Exit Without Regret: When is the right time to sell your business?

People ask me all the time, “How do you know it’s the right time to sell your business?” The truth is, there’s never going to be a perfect time. But what you can do is put a plan in place that helps you stay ready, no matter what’s happening in the economy or in your personal life. A little preparation today can help you avoid regrets about your business sale later.

When market conditions are strong, it can be tempting to speed up or slow down your timeline. Think about the COVID-19 pandemic, when lumber prices spiked. For some business owners in that space, the opportunity to sell at a premium might have been irresistible. Others may have felt reinvigorated by the boom, choosing to push back their planned retirement.

Every business owner is different, and so are their retirements. That’s why, when it comes to deciding when to sell your business, I believe the most important factor is ensuring you can exit on your own terms. You need a business exit plan that gives you the flexibility to decide whether you want to sell now or later, instead of being forced into a corner by your health, market conditions, or other circumstances outside your control.

Unfortunately, I’ve seen too many cases where owners waited too long to sell or transfer their business. Passion fades, health issues arise, or energy runs low. In those situations, businesses often sell for less than they would have if the owner had transitioned earlier, on their own schedule.

4 Steps to take now that will help you sell your business at the right time

1. Create a buy-sell agreement

A buy-sell agreement spells out how ownership will be transferred and under what conditions. It provides a roadmap so you aren’t caught off guard by unexpected changes.

2. Build a contingency plan

Life is unpredictable. A contingency plan protects you from being forced into a sale because of illness, burnout, or sudden market changes. With a backup plan, you stay in control even when circumstances shift.

3. Monitor market and industry conditions

Pay attention to your industry’s activity and overall economic conditions. A booming market or active M&A environment might create opportunities, while downturns can lower valuations. Understanding the timing dynamics helps you decide when to act.

4. Define your next chapter

Know what comes after the sale. Whether it’s retirement, a new venture, or simply more time with family, having a clear, values-based vision for retirement helps you make confident decisions about when to exit.

The economy will rise and fall. Industries will have hot streaks and quiet periods. But if you’re prepared, you don’t have to wait for a “perfect” time—you can sell when it makes the most sense for you and your goals.