just started becoming a thing.

After grad school, I was working for a styling company in Boston, and I started running the owner’s social accounts. It helped her get new clients. Back then, nobody really understood social media yet. Nobody respected it as a job. People would basically be like, Oh, you tweet for a living? And I’d be like: there is actually a lot that goes into this.

Eventually I decided I wanted to move to New York. I interviewed for 38 jobs, going back and forth between Boston and New York. I had one friend here, moved onto her couch, and told everyone I was giving myself 30 days.

If I didn’t get a job, I’d go back to Boston.

I started looking at magazine mastheads, finding journalists on Twitter, cold DMing people, guessing their email addresses. I was basically like, I will do anything. I’ll assist at a shoot. I’ll write. Whatever you need.

And on essentially the last day of that 30-day window, I got a job at American Salon magazine as their first digital editor. That was really where I had to learn what an actual social strategy looked like.

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How did you end up eventually at Nasdaq doing social media?

Kelsey: At one point, I interviewed for a social role at Vogue and got down to me and one other woman. She got the job. At the time, obviously, I wanted it. But looking back, it was the absolute best thing that could have happened to me. Because if I had worked at Vogue, I probably never would have ended up at Nasdaq.

After that, I took a role at LearnVest, which was acquired by Northwestern Mutual shortly after I started. That gave me an entirely different set of marketing skills. I learned large-scale campaigns and what it was like to work on a big corporate marketing team.

Eventually, an acquaintance I’d stayed in touch with was leaving Nasdaq, and I asked if she would pass along my résumé. I interviewed and got the role.

I went from senior manager to eventually becoming the global head of social media. By the time I left, I was a VP. When I started, it was basically me and one other person. By the end, I was overseeing a global team of 16 across organic social, paid social, influencer marketing and executive social.

Nasdaq was absolutely the best job I ever had, and it was also the most challenging.

That’s what I find so interesting about your story, and I can relate to it. You left a job that you were technically good at and succeeding in.

When did you realize it was time to go?

Kelsey: There were two things.

The first was that I didn’t feel challenged anymore. I had grown the team. I had built the strategy. At a certain point, it felt like everything was activating on its own.

And the second was that I was trying really hard to get pregnant. My team was global, so I was waking up really early, going to bed really late, just constantly grinding. My cortisol levels were incredibly high, and my doctor basically told me something needed to change. And I wanted to be a mom more than anything.

So I left.

And I got pregnant two months later.

I keep thinking about what you said about being bored, because we don’t talk about boredom as part of burnout enough.

Kelsey: Social media has such extremes.

You’re either on a huge team where you own this tiny little piece of the strategy and become an expert in one platform or one area—or you’re one person doing six different jobs. And because everything changes constantly, there’s always this churn.

For me, I would eventually reach this point of: I’ve learned everything I can learn here. I’ve done everything I can do for this brand. I’m ready to try it somewhere else.

So you leave Nasdaq. Why Grey Areas?

Why not do the potentially obvious thing and become a freelance social media consultant?

Kelsey: I actually had the idea for Grey Areas years earlier.

I was experiencing situations at work where I kept thinking: Why isn’t there somewhere I can talk about this? Why can’t I ask other women who have been through this how they handled it?

There were so many workplace situations that felt toxic or antiquated, and I knew I couldn’t be the only person dealing with them.

I even bought the Grey Areas domain years before I left corporate because I didn’t want anyone else to take it.

But while I was working at these companies, I didn’t have the time to actually build it. There was also an obvious conflict of interest in writing about workplace issues while working in corporate America.

Around the time I decided to leave Nasdaq, I joined a six-month mastermind for women entrepreneurs. That gave me a container. I had six months to figure out what this thing was. I had an accountability group. I could learn the practical parts of entrepreneurship: what tech I needed, how to set up the business, how to find clients.

I started posting on LinkedIn and eventually got my first coaching clients.

I did try one freelance social project and I hated it. I felt micromanaged, and I remember thinking: I’m doing the exact work I was doing at 24. Why am I doing this That made it really clear that wasn’t what I wanted to build.

I love the idea of giving yourself a container to figure something out. Because you did that when you moved to New York too: “I’m giving myself 30 days.” And then again: “I’m giving myself six months to build this.”

