I met a man at a business event a few years ago. He’d just sold his company. Twelve years of work, a clean exit, a number that would have made most people in that room go quiet.
Someone asked him what he was going to do next.
He looked genuinely startled. Not overwhelmed. Not emotional. Just... blank. Like the question had never occurred to him.
“I don’t know,” he said. “I suppose I’ll start another one.”
He wasn’t being humble. He wasn’t deflecting. He meant it. The business had been the answer for so long that he’d forgotten what the question was.
I’ve thought about that moment a lot.
There’s a version of entrepreneurial ambition that’s really just forward motion dressed up as purpose. You’re working hard, building something real, hitting milestones — and it all feels meaningful because it’s difficult and consuming and the numbers are going in the right direction.
But difficult isn’t the same as purposeful. Consuming isn’t the same as fulfilling. And a number going in the right direction is only useful if you know what you’re pointing it at.
Most entrepreneurs I’ve known — and I include my earlier self in this — can answer the what without hesitation. What are you building? A technology business. A services firm. A brand. A team. Fine. Good. All accurate.
Ask them what for and the answer gets murkier.
“Financial security.” Okay — but what does that look like on a Tuesday afternoon when you’re sixty?
“To prove something.” To whom? And once it’s proved, then what?
“Because I love the challenge.” That’s a personality trait. It’s not a destination.
None of these are wrong answers. But they’re not complete ones either. And if you’re spending ten or fifteen years of your finite life building something, incomplete probably isn’t good enough.
Here’s what I’ve come to think.
The business isn’t the point. It never was.
The business is the vehicle. It’s the thing that generates the resources — financial, but also experiential, relational, psychological — to fund the life you actually want. And if you haven’t defined that life with any clarity, then you’re essentially building a very sophisticated machine with no idea what you’re manufacturing.
You can do that for years. Decades, even. The machine will keep running. You’ll keep feeding it. And one day someone will ask you what you’re going to do next, and you’ll look startled, because the machine was always the answer and you forgot to write down the question.
I’m not telling you to stop building. I’m asking you to run both things in parallel — the business and the life you’re building it for. Not sequentially. Not “I’ll figure out what I want once I’ve exited.” Now. With the same rigour you’d apply to a revenue target or a hiring decision.
Because here’s the uncomfortable truth: the clearer you are about what you’re building for, the better the business decisions get. You stop chasing contracts that pay well but cost you everything else. You stop building teams in a shape that serves the business but not the exit. You start making choices that compound towards something you’ve actually chosen, rather than defaulting to whatever’s in front of you.
Keep reading with a 7-day free trial
Subscribe to The Long Run Mindset to keep reading this post and get 7 days of free access to the full post archives.