Someone will describe the service they offer, for example a blog post, an edited report, a newsletter, or a website rewrite, and then explain how they market it. Often, that marketing looks like, “I write blog posts for legal clients.”

Now, knowing what you do and who you do it for is important. But there’s nothing in this statement that sets you apart from most other writers. It doesn’t show your potential clients that you understand them beyond the fact that they might want some blog posts.

I don’t know that any of my clients has ever woken up one morning and thought, “What I need today is a 1,200-word blog post.” That’s not what keeps them up at night (it’s what keeps me up at night, but that’s because I’m the one writing the post). Instead, what keeps them up at night is that they need more visibility, stronger search results, more leads, or better engagement. And they need that because they want their business to grow (or they want to find premium clients, or they want to establish thought-leadership).

The blog post is one way to get them there.

The same applies to editing. A client may hire you to edit a report, but the report itself is usually connected to something bigger. The report may help them to get research approved, support a funding application, or help them move their career ahead.

The work freelancers produce usually isn’t the end goal by itself; it has its own job to do once it’s published. Understanding that job is the key to marketing yourself. That’s where you show your clients you understand their pain points, needs, and goals.

Your client may be buying a well-written or professionally edited document. But what they need is:

• a more credible reputation

• a successful launch

• better search visibility

• more qualified leads

• approval for an idea or project

• progress in their career

• income from a new offer

• a book that’s ready to go to the publisher

Show that you understand why the work is important to them, and show the link between having, for example, a well-written blog post and achieving their goals.

This doesn’t mean you have to rethink your entire marketing strategy. But you may want to think one step further than you have been. Instead of asking, “What do I do and who do I do it for?” You may want to ask, “What does my work help the client achieve?” or “How does my work help them advance?”

For example:

• “I write blog posts” might become “I help organizations create useful SEO-focused content that brings the right people to their websites.”

• “I edit research reports” might become “I help researchers present complex findings clearly so decision-makers can understand and act on them.”

• “I edit non-fiction business books” might become “I help thought-leaders turn promising drafts into books that help them advance their career.”

This framing helps potential clients recognize how your work connects to what they’re trying to accomplish. “This person understands what I’m trying to do” is a much stronger response than “This person writes blog posts.”

That’s how you differentiate yourself and connect with your ideal clients.

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How do you figure out the want behind the want?

If possible, ask your existing clients and reach out to people in your network who are in the industry. Find out what their main pain points are, what they need their content to do for them, and what the end goal is. Ask about their key performance indicators (KPIs), if they have any (the KPIs they monitor will tell you a lot about their overall goals). Industry groups on social media can offer insights, as can following people on social media to see what struggles they’re posting about.

Determine the larger goal the work is meant to support, then make sure your marketing shows clients how your work supports their goals.

Here’s to closing out 2026 strong!

Heidi

Co-working sessions

Paid subscribers get a standing invitation to fill that gap. Most Wednesdays at 10:00 am Pacific (1:00 pm Eastern), we meet on video for co-working. We start with a short hello, then hop into a 45-minute (off-camera) work session followed by a 10-minute break to chat. We finish with another off-camera 45-minute work session.

What you work on is up to you. Client projects, invoicing, marketing, a proposal, or cleaning your office all count.

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What we talk about at the break

During the break, participants have a chance to talk about whatever it is they want to talk about. Sometimes we answer questions about reaching out to past clients or quoting on complex projects. Other times we share our celebrations or odd stories from our projects.

Showing up regularly means you get to know the other freelancers, and they get to know you. It’s a nice way to feel a bit less alone, and to break up your week.

Monthly Let’s Do Marketing! session

Once a month, we hold a Let’s Do Marketing! session, an hour for the marketing tasks we keep putting off. Pick a task or two, whether that’s a pitch, a social media post, a website update, or a note to a past client, and work on it while other freelancers do the same (off-camera, of course).

At least you know that once a month, you’ll have some time focused on marketing your business.

A good way to end the year

The last few months of the year tend to disappear quickly, and December often shows up before we’ve even taken down our Halloween decorations (just me?). A standing Wednesday session gives those months some structure. It also gives you an opportunity to get to know other freelancers and feel part of a group that’s cheering you on.

How to join

If you’d like regular company, a bit of structure, and a place to get to know other freelancers, upgrade to a paid subscription. You’ll get the meeting links so you can join us.

And all sessions are virtual, so if you’re wearing your pajama bottoms (like me, pictured) no one has to know.

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Here’s to finishing 2026 strong!

Heidi

The vast majority of businesses use written communications in some way, from reports to proposals to websites and internal documents. Every document they publish reflects on that business. A typo in a marketing material looks unprofessional. An error on a website undermines credibility. That’s why they need someone to catch mistakes before they spend large budgets publishing documents with errors that can hurt their business in them.

Proofreading is also a skill AI still can’t do well, making it a valuable offering (especially if you have an eye for detail and love consistency). Beyond that, businesses and ad agencies value confidentiality and trade secrets, so they don’t want to share their content with AI. Many businesses that won’t pay for a full edit still want a set of eyes on their reports, websites, and marketing materials to make sure everything looks professional and error-free. Proofreading (done by a human) fits their needs perfectly.

If you’re already working as an editor, proofreading might seem like a natural add-on. It is, but it’s also its own skill. While some of the editing and proofreading processes overlap, there are important differences. If you’ve never proofread professionally there are ins and outs worth learning before you offer it as a service.

Sharon McInnis has been proofreading for corporations, ad agencies, and businesses for years under the business name Proofing Queen. She created her course, “Proofreading for Businesses and Ad Agencies,” to help freelancers offer proofreading and fact checking to corporations and agencies. I was given free access to review the course, and I came away impressed, more informed and (alarmingly) humbled.

For those of you looking to make a change or add a new skill (or possibly work in a new market) this course could be exactly what you need. As a bonus, Sharon is a perfectly delightful instructor. She shares some fun stories from her freelance experiences and tips on ways to manage proofreading projects.

Registration is now open for the next session of Proofreading for Businesses and Ad Agencies, which starts on Oct. 7.

In the meantime, I asked Sharon a few questions about proofreading, her course and what students can expect to learn.

What’s your background, and how long have you been doing this work?

After several years doing secretarial and temp work, I started to work in an ad agency in 1976. That launched my marketing and communications career, that later included being a product manager for two national trust companies, a marketing manager for a large credit union, and a studio and production manager for a graphic design firm, followed by several years providing freelance writing, editing and production services. As I started ProofingQueen in 2002, that means I’ve now been providing proofreading and fact-checking services to clients for 24 years!

How did you get into proofreading, and what made you stick with it?

I’ve always had a knack for proofreading, but I only proofread items occasionally as needed, up until 2002 when I found myself in-between jobs. My friend Cathy, who was a production manager at an ad agency located near my home, knew I was “at liberty”, so she asked me for a favour - to proofread an annual report for her. Of course, I said yes. I picked up the printouts, found quite a few errors, marked up the printouts with a pencil (very high tech!) and walked them back to her the next day. She then changed my life by saying, “Thank you - how much do I owe you?”

I hadn’t even thought about charging her, as she had asked me for a favour! But I named a small amount and she organized payment for me. Then she changed my life even further by telling production manager friends at other Vancouver agencies that I was offering proofreading services. Those other production managers proceeded to hire me for projects and - many projects and dollars later - I finally realized that I no longer needed to look for a job. I was now self-employed - for the first time in my life!

For people who aren’t sure, what exactly does a proofreader do—and how is it different from editing?

In my world - as a corporate proofreader working with businesses and ad agencies - I’m usually the last person to review material before it goes to print or is released online. So, essentially, I’m checking to make sure there are no errors, no typos and no incorrect facts, and that it’s appropriate for the target audience. A proofreader wouldn’t make major changes and wouldn’t rearrange sections, whereas an editor might do that.

What kinds of clients or projects do corporate proofreaders typically work on?

As I don’t know if there are other corporate proofreaders, I can only reference my clients and projects. My clients are large businesses, local and national corporations, private schools, real estate marketing firms, ad agencies, graphic design firms and communication consultants. Projects run the gamet from annual reports and sustainability reports to corporate magazines and websites and everything in between.

Why do businesses and ad agencies need proofreaders when they already have writers and editors on staff?

In my experience, although most businesses and ad agencies work with staff or freelance writers, very few work with editors.

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Who is this course for, and who might it not be right for?

This course is designed for beginning and experienced editors and proofreaders who would like to add corporate clients to their roster. As I’m not a marketing or sales expert, I don’t provide any marketing or sales advice - so it’s probably not the right course for an editor or proofreader who wants also help finding and landing corporate clients.

What can someone expect to walk away with after five weeks?

If they do all of the self-marked assignments, they should have a basic understanding of the skills and tools that would support their work with corporate clients.

The course also goes into fact checking. Why is that important and is it still a beneficial service to offer?

As I mentioned above, most (if not all) corporations and creative agencies do not work with a staff or freelance editor. And, as an editor would normally take care of the fact-checking, that’s a task that I firmly believe that a corporate proofreader needs to do. Grateful clients tell me how pleased they are when I find incorrect facts. (When I started the business, I didn’t realize that ’traditional’ proofreaders - in the publishing world - didn’t check facts. I just knew that, as my clients were paying me to make sure everything was correct, that included the facts!)

If you’re interested in offering proofreading as a service but aren’t sure what it entails or how to manage projects, Sharon’s course provides a fantastic breakdown. You’ll do exercises to practice the various processes involved in proofreading and fact checking, learn how to use different platforms (Word, Adobe in the process), and explore how Sharon manages her proofreading projects (including communicating with clients).

Learn more about and register for Sharon’s course here.

I’d built a website, sent a few emails to potential clients, and even posted on social media a few times. And then I’d sit at my desk checking my inbox every twenty minutes, sure that at any moment my perfect client would email me offering exactly the kind of work I wanted at the rate I deserved.

Of course, I didn’t get the result I was expecting.

Instead, I watched other freelancers land great projects while I sat there feeling increasingly bitter about their success. It wasn’t a great feeling, but it allowed me to avoid facing an important truth: I was waiting for opportunities to land in my lap, rather than finding them.

For most of us, marketing means being uncomfortable

Marketing my business meant doing things that make me deeply uncomfortable, including being visible, reaching out to people I don’t know, and risking rejection (which feels absolutely terrible, regardless of how positively you try to spin it). I also had to attend networking events, where I stood awkwardly by the snack table trying to gear myself up to start conversations with people I didn’t know about topics I wasn’t sure I understood. And I had to explain what I did over and over, which felt repetitive.

None of it felt natural to me (I’m not the type of person to charm a room with my ease and eloquence). I often felt like I was trying too hard. But I kept doing it, because sitting at my desk while constantly refreshing my email wasn’t getting me anywhere.

It took a few months before anything started happening. More than once during those months I felt awkward and uncomfortable, and I went back and forth for days before posting something to social media. I freted endlessly about the people who ignored my connection requests.

But over time, my efforts started paying off. People started reaching out to me, asking if I was available. And I started to feel less uncomfortable sending connection requests to people who didn’t know me.

The client I almost missed out on

One of my best long-term clients found me because I took uncomfortable action.

He had looked at my LinkedIn profile and then did nothing. He didn’t connect with me, send a message, or reach out in any way. He simply viewed my profile and disappeared.

I could have left it alone, but instead I sent him a connection request with the note, “Hi [name], I saw you were checking out my profile. I’d love to connect, and learn more about what you do!”

He accepted my request and noted that he was looking for a Canadian writer for his marketing agency. We talked initially through LinkedIn and then through email. Ultimately, he hired me for the project and I wound up working with his firm on various projects for almost five years.

If I hadn’t sent that connection request, I might have misssed out entirely. But, he likely would never have come across me in the first place if I hadn’t been somewhat active on LinkedIn, which made it possible for him to find me.

What’s worked for me

I don’t have a formula that will absolutely work for everyone, but I do know what’s worked for me.

• Talk about what you do in regular conversations. It doesn’t have to be pushy or forceful, just tell people what you do, how it helps, and who you work with. You never know who’s going to remember that six months from now when they need someone or when their colleague mentions they’re looking for a writer or editor.

• Ask questions. The more you understand what someone needs, the better you can tell if you might be able to help them. And if you can’t help them yourself, point them in the right direction wherever possible. People remember that sort of helpfulness.

• Don’t let assumptions stop you. When I saw that profile view, I could have assumed he’d already found someone, or wasn’t serious, or saw something in my profile that convinced him I wasn’t right for him. Reaching out cost me nothing. In the worst-case scenario, he would have ignored me, but that wouldn’t have imploded my world (at least, it shouldn’t implode my world).

What people forget about taking action is that you get more comfortable with an activity by doing it over and over, not by avoiding it.

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Your clients are looking for you, too

Have you ever had to hire a contractor (for work or personal projects)? Remember that feeling of wishing something would make the process easier? Maybe (like me) you wish the right option would magically appear in front of you, so you don’t have to put too much time or energy into vetting the choices.

Your ideal client is likely sitting at their desk hoping the perfect writer or editor will find them.