Kelsey: Yes. And with the business, it also gave me permission to not be perfect.

It was basically: I’m giving myself this amount of time to fuck up.

Hopefully by the end of those six months I would have one or two clients and at least feel confident saying, Okay. I run a business now.

Obviously, it grew from there.

What does Grey Areas look like now?

Kelsey: Most of my clients are directors and above, all the way up to EVPs. A lot of them work in marketing, journalism, agencies or adjacent industries.

They’re extremely smart.

They’re extremely driven.

And they’re probably a little more burnt out than they realize…

When we start working together, the first thing we do is really dig into their values. What do you actually want from your life? What are the biggest challenges you’re dealing with? Where do you want to be six months or a year from now?

Then we build a strategy around that.

Sometimes they want to leave.

Sometimes they want to stay and continue climbing.

At the director level and above, so much of your job becomes less about doing the work and more about leadership: managing down, managing up, navigating politics, managing perception.

And one of the biggest things I’ve learned from working with all these women is that most of them already know what they want. They just need someone to tell them they can do it. They’ve talked to their therapist. They’ve talked to their friends. They’ve talked to their husband or partner. And then they come to me, and I’m the fourth-plus person they’ve talked to about this.

Sometimes they just need someone to say:

Yes, it’s okay to leave your job.

Yes, it’s okay to want something more.

Yes, it’s okay to ask for more money.

These women are so fucking smart. And yet sometimes you need to hire someone to basically tell you that you’re allowed to do the thing you already know you want to do.

Can we talk about the marketing girlies all leaving their jobs?

Kelsey: I think it’s bigger than marketing. During the pandemic, it became incredibly obvious that women could be very good at their jobs, work from home, be productive—and also live their lives. Now a lot of people don’t want to give that up. They want control, autonomy, and agency over their lives and their work.

I don’t think women are necessarily leaving traditional jobs because they don’t want to work. A lot of them are leveraging their networks, starting businesses, launching Substacks, building things that don’t look like the traditional way of working.

Marketers might just have an advantage because we know digital. We know social. We know how to market something online.

One of the most surprising things to me about trying to figure out what I want next has been realizing that changing careers doesn’t necessarily mean throwing away everything that came before.

Do you feel like social media prepared you to become an entrepreneur?

Kelsey: Absolutely. Entrepreneurship is very similar to social media because you have to pivot constantly and every day feels different.

In social, one day all your analytics are terrible and you’re like, I’m awful at my job.

Then the next day something goes semi-viral and you’re like, I’m fucking soaring.

That’s entrepreneurship too, a roller coaster. If I hadn’t spent so many years in social media constantly responding to things changing, I don’t know that I would have believed in myself as much while building a business.

I love that entrepreneurship means I never stop learning. That’s something I really need.

What are you soft launching right now? What’s the half-baked idea? The thing you’re experimenting with? The thing that’s still percolating?

Kelsey: I want to build some kind of community around Grey Areas.

My one-on-one coaching is going really well, but there are people—especially more junior women—who reach out to me and want help but can’t necessarily afford private coaching.

I want somewhere they can go and say, I’m dealing with this really hard thing at work. Has anyone else experienced this? How did you handle it? And someone can say, Actually, yes. Here’s what I did.

I’d love it to be a community where there’s no judgment and people from different industries can share their perspectives.

I’d also love to host monthly conversations and bring people from my network in to talk about everything from writing thank-you notes to dealing with workplace bullying or retaliation. It’s still very early and I don’t know exactly what it is yet. I don’t know where it’s going to live or exactly how people will get there.

But that’s what I’m figuring out!

✨Connect with Kelsey✨

Instagram

Substack

LinkedIn

Grey Areas

Liked this post? Be sure to hit the “like” button. It seriously helps show my content to more people. And if you really, really loved it, feel free to share my Substack with a friend 💗

The pool on the roof of my parents’ building is so much more than an escape from the oppressive heat of summer in NYC.

It all began for me in summer 2020. My parents had had their apartment in the city for a few years at this point, their reverse weekend ho…

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It’s been a minute since we’ve done a casual catch-up. Let’s chat about how things are going on a GLP1 for endometriosis, the latest stop on my never ending medical mystery tour, how I’m really feeling about work, and life post-wedding….

