10 Business Exit Mistakes - 3. Waiting Too Long to Sell

An unexpected downturn or illness can destroy value

Most business owners don’t sell the day they decide they’re ready. Often, they wait, telling themselves they’ll exit “in a few years,” or “once things settle down,” or “after one more good year.”

But time has a way of slipping by. And while patience can be a virtue in many parts of business, waiting too long to sell can quietly chip away at the value you’ve spent years building.

Sometimes the delay is strategic. But more often, it’s emotional the fear of letting go, or the belief that next year will always be better. Unfortunately, the future doesn’t always cooperate.

When Life Happens

Here’s the reality unexpected events happen. A health scare. A personal crisis. An economic downturn. A shift in your industry. None of these arrive with a warning and when they do, they can instantly change the outlook of your business.

If you haven’t planned ahead, you might find yourself forced to sell at the worst possible time, when profits are down, when your role is still too central, or when buyers smell urgency and lower their offers accordingly.

It’s not just about price, either. It’s about control. In a distressed sale, you don’t get to call the shots. You’re reacting, not choosing. That’s a difficult way to end something you’ve worked so hard to build.

Value Is Fragile - Especially Without You

Many small to mid-sized businesses rely heavily on their owners. You might be the rainmaker, the decision-maker, the engine behind the brand. If something takes you out of the business suddenly, whether for a few months or permanently, value can erode quickly.

Revenue might dip. Team morale might drop. Key customers could get nervous. And buyers? They’ll hesitate.

Even if the business has strong fundamentals, the perception of risk can drive down price or push buyers away altogether. What was once a valuable, stable business can quickly become a liability in the eyes of the market.

Selling From a Position of Strength

The best time to sell your business is when things are going well, not when you’re tired, under pressure, or caught off guard.

When you sell from strength

• You have time to prepare the business properly

• You can be selective about the buyers you engage with

• You’re more likely to get a fair, even premium, valuation

• You can negotiate terms that reflect your goals, not just your needs

This doesn’t mean you need to sell tomorrow. But it does mean starting the planning process well before you feel desperate to leave.

Exit planning isn’t just about the final transaction, it’s about making sure your business is ready, your mind is clear and your options are open.

Avoiding the Trap of “Just One More Year”

Many business owners fall into the “one more year” trap. It’s understandable. Maybe there’s a new opportunity just over the horizon. Maybe profits are trending up. Maybe things just don’t feel ready yet.

But one more year easily becomes five. And by then, energy wanes, markets shift, or personal issues arise. You may still sell, but the result won’t be the same.

It’s not about being pessimistic. It’s about being prepared.

Final Thoughts

Selling your business is one of the biggest decisions you’ll make. Waiting too long might feel like you’re staying in control, but in truth, it could put your legacy, your wealth and your options at risk.

The smartest exits aren’t rushed, but they are planned. Start the conversation early. Understand your options. And give yourself the time and clarity to exit on your terms, not someone else’s.