December 13, 2025

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Five months ago, I watched a popular creator (and friend of mine) announce he was pausing his newsletter and podcast after ten years of consistent publishing.

His reason? It no longer brings him the feeling of "aliveness."

The comments were predictable. His fans were shocked. Other creators called him crazy for walking away. But I didn't think he was crazy at all. I thought he was honest.

And the thing that seemed to go over most people's heads is that he wasn't quitting. He was just evolving.

Three months after that announcement, he launched a completely different business in a different space. His content took on a new format, he built a new audience, and he had a brand new energy. He'd been curious about the topic for the last few years, but kept telling himself he couldn't abandon what he'd been working on for a decade.

Turns out, he could.

His pivot got me thinking about something I don't hear people talk about much:

How do you know when it's time to evolve?

When obligation replaces curiosity

Another friend of mine has 80,000 newsletter subscribers. She kept publishing every week for more than a year after she stopped enjoying what she was writing about.

"I felt like I owed it to my audience," she told me a few months ago. "I kept waiting to feel excited again. Like maybe if I just pushed through, the creative juice would come back."

It didn't.

She described what that year felt like, and it sounded miserable. Sitting down to write and immediately thinking about everything else she should be doing instead. Hitting publish and feeling relieved instead of proud. Reading replies from subscribers and feeling guilty instead of grateful.

The words she finally landed on to summarize the whole experience were "mailing it in."

Her open rates dropped from 55% to 39% during that year, and her audience could tell something in her energy had shifted.

Now that she's stopped writing and is trying something new, she said, "I wish I'd paid attention to what I was getting curious about instead of what I felt obligated to keep doing."

Because the whole time she was grinding through newsletters she didn't want to write, she'd been getting excited about something else entirely. A different curiosity she felt compelled to follow. But she dismissed it as a distraction for a long time.

Turns out it was a signal.

What this looked like for me

I've been through this a few times already. I just didn't recognize it as evolution at the time.

When I started posting online six years ago, I talked about healthcare sales and marketing. That's basically what my entire career had been for sixteen years. That's what I thought my "thing" would be forever. I did that for about a year before I started getting curious about something else.

Weirdly, it was LinkedIn that I got curious about, because I seemed to crack the early code for gaining followers. So I started writing about the platform itself. How it worked, how to grow on it, and what made content perform. I did a 180-degree pivot away from healthcare and talked about LinkedIn and audience growth for two years. I built a massive following, created the world's most popular LinkedIn course, and probably could have done that for another decade or so.

But I got bored.

While I love figuring out how social media works, I didn't want to spend the rest of my career as the "LinkedIn guy." I became less interested in the platform tactics and more interested in the bigger picture. What does it actually look like to build a business by yourself? And how do you do it without burning out or hating your life?

So I shifted into solopreneurship and became somewhat synonymous with the word itself.

But (as you may have noticed), in the last year or two, I've found myself pulled toward something broader. The philosophy behind the tactics. How to build a business that actually supports the life you want, not one that slowly consumes it. Less "here's how to grow" and more "here's why any of this stuff matters."

Each time I made one of these shifts, I definitely lost some readers. The healthcare folks didn't care about LinkedIn strategy. And the LinkedIn crowd probably doesn't care all that much about my philosophy on life and business.

But I kept a lot more readers than I lost. And if the replies to my newsletters are any indicator, it's because the ones who stayed weren't following me for a specific topic. They were following for how I thought about things.

My own curiosity has continued to be the signal.

What's pulling me now

Interestingly, after two years of leaning into philosophy around life and business, I'm starting to feel the pull again. Back toward strategy and tactics.

Not because I'm bored with the bigger questions. I'm just getting started sharing my perspective on that.

I'm feeling pulled because I'm getting more curious about how I can help people more practically. What actually works right now for people building lean, healthy, profitable businesses online? Not the old growth-at-all-costs playbook. Not the 24/7 hustle bro BS. The stuff that supports a life well-lived, and not one that is sacrificed for revenue.

Over the course of my solopreneur journey, I’ve built a relationship with a team of smart people who have a behind-the-scenes look at what's working in the online business world right now. The more I learn, the more excited I get about how I can impact people who need help sharing and monetizing their expertise online. And after spending last week in California with them, I'm buzzing with excitement.

That excitement? That's the signal I've learned to pay attention to.

The thing nobody tells you

The truth is, your interests evolve. The topics that energized you three or five years ago might not be the same things that light you up now. You've probably read different books, met different people, and solved different problems. You've changed. But maybe the thing you're known for hasn't.

Most people dismiss these signals as impractical. They convince themselves that they've already built something (a brand, a business, etc.) and that moving, even slightly, in a different direction would ruin it all.

And maybe in certain cases, pivoting would hinder your progress. I’m not suggesting that isn’t a possibility. But I can tell you from experience that the curiosity won't go away. It just gets harder to ignore.

My friend with 80,000 subscribers spent a year ignoring what she was curious about because she felt obligated to keep doing what was working. By the time she finally made the change, she'd lost a year she would love to have back.

The bottom line

Your online business, your creative work, whatever you're known for, it's not a life sentence. Think about it as a season of your life.

And when new curiosities start pulling at you, they may not be a distraction. It could be information worth paying attention to.

So here's my question: What have you been getting curious about that doesn't fit neatly into what you're currently doing? What ideas excite you that you keep dismissing because they don't match what you're known for?

Reply and tell me. While I can't write back to everyone, I read every response.

That's all for today.

See you next Saturday.

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