The short version? Nothing is magically fixed or completely figured out. But for the first time in a while, I’m feeling cautiously optimistic.

Shall we?

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Hiii friends! How was your week?

I’m honestly feeling a little… overwhelmed.

Even admitting that gives me the ick. Who am I to be overwhelmed? I don’t have kids. Or a full-time job.

I’ve had far more plates spinning than I currently do. I think back to the da…

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Even though I’m in denial that we’re creeping towards fall, one thing I am excited for is all the new books coming out between now and the end of the year.

Here are my picks for 30 new books to read this fall.

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See You Next Tuesday by Kate Stayman-London — A romance about two political campaign staffers who are politically aligned, but disagree about everything else. Kate’s background is in working on political campaigns, including Hillary Clinton’s 2016 run for president, and I just know there’s going to be fantastic, gritty details.

Hollow Bones by Jodi Picoult — (Out 9/15) Jodi Picoult’s 30th novel is an epic story told in multiple timelines about the lies we tell ourselves and what we will do to protect loved ones from a crisis. Apparently, it was inspired by a Post Secrets thread that said everyone who knew me before 9/11 thinks I’m dead.

My Person by Téa Mutonji — After two decades of friendship, one of them abruptly suggests a friendship break-up. I’m especially intrigued by a book that centers around female friendship over a romantic relationship, and how a friendship break-up can be just as emotionally challenging.

Back Where We Started by Becca Freeman — (Out 10/13) A second-chance, dual-timeline romance about a small-town girl turned Hollywood star and the best friend from childhood turned boyfriend who broke her heart. I had the opportunity to read an advance copy and absolutely loved this book, which also explored fame and identity as an actor. And fun fact — Becca interviewed me about my experience studying theater at NYU/Tisch, and a nod to a few of my own stories made it in!

Lina & June by Genevieve Wheeler — (Out 12/8) Two best friends from college go through a bitter break-up after years of little things adding up. Genevieve’s debut novel, Adelaide, is an absolute fave of mine, and I’ve been so excited to see what she does next. I just finished this book this week and ADORED it — it’s beautiful, raw, and emotional, and such a good dissection of platonic love.

Bad Words by Rioghnach Robinson — (Out 10/6) A much-anticipated and very hyped up romance about a writer and the critic who wrote him a brutal review. I haven’t read this book yet; there’s an advanced copy waiting for me on my shelf that I still need to crack open, but based on the way this book is being heavily marketed, I have a feeling it’s going to be a huge romance.

Rabbit Rabbit by Jennifer E. Smith — (Out 10/15) On New Year’s Eve, a single 39-year-old decides that this is the year she’s going to have a baby on her own. And then less than an hour later, she meets a man who seems perfect… but doesn’t want to have kids. I’m curious to read this romantic novel as someone who has been through a similar journey in my own relationship.

Off Season by Frankie Caracciolo — (Out 12/8) A therapist starts working for a baseball team and is challenged to finally confront her own grief… but then ends up falling for one of her patients — the pitcher with a case of the yips.

If Not You by Ellen O’Clover — (Out 9/15) Rival copywriters with a deep-rooted history end up on a road trip together.

Looks Perfect by Jessica Siskin — (Out 10/6) An influencer’s perfect online presence starkly contrasts with how her life looks offline. Through an anonymous dating app, she connects with a stranger who takes her down a path she didn’t expect.

Thank You for Remembering by Emily Harding— (Out 9/15) A modern amnesia romance about getting a fresh start. A 30-year-old wakes up in the hospital with no memory of how she got there or what’s happened over the last year. The man who was her boyfriend insists that they broke up months ago. She starts to retrace her steps… and also begins to fall for her very attractive neighbor.

Never Lasting by Angela Bourassa — (Out 9/22) A recent law student with plans to move abroad has a summer fling with a caterer focused on opening a small-town restaurant. They know it’s going to be a short-lived thing with an expiration date, but then it starts to become something more

The Thoroughbreds by Elin Hilderbrand and Shelby Cunningham — (Out 9/15) The second book in Hilderbrand’s boarding school series, co-written with her daughter. I’m particularly excited to finally uncover what was in Cinnamon’s email to Dub.