When that client looked at my LinkedIn profile, he was actively looking for someone. Nobody wants to review fifty profiles or email twenty freelancers hoping one of them turns out to be right. They’ve got a million other priorities, so they want the right person to be immediately obvious and easy to find. When I reached out, I made it easy for him. I kept that up by answering his questions quickly and getting him the information he needed. His search was over and my work was begining.

That’s what marketing is, at its most basic. It’s making yourself findable so the people who need you can find you without having to work too hard at it.

Most people quit too early

A lot of freelancers leave because they set up a website, sent a couple of emails, didn’t get the immediate results they wanted, and decided there were no clients out there.

The freelancers who are successful long term are those who kept going even when things didn’t happen immediately. They tried something, reviewed the results, and adjusted. They reached out when it felt awkward and posted even when no one was reading.

I’m not saying it’s easy, because it isn’t. It’s uncomfortable and slow, and you have to learn to tolerate rejection (or no response).

But when you focus on making it easy for your potential clients to find you, rather than focusing strictly on marketing, it can feel a little less unnatural and a little more like you’re helping.

Your ideal client is out there looking for someone like you right now. Make sure they can find you.

Let’s finish 2026 strong!

Heidi

There’s no single right way to build a successful freelance business.

I’m Heidi, and I’ve been freelancing as a writer and editor for 20 years. I also teach editing and write this newsletter. Throughout my career I’ve heard lots of good advice (some of which worked out for me and some of which didn’t) and lots of bad advice that probably doesn’t work well for anyone.

One of the most important things I’ve learned is that knowing how to do something is only part of running a successful freelance business. You also have to figure out what makes sense for your business and move through the discomfort to take action (and yes, there can be a lot of discomfort in freelancing).

That’s what Happy Freelancing is about.

There’s no shortage of free advice online. And while that advice isn’t necessarily bad, it’s much less useful when we treat it as a rule, rather than considering whether it fits our unique circumstances, goals, clients, finances, personality, and business.

At Happy Freelancing, I absolutely share advice, including practical strategies that worked for me, on topics such as finding clients, marketing, systems, boundaries, and client relationships. I’ll share strategies that have worked for me, things I’ve tried that haven’t, and lessons I’ve learned over 20 years of freelancing (and talking to other freelancers).

But I’ll also help you think about that advice within your context:

• Should you niche down? It depends on your goals, your market, and what you enjoy (and are good at).

• Should you post on LinkedIn? Maybe, if it fits the work you do, the clients you serve, and how you want to market yourself.

• Should you raise your rates? Let’s think through your financial needs, your positioning, and how you currently approach rates.

Why might one approach work better than another? What are the trade-offs? What does your business need right now? What are you trying to accomplish?

I’m here to help you think strategically about your business, make informed decisions based on your circumstances, and trust your judgement enough to take action, rather than getting stuck in analysis paralysis.

Because ultimately, the goal is to build a business that works for you.

What you’ll find at Happy Freelancing

This newsletter shares my experience built over 20 years of freelancing and mentoring freelancers: what I’ve tried, what worked, what didn’t, and what I’m still learning. Some issues dig deep into a topic, like setting boundaries with clients or finding a sustainable way to market yourself. Others simply share something I’ve noticed or a decision I’m working through.

The Happy Freelancing community is a paid tier that includes weekly coworking sessions, monthly marketing sessions, and quarterly business planning (plus other workshops and sessions). This is where you get accountability, build your momentum, and connect with other freelancers who are actively building their businesses. These sessions give you structured time to work on your business, space to talk things through, and and a chance to make freelancing feel less lonely (because freelancing can be an incredibly lonely career).

Guides, workbooks, and other paid resources offer practical help when you want to tackle something specific on your own, whether that’s improving your LinkedIn profile, writing your website copy, or building better systems.

And when you need more individualized support, mentoring gives us the opportunity to sit down together, explore what’s going on in your business, and work through the decisions or challenges that are keeping you stuck.

Where to start

Start by reading the newsletter. See if the way I think about freelancing resonates with you; whether the questions I ask help you think about your own business differently or help you to make important decisions.

Join the Happy Freelancing community to get access to coworking sessions, marketing sessions, and business planning sessions. These give you some extra support and the opportunity to talk to other freelancers who have likely experienced the same challenges you experience.

Grab a guide or workbook when you want practical help tackling something specific. Book mentoring when you’re dealing with a problem or decision that would benefit from having an experienced freelancer sit beside you, ask questions, and help you work your way through it.

If you have a question, topic, or challenge that you’d love to see covered in Happy Freelancing, fill out this form.

Let’s make 2026 your best year yet!

Heidi

This is, by all objective standards, especially ridiculous because invoicing is one of the essential parts of getting paid. Clients generally can’t send you money unless they know exactly how much to send and where to send it. They like to have an invoice so they can justify the expense to their accountant (or their accounts payable department).

At the time, invoicing was a bit of a production. I had an invoice template, but I had to enter everything manually, calculate the totals myself, send the invoice, keep track of whether it had been paid, and follow up if it hadn’t.

Individually, none of those tasks was particularly difficult. But put together, they created just enough friction that sending an invoice became the sort of task I told myself I’d do “tomorrow, when I have more energy.” I never magically had more energy tomorrow, but ultimately I’d send the invoice when I got panicky about my bank account, which also meant I was frustrated when clients didn’t pay me immediately upon receiving my invoice.

Then a colleague pointed out something I hadn’t considered: clients need us to invoice them promptly. Yes, we benefit from invoicing because we get paid. But they benefit because they have finances to manage and expenses to allocate. An invoice that unexpectedly appears weeks after the work was completed can make budgeting, expensing, and money management more difficult for the client.

So I committed to sending invoices immediately upon completing a project.

But that wasn’t the only change I made, because I also realized that part of the reason I was delaying invoicing was that there was too much friction around the process. So I took one more step: I paid for invoicing software to make the entire process smoother for me.

Just like that, invoicing became a regular thing I did. I was truly surprised at how quickly invoicing stopped feeling like a massive chore. Having the calculations automatically done, a portal to send the invoices through, and a way of tracking the invoices made the process much easier for me. Once it was quick and easy to do, it was also much harder to justify avoiding it. I literally have no reason to wait until I have “more energy” (or until I’m in a panic over my bank account balance), because I need virtually no energy to get the invoice completed and sent.

What I’d blamed on a lack of discipline was instead an issue with my processes.

Since that time, I’ve noticed how easy it is to confuse the two. When we repeatedly procrastinate or delay doing something, we often assume we need to be more disciplined. When we think the problem is internal (lack of organization, discipline, or commitment), we attack the problem internally. We try to get more organized, push ourselves to be more disciplined, or adopt a just do it attitude.

Automatically blaming our procrastination on a lack of discipline can stop us from looking more closely at what’s really going on with us.

For a long time, I would have described my invoicing procrastination as a lack of discipline. But “I’m not disciplined enough” isn’t an explanation for why I kept putting it off, it was more of a judgement I’d made based on the fact that I kept delaying invoicing.

There’s an important distinction there. If I decide the problem is a lack of discipline, the obvious solution is to become more disciplined; to force myself to do the activity. Try harder, or stop procrastinating, or send the invoice already.

Sometimes becoming more disciplined works, but often it only works for a short while before we revert to our earlier behaviour. Why? Because we haven’t solved the root problem.

A more useful question for me was: What is making this so hard for me to do?

That question gave me something concrete to investigate. In the case of invoicing, the answer was (embarrassingly) mundane: there were too many little steps involved in a task I didn’t particularly enjoy doing. Once I understood that, I could stop relying entirely on discipline and start looking for ways to make the process easier.

One of the things I’ve been more focused on as I’ve progressed in my career is designing systems around my own behaviour, rather than trying to correct that behaviour.

It’s not that I think my behaviour is above reproach or that I should never have to change. I’ve had to develop better habits and get comfortable doing things that make me uncomfortable. But I also think that if my business is going to be sustainable, the systems I use to run it have to work reasonably well with who I am. They can’t depend on me becoming a completely different person.

If I notice I’m repeatedly avoiding something that needs to be done, I try not to assume I need to become more disciplined. Instead, I look at the process itself and ask what’s making it difficult for me to follow through. Then I explore whether I can do anything to make that process easier.

That’s why the follow-up question is so important: What would make this easier for me to do? The answer to that question gives you potential solutions to explore and evaluate, rather than forcing yourself to change.

Sometimes that means taking the friction out of a process by paying for a service or platform. Sometimes that means using a template or setting up a checklist. Sometimes that means batching certain types of work. The solution depends on what’s making the task difficult for me in the first place.

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These days, clients get their invoices as soon as a project is completed. That’s not because I’ve developed a desire to invoice or because I’ve become incredibly disciplined about it. It’s because I took some of the friction out of the process, so sending an invoice no longer feels like a whole thing.

If there’s a task you repeatedly put off, and trying to be more disciplined hasn’t changed that, maybe it’s worth exploring why you keep putting it off and whether there’s a way to make it easier on yourself.

Let’s make 2026 your best year yet!

Heidi

Speaking of making things easier to do…

One of the ways we make things easier to do is by doing things together. Happy Freelancing paid members meet weekly for coworking, monthly for dedicated marketing time, and quarterly for business planning.

Get work done and feel less alone! (I promise, we’re all friendly!)

If that sounds like something you’d like to be part of, join the Happy Freelancing community.

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Warm greetings! My name is Rachel, and I am reaching out because I was intrigued by your professional background and experience. I'm from Sparkle Group hiring for a Technical Writer role on behalf of a client, and I believe it would be a good match for you!

I understand that you help solopreneurs and business owners articulate their unique stories. This skill is valuable, especially in a role where clear communication is key. Your ability to help clients express their depth and attract the right audience could be a strong asset in this position.

To understand this role better, I'd suggest setting up a meeting to discuss it in more detail. Please let me know if you are interested, and we can schedule a call at your convenience.

My immediate reaction was both interested and skeptical. I haven’t lived under a rock for the past few decades, so I know social media is full of stories about people being scammed by fake recruiters. And, while I have zero intention of handing over personal information to strangers, I’m also aware that scams can unfold in seemingly innocent ways: you answer a message with a “sure let’s chat” and next thing you know, you’ve sold your house to the prince of an imaginary country for less than the cost of a loaf of bread (or something like that).

Of course, one of the cruel ironies of scamming is that legitimate opportunities get ignored. We might dismiss a real recuriter or potential client because we’re afraid of becoming a cautionary tale. That fear leads to infinite second-guessing every time a message comes in. Is this opportunity real? If I follow up, will I look like a complete moron in four weeks’ time? Or could I potentially miss out on a great chance?

Alex Benarzi

A Freelancer’s Questionable Guide to Trust

You’re plugging away at work, trying to block out all distractions, when you phone rings. For that split second, you oscillate between answering and whipping you phone (gently—knowing that there is a soft place to land) across the room.Thanks for reading! Subscribe for free to receive new posts and support my work…

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3 months ago · Alex Benarzi

Here’s how I evaluated the message, step by step. (Important caveat: this guide is about protecting yourself from people trying to steal your money or personal information. These tactics won’t necessarily help you identify real clients who simply want free work. That’s a different article.)

Evaluate messages for signs of a scam

When an unsolicited message lands in your inbox (email, DM, or otherwise), you’re looking at several layers:

• The sender: Are they who they claim to be?

• The company or organization: Does it exist? Is it legitimate?

• The message itself: What can you learn from the tone, content, and structure? What are they offering and how urgently?

• Any links or attachments: Are they safe to click? (Verify this before clicking anything in the email.)

Here’s how to work through the layers.

Evaluating the sender

Start with the person who contacted you. On LinkedIn or other social media platforms, this is relatively easy; if they’ve contacted you through email, do a social media search for them.

Check their profile. Is it established? A legitiate contact—whether they’re a recruiter, content manager, or agency owner—will have:

• A reasonable connection count (more than 12 connections)

• Endorsements and recommendations

• A clear work history with the company they claim to represent

• Somewhat regular activity (posts, comments, shares)

Sparse profiles with generic stock photos, vague job titles, or zero work history are red flags. So are profiles created recently with seemingly rapid career progression.

In my case, Rachel had a history on LinkedIn with the company; she also had posts about awards she’d won from her employer and congratulations from other people linked to the same organization.

Verify their domain. If you have their email address, it should match the company’s official domain. A recruiter or representative from Sparkle Group should email from [@]sparklegroup.com, not [@]gmail.com or [@]sparkle-group.net. Double check the company’s official website to ensure you know their domain and compare it with the person’s contact into.

That said, legitimate overseas agencies or smaller companies sometimes use generic email domains initially. This isn’t an automatic disqualifier, but you may need to check other details more carefully.

Is their email address consistent with other internal emails? For example, if you can tell that other employees at the company have an email using their first initial and last name at the company (hturner@sparklegroup.com, for example) is this consistent with that convention?

Cross-reference contact information. If they include a phone number, check the area code. Does it match with where the company operates?

Evaluating the company

Assuming the sender’s profile checks out, turn your attention to the organization.

Visit the website directly. Don’t click any links in the message. Instead, type the company name into your browser or search for it. Once you’re on the site, look around. Does it look professional? Do they have client testimonials and contact information? Is there a portfolio? Are there red flags on the site?

