09/27/2026
Two people I know walked away from their work this year. Neither of them sold a company. Both of them had built the exit long before they needed it.
There's a question I've been dodging for about a decade. This month it cornered me from four directions at once.
It showed up in a podcast conversation with my friend Stephen. It showed up in a note from a stranger on Substack. It showed up while Todd and I were recording Sunday, Unedited, when I heard myself say something out loud I'd never quite admitted. And it showed up in my own body, which decided to remind me who's actually in charge.
The question is simple: if you had to walk away tomorrow, could you?
Not quit in a huff. Walk away calmly, because the thing no longer fits, and be fine.
I recently recorded an episode with my friend Stephen about his retirement. I wrote about that conversation here. What stuck with me wasn't that he retired. It was how.
Things at work got out of alignment. Most people in that spot run the numbers and decide to grit their teeth for five more years or find another job. Stephen didn't have to. He'd been planning financially for decades, quietly, long before he had any reason to.
So when the job stopped fitting, he had a choice most people never get.
That's the part nobody posts about. The decision took a moment. The option took decades to build.
A few days later I read a note from Marcelo Oliveira that told the same story from the other direction.
In 2025, at 57, his company moved him to success-based compensation only. In plain English, a layoff. His first instinct was the one we'd all have: update the resume, call the network, find the next job. That’s what I’ve done, multiple times.
Then he looked at the other side of the ledger. Just owning their Fort Lauderdale condo, between the mortgage, the association fees and property taxes, ran about $80,000 a year before a single grocery run. Health insurance quotes for him and his wife, both too young for Medicare, came in around $2,500 a month.
So instead of asking how to replace his income, he asked how much of it they actually needed. They sold their house, moved to Portugal, and rebuilt their expenses around the life they wanted. He still prospects a few hours a week. Most days, he considers himself retired.
Stephen raised the ceiling. Marcelo lowered the floor. Same outcome: the freedom to walk away from something that stopped fitting.
If you're a founder, you already know these two levers. You just call them something else: raise and burn. Most of us pour everything into the first and barely look at the second.
Here's what I admitted to Todd on Friday’s podcast recording session.
For years, I've chased business models I wanted to work in. Models that sounded right and fit the story I had about myself. Meanwhile, one of my businesses quietly did something the others never did. It made sales whether I promoted it or not. Ten thousand dollars plus per year with no effort.
That's the clearest sign a business can scale. Not how excited I am about it. Not how well it fits my identity. Whether it keeps working when I stop pushing.
I ignored that signal for a long time, because the business that worked wasn't the one I would have picked. I'd bet some of you are doing the same thing right now.
Which brings me to what I'm actually wrestling with.
My GTM brand is finally moving. After a long stretch of pushing, it has real momentum. And that's exactly what's making me question it.
Momentum in a model that trades my time for money just means more of my time gets traded. Every new client adds hours, not leverage. I've done that work, and I've been good at it. I don't want to build my next decade on it.
So here's the test I'm applying, and it's the one I'd give any founder with early traction: **when revenue grows, do your hours grow with it?** If they do, you haven't built an exit. You've built a better-paying job.
I don't have the final answer yet. But I know "it's working" isn't reason enough on its own. Stephen and Marcelo didn't get their freedom by following whatever happened to be working. They built toward it on purpose.
This month, my gut issues (churning & bloating, not the real ugly stuff 💩, fortunately) came back, and I still can't tell why. It's exhausting. Even as I’m writing this it’s starting to flare up.
It's also clarifying. When your body goes sideways, you find out fast which parts of your life need you to show up and which keep running without you. Any business that needs you every single day is one bad month away from stopping.
Stephen planned for the day work stopped fitting. Marcelo adapted to the day the paycheck stopped. Most founders never plan for the day they can't be there at all. Your health is the one asset you can't delegate.
Here's the one thing I want you to take from this.
Once a quarter, take one week where you stop pushing. No posts, no outreach, no launches. Then look at what still sold. That’s today for me.
Whatever kept moving is your real business. Whatever stopped is either a job you've given yourself or an idea you haven't validated yet. Both are fine to have. Neither is an exit.
If you're staring at a few ideas and can't tell which one deserves your next year, that's why I put the idea-validation resources and the business plan template into the Ultimate Entrepreneur Toolkit. They're built to get you to evidence faster than enthusiasm does.
Stephen took decades. Marcelo took a hard year of rethinking. I'm starting this week. The best time to build your exit is while you still don't need one.
