The Exit Nobody Plans For

Here's something most business owners don't want to hear: you're going to exit your business. The only question is whether it happens on your terms or someone else's.

Retirement, burnout, health problems, family crisis, market shift, better opportunity, boredom. Something will eventually push you toward the door. And when that moment comes, most owners discover they have no plan, no options, and a business that's worth a fraction of what they assumed.

I once watched a founder try to "flip a switch" when it came time to leave. No handover. No preparation. No buffer. It was chaos. Employees were confused. Clients started calling asking what was going on. The value of the business cratered in a matter of weeks. Everything he'd built over fifteen years nearly disintegrated because he'd never thought seriously about what happens after him.

He's not unusual. He's the norm. The vast majority of small businesses have no exit plan. And the ones that do often have something so vague it's basically a wish written on a napkin. "I'll sell it when I'm ready." Ready for what? To whom? For how much? Under what terms? These are the questions that eat people alive when the moment actually arrives.

The mistake is thinking of exit planning as something you do at the end. It's not. It's something that should shape how you run the business from the beginning. Or more precisely, from the moment you realize you want the business to be worth something beyond the paycheck it gives you today.

Think of it this way. If you're building a house you might sell someday, you don't wait until the day you list it to fix the foundation. You build it right from the start. You make choices along the way that keep options open. You maintain it. You improve it. The house is always being built to be sellable, even if you never sell it. Because the things that make a house sellable, solid structure, good systems, nothing falling apart, are the same things that make it a great house to live in.

Businesses work the same way. The things that make a business attractive to a buyer are the same things that make it a pleasure to own. Clean financials. Predictable revenue. A team that operates without constant oversight. Documented processes. Diversified customer base. These aren't just "exit planning items." They're just good business. The exit plan and the operating plan are the same plan.

So why do most owners avoid this? I think there are three reasons.

First, it feels morbid. Planning your exit feels like planning your funeral. Nobody wants to sit down and think about a world where they're not running the thing they built. There's an identity issue here that most people don't acknowledge. For a lot of founders, "I run this business" isn't just what they do. It's who they are. Thinking about the exit means thinking about who you'd be without it. That's scary.

Second, it feels premature. "I'm only 45. I've got twenty years." Maybe. But two years of preparation time is the minimum for a decent exit, and that's if things go smoothly. Most good exits take three to five years of groundwork. If you wait until you're burned out or sick or just done, you've lost most of your leverage. You make terrible decisions when you're exhausted. Desperation doesn't negotiate well.

Third, it feels complicated. Valuations, tax implications, legal structures, buy-sell agreements, succession candidates, ownership transfer mechanisms. It's a lot. And because it's a lot, people just don't start. They kick the can. They'll get to it next quarter. Next quarter never comes.

Here's the thing I want people to understand: exit planning isn't about leaving. It's about having options. The best position you can be in as a business owner is one where you could leave, could sell, could hand it off, could keep running it, and any of those choices would be fine. That's freedom. That's what a well-run business gives you.

The owners who are most stuck are the ones with no options. They can't sell because the business depends entirely on them. They can't hand it off because there's no one ready to take it. They can't even take a proper vacation because things fall apart when they're gone. So they just keep grinding, year after year, until something forces the issue. And by then, their negotiating position is terrible.

I've seen what happens when someone plans well and when someone doesn't. The gap is enormous. Not just financially, though the financial difference is real and significant. The emotional difference is what gets me. The planned exit is calm, intentional, even exciting. The unplanned exit is frantic, stressful, and usually ends with regret.

If you're a business owner and you haven't started thinking about this, today is the day. Not because you need to leave. Because you need to build the kind of business that gives you the choice. Start with the basics: know what your business is actually worth, not what you hope it's worth. Identify the gaps between where you are and where you'd need to be for someone else to run it. Get honest about your timeline. Talk to someone who's been through it.

The exit nobody plans for is the one that plans you. And by the time that happens, most of what you could have done to protect yourself is no longer available.

Two years. That's the window you need. Not to execute the exit, but to build the business into something that gives you options when the time comes. Whether that's next year or next decade, the preparation is the same. And unlike most things in business, this is one where starting early has almost no downside and waiting has almost no upside.

The best time to start was five years ago. The second best time is now.