Search “[company name] scam” (or “[company name] reviews”). A quick search might bring up complaints or warnings from others. If the company is real and reputable, you’ll find normal reviews and discussions. If it’s a known scam, you’ll find warnings. Some large companies will also have a page on their website dedicated to fraud alerts, including tips on avoiding people impersonating their employees. These can be helpful.

Evaluating the message

Does the message itself raise any red flags?

Look for personalization. Does the message reference your work or experience? In my case, the recruiter mentioned my work helping solopreneurs share their stories and how that was relevant to her opportunity. A content manager might write, “I saw your article on [topic] and think your expertise would fit our clients in [industry].”

Details pulled from your LinkedIn or website increase the chances this is legitimate (scammers don’t want to spend too long on something that might not pan out). Generic messages with no context (“You have an impressive background”) are easier to fake.

Check spelling and grammar. Not everyone’s a gifted writer or editor, but some level of professionalism should be clear in the message.

Watch for overly flattering language. Phrases like “You’re the perfect candidate” or “Once-in-a-lifetime opportunity” often suggest manipulation. Real recruiters will be interested and they’ll want to promote the opportunity, but they usually won’t oversell it. It’s in their best interest to get the right person for the role, which means being honest about it. Rachel mentioned that my previous work could be a good match for the role, but she never suggested I was perfect for it, just that my skills might be a good fit.

Pay attention to what isn’t in the message. Does the message include any specific details or is it all incredibly vague? In my case, the recruiter included the name of her company and the role she was hiring for (technical writer). Later, in our chat, she spoke more openly about the client she was hiring for.

Notice how urgently they push the offer. A legitimate recruiter will ask for a phone call or video chat to discuss the role (yes, this is a normal request). They may also request your resume or portfolio, your rates, or your availability to take on a project. They won’t ask for sensitive personal information before you’ve chatted, money for any reason, or immediate action (“respond within 24 hours”).

Evaluating links

This is where things get technical, but this is also one of the most reliable ways to spot a scam.

Let’s say the recruiter includes a link to schedule a meeting. Before you click, always verify the URL.

Read the domain from right to left. The critical part of any URL is the main domain; the domain name (sparklegroup) plus its extension (.com, .org, .ca, or .net, for example). Everything to the left of that is either a subdomain or part of the parth.

For example:

• https://talentassistant.sparklegroup.com/assistant/bookings/12345

• Reading the domain right to left: .com → sparklegroup → talentassistant

• Main domain: sparklegroup.com

• Subdomain: talentassistant

If you know that Sparkle Group’s website is sparklegroup.com (which you know from doing your research above), then you can tell this is legitimate. Only the owner of sparklegroup.com can create subdomains like talentassistant.sparklegroup.com.

Watch for lookalike domains. Scammers get creative with domains that look similar but aren’t official. There will always be something slightly off, such as a hyphen, a different domain extension than the official website uses, or extra words:

• sparklegroup-careers.com (in this case, the main domain is sparklegroup-careers.com not sparklegroup.com)

• sparkle-group.com

• sparklegroup.net

• sparklegroup.com.jobs-portal.com (sparkle group.com is not the main domain here; jobs-portal.com is).

Hover over the link before clicking. Your browser will show you the destination URL (not just the linked text) usually in the bottom corner of your screen. If it raises your suspicions, don’t click.

In my case, the URL was to talentassistant.sparklegroup.com, which was a legitimate URL.

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If you’re still unsure whether it’s a scam

You’re never obligated to return an unsolicited message immediately. If something feels off, you can decline or request time to review the details. And if you do wind up on a call with someone and it still feels off, you’re allowed to excuse yourself from the call. No one can force you to continue a process if that process becomes uncomfortable or raises your suspicions.

In my case, the recruiter turned out to be completely legitimate. We chatted, but her client needed an experienced technical writer who was highly familiar with a platform I’d never heard of before. So I thanked her for thinking of me and she asked me to send her a CV in case something in my expertise came up.

Some unsolicited messages will be obvious scams, but others will be less straightfoward. Rather than constantly second-guessing or going back and forth in your mind about whether to move forward, take the time to do some reviewing so you can protect your time, your information, and your sanity. Then be proud of yourself for making an informed decision.

If you’ve ever hesitated over responding to a lead because you weren’t sure it was legitimate, you’re definitely not alone. I think most freelancers have had that moment. If you’ve developed your own process for verifying unsolicited leads, I’d love to hear it, and I’m sure others would as well.

Here’s to making 2026 your best year yet,

Heidi

The advice covers everything from what you should wear when you sit at your computer (professional clothing or you don’t take your business seriously enough) and what time you should start your workday (9:00 AM at the latest or your business will implode almost immediately) to how you should find clients, what you should charge, which services you should offer, and how you should structure your entire business.

Freelance advice often sounds more universal than it is

The problem isn’t necessarily the advice itself; it’s that the advice is often shaped by a specific set of circumstances even while it’s being framed as universal.

• Post every day

• Niche down

• Raise your rates

• Never charge hourly

• Cold pitch

• Build relationships

• Diversify your income streams

On a surface level, there’s probably nothing inherently wrong with any of this advice (though I may have a vested interest in writing that because I’ve given it myself). But what is a problem is the missing context. For the sake of being concise and engaging to readers, the advice tends to be shortened from “This works well for people in X circumstances who are trying to achieve Y…” to “All freelancers should do this…” (or “If you want to be successful do this…”).

Once a piece of advice gets adopted as an idea by enough freelancers — or when someone says something confidently enough — it tends to get treated as a rule and then people stop asking whether the assumptions behind the advice apply to them, individually. Instead, it becomes a blanket rule for everyone in the industry to follow.

That makes sense on one level; if enough freelancers have had success following that advice, then it seems as though everyone will.

But your business might have a different audience, different skills, different financial needs, different goals, or different challenges than others. Something that worked incredibly well in one business might work just as well for you. Or it might be completely wrong for your circumstances (or something in between, as we’ll see).

Good business advice isn’t necessarily good advice for your business.

Why we’re so tempted to follow the rules

Despite the fact that we often get into freelancing so we can make our own decisions, chart our own brave path forward, and decide what works for us, it’s still very appealing to have someone confidently say to us, “Here’s how you address this problem.”

It means we don’t have to come up with a plan ourselves (and conduct the necessary research, evaluation, and organizing). It also means we don’t have to make decisions. Our path forward is set out for us.

Additionally, when we’re new to freelancing, it’s helpful to learn from the people who have been there before us and succeeded. They know the industry conventions and common practices, and they have experience figuring out what has and hasn’t worked for them. That experience carries a lot of weight for freelancers who don’t yet have as much experience of their own.

At some point, however, becoming better at freelancing means becoming better at making decisions based on you and your business.

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Evaluate common advice

This isn’t to say that any of the advice online is necessarily bad advice. The point isn’t to throw it all out; the point is to take any freelancing advice you encounter and ask when that advice makes sense for you and when it doesn’t.

For example, “Post every day” might make sense if:

• visibility is an important part of your client acquisition strategy;

• your audience is active on a platform;

• you have something useful to say that frequently;

• you’re getting the engagement and results you need;

• you can sustain it without taking time away from higher-value activities.

It might not make sense if most of your business comes from referrals and you’ve already got a waiting list of clients eager to work with you. It might also not make sense if posting twice a week produces essentially the same results.

The question isn’t “Should freelancers post every day?” because there’s no right answer to that. Whether you should post every day depends on your circumstances.

Instead, it’s worthwhile to ask “What am I trying to accomplish by [doing this thing], and will it help me accomplish that goal?” This allows you to determine what your goals are, how this task helps you meet those goals, and whether a modified version of that rule can get you the same results.

Most advice comes with a tradeoff

What often gets forgotten when advice becomes a rule is that every business decision you make has an opportunity cost.

For example, “Post every day” means you’re creating and posting social media content instead of doing something else. “Niche down” means choosing some marketing opportunities while potentially ignoring others. “Raise your rates” may mean earning more per project but potentially accepting a lower conversion rate or losing some current clients.

That means that any rules or advice can’t be evaluated in isolation; everything you say “yes” to means you’re saying “no” to something else. That’s not to scare you, but to highlight a reality. The things you’re okay saying “yes” and “no” to might be different from the person giving the advice. And what your business needs might be different from what their business needs.

A good question to ask is, “If I follow this advice, what am I choosing it instead of?”

A simple framework for evaluating freelance advice

Rather than simply following what other people tell you to do, run through a series of questions to see if the advice is fully, partially, or not at all applicable to you:

1. What problem is this advice supposed to solve?

2. Do I truly have that problem?

3. What assumptions does this advice make about my business?

4. Do those assumptions apply to me (that is, are they accurate)?

5. Are there specific and important context factors about the person giving the advice and do those factors apply to me (or can the advice be tailored to my situation)?

6. What would following this advice cost me, in time, money, energy, or other opportunities?

7. What evidence would tell me it’s working?

8. Could I test it before committing to it?

9. How does it move me towards my goals or help me overcome a challenge?

10. Is the person charging me a lot of money for something that worked for them but isn’t generalizable? (very important to ask before shelling out money)

Your answers to those questions will help you determine whether the rules or advice will work for you (and whether it’s worth it to pay for that advice).

You’re allowed to take the part that works for you and discard the rest

Most freelance advice isn’t all or nothing. You don’t have to either follow it to the letter or reject it entirely. You can take it, figure out what works for you, and leave the rest.

Advice about posting every day might help you realize you haven’t been visible enough, even if you only want to post twice a week. Perhaps you’re not ready to raise your rates but evaluating your rates makes you realize you could increase the project minimum or the deposit you charge.

You can understand the principle behind someone’s advice without adopting their rules in full.

Take their lesson and make your own decision about what (if any) works for you.

Evidence something can work isn’t proof you should do it

There is plenty of solid freelance advice available. There are also people whose business have grown and survived because they posted every day, niched down, raised their rates, cold pitched, built passive income, or did any number of things.

There experience is evidence something can work, but it isn’t proof you have to do it.

You’re unlikely to ever find one person who can give you the perfect set of instructions to run your business. And even if you did, those instructions would eventually need to change as your business, goals, clients or the market changed.

Rather than finding the best rules to follow, focus on getting comfortable deciding what makes sense for you.

Listen to people with experience. Learn from what has worked for other freelancers. Pay attention when someone challenges the way you’re doing things. But then take that information and evaluate it against your own circumstances, goals, and experience.

Sometimes, you’ll decide to follow the advice exactly as it is. Sometimes, you’ll modify it based on your needs. And sometimes, you’ll decide it isn’t right for you at all.

The important thing is that you’ve made these decisions intentionally.

It’s your business. The more capable you become at evaluating advice and making your own decisions, the less you need other people to give you the rules for running it.

Want to make more confident decisions about your freelance business?

That’s what I’m exploring here at Happy Freelancing. Not more rules about how you should freelance, but the questions, frameworks, and tools that can help you figure out what works for you, and then take action on it.

If that sounds useful, make sure you’re subscribed. There’s lots more to come.

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Here’s to making 2026 your best year!
Heidi

When you’re ready for more, I also offer:

• Mentoring sessions to help you get unstuck on specific business challenges and move your business forward.

• Freelancing resources designed to help you run your business, market your services, and use LinkedIn with confidence.

  • LinkedIn Profile Cheat Sheet (free)

  • 6 keyword tricks for boosting your LinkedIn profile ($5)

  • LinkedIn templates and frameworks ($6)

  • LinkedIn posting for quiet freelancers ($19)

  • From blank page to consistent posts: How I come up with a never-ending list of LinkedIn topics ($19)

  • LinkedIn Success Bundle ($39)

  • Words that attract clients: A guide to writing about you and your business ($14.99)

For those who have a regular, stable income, that question might not be as difficult to answer. But when you run your own business and income is about as even as a roller coaster in a tornado during an earthquake, it becomes a complex problem. Do I:

• Save this money for the inevitable dry spell?

• Invest in a course/tool/support I’ve been considering?

• Pay myself a bonus or splurge on something I’ve always wanted?

• Pay off debt?

• All of the above?

Each of these possibilities might feel like a huge priority. After all, a decent payday today doesn’t mean the good times will last. At some point, things will slow up and you’ll need to rely on your savings, so best to build that up. At the same time, perhaps a course, tool, or outside support will help you stabilize your business so the dry spell is less likely (or further away). But you’ve been working hard and possibly living from paid invoice to paid invoice. Treating yourself is a nice way to celebrate that hard work. And, if you’ve built up some debt, well you probably want to get that paid off, too.

Before we get into some ways to approach this question, it’s important to keep in mind that there is no one-size-fits-all answer. Your financial needs depend on your personal risk tolerance, business stability, life circumstances, and a variety of other factors that are entirely unique to you.

A framework for where to put your money

Start with your personal runway (how much money you need to save): This depends on how many months of basic living expenses you need saved to sleep comfortably at night. Some people sleep well with three months of expenses, others need six months or more. There’s no wrong answer, it’s about what feels secure to you.

Factor in your debt situation: This depends on how much high-interest and low-interest credit card debt you have. High-interest debt (such as credit cards) might need more attention. Low-interest debt (line of credit or business loan) may be less urgent. Your need to pay off your debt will depend on your comfort with that debt and how much of your income your monthly payments take from you.

