The Psychology of Selling a Business
If you can’t picture life after the sale, we need to prepare you to sell.
You’ve worked hard.
You have spent 20, 30, maybe 40 years building your business.
It has your fingerprints on every part of it from the way customers are greeted, the systems you designed, even the quirks of the office coffee maker. One day, you decide it’s time to sell. You expect the hardest part to be getting the numbers right. But the real gut-punch comes when a buyer asks, “How will this company run without you?”
That’s when you realize selling a business isn’t just a financial transaction. It’s a psychological one.
The problem many owners face is simple: they underestimate the emotional weight of letting go. Owners sometimes sabotage deals, not because the offer was bad, but because they weren’t ready to separate their identity from their company. The fear of being “less than” without the business can be paralyzing.
It gets worse. When emotion enters the room unchecked, rational decisions go out the window. I’ve watched sellers cling to unrealistic valuations because “that number feels right.” Others walk away from qualified buyers because