Sophie Standing There by Meg Mason — (Out 9/29) A book-lover with a dream job and a seemingly perfect life finds herself living alone, estranged from her loved ones, and on the verge of getting fired. It’s supposed to be a tender yet funny novel about heartbreak and the journey from loneliness to belonging.

Hollywood, Ending by John Green — (Out 9/22) A behind-the-scenes Hollywood love story about the stars of an Andy Warhol biopic, told in dual POVs. I somehow haven’t read anything by John Green... but I’m such a sucker for a love story about celebrities and their private vs. public life, and this sounds very up my alley.

It’s Only Dancing by Jasmine Guillory — (Out 10/6) One of my favorite romance authors making her YA debut, AND it’s inspired by one of my all-time favorite movies, Dirty Dancing? Yes, I’m sold. The summer before senior year, a high schooler is forced to spend the summer with her family at a camp in Southern California, where she stumbles upon a staff party with something she’s deeply missed: dance, and the handsome hip-hop instructor who is trying to reignite her love of dancing.

The True Confessions of First Lady Freeman by Deesha Philyaw — (Out 9/29) The wife of a mega-church pastor’s past secrets start to come out. It sounds incredibly juicy, and the main character sounds brash and also someone you’ll adore and root for.

Once, Again, Always by Amanda Gayle — (Out 10/6) A second-chance romance following a woman with no memory of the last six years who wakes up in the hospital married to her high school nemesis. I find it interesting that there’s more than one romance with an amnesia plotline this fall!

Friend and Family by Natalie Baszile — (Out 10/6) Two women who became best friends thanks to their kids now find themselves at odds after the cops are called on their kids, and one of their sons has a traumatic police encounter as a young Black man.

The Apparent Trap by Ali Rosen — (Out 11/1) A workplace romance about two coworkers meddling in their parents’ age-gap romance… only for them to start to fall for each other. A fun adult spin on The Parent Trap.

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Once in a Timeline by Iman Hariri-Kia — (Out 10/13) An aspiring lifestyle influencer gets caught in her own “A Day in My Life” video. I’m excited to see Iman tackle influencer culture from this lens and blend in a romance element.

Fetal Position by Carolyn Huynh — (Out 12/1) It’s the near future. Birth rates have plummeted, and the male loneliness epidemic is at its peak. A start-up starts to recruit “high-value: women with the promise of trading your demanding work life for subsidized security, a home, and a robotic butler to handle all your needs. It’s giving me Don’t Worry Darling with even more bite, edge, and social commentary.

In Every Future It’s Us by Kate Naymon — (Out 12/1) Childhood best friends made a pact that every year at their parents’ New Year’s Eve party, they’d write down five secrets about the other’s year ahead. Whoever got the most right would get to make a big decision for the other. They kept up the tradition for the last 10 years… until something came between them. It sounds very much like my kind of second-chance, friends-to-lovers romance with resolutions and dual timelines.

The Only Things There Is To Want by Sarah Hepla — (Out 9/29) A searing memoir about the three loves that have defined Sarah’s life. I don’t read a ton of memoir or non-fiction, but I read this as part of a work assignment and found myself totally sucked into the writing and storytelling. I think fans of Three Women and those who loved the openness of Strangers will find this equally as compelling.

Proof of Progress by Elizabeth Castellano — (Out 9/15) A former popular actress has survived the challenge of aging in Hollywood and finds herself back in the spotlight. Turns out, 37 years ago she was supposed to turn in a transcript to her publisher, and she’s still expected to fulfill her contract. What she delivers is a series of bite-sized, revealing anecdotes about her life.

The Mother-in-Law Book Club by Kate Hash — (Out 10/13) A soon-to-be divorcee is invited to join a book club of gossipy seventy-something women, who she finds an unexpected bond with. I love an intergenerational female friendship, especially one centered around books.

I Never Knew You At All by Christine Pride and Jo Piazza — (Out 10/13) A Black woman’s interracial marriage is rocked when an investigation is opened about a murder tied to her wealthy husband’s family.

Peck & Peck by Bonnie Garmus — (Out 10/13) This is the second book from the author of Lessons in Chemistry. It’s the 1980’s in NYC. A young man gets a prestigious job at a secretive and also dysfunctional poetry journal.

Under Story by Chloe Benjamin — I’m not gonna lie, I’ve heard many people talk about this book, and I still can’t tell you what exactly it’s about. I can tell you it’s a sci-fi fantasy blend and will be a very big book this fall.