Factor in your income patterns: If you’ve been freelancing long enough, you’ll have some history to look back on. If your work is genuinely cyclical (that is, summer is always slow or Q1 is quiet), you’ll need to save during your busy months to cover those predictable gaps. Knowing how long those gaps typically last will help you to predict how much money you need set aside.

If you don’t have enough history yet to know your patterns, it’s probably a good idea to err on the side of saving more until you do.

Separate business operating costs from investments in growth: Some costs are crucial, such as having internet access or keeping your website running. Those are operating costs and they’re always your first priority when it comes to business spending. After all, you don’t have a business if those aren’t paid. Growth investments (courses, hiring consultants, coaching) are important if you need your business to grow or are considering a pivot and need to expand your skills.

A little celebration is okay: Not every cent needs to be allocated to major financial goals. If you’ve been white-knuckling it through lean months, sometimes the smartest thing you can do for your business is remind yourself why you’re doing this. Maybe that’s a nice dinner, a weekend away, or replacing a device that’s held together with duct-tape and optimism.

The both/and/also approach: You don’t have to pick savings or reinvestment or debt reduction. You can allocate percentages to each. For example, maybe 50% of any income above your baseline goes to savings until you hit your runway target, with another 25% going to debt and the rest invested in your business and a tiny bit for a splurge. Once you’ve hit your runway, you can shift the percentages as needed.

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Don’t forget to reinvest

One thing I’ve noticed is that freelancers often focus heavily on debt and savings — both of which are important — but underinvest in their businesses. And I don’t just mean courses (although those can help). I mean things that free up your time or energy: a bookkeeper, a VA, better software, or outsourcing the activities you strongly dislike.

For years I took courses on aspects of marketing I don’t love, thinking I just needed to learn them better. What I actually needed was to hire someone who does love that work and let them handle it while I focus on what I’m good at (which, ironically, is exactly what I want my clients to hire me for — doing the things I love so they can focus on what they’re good at). That’s an investment that pays off in ways a course doesn’t always.

The tricky part is knowing when you’re ready for that kind of reinvestment. If you’re still building your runway or paying down high-interest debt, it might not be time yet. But if your business is stable and you’re just working harder rather than working smarter, it might be worth reallocating some of that savings toward buying yourself back some bandwidth.

Don’t forget taxes

Taxes are also important and easily forgotten. Before you save, reinvest, pay down debt, or celebrate, make sure to keep money set aside for income tax. A good rule of thumb for Canadian freelancers is 25-30%, though your actual rate might be different. Check with an accountant for guidance.

As mentioned above, what works for one person won’t work for everyone. It depends a lot on how well you sleep on a thin margin. Know yourself and what stresses you out financially, and use that as a guide.

Your life stage and business stage matter, too. A freelancer in year one with no client base might need to invest more aggressively in marketing and systems. A freelancer with 10 years and steady clients might prioritize savings and bonuses. Someone carrying debt might need to prioritize stability over expansion until the weight lifts. Someone close to retirement might be thinking about whether they have enough to pull back on work.

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Revise as your career unfolds

As much as there’s no one-size-fits-all solution, there’s also likely no life-long answer for you. Your approach in year one might change as your circumstances change, so revisit this question throughout your career. What’s more important than having a magic percentage in your head is figuring out what helps you feel stable enough to do your best work.

Have you learned any lessons about where to put your money when things are going well? I’d love to hear how other freelancers think about this.

August co-working and marketing sessions

Paid subscribers have access to weekly co-working and monthly marketing sessions. These are structured time for you to work on client work, administrative working, or marketing activities, especially those you’ve put off. Along with the structured work time, you get time to meet other freelancers, ask questions, and get insights into running a freelance business.

If you’d like to join us, upgrade your subscription.

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Here’s to making 2026 your best year yet!

Heidi

Typically, urgency has three components: time sensitivity, important enough to prioritize, and a significant consequence if it is delayed. By saying a project is urgent, the client is implying that all three of those components have been met.

In my experience, clients use the word urgent when they really mean, “it would be convenient if we could have this done quickly.”

It happened to me (again) last week. A marketing agency I often write for sent me a request for two 1,500-word articles. The deadline was less than a day. That’s right, less than a day to write 3,000 reasonably engaging, polished words. So I replied to let them know I couldn’t get the project completed on that deadline and would need until the end of the week (which was still tight, but doable). “If that deadline works for you, then I’m happy to take that on. But if it’s a firm deadline for tomorrow, I won’t be able to complete the project on time.”

The marketing agency wrote back with an apology and asked if they could get at least one article a bit sooner than Friday, and they noted that the request from the client said the client needed it “urgently.”

Now, I’m always highly skeptical of urgent requests, mainly because almost nothing in writing is truly urgent. We are not performing life-saving surgery or protecting Gotham from evil villains dressesd up in ridiculous costumes.

The client approved a slight extension. And it’s a good thing, too. Because one of the “urgently needed” articles (and keep in mind, this is July we’re in) was about planning your company’s Christmas/holiday party.

Friend, I have wracked my brain but I can truly see nothing that would be urgent about a posting an article in July on planning a December Christmas party. Even giving them massive benefits of the doubt, there is no world in which that article needs an 18-hour turnaround time.

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Why saying no is hard

As freelancers, we’re used to figuring out what people want and delivering it, on time. That’s a strength, but it also means our gut reaction to “I need this urgently” is often “How can I make this work?” rather than “Does this make sense for my business?”

For years, when I got urgent requests, my first instinct was to immediately open my calendar and look for ways to make sure I could take on the project, even if that meant shifting my entire schedule or working until 3:00 AM.

After all, why would they say they needed something urgently if it wasn’t urgent?

It took me years to realize that ‘urgent’ is often just someone’s way of making their poor planning my issue to solve. And it took me a while to get comfortable acknowledging that their timelines didn’t always work for me. Sometimes a lady wants to get her 8 hours of shut-eye and not have to justify it.

If you’re someone who hates disappointing people or worries about coming across as difficult, I hear you. But advocating for reasonable timelines is about you being intentional when it comes to your business and not subject to someone else’s whims.

If you’re constantly responding to urgency, then you’re always at the mercy of other people’s whims.

The cost of saying yes to fake urgency

Sure, you might get the project finished on time. And maybe they come back to you next time. But there are still costs to saying yes to these scenarios with zero pushback.

You train clients to expect the impossible. If you keep saying yes to these scenarios, the client has no reason to ever plan ahead or give you more time. They’ll come to expect that you’ll do everything for them last minute. That might work out well in the short term, but over the longer term and over multiple clients, it’s rarely sustainable.

It’s hard to do high quality work on a short turnaround. I know that if I had done a poor job on those articles, the client wouldn’t have said, “It’s our fault for not giving her enough time.” They would have blamed me for not doing a good enough job.

You’re giving up your personal time, sleep, or other projects for someone else’s poor planning. You’re teaching yourself that their messes are yours to fix, and you’re teaching them that you’ll clean up their messes. You’re also telling yourself that your time isn’t as important as theirs.

You never learn how to push back. Pushing back (even gently) is a bit like a muscle you need to train. It’s uncomfortable at first, but it won’t magically become comfortable unless you start doing it. Every time you say yes to unreasonable deadlines without pushing back, you’re reinforcing the habit of not advocating for yourself. Every time you do push back, you get a little more comfortable doing it.

Advocate for yourself

Your clients won’t advocate for you. They aren’t worried about your mental health, your work-life balance, or your need for sleep. When it comes to deadlines, common sense often flies out the window. (How many rational people would ever claim an article about Christmas parties is urgent in July?)

You can tell yourself these urgent requests are a one-time thing, but they won’t be. They will happen again and again over the course of your career (ask me how I know).

That’s why it’s important to be willing to push back. You don’t have to be rude, argumentative, or aggressive. You just have to be clear, concise, and firm. I don’t apologize or overexplain. I simply state the terms I’m willing to move forward with if I’m willing to move forward. Otherwise, I pass on the project.

(In this specific case, I had plans that night I wasn’t willing to miss, so I didn’t offer to take the project on at a higher rate. On another occasion, I might have decided it was worth it to do the work but charge a premium for the rush.)

Assess the urgency

When someone comes to me with something they claim to need urgently, I take a deep breath first. Reading ‘ASAP’ often gets my pulse going and feeds my people-pleasing instincts. So I pause, breathe, and ask myself some questions:

1. What happens if this deadline shifts by 24/48 hours. If the answer is “nothing catastrophic” it’s not urgent. After decades of freelancing, there has never been a catastrophic result to a slightly later deadline. I’m sure it could happen in some universe, but it hasn’t been my experience.

2. When did the client know they needed this or when should they reasonably have been expected to know? We all know when Christmas is, and they know their article pipeline. So if they needed an article in July about Christmas, they really should have requested it in June. If they’ve sat on it for months, it’s not urgent.

3. Is there a hard external deadline? For example, is this going to a print shop? Are there regulatory deadlines they need to meet? Genuine urgency usually has a concrete deadline.

4. Am I being asked to rush so someone else can take their time? I’m not giving up my sanity so your team can take five weeks to approve an article, Linda.

Asking those questions doesn’t change whether I’ll push for a later deadline or charge a rush fee. Urgent or not, I’m charging that fee. But it helps me to remember that the client likely doesn’t have a truly urgent scenario, which makes it easier for me to advocate for myself.

Scripts I use in these scenarios

The response I use in these scenarios depends on the context.

1. I would take the work on if the deadline were moved

“Thanks for thinking of me for this project. Unfortunately, I’m booked up for the next [X days/X weeks] and can’t meet your deadline. I would be able to take this on if the deadline can be moved to [give reasonable date]. If that deadline doesn’t work for you, I understand.”

2. I’ll do it, but I’m charging a rush fee

“Thanks for thinking of me for this project. Because your deadline is so tight, I do charge a rush fee [state rush fee or percentage]. If you can move the deadline to [state more reasonable deadline] then there would be no rush fee charged. Let me know how you’d like to proceed.”

3. Where they haven’t given enough information to make a decision

“Thanks for thinking of me for this project. Before I can commit, I need a bit more information. [List questions]”

4. Where I’m not going to take this on

“Thanks for thinking of me. Unfortunately, I’m booked up for the next [X days/X weeks] and won’t be able to make your deadline. Please feel free to reach out in the future if you need my services.”

Pushing back by stating your terms doesn’t make you difficult, unprofessional, or aggressive. You’re a business owner, and you have to be willing to set boundaries that protect your time, quality of work, and sanity. The first time you do it might feel uncomfortable, but the tenth time will feel a little easier. Eventually, it becomes a normal part of how you run your business.

When faced with these situations, pause, think strategically, and make an intentional decision rather than simply reacting to what’s immediately in front of you.

And remember, as always, poor planning on their part doesn’t constitute an emergency on yours.

A quick note: paid subscribers get acccess to weekly coworking sessions, most Wednesdays at 10:00 AM Pacific (1:00 PM Eastern), plus monthly marketing sessions. This month’s marketing session is Thursday, July 30, at 11:00 AM Pacific (2:00 PM Eastern). If that kind of support would be helpful, upgrade your subscription to join us.

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Let’s make 2026 your best year yet!

Heidi

Motivation is one of the topics I’m asked about most frequently, behind “Have you written any books I’ve read?” (sadly, no) and “Can you really earn a living as a writer?” (really, yes).

I understand the question. We’re conditioned to believe that without a supervisor watching us we’ll lose the ability to be productive human beings. Faced with a never-ending list of Netflix shows to watch and a big comfy bed that’s perfectly set up for nap time we’ll stop functioning entirely.

Motivation is baffling to us. We think that much like the gift for being a skilled and engaging conversationalist, some people are born motivated, and others aren’t. The motivated ones wake up every day, ready and excited to work, filled with a deep yearning to create, to get their thoughts on paper.

But the question misses something important. What we think of as being motivated is often just repeatable routines, systems, and habits that can be relied on instead of waiting for inspiration to strike.

To take an example from outside work, I walk every morning. But I didn’t used to. Although I knew exercise was important, I usually only exercised when I felt motivated to do it. That typically meant I had bursts of motivation followed by long periods of never doing anything, because if I asked myself “Do I really feel like doing this?” the answer was usually, “Hard pass.”

It wasn’t until I got a dog and he needed daily walks that I built a habit of waking up, putting on exercise clothes immediately (no time to think about whether or not I felt like it), and going for an hour walk. Now that he’s gone, I still go for my hour walk in the morning because it’s a habit I’ve built. I don’t even think about whether I feel motivated. The habit does all the work for me.

And I think that’s a key difference with successful freelancers. They aren’t more motivated than anyone else. Instead, they’ve built businesses that don’t rely on motivation.

Freelancing goes through many cycles of success and stress. But there are also long stretches where a Wednesday is just another boring Wednesday staring at a computer screen. Where you’re waiting on information from clients, and your social media hasn’t really had any impact, and it’s taking hours to get your website updated. Where everything just feels like a slog.

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This is where habits beat motivation

Habits become automatic. They don’t require motivation. They don’t need you to magically feel like doing something. They just happen.

Think about brushing your teeth. You likely don’t wake up every morning with the sun in your eyes, a song on your lips, and motivation to brush your teeth in your heart (although if you do, kudos to you). You do it without much thought. That’s because you’ve created a routine.

The same process will help you in your business: create habits, patterns, systems, and routines so you’re not relying on motivation to post on social media, follow up with leads, market yourself, invoice clients or do any of the activities you hate doing, but need to be done.

Routines reduce decision fatigue

Instead of constantly asking yourself Do I feel like doing this right now? or When should I do this?, you’ve already made the decision. It’s one less thing competing for your attention in a day that’s already full of decisions.

Some of the habits that have helped me avoid over-reliance on motivation:

Tying one task to another. I create the invoice as soon as the project is agreed to. I send out the final invoice when I submit the first draft. Those milestones become triggers for the next step, especially for tasks I used to procrastinate on. If completing Task A always leads to Task B, then Task B is much less likely to be forgotten or put off.

There are practical benefits, too. For example, creating the invoice right away means I don’t have to rely on my memory weeks later or dig through old emails to confirm what we agreed to. The information is fresh and the paperwork is already done, so I can focus on the work itself. And when the time comes to send the invoice, all I have to do is hit “send”.

Giving recurring tasks a spot on my calendar. Rather than fitting marketing in whenever I feel inspired, I schedule dedicated time each week. I also schedule time for administrative work and for business planning.

Setting policies. My policy is to reply to new client inquiries and send followups within a certain timeframe so I’m not trying to remember when the last time I reached out was (or whether I reached out at all). I also have policies around not having the tv on throughout the day, so I can’t be distracted, and being at my computer certain hours, even if I don’t have a project on the go. Just make sure you hold yourself accountable for the policies you’ve set.

Designing my environment to support my work. My office is tidy comfortable, and free from distractions. If I need to, I can close the door as a signal to others that I’m not to be disturbed. I also often put my phone in “Do not disturb” or leave it out of the office entirely.

If you don’t have a dedicated office, create a cue that tells your brain it’s time to work, and lets other people know you can’t be disturbed. Putting on your noise cancelling headphones, popping a knickknack in front of your computer, or playing classical music can all help.

Building in something to look forward to. I block out time to work on projects I enjoy, like this newsletter. Knowing there’s something rewarding in my day makes it easier to get through the less exciting tasks.

Take one small step today

Make starting easier than waiting for motivation. If a task regularly gets postponed or ignored, figure out what it is that’s blocking you from doing it when it needs to be done. Then, determine the workaround that will make it easier for you to complete the task. Create a template, tie the activity to a related task, or block space in your calendar. Often, a small change to your process is all it takes to turn something you keep putting off into something you do automatically.

You don't have to become a more motivated person to build a successful freelance business. You need to become the kind of business owner who creates systems that make progress possible, even on the days when your motivation is nowhere to be found.

Motivation comes and goes. The habits you build are what keep your business moving forward.

Here’s to making 2026 your best year yet,

Heidi

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Case in point…

…a few years ago I was at a Christmas party. One of the hosts owned a construction company and needed an important advocacy letter written. When he found out I’m a writer, he asked whether I could take it on.

“Sounds good,” I said. “When do you need this done?”

“Tomorrow morning,” was his response.

“Great!” I said. “I have a $1,000 overnight fee on top of my regular fee for the work.” I was only half joking.

In the end, he didn’t actually need the letter for another 10 days. He just wanted the letter by the next morning. Because why wouldn’t he?

Setting boundaries with clients is deeply uncomfortable, right up there with talking about your prices, accidentally sending a personal text to a colleague, or admitting you love reality tv in a room full of academics.

Especially when you’re new to running a business, you want to be known as a yes person so you can keep clients happy and coming back to you. You want to go the extra mile, all the time.

The thing is if you go the extra mile every time, you’re no longer going the extra mile, you’re moving the finish line. You get comfortable being accommodating, and that becomes a difficult habit to break. In the end, you build the “yes” muscle and the “this isn’t right for me” muscle withers away.

Saying yes to everything every client wants is a surefire path to burnout

Clients will push for the most work done in the least amount of time for the lowest price possible because that’s how humans work. Without boundaries, we tend to take advantage of others because we assume the answer will continue to be yes until we finally hear no.

“She said yes to completing a 12-page report overnight five times already, she’ll have no problem saying yes a sixth time,” is the thinking.

This doesn’t make clients bad, necessarily. They have budgets to follow, competing priorities, and deadlines of their own to meet. Often they put things off until the last minute and then leave it to you to scramble. If they have staff of their own, they’re likely used to their staff saying yes to their requests, because that’s what employees do. Or they think they need something ASAP because that’s their normal method of operation.

Often, however, when it comes down to money or time, money often wins out. Clients will agree to a longer deadline to save money. Or they’ll decrease the scope of the project, because budgets are almost always the most important factor.

But you’ll never know that if you keep accommodating everything, without asking for anything in return.

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It’s up to you to push back

The thing is, you won’t magically become comfortable setting boundaries or pushing back with clients. If your default is to accommodate everything, you’ll feel more comfortable saying yes and dealing with the burnout later than you will setting boundaries, even though boundaries protect you and keep your business more sustainable in the long run.

It’s something you have to practice so you can get comfortable with it, which means you have to be willing to be uncomfortable for a while. Like so many uncomfortable things in life, it requires effort and a willingness to push yourself.

The good news is setting boundaries doesn’t mean always saying no, it means figuring out what circumstances make “yes” worthwhile for you and leaving it up to the client to decide whether that works for them or not.

And, you don’t always have to spell out the boundary. Sometimes your action or inaction sends a message. For example, I don’t respond to client emails outside of Monday to Friday, 9-5. I can tell clients that policy if I want, but by only responding during regular work hours, I send the message that’s how I run my business.

Get comfortable setting boundaries: A process

1. Figure out what your boundaries are and what would make it worthwhile to you to be flexible.

This includes parameters around things like rushed projects, expanding the scope of a project, or clients making demands on your time (such as wanting many long, tedious and unnecessary meetings). Give the client the choice of either meeting your requirements (more money, for example) or being flexible with their needs (fewer meetings). That way, it’s up to them to set the priority and you aren’t turning down work.

In the Christmas party example, if the client had paid an overnight fee of $1,000 plus my regular rate, I would happily have gone home and written up that letter for him. $1,000 for a few hours of overnight work? That would have been worthwhile. But it wasn’t worthwhile to give up a fun night for my regular project rate. I gave him both options—pay me a much higher rate so he can get what he wants or pay me the regular amount and give me a few days to complete the project. Predictably, he chose to save money and I got to stay at the Christmas party.

2. Set policies for yourself about hours you’ll work, what constitutes a rush job, and when you’ll respond to clients.

Stick to them. Don’t let their behaviour push your boundaries. If you decide not to respond to emails outside of work times, then don’t unless it’s an absolute emergency (spoiler alert: in writing and editing, it’s rarely an actual, genuine emergency). They might send you an email after your work hours because that’s when they’re thinking about your project, but you don’t have to respond.

My favourite phrase to keep in mind was a sign on the door of a teacher’s room at school: Poor planning on your part doesn’t constitute an emergency on my part.

3. When clients come to you with an urgent situation, manage expectations.

Sometimes clients come to me one day (let’s say Monday) wanting something completed ASAP (which is vague as a deadline). I’ll often respond with, “I’m happy to work on this for you and I’ll have the time to focus on it this Wednesday.” Or, “I’m booked up for the rest of this week, but I can make it a priority next Monday.” Then it’s up to them to figure out if they’re okay with that. They almost always are.

4. Remember: It’s not your job to accommodate every request. It’s your job to build a sustainable business. Saying yes to everything isn’t conducive to sustainability.

While you might worry about losing business—and income—by saying no to clients, the truth is that unless you push back a little, clients will try to get as much out of you as they can for as little as possible. You’ll be limiting your income by saying yes to everything. Additionally, the harder you work for less money, the less time you have to find clients who respect your time and value your work.

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Boundaries aren’t about controlling clients. They’re about creating a business relationship that works for both of you, rather than one built solely around the client’s needs. Good boundaries protect your time, energy, and business while giving clients clear expectations about how you work. That’s part of running a sustainable business.

Every time you set a thoughtful boundary, you’re practicing something much bigger than saying no. You’re making a deliberate business decision instead of reacting in the moment. And every one of those decisions helps you become the kind of business owner who builds a business intentionally, rather than one that’s shaped by everyone else’s expectations.

Here’s to making 2026 your best year yet,

Heidi

You have to invoice clients if you want to get paid.

This is both true and complicated, especially if you’re in the early parts of your freelance career. I say that with no judgment. As I’ve told people at our weekly co-working sessions, in my early years as a freelancer, it sometimes took me weeks after a project was completed to send invoices to clients.

I’d finish a project, think about invoicing, and then put it off. Sometimes for a few days, sometimes for up to six weeks. This did no favours for me or my bank account, and it didn’t help my clients, either.

I can’t fully explain where the hesitation came from. I’ve never been especially good at discussing money, and nothing feels quite as aggressive, from a money perspective, as reminding someone that they owe you some. So maybe my discomfort around money was bubbling up every time I opened my invoicing software.

I also worried, deep down, that sending the invoice would somehow remind the client of something they didn’t like about my work. As if they’d see an invoice from me and think, “Oh yeah, we approved that article, but now that the invoice is here, we remember that one sentence we didn’t love and we’ll never work with her again.” Which, in retrospect, would make them exactly the kind of client I wouldn’t want to work with again anyway.

Sometimes, the work of creating and sending the invoice felt overwhelming. If I left invoicing until the last thing on Friday, sure enough, Friday afternoon would roll around and I’d think, “I’m too tired right now. I’ll do this Monday morning, when I have that fresh-off-the-weekend energy.”

Reader, I almost never had that energy. So the invoices kept getting put off, in the same way I put off emptying the dishwasher or preparing my taxes.

Eventually, I’d end up batching invoices, which meant invoicing became a much bigger, more drawn-out process than it needed to be. And because it felt like a bigger process, I put it off even more. By the time I finally sat down to create the invoices, I’d often forgotten important details. I’d have to search my inbox for the purchase order number, the exact quote we’d agreed to, the payment terms (if we had negotiated payment terms), or whether the invoice was supposed to be in Canadian or U.S. dollars. Which, of course, made the whole thing take longer.

And so weeks would go by before I sent an invoice.

That delay didn’t make things easier for my clients, either. Many clients work with budgets, and once money has been allocated to a project, they often want to pay it and close the loop. They don’t necessarily want that amount sitting in their system for weeks while everyone moves on with their lives and new bills come due.

And, because many clients don’t pay on receipt of invoice—they have their own payment terms—waiting several weeks to invoice meant I sometimes wouldn’t get paid until more than two months after a project was done. Not great for my credit card, my cash flow, or my confidence.

Looking back, I realized it wasn’t just about the invoices; I was avoiding the discomfort that comes with asking to be paid. The best way to deal with that discomfort is to set up systems that do the heavy lifting for you.

These days, I have a firm policy for creating invoices and following up on payment. It means I get paid much faster and I’m not spending hours searching my inbox for crucial details I promised myself I’d remember.

Here’s what changed

I use an invoicing system

Yes, my invoicing system costs about $50 a month. And yes, it’s worth it. The time and mental energy it saves me more than make up for the cost, especially because it removes so many energy-sucking decisions from the invoicing process.

Each client has its own payment terms, tax settings, currency, and billing details. That means I don’t have to remember whether this client pays in 15 days or 30, what that client’s tax status is, or whether the invoice should be in Canadian or U.S. dollars. The system remembers for me, which is good, because my brain is too busy remembering where I last saw my phone.

I write up the invoice as soon as the project is approved

Once I have approval to go ahead with the project in my inbox, I go straight to my invoicing system and create the invoice.

This is the step that has probably made the biggest difference. When the project is newly approved, all the details are still easy to find. The quote is recent and the purchase order number, if there is one, is usually in the latest email thread. I’m not trying to reconstruct the project from memory three months later while searching my inbox for the specific email where we laid out the terms.

Creating the invoice right away also means the hard part is already done. When the project is finished, I just log into the system, review the invoice to make sure it’s still accurate, and hit send. I literally have no excuse not to send it right away.

I charge a deposit

Charging a deposit helps weed out clients who may not be serious about paying. It also smooths out my cash flow, which is not a small thing when you’re self-employed. But it also forces me to create the invoice immediately.

When the final invoice goes out, the client can see the amount already paid and the balance owing. I don’t have to do the math manually or remember what was paid when. I don’t have to create a second little spreadsheet that I will definitely forget exists. The system handles it.

And because the client has already paid something, the final invoice feels less emotionally loaded. The payment relationship has already begun. I’m not suddenly introducing the idea that my work costs money.

I send the final invoice immediately after submitting the work

The rule I follow is that once the work is submitted, the final invoice goes out immediately. No putting it off until tomorrow or Friday or when I’m desperate for money.

What I may not have wanted to admit to myself is that there’s an awful lot of mental energy that goes into not invoicing people. Because every time I thought about it, I’d weigh whether or not I had the energy to send the invoice, feel guilty for not sending it, then negotiate with myself when I could send it. Now, there’s almost no mental energy required for the process.

