Timing the Market vs. Timing Your Life
When to Sell
“I should’ve done this three years ago”
I sat across from a seller who looked like he’d just aged five years in five minutes. We were discussing he was halfway through due diligence when he leaned back and sighed, “I should’ve done this three years ago. I had more energy. I cared more. I waited for the right number, and now I don’t even care about the money.”
That sentence stuck with me.
Because in this business, both in buying and selling companies, we’re taught to optimize everything: EBITDA multiples, market timing, deal structures, tax strategies. But what’s almost never optimized is the seller’s life. Their emotional energy. Their alignment with what’s next. Their clarity on why they’re selling at all.
Let me be blunt: most owners don’t sell too early…they sell too late.
They stay too long trying to “time the market,” as if a few more turns of the business cycle will finally produce that perfect number.
And when they do sell, it’s often under duress, burned out, bored, battling declining performance. That’s not a strategy. That’s an exit under pressure.
Now, don’t get me wrong. Of course macroeconomic timing matters. A strong M&A market can increase valuation. Interest rates affect buyer financing. Strategic buyers may be more acquisitive during growth phases. But none of that matters if you are done.
Because selling a business isn’t a spreadsheet decision. It’s a life decision wearing a suit.
You can’t time the market. But you can time your life.
And that’s how real exits happen: clean, profitable, liberating ones.
Trying to time the market
I’ve had the privilege of speaking to dozens of Main Street and lower middle market founders. What I learned is the most successful exits, both financially and emotionally, weren’t timed to the market. They were timed to the founder’s life arc. Their energy. Their clarity. Their next chapter.
One owner sold in a so-so market because his daughter just had twins, and he wanted to be present. Another left a thriving firm to go build a nonprofit that had been tugging at him for years. One had no big plans other than to fulfill a dream to wake up without email for once.
Every one of them told me later: “I’m glad I didn’t wait.”
Compare that to the owners who wait for “just one more year of growth.” That one year becomes three. The team gets tired. Culture slips. Their health wavers. They lose key staff. By the time they’re ready, the business isn’t.
Buyers can smell fatigue. And if the owner seems like they’ve mentally checked out, it will impact price, terms, and deal confidence. That’s the dirty little secret no spreadsheet shows.
So how do you know when it’s time to sell?
You check your life, not the market.
Ask:
Am I still emotionally invested in this business?
If I were free tomorrow, what would I do?
Do I want to manage people or mentor someone who will?
Would a liquidity event free me to pursue something that matters more?
If the answer to any of these is yes, it might be time. Not because the Fed made a decision or the market hit a high. But because you’re ready. And readiness…real, internal readiness…is the most underused asset in any deal.
My advice? Build the business so it’s always ready to sell, but don’t wait until you have to.
If you’re tired, bored, or trapped: you’ve already waited too long.
If you’re clear, energized about what’s next, and your numbers are strong? You’re right on time.
David Hermann, CEO of hermanngroup and M&A Advisor/Broker at Sunbelt Business Brokers of Colorado
David Hermann is a transformative advisor and strategist who turns complex business challenges into extraordinary successes. Known for driving over $500 million in documented financial improvements for clients, David partners with C-suite leaders to unlock their full potential. With 60+ speaking engagements, numerous publications, and a spot in the top 1% of Consulting Voices and top 1% of the Social Selling Index on LinkedIn, he’s passionate about making strategy, change leadership, and operations insightful and accessible.