First Famous Christmas by Carrie Wittmer — (Out 11/3) A famous pop star returns to her hometown for the holidays and runs into her high school crush.

Any other new or upcoming books you’re excited to read this fall?

Leave a comment

💗 Kayla

PS — I love sharing reading guides, and this type of content will always remain free… but they also can be a bit of a beast to put together. If you enjoy the content I share, please consider becoming a paid subscriber. It’s a simple way to support this newsletter and the content I create.

If you’re not in a financial position to subscribe at this time, please consider sharing this with a friend or restacking. It makes a huge difference.

Thank you, as always, for being part of this community.

Okay, the back-to-school energy is hitting me hard. Even as a Summer Girlie™️, I do love a new notebook, an elaborate list of things I want to accomplish, and leaning into the fresh vibes of a new season.

I tend to try to do all! the! things! Which then leaves me burnt out and doing none of the things. I’m working on being a bit more realist…

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Hiii friends! How are you!?

I’m writing and scheduling this a bit earlier than usual so Jeremy and I can go on a little adventure today.

He’s been off from work for the last two weeks, as it’s the downtime between his summer job at cam…

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Sometimes this is useful — I don’t wait all that long before I decide to do something. Like starting a blog when I was in college, which is the whole reason I’m still here today talking about my life on the internet. I’m glad I didn’t patiently wait until I had the perfect name and a well-thought-out content plan and strategy.

But this impatience, wanting things now and to make moves as quickly as I can, sometimes bites me in the ass.

Everything can feel so urgent.

This summer, I found myself frantically researching life coaching programs like there was a ticking time bomb. This fear that if I didn’t start ASAP, I was just wasting even more time.

That same urgency hit me when I quit my job. I wanted to launch a YouTube channel as quickly as possible. Start a podcast here on Substack. Crank out content across multiple platforms… which ironically is exactly what burnt me out at my full-time job…

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There’s a lot I want to do… or at least try…

Write a book.

Delve into coaching.

Turn paid subscriptions back on here… but also make it genuinely valuable to y’all.

Create a course. Or a digital book.

Travel. A lot more.

And… I also want a life that’s full of rest and space for creativity. And y’know, seeing my husband, family, and friends.

Sometimes I get worried that if I don’t act on the impulse, the energy, the excitement, right away, then it’s never going to happen.

I’ve had to start to shift how I think about that… just because I’m not doing something right now doesn’t mean that it won’t happen eventually.

Telling myself this? Oddly, a huge relief. It’s allowed me to map out the rest of my year more realistically. Instead of treating every idea like it’s this urgent thing I MUST do now, I’m pausing and asking myself:

Okay, what deserves my energy right now… and what can I trust myself to return to later?

So, as we head into September, this is my plan…

I’m soft-launching a new era [heh, get it?] with soft being the keyword here. I want September to feel like experimenting and learning… and not immediately feeling like I need to act on every new interest or business idea.

I’m asking myself these 5 questions:

1. What matters most this month?

2. What can wait?

3. What am I exploring?

4. What will be enough?

5. What do I want more of?

✨ What matters most this month?

Showing up for the work I’m already committed to: My part-time jobs plus some exciting upcoming brand partnerships.

[Re]launching a paid tier here on Substack. Okay, this one has been on my mind for a bit… and I keep going back and forth on it. I know this is something I’ve done before, but this time around I’m in a better place physically : ) and feel more ready.

Starting today, I’m officially turning paid subscriptions back on here at Soft Launch.

The plan is to start simple: The plan is to start simple: paid subscribers will receive two additional posts each month—one monthly check-in like this and one deeper, more personal essay.

My regular free posts and Logging Off aren’t going anywhere. But if you enjoy my work and have the means, it’s simply a way to support what I do and create, and I’d love to have you.

If you have anything you’d love to see, please let me know. And if you have any questions or concerns about prior paid subscription charges, please reach out.

And with that… here’s the paywall!

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Hiii friends! How was your week?

The highlight of mine was undeniably seeing Harry Styles as he began his Madison Square Garden residency. I joke that I’m a late in life one direction fan. It wasn’t until I read The Idea of You, which has a character loosely based on Harry, in 2…

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