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I follow up before I’m annoyed

In the past, I’d avoid sending the invoice, then avoid checking whether it had been paid, then suddenly realize the payment was late, then put off following up until I was cash-strapped and resentful. Which meant my first follow-up came from a place of irritation.

These days, I try to make payment follow-up boring. If an invoice is approaching its due date, I check the status (and yes, my invoicing system tells me when payments are overdue). If the client hasn’t yet viewed the invoice, I’ll send a quick email to confirm they’ve received it, double-check the correct email to send it to, and offer to resend it if they can’t find it.

If it’s overdue, I send a polite follow-up.

Hi [Name],

I’m following up on invoice #[number], which was due on [date]. Could you let me know when I can expect payment?

Thanks so much,

[Name]

Invoicing is part of the project

For a long time, I treated invoicing as separate from freelancing.

But invoicing, following up on payment, and having a system are all part of the work of freelancing. Invoicing is the administrative step that allows the business relationship to function. Reframing it as part of the work has helped me be more systematic about it. If they’re professionals, they should be expecting an invoice, not praying it won’t come (and if they are praying it won’t come, they probably won’t make for great repeat clients).

You did the work. Now the client needs the invoice so they can pay you for it.

Start small:

• Create the invoice as soon as the project is approved so you aren’t relying on memory.

• Send it as soon as the work reaches the agreed invoicing point.

• Use software or templates so you’re not constantly building from scratch.

• Follow up calmly when payment is late.

Your system doesn't have to look like mine. You might use accounting software, manually-built templates, or a spreadsheet. The important thing is building a system that doesn't rely on you feeling motivated or excited to do an uncomfortable task.

Can you believe we’re half-way through 2026?

One minute we’re in December looking forward to the year and optimistically planning how we’ll make 2026 our best year ever, and the next, we’re halfway through, wondering what happened to the first six months.

This is a good moment to look at your freelance business beyond the next invoice.

Invoices are important, for obvious reasons. They pay for groceries, software subscriptions, taxes, and the occasional fancy dinner. But when our whole business is viewed invoice by invoice, it can start to feel like we’re constantly reacting to our balance sheet. Finish the work, send the invoice, follow up, check the bank account to see if payment’s come in yet. Repeat until retirement, or at least until the next CRA instalment reminder.

Thinking in quarters gives us a slightly wider lens through which to view our business.

Why quarterly planning works for freelancers

A quarter is long enough to see patterns, but short enough to feel immediate.

An annual plan can become an outdated document that lives in a folder, alone, ignored and unopened like a new year’s resolution. No matter how far off the rails things go, everything feels like a problem for November-you to sort out.

A monthly plan can feel too immediate. After all, all it takes is one delayed project, one slow-paying client, one family emergency, or one week of feeling like your brain has been replaced with oatmeal, and the month is suddenly way off track.

A quarter gives you a useful middle distance. You’re still close enough to the work to make practical decisions, but far enough out to see what’s forming. Over three months, you can start to notice what needs attention before it becomes urgent: the pipeline that’s gone a little thin, the payment terms that need tightening, or the workload that’s creeping past capacity.

That wider view can make the business feel less reactive.

That might mean:

• building a healthier pipeline things slow down

• reviewing whether current clients still fit your goals

• setting aside time for admin before it becomes a paperwork mountain (I’m committed to spending more time filing my receipts and invoices so tax time is less of a nightmare)

• planning rest before your body forces you to

• deciding which offers, services, or relationships deserve more attention

When I only look at the next invoice, every decision feels urgent, because every decision is focused on landing that next client.

That urgency makes sense. Freelancers have bills, tax instalments, and moments of wondering whether time spent refreshing your inbox counts as a billable hour. But when all you do is focus on the next invoice, it’s easy to miss the patterns forming underneath your work.

A quarterly view gives you a bit more distance. You can still pay attention to cash flow, while also noticing whether the clients, projects, timelines, and energy demands are adding up to a business you want to keep running.

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I’ve been thinking about that message a lot the past few days. Partly because it was
kind and unexpected, and partly because I am always a little startled when
something I’ve shared helps someone else feel less alone. I think as
freelancers, because we work in alone we also think we experience things in
isolation. We’re the only ones going through it, so we’re surprised to hear
that someone else has been thinking the exact same thing.

When I do go through something tough, my instinct is usually to wait until I’ve made it through to the other side, learned my lesson, taken stock of my emotions, and can present the whole thing like a tidy story with a beginning, middle, and end. It feels better to say, “I’ve gone through this and I know from experience you can, too. Here’s how I know.”

But freelancing doesn’t always give us tidy stories with a lesson learned like an after-school special. Often, it gives us cycles.

Freelancing has cycles

Too much work, followed by not enough, followed by too much, followed by not enough. Burnout, then anxiety. A full calendar, then an empty one. A period where
everything feels easy, followed by a period where you start wondering if all your clients have fallen into a collective coma, that’s how little you hear from them.

If I’m being honest — and why not? — I’ve been feeling stuck lately. There hasn’t been one dramatic event so much as a pileup: clients ghosting, projects changing direction, budgets shrinking even though those clients have more money than some small countries, and personal losses taking up all my available headspace and energy. On their own, those things would be more manageable, albeit still daunting. Together, they’ve made it harder and more exhausting to find my footing again.

Listen, freelancing has plenty of obvious perks. You can work from home. You get to choose your own clothes. If you feel professional, you can dress up, but if you’re not feeling it, hello pyjama day. You can make coffee whenever you like and snack on the chips in your cupboard throughout the day. You can eat lunch at 11:00 am or 2:00 pm, or whenever your stomach decides it needs nourishment.

And yet, it wears on you.

The stress of doing it all yourself

You’re constantly looking for clients, managing the clients you have, wondering if you
have too much work or too little, and trying to keep your business visible without turning into a content machine.

You pitch and follow up. You network and send letters of introduction. You take
meetings, then check your inbox constantly hoping you proved your worth to them.
You do the work, then you look for more work, then you wonder if the work
you’re doing now is getting in the way of the work you need to find next.

Some months you’re burned out. Other months you’re riddled with anxiety that you’ll never work again. Many months, you’ll feel both. Every decision you make is filled with anxiety, uncertainty, and indecision.

Should I have taken that job? Should I have walked away? Should I have charged more? Should I have charged less? Was that comment by the CEO a sign they’re going to avoid payment? Has that past client I just pitched at their request ghosted me or are they planning on coming back in six months for me to finally do the work like they did last time? (This last question is based on personal experience.)

And right now, in many industries, it’s a very slow time. The economy is tough, communications departments are being slashed, those that are intact are being asked to do more with a smaller budget, and because so many communications people are losing their jobs, there’s more competition for freelance work.

Slow periods feel permanent, even if they aren’t

I know freelancing has cycles. I’ve been through slow times before: recessions, Google algorithm changes, COVID, mass communications department layoffs. I’ve lost clients before, sometimes a few all at once. I’ve had work disappear, budgets shift, priorities change, and promising conversations result in zero work.

When all those things pile on, it’s normal to feel stuck. And when you feel stuck, it’s hard to imagine you’ll ever feel unstuck again.

You can remember that things have changed before and still feel hopeless. Even if you know you have skills, experience, and resilience, you can still wonder whether you’ll be able to build momentum again.

This is where a lot of freelance advice starts to feel somewhat irrelevant: Charge more, protect your time, build a pipeline, post consistently, diversify, niche down, niche up, and niche sideways (I’m only partly joking here).

There’s value in that advice. But when you’re anxious, depressed, grieving, lonely, financially stretched, or simply tired of making every decision yourself, advice that assumes you have energy falls flat. After all, if you can’t imagine yourself ever finding clients again, how motivated are you to post on social media?

Find a little breathing room

Sometimes the first helpful move is to ease the pressure.

For me, easing the pressure has meant I’ve been looking at part-time job options, changing parts of my business, and making a more deliberate effort to find joy outside my work. That last one sounds simple, and also like something printed on a mug, but it helps (and sometimes the mugs are right!). When work is uncertain and life has already taken a lot out of you, you need places where every moment isn’t about solving, deciding, rebuilding, or bracing for the next thing.

For another person, easing the pressure might mean taking on a contract that creates
stability, reducing expenses for a while, reaching out to past clients, talking honestly with another freelancer, applying for a job, changing services, resting before making another big decision, or getting support for anxiety or depression.

All are valid, and all can help.

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You have options

If you’re feeling stuck or in a low cycle right now, I hope you can give yourself a little grace. It makes sense if you’re exhausted or if freelancing is getting to you. It’s getting to me, too. It’s normal to love freelancing and still wish that someone else could be responsible for literally anything. At this point, I’d take a magic 8-ball making decisions for me, although I suspect if I asked it if it would make decisions for me, the answer would come back “Don’t count on it.”

Feeling stuck can make optimism feel impossible. Taking action, even when the action is small, can remind you that you have some control in your business. And feeling that you have some control can lead to feeling more optimistic.

Look for a bit of breathing room, whether that’s a conversation with someone who hears you, a small change you can make that doesn’t feel overwhelming, or a practical option that eases some of the immediate stress. And, if at all possible, try to find some joy outside work, so that the burden of work doesn’t overtake your entire life.

A question I ask myself when I’m feeling stuck (after I’ve let myself feel sad for a few days) is “What is causing me the most stress right now and what is the simplest way to ease that stress?”

And, for what it’s worth, every slow cycle I’ve ever been through has been followed by a very busy cycle. Things have shifted before. They can shift again, although it will most certainly take longer than any of us would like.

In the meantime, be kind to yourself and remember, you’re not alone.

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It was a solid offer. Left to my own devices, I would have accepted it right away. My exact words to myself after seeing the offer in my inbox were “Let’s do this.” Not so much because it was a decent offer (although even at $30,000 under asking, it was decent), but because accepting it would have ended the uncertainty and emotional roller coaster that go along with selling the family home after a death.

There would be no more worrying that I couldn’t sell the home, no more anxiety over our beloved property sitting empty, and no more crying every time I thought about strangers walking through the house, judging every decision my parents had made in building it. I could be done with trying to carry on with normal life while one of the biggest emotional and financial decisions I’ve ever made sat there, unresolved, taking up precious room in my brain.

I was fully ready to accept the offer, move to the next step of settling my sister’s estate, and be done with this particular stretch of uncertainty.

Then I talked to my realtor.

She didn’t pressure me. She said it was up to me, and that it was a good offer. Then she added, “It’s only been on the market for two days. We’re showing your house six more times tomorrow, so maybe you want to wait a day before you make a decision.”

The next day, I got an offer $1,000 above asking ($31,000 above the original offer, for those who like math).

Since last weekend, I’ve kept thinking about how easily I could have missed out on $31,000 simply because I wanted the discomfort to be over as quickly as possible, and how my tendency to seek certainty and avoid discomfort has been a hindrance in my professional life (this experience just magnified it about 1,000 times).

We hate discomfort

When freelancers talk about undercharging, we often focus on confidence, experience, or market rates. While I absolutely believe those play a role in our charging, I don’t think they always explain the whole thing.

Sometimes we quote lower than we would like because we’re afraid of rejection or we’re people pleasers at heart. Sometimes we do it because the client seems nice, the project sounds meaningful, or the economy is tough.

And sometimes we lower the price because we want to avoid the discomfort that comes with waiting for someone to approve our price.

Sending a quote creates a limbo. The number is out there, and now the client may say yes or they may say no. They may ask to negotiate. They may disappear into the professional void, never to be heard from again.

What makes that limbo so uncomfortable is that we’re not only waiting for a yes or no, we’re waiting for someone’s judgement on our pricing. We’re waiting to find out whether they think the number is fair, a bit high, or completely detached from reality. Pricing can make even experienced freelancers feel exposed, especially when part of us is wondering if the client has opened the quote and thought, “Is this person out of their mind?” or worse, “Are we insane for thinking we could work with her?”

To avoid this, our brains can start looking for a way to eliminate the discomfort. A lower price can seem like the fastest route to an easier yes. We may tell ourselves we’re being strategic, and sometimes we are. But other times, we’re choosing emotional comfort over a healthy bank account.

Emotional comfort can get expensive

There’s a very human reason a lower price is appealing: it minimizes the discomfort.

• If I lower the quote, I might get a faster yes.

• If I ask them what they’re willing to pay, I know what I have to tell them to get a yes, so I don’t have to guess at my price.

• If I accept the offer, I can stop waiting.

• If I make the number easier for the other person to accept, I can avoid the vulnerability of having someone look at my price and decide whether I’m worth it.

It provides immediate relief, but it’s also a trade-off: emotional comfort now in exchange for financial pressure later.

This is where undercharging gets tricky, because the emotional payoff is immediate. The lower price may calm the nerves, end the limbo, or settle the decision. The financial cost appears later, when the project takes longer than expected, when there isn’t enough room for better-paid work, or when you need to take on more projects to reach the same income.

That doesn’t mean every lower price is a mistake. Sometimes a project fits a smaller budget because the scope is smaller. Sometimes a discount has a clear reason and a clear boundary. Sometimes the money is not the only factor, and that can be a valid choice.

But it helps to be honest with ourselves about what we’re choosing and why. Am I offering a lower price because the scope is smaller, the client relationship has earned some flexibility, the project has a clear strategic benefit, or I’ve decided this discount fits within my business? Or am I lowering the price because I don’t want to wait, I’m worried they’ll think I’m out of my mind, or I want the discomfort to end?

A lower price may buy immediate relief. A healthier price may require sitting with uncertainty a little longer. But the longer you put off sitting with the discomfort, the longer it’ll take you to get comfortable with it.

The pause before the price drop

I don’t think the goal is necessarily to become someone who feels perfectly calm while waiting for a client’s response. If that person exists, I hope they’re using their powers for good and also teaching the rest of us how they sleep.

For most of us, pricing will probably always involve some discomfort. There may be a stomach swoop after sending a quote. There may be a strong urge to lower the price, accept the first offer, or make the conversation easier so the uncertainty ends.

Discomfort can provide useful information, but it’s a terrible deciding factor. It may be telling us to slow down, check the numbers, revisit the scope, or ask a better question. But if it becomes the only reason we’re choosing something, we’re no longer pricing the work, we’re pricing the fastest route out of an uncomfortable feeling.

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It’s useful to ask whether a lower price is solving a business problem or an emotional one.

• If the scope is smaller, a lower price may make sense.

• If the client is trusted and there’s a clear reason for a discount, it may make sense.

• If the project genuinely fits your business at that rate, it may make sense.

But if the lower price is mostly there to end the waiting, avoid rejection, or make someone else happy at your expense, it may be worth pausing before you send it.

A few things to remember:

• A fast yes can feel good and still be costly.

• A good offer can still be lower than the right offer.

• Discomfort provides useful information, but not the rationale for the entire decision.

Outside perspective can interrupt the pattern

What helped with the house offer was talking to someone about it who guided me without telling me what to do. My realtor didn’t say, “Reject this, we can do better.” She simply added information I didn’t have and showed me that waiting wouldn’t be the end of the world.

“This is your call. Also, there are six more showings tomorrow.”

That sentence gave me room to think past the initial relief (and excitement) that the process might be over. Rather than falling into my familiar habit of rushing to accept whatever was in front of me, I took a breath, listened to what she said, and waited a day before deciding. And yes, it was a day filled with discomfort and second-guessing whether I should have taken that first offer. But I survived it.

Freelancers often need that same kind of pause. A mentor, peer, or trusted business friend can help us see the full picture when our own discomfort is pushing us toward the fastest resolution.

Someone outside the moment can say:

• “Have they already rejected the higher price, or are you lowering it before they’ve had the chance?”

• “Is this a discount you want to offer, or are you trying to get out of the waiting?”

• “If their budget is lower, could the scope be smaller?”

• “Would you still feel good about this rate halfway through the project?”

• “When you’ve lowered your price in the past, what has the result been?”

Those questions are useful because they don’t shame the impulse, they simply slow it down. Sometimes slowing down to take a moment to think is enough.

And yes, if you’d like, I do offer mentoring sessions.

Let’s make 2026 your best year yet,

Heidi

Of course, writing and editing aren’t the only part of running a freelance business. There’s also the business part of it: setting prices, managing clients, making decisions, planning capacity, marketing, and overseeing cash flow. That’s the stuff CEOs do, even if you’ve never once referred to yourself as a CEO without making a face or gagging a little.

As I start this series about managing your own business (or being your own CEO), I thought we’d start with something lighter: A fun, unofficial self-assessment.

This isn’t a diagnostic tool; I wouldn’t go around putting the results on a business card or adding them to a LinkedIn profile. But it might help you notice the patterns you bring to your business, including those that help you and those that might be getting in your way.

Answer these questions honestly and read on for some thoughts about the different CEO styles. For paid subscribers, there’s a link to a guidebook that goes more in-depth into the CEO types, what to watch for, what questions to ask, and strategies for working with your natural style.

1. When you look at your business, you’re most likely to notice:

A. What it could become

B. What needs to run more smoothly

C. What you’ve been putting off

D. What needs fixing right now

E. Who needs something from you

2. Your business planning style most frequently involves:

A. A burst of ideas in a notebook, app, or random email to yourself

B. A list, calendar, spreadsheet, or workflow

C. A vague intention to think about it later

D. Responding to the most urgent problem first

E. Planning around other people’s needs

3. Your clients probably appreciate that you are:

A. Creative and forward-thinking

B. Reliable and organized

C. Thoughtful and skilled

D. Resourceful and responsive

E. Generous and caring

4. The pattern that most often gets you into trouble is:

A. Starting too many things and not finishing them

B. Carrying too many things at once

C. Avoiding too many things and feeling panicked

D. Rescuing too many things that weren’t your mess to begin with

E. Giving too much away for free

5. Your business would benefit most with more:

A. Focus

B. Space

C. Confidence

D. Boundaries

E. Clear expectations

Mostly A: The visionary CEO

You’re energized by possibility. Watch for idea sprawl. Try choosing one main priority for the next 90 days.

Mostly B: The operator CEO

You know how to get things done. Watch for becoming the engine of everything. Try protecting time for strategy, not just delivery.

Mostly C: The reluctant CEO

You care about the work, but the business-owner parts may feel awkward. Watch for avoided decisions. Try a simple monthly CEO check-in.

Mostly D: The fixer CEO

You’re excellent when things are messy. Watch for building a business around urgency. Try separating true emergencies from habits of responsiveness. Not every crisis is yours to fix.

Mostly E: The overgiver CEO

You care deeply and want clients to feel supported. Watch for blurred scope and emotional overextension. Try defining what is included, what costs extra, and what needs a separate conversation. Then hold those boundaries.

If you found your CEO type and immediately thought, “Oh no, that explains a few things,” I’ve created a deeper companion guide for paid subscribers.

Inside, I break down each CEO type with:

• What you’re probably already good at

• The patterns that may trip you up

• What to watch for when business gets busy, stressful, or weird

• Small strategies to help you work with your natural style instead of fighting it

You can read the full companion guide by becoming a paid subscriber.

Subscribe now

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We schedule meetings, write proposals, market ourselves, develop routines, and slowly assemble the pieces of a business.

All of those activities matter. It’s hard to run a freelance business if you can’t send an invoice, book a meeting, or explain what you do without sounding like you’ve been spontaneously pulled into an improvised comedy sketch without being told what the scene is.

But over time, we start to realize the visible task is rarely the whole deal. There’s a lot more underlying every activity we undertake.

Take scheduling

On paper, scheduling looks simple. Someone wants a meeting with you and you’re free, so you book the meeting. Or you’re not free, so you suggest another time. But that’s like saying writing an essay is easy because you know how to write sentences.

In real life, you’ll be asked to decide things like

• whether to wake up at 5:00 am to meet with a client from a different time zone because they can’t make any other time work

• whether to accept the fifth meeting in two weeks with a micromanaging client

• whether to give the person who flaked on two previous discovery calls a third chance because the project sounds fun, if only you could get them on a call

• whether to prioritize the edit due Tuesday or make room for a promising potential client

And you’ll be making these decisions (and many more) again and again (and again and again) throughout your career.

As my career progressed, I noticed the visible task—the action we take—is rarely the whole task. The parts that wear me down are often the decisions underneath it: when to follow up, when to hold firm, when to be flexible, what’s worth fighting for, when my availability helps me and when it hurts me.

Pricing isn’t just choosing the number to charge; it’s being willing to say the number out loud, hold firm when you get pushback, and stop treating every “that’s outside our budget” as a problem only you can fix.

Invoicing isn’t just writing and sending the invoice; it’s noticing when it hasn’t been paid, deciding when to follow up, keeping track of how many reminders you’ve sent, and figuring out what to do when a client who was very reachable during the project pulls a Houdini when the payment is due.

Marketing isn’t just having a website or a LinkedIn profile; it’s about showing up before you feel completely ready and continuing when a post (or three) fails to summon a never-ending list of your ideal clients.

You decide how your business looks

I thought freelancing meant no one else got to tell me what to do. Eventually, I realized it also meant no one else was coming to make the hard decisions for me. I’m the one weighing every single trade-off and deciding whether or not it’s worth it.

And there are many trade-offs.

“If I take this 5:00 am call, I might land the client, but then they might start to expect more 5:00 am calls. If I don’t take this call, I might not land this client, but do I want a client who expects me to be functional before the birds are even awake? Technically I can wake up for 5:00 am, but should I?”

And that’s just your first decision of the day.

A business gets shaped either intentionally or accidentally. When we make informed decisions based on the long-term sustainability of our business, hold our boundaries, and stand firm even when things are tough, we’re shaping the business.

But when we avoid decisions, when we let other people’s priorities and urgency become ours, the business gets shaped by those forces instead. We may still be doing the work, sending the invoices, and answering the emails, but the direction of the business starts coming from other people’s expectations.

Intentionally shaping a business takes energy. It can mean saying no, setting firmer boundaries, raising rates, rethinking old offers, and letting go of work that no longer fits. And because that work is hard, it’s tempting to hope something outside us will make everything easier. A dream client will appear, offer a mind-boggling amount of money for reasonably easy work on a fun long-term project, and pay early without being asked.

Essentially, we’re hoping for someone to rescue us so we don’t have to make the hard decision or take the uncomfortable action.

I know this because I have tried several variations of waiting to be rescued, all without success. I have:

• Waited for clients to indicate they’re willing to pay more before raising my rates.

• Hoped no one would test my boundaries so I wouldn’t have to enforce them.

• Opened my inbox hoping a dream client had appeared through sheer force of optimism, despite the fact that I had done very little marketing. A bold strategy, and not one I would recommend building a pension plan around.

• Taken courses expecting they would share the magic formula that would make everything come together seamlessly, with little discomfort on my part.

• Stared at my computer screen wondering “why can’t this just magically be easier?”.

The hard part was admitting that none of those were business strategies. They were just ways of avoiding the discomfort of choosing.

The problem with autonomy

Many of us get into freelancing because we want to be our own boss. We want fewer unnecessary meetings with no one hovering over our shoulder and no performance review written by someone who views Bill Lumbergh as inspirational.

But being your own boss still means someone has to be the boss. Someone has to notice when the marketing has stalled, the rates no longer pay the bills, the client hasn’t paid, and the entire business is held together by a unicorn’s dream.

I was used to wanting autonomy. I was less used to being the person who had to decide what to do with it.

The reasons we get into business for ourselves—to be in control, have autonomy, make decisions based on goals we’ve set—come with responsibilities we may not fully appreciate at the start of our business.

It’s easy when you’re employed to look at decisions your employers make and think, “that’s not how I’d do it.” But when you’re the one making the decisions, you discover they come with a long list of trade-offs, and you’re the person who has to weigh all of them and set the priorities.

That responsibility can feel overwhelming. It means there isn’t always someone else to ask for permission, overrule us, or make the difficult call. I can ask for help. I can gather information. But I’m still the one who has to choose what kind of business I’m building and what I’m willing to do to support it.

That’s where the freedom is and also the responsibility: I get to shape the business, and I’m responsible for the shape it takes.

More articles on freelance decision-making:

Here’s what’s coming up in May:

If you’re a paid subscriber to Happy Freelancing, you have access to:

• The “Be Your CEO” series: A new series designed to help you step back from the day-to-day and run your freelance business with more intention and clarity. This will include articles, templates, worksheets, and guides to help you feel more in charge of your business.

• Weekly coworking sessions: Where we answer questions, talk through business issues, and get work done together.

• “Let’s Do Marketing” sessions: Focused time to tackle marketing questions and do concentrated outreach work.

  Subscribe now

  ---

I’m Heidi, founder and writer of Happy Freelancing. I’m a freelance writer and editor with 20 years’ experience, winner of the Abbotsford Arts Council award for Outstanding Artist in the Literary Arts, and I’ve been mentoring writers and freelancers for 15 years.

When you’re ready for more, I also offer:

• Mentoring sessions to help you get unstuck on specific business challenges and move your business forward.

• Freelancing resources designed to help you run your business, market your services, and use LinkedIn with confidence.

  • LinkedIn Profile Cheat Sheet (free)

  • 6 keyword tricks for boosting your LinkedIn profile ($5)

  • LinkedIn templates and frameworks ($6)

  • LinkedIn posting for quiet freelancers ($19)

  • From blank page to consistent posts: How I come up with a never-ending list of LinkedIn topics ($19)

  • LinkedIn Success Bundle ($39)

  • Words that attract clients: A guide to writing about you and your business ($14.99)

Additionally, I’ve taken courses, spoken on panels, led countless workshops, guested on podcasts, been interviewed, taught courses, and written many articles and guides about writing and editing.

I don’t say any of this to brag, but to underscore the following statement:

Even with all that experience, I still struggle to see myself as an expert.

When I meet with potential clients, I still feel as though I have to prove something to them. When clients tell me they want something, even if everything in me says, “that’s not the best call,” I struggle to speak up. I’m better than I used to be, but I still find it hard. I can refer to myself as an expert because I know after 20 years in two industries I must be, but knowing I fit the parameters and behaving like an expert—feeling it in my bones and letting that fuel conversations—is an entirely different matter.

To be clear: I don't think experts have all the answers. They have experience, perspective, and judgment, and they know what they don't know. In content especially, where the variables are endless and outcomes unpredictable, certainty isn't the goal. Good judgment is.

But even given that I don’t expect experts to have all the answers, I still struggle to feel like one.

While it might not seem like a big deal, not feeling like an expert can hold a business owner back. If you don’t feel like the expert you are (and you don’t need 20 years of experience to be an expert) you likely:

• Undercharge for the work you’re doing

• Don’t speak up when you see a potential issue

• View yourself less as a collaborator or partner and more as a service provider

• See a power imbalance between yourself and your clients

All of this adds up: you end up underpaid, overworked, and stuck in a dynamic where the client holds the power and you're just there to execute.

A note about imposter syndrome:

I don’t think this is imposter syndrome, at least not directly. I’m not afraid clients will find out I’m faking anything, because I’m not. I know I’m good at what I do—I have plenty of testimonials and repeat clients to bolster my confidence. But when clients push back, I tend to second guess myself. When they want something that deep down I know isn’t going to help them, I hesitate before suggeting other options. I defer to their ideas and opinions, even when I have my own, telling myself they know their business better.

But they hired me because I know something they don't.

Where does this feeling come from and what can we do about it?

There are a few places not feeling like an expert could come from:

The power dynamic of being hired versus being the hirer

Potential clients reach out to us to determine whether they should hire us. That puts us in the position of proving to them we’re worthy of the job. They have the power to decide whether or not to work with us. When they decide not to work with us, it's easy to take that as evidence we're not good enough, and that chips away at how we see ourselves.

What to do:

It’s important to be in the driver’s seat sometimes, so you remember you have some power as well. Evaluating potential clients to see if they’re a good fit and turning them down if they’re not, for example. This means you’re not only on the defensive, proving your worth to potential clients.

Once you're hired, that same principle applies: make your expertise visible to keep yourself in the driver’s seat. Document your reasoning for clients. Before, when I made changes or decisions, I simply took the action: changed the wording, altered the heading, added in a section. When clients didn’t like it, they often changed it back or rejected it, which undercut my feeling of expertise. Now, I explain my reasoning in the comments. That has decreased the amount of pushback I get because they understand the logic behind my decision.

For example, I might write, “You had ‘fees’ in the brief for this header, but given you previously stated you don’t like the word ‘fees,’ I’ve changed it to ‘costs.’” This shows I’m not arbitrarily changing things; I’m paying attention to what they’ve indicated they want and making decisions based on the information I have.

It also shifts the dynamic: instead of waiting for them to approve or reject my work, I’m showing why I made the call.

Along the same lines: watch how you frame your decisions. Asking “Are you okay with this?” or “Is this all right?” invites pushback and positions you as someone seeking permission. You're not. You made a choice based on experience. If they disagree, they'll say so. You don't need to ask.

The fact that everyone learns English

Anyone who’s graduated in Canada (or the US) has learned at least some English, including how to write. While they may not do it as well as we do, they still feel they know it and can do it. Add to that the fact that AI can now do some of it (regardless of whether you think AI could do it well), and it seems to some people like a job anyone can do.

I’ve had potential clients say to me “I could do this, I just don’t have time.” They have that confidence because they took an English class or two. Worrying that anybody with a keyboard and an English class or two under their belt can do your job will definitely undermine expertise.

What to do:

Yes, we write and edit. But that’s like saying a chef “cooks food.” Technically true, but it misses everything underneath.

We understand how an audience will read, interpret, react to, and act on a piece of text, and we write or edit accordingly. We know how to weave tone, voice, and style into a cohesive experience. We see where each document fits in the reader’s journey, and what this piece in front of us needs to do to move them forward.

Writing a sentence is the surface. Knowing which sentence, where, and why is the work. Talking about these layers publicly (on social media, in conversations with clients) helps both you and your potential clients remember that “I took English” isn’t the same as “I can do what you do.”

How we attribute our successes and failures

We have a tendency to attribute our successes to luck and our failures to lack of skill. That means we have no ownership over our successes and full ownership over our failures.

What to do:

The truth is probably a balance of the two: our successes might have an element of luck but also skill, hard work, and expertise. Our failures may have an element of bad timing and bad luck, and possibly having rushed through a project, not paid enough attention, or having taken on a project that wasn’t the right fit.

Failures and successes often have the same mix of internal and external factors, we just weigh them differently.

When you assess your wins and losses, include both internal and external factors. You'll start to see where your hard work and expertise moved the needle—not just where you got lucky. And when something doesn't go well, look deeper than “I'm bad at this.” What else was at play? What can you carry forward? What can you do differently next time? When you focus on lessons that can be learned, as opposed to simply “I”m not good at this,” you reframe your failures.

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The absence of external scaffolding

Employees get recognized for their successes with promotions, new titles, performance reviews, and pay increases. They get external signals that indicate they’re building expertise. Freelancers get paid. And then we start the next project from zero again.

What to do:

Without external recognition, our expertise has to be internally claimed.

Build your own scaffolding, as much as you can. Track milestones, including projects you’re proud of, dream clients you’ve landed, and outstanding results. Keep a folder where you mark your wins and do your own performance review (maybe every quarter or twice a year). Go over what went well, what you’ve learned, and where your greatest successes were.

You can also seek external recognition by applying for awards, pitching to speak at conferences, and asking for testimonials (and reading them).

And remember, that anyone with 10+ years in any industry would be considered at least advanced if not expert.

So where does this leave us?

I don’t think the goal is to suddenly feel like an expert. I’m not sure that day comes. But I do think we can act like one, even when the feeling lags behind. And we can do it without necessarily “faking it.”

I’ve started small:

• Documenting my reasoning for clients, so my expertise is visible.

• Giving myself permission to say “I need some time to consider this” instead of reacting in the moment when I’m caught off guard.

• Asking questions like, “Have you considered…” instead of saying, “Here’s what I think you should do…” It feels less forceful while still demonstrating that I’m engaged, thoughtful, and bringing ideas to the conversation.

These aren’t huge shifts, but they’ve made a real difference in how I view myself and my expertise. I stand firm more and second-guess myself less.

That’s the work, I think. Not waiting to feel like an expert, but practicing what it looks like to be one.

What’s one step you could try this week?

Give this a read

If you’re looking for a bit more money guidance (and who among us isn’t?), check out this fantastic article from Dear Money Letters: You’re Not Bad at Money, You’re Just a Freelancer.

Dear Money Letters

You’re Not Bad at Money, You’re Just a Freelancer

Dear reader…

Read more

7 months ago · 7 likes · 5 comments · DearMoney Letters

Here’s what’s coming up in May:

If you’re a paid subscriber to Happy Freelancing, you have access to:

• The “Be Your CEO” series: A new series designed to help you step back from the day-to-day and run your freelance business with more intention and clarity. This will include articles, templates, worksheets, and guides to help you feel more in charge of your business.

• Weekly coworking sessions: Where we answer questions, talk through business issues, and get work done together.

• “Let’s Do Marketing” sessions: Focused time to tackle marketing questions and do concentrated outreach work.

Subscribe now

When you’re ready for more, I also offer:

• Mentoring sessions to help you get unstuck on specific business challenges and move your business forward.

• Freelancing resources designed to help you run your business, market your services, and use LinkedIn with confidence.

But the more I think about it, the more I suspect that many say lonely when they mean isolating.

It can be deeply isolating to work for yourself from home, because you can be surrounded by people and still feel that you’re doing everything alone. And, technically, you are.

Decision-making isolation

In a traditional job, whether you’re in an executive role or reporting to higher-ups, you likely have people to confer with about projects, decisions, and problems. Even if you’re the one expected to make the final decision, you can usually talk it through with someone who has inside knowledge of the situation and the stakes.

As a freelancer, you’re making every decision on your own. That can make even small decisions feel more overwhelming than they need to, not because all decisions are difficult, but because there’s no one else to share the weight or the context with.

Structural isolation

When you have an employer, you have someone setting your goals, priorities, and parameters. There are deadlines you didn’t invent, policies you didn’t write, and expectations that exist whether or not you feel like revisiting them at 10:40 on a Tuesday morning.

When you work on your own, you set the priorities, which also means you can change them at a moment’s notice. You can create a policy and immediately abandon it five minutes later without checking with anyone.

That flexibility is part of the appeal of freelancing. It’s also part of what makes it isolating.

Without external structure, everything depends on your ability to decide, define, prioritize, and follow through. You are the boss, the manager, and the employee. There’s no shared system to lean on when you’re tired, unsure, or distracted. There’s just you, making yet another decision and then determining whether or not it was the right call.

Professional and cultural isolation

You may have people around you all the time: a partner working from home, kids in and out of the house, friends you text regularly, and a dog faithfully sleeping at your feet while you invoice (technically not a person, but close enough). You might have a social calendar that, technically speaking, contains a reasonable number of human beings.

And still, your work life can feel oddly cut off.

That’s because a workplace provides more than social company; it provides context. You’re surrounded by people who understand the rhythms of the work, the pressures, the deadlines, the annoyances, and the shorthand. You don’t have to explain why a small client request can derail an afternoon or why one negative email can tank your mood more than any adult should probably admit.

Freelancing removes a lot of that by default.

You’re still working. You may even be happier working this way. But you’re doing it without the casual conversations, shared reference points, and background sense of “we’re in this together” that many traditional jobs provide.

For example: I’m friends with many teachers and school administrators. Even when they don’t work at the same schools, they share reference points. When I host an event and a bunch of them are there, the conversation always drifts into school talk: gossip about administrators, whose classes are doing what, and how the parents are behaving (apparently, not well).

That kind of shared shorthand is normal in many professions. People who do similar work can slip into conversation because they already understand the landscape.

Freelancing doesn’t always offer that. Very few people in my life can talk with me at length about my business, the decisions I’m weighing, or the frustrating little dramas of client work. The only time I’m regularly in a room with other freelancers is when I’m at a freelance-specific event.

Loneliness and isolation

Loneliness and isolation overlap, but they aren’t the same thing. You can feel lonely because you’re isolated. You can also feel isolated without feeling lonely at all, especially if you share a living space with someone else (who’s always around, wondering outloud where the bread is kept) or you manage a full social calendar.

That distinction matters because the fixes are different. If what’s missing is companionship, the answer may be more human contact. If what’s missing is shared context, feedback, accountability, or a sense of professional belonging, then “try being more social” is not especially helpful advice. “More friends” doesn’t help you if they can’t relate to you.

Is it loneliness or isolation?

If your work-from-home life feels off, it might help to get more specific about what’s going on.

You might be dealing with loneliness if you’re asking:

• Do I miss being around people, full stop?

• Am I craving company?

• Do I feel emotionally disconnected or unseen?

• Am I itching for conversation with someone other than my dog?

You might be dealing more with isolation if you’re asking:

• Do I miss having colleagues who understand my work without a long explanation?

• Do I feel like I’m making every decision in a vacuum?

• Am I missing feedback, perspective, or shared context?

• Do I feel like no one I talk to understands my situation?

And of course, it can be both, because in freelancing very little is always either one thing or the other.

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What to do when freelancing feels isolating

As mentioned above, I don’t think the fix is simply “be more social.” That advice tends to be both annoying and frustratingly unhelpful. If you’re already busy, it can also feel like being handed another task by someone who isn’t volunteering to take any of the workload off your shoulders.

What helped me more was understanding what I was craving.

Was it casual conversation? A sounding board? Accountability? Industry perspective? A sense of belonging?

Once you know that, you can build for it more deliberately.

• If what you miss is connection, maybe that looks like setting up a regular coworking date or a coffee with another freelancer.

• If what you miss is perspective, maybe it’s a small peer group of freelancers who can talk through business decisions with you.

• If what you miss is structure, maybe it’s a regular check-in with a coach, colleague, or accountability partner you can bounce ideas off of, who understands the nature of freelancing.

• If what you miss is community, maybe it’s less about meeting more people and more about joining a professional organization or community of people at about your career level who can share their stories and insights, and listen to yours.

You aren’t trying to recreate an office, especially if leaving one was the whole dream. Instead, you’re recognizing which parts of working life supported you more than you realized and rebuilding that portion to fit your freelance life now.

You haven’t made a mistake

Sometimes people leave traditional jobs because they want freedom. Sometimes they leave because they want peace. Sometimes they leave because one more round of office politics might send them screaming out the door.

And then, after they start freelancing, they find themselves missing pieces of that world they never expected to miss: the built-in conversations, the shared understanding, the accountability, the comfort of not being the only person holding the whole thing together.

That can be disorienting and it can make people wonder whether they made a mistake.

It doesn’t necessarily mean freelancing was the wrong move. It usually means the parts of working life that supported you were less obvious than the parts that drained you; without those other parts draining you, you now have the ability to focus on what’s missing.

And once you know that, you can start rebuilding the supports you need in ways that fit the life and business you want.

Heidi

*If you’re a paid subscriber to Happy Freelancing, you already have access to resources that can help with some of this, especially around accountability, connection, and building a freelance life that feels more supported.

Subscribe now