The morning of New Years Eve day – I hit refresh on my browser like 17 times….and there it was. Seven figures. The business I’d helped build was sold. Everything I’d been working towards—done.
Packed up and went to my favorite restaurant. Ordered the expensive wine. Felt like I should feel something big. Triumphant, maybe. Relieved, definitely.
What I actually felt was: Now what?
The Finish Line That Isn’t
The truth is that while exits sound exhilarating: they’re often exhausting and anticlimactic. You spend years building toward this moment—the payout, the validation, the freedom. And then it happens and you’re… still you. Same problems. Same insecurities. Plus a non-compete agreement and either a lot of unstructured time or a new boss with capped earning potential.
Of the many owners I’ve worked with who’ve sold. Maybe a third of them look back and say it was exactly what they needed. The rest? They’re somewhere between “it was fine” and “biggest mistake I made.”
- The ones who regret it usually say similar things:
- “The process (lawyers, brokers, etc) ruined the experience.”
- “I thought the money would feel different than it does and a huge chunk went to lawyers, brokers, taxes.”
- “My team looks at me different, and I’ve lost part of my identity.”
Don’t get me wrong, the money can matter—security, options, peace of mind. But it doesn’t provide purpose. And if you built your identity around your business, selling it can feel like losing part of yourself.
Two years after my exit, I left the business and was asking myself: What am I actually doing with my life? I had resources but no real mission. Freedom but no direction. I’d achieved the goal but just felt off.
The Path Nobody Talks About
Here’s the thing I’ve learned since: not selling can be just as aspirational as selling. Maybe more.
What if instead of building to exit, you built something sustainable? Something you could run indefinitely—not because you’re trapped, but because you genuinely want to?
I’m working on that now. Building businesses I plan to operate way past any reasonable
retirement age. Not because I have to. Because the work gives me purpose, the structure gives me meaning, and the financial rewards are significantly better than any pile of cash in a stock portfolio.
One owner I worked with recently is mid 50’s and runs a $3M business. Could sell tomorrow if he wanted. Doesn’t want to – in fact, he bought out his partner who wanted to exit. He works three days a week, travels when he feels like it, and spends his time on the parts of the business he actually enjoys and other interests. His kids aren’t interested in taking over, and that’s fine. He’s using the cash flow to build a financial structure for his life that doesn’t require selling.
He’s not building an exit. He’s building a life.
The Real Question
If you’re thinking about selling, here’s what I’d ask: Are you running toward something or away from something?
If you’re burned out or trapped in a business that doesn’t fit you anymore—an exit might be exactly right. Sometimes the best decision is to let go and start fresh.
But if you’re selling because you think that’s what you’re “supposed” to do? Because everyone talks about exits like they’re the only finish line that counts?
Consider another option: build something you don’t want to exit from.
Build a business that gives you flexibility and purpose. That lets you work on what energizes you and delegate what drains you. That pays you well for the value you create and doesn’t demand everything you have.
That’s not settling. That’s building something rare.
Like many others, I spent years chasing the big payday and realized what I actually wanted was a business aligned with how I want to live—not a payout that let me stop living it.
You can build toward an exit if that’s your goal. But you can also build something you never want to sell. Both paths are valid. Both can be financially rewarding.
The question is: which one actually fits the life you’re trying to create?