Bored to death.

At some point in the last few years, I got really good at my job.

I don't say that to brag. I say it because “getting good at something” is everybody’s goal, but people rarely talk about what happens after that.

By early 2022, I had most things in my business firing on all cylinders. I’d figured out how to create content that resonated, how to generate leads for my products, how to collect information about my leads, how to make sales with custom pitches, and how to do all of that on repeat.

Revenue was predictable, and I could log into my Kajabi dashboard at 8 am, noon, and 4 pm and tell you almost down to the dollar where the numbers would be.

That's supposed to be the dream, right? Predictable, repeatable income from an automated process.

But I can remember sitting at my desk one morning, coffee in hand, looking at the 8 a.m. revenue and feeling numb to the numbers. Not ungrateful or disappointed. I know how fortunate I’ve been. But somewhere along the way, my calendar started to feel more like an assembly line than a creative endeavor. I was going through the same motions and producing the same outputs.

The creative parts of my work that once lit me up had completely disappeared.

The boring kind of burnout

You might assume folks lose motivation because something goes wrong. Their businesses failed, or the market shifted, or something “bad happened.” But there’s a version of burnout that’s less common (or at least talked about less).

The version where everything’s pretty much fine, numbers are as good as ever, and you’re just bored out of your mind.

This happens in all kinds of jobs. My friend Jason is a financial advisor who spent ten years building his firm, and he can do the job in his sleep. It’s paying the bills, and he goes on great vacations. But he doesn’t enjoy the work anymore. Hell, I spent years selling to physicians who wanted to grow their practices for financial reasons, but didn’t even love seeing patients.

Sure, money and success are important. But monotony is poison for the spirit.

You get good at the things that make your business succeed. But reaching that level kills some part of the work that makes things interesting. And then, there you are, going through the motions, day in and day out. And feeling guilty about not liking it anymore.

I was thinking about that as I read my buddy Brad Stulberg’s new book, The Way of Excellence (not surprisingly, an excellent book). He talks about how when you're early in some sort of journey, the progress itself keeps you going. You're getting better every day, and you can feel it. But eventually progress levels off, and the honeymoon fades. We call that “being able to do this in your sleep.”

The people who keep going after that are the ones who fall in love with the joy of their craft and the people they do it with.

That hit me because I’m one of those people who almost didn't make it through the honeymoon.

500 replies

Deep into 2025, my assembly line was humming along fine. I was writing about the usual topics my audience expected: solopreneurship, reverse engineering social media, selling products, and the new trend, AI. Those topics are all fine, and that tactical stuff performed well enough.

But my work was feeling less like “the real me” with every new issue.

I think back to when I started doing this work. The dozens of people building alongside me on LinkedIn and Twitter. Most of them are gone now.

They burned out, or got jobs, or took a break, and I just never saw them in my feed again. I doubt any of them “failed” in the traditional sense. I think the honeymoon phase just expired, and they didn't find a way through it.

And I felt myself being pulled in the same direction.

Then, I wrote a newsletter that was different from what I’d been publishing. It was about how I'd spent twelve months pretending I’d eventually organize my garage, when I was never actually going to do it. It’s about deferring decisions and the things we push to "someday.”

That newsletter issue didn’t have much to do with social media strategy, pricing, or solopreneurship. Not on the surface, at least. It was personal, a bit philosophical, and kind of uncomfortable to share out loud. I was nervous about how it might land with my readers.

My newsletters up until then had averaged around 45 replies per issue. And that particular issue got over 500 replies! And they weren't the usual "Great tips, thanks." kind of responses. Readers penned heartfelt paragraphs. They told me things they’d never told anyone, treating the reply to me like a journal. People said I’d made them rethink decisions they'd been sitting on for years.

I’m back again

I loved writing that newsletter, and my audience was asking for more. I honestly hadn't felt that combination in a long time. It wasn’t necessarily a lightbulb moment, but more like a jolt of creative energy I hadn't experienced in so long.

I hadn't shared the issue with Jennifer beforehand, which is unusual in our process. She hadn’t seen it before it came out, and I remember her reading it and walking into my office.

She said something like "I love the new issue, but it's sort of different from what you've been writing. But different in a good way."

And that was it. Jennifer didn't ask about why or what I was writing about next. She was commenting about the energy she could feel from it. I felt back again.

When she edited the next issue, she liked the direction again. "More fun to read than the tactical stuff."

That’s when I admitted I wasn’t feeling the tactical stuff anymore. I want to write about the intersection of life and business, or whatever you call these essays. This detour might not generate the same revenue (it doesn’t), but it’s what lights me up these days.

So I’m going there.

A trade that’s worth it

When I decided to walk through a new door, business was fine. The stuff I was supposed to care about was humming along. But I felt like I was losing my craft. My assembly line had chewed it up and spit it out, and I wasn’t excited to get out of bed anymore.

The thing that saved me wasn't optimizing that machine or grinding harder through the boredom of “staying on brand,” or outsourcing it to a bunch of employees.

What saved me was letting go of the stuff that made strategic sense on paper, and writing what I really cared about instead.

That's what success over the long run is really about, I think. Maybe not in the early stages where everything is exciting, and the growth feels electric. But the part after that. The part where you have to find a different reason to keep going. The part where the only reason that actually works is caring about the work itself.

I’ve given away a lot of revenue by venturing away from solopreneur tactics. But in exchange, I love to sit down and write again. Working on this newsletter is a pleasure every week. And hearing back from so many readers is a real “wow” factor. You wouldn’t believe the personal stories people share with us. Moving, interesting, inspirational, and even embarrassing stories.

Reading your replies has become a big part of our newsletter process that we love most. And I can tell you that didn’t happen when I was writing about social media and landing pages.

The bottom line

I could still be running the assembly line. The numbers were good, the system was working, and nobody was asking me to change. But I think I would have become one of those people who quietly disappeared. Eventually, I would have given in to work I wasn’t excited about.

If you've been doing something long enough that you've mastered it, and the mastery feels more like a trap than an achievement, that's probably worth paying attention to.

The thing that got you here, the challenge, the curiosity, the figuring-it-out stuff, might need to come from a new place now.

I’m very systems-oriented, and I still have an assembly line, of sorts. I just stopped letting it dictate what I make.

So here's my question for today:

Where have you lost the creative spark in your life or business? And what could it look like to bring raw creativity back?

Reply and tell me. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you.

That's all for this week.

See you next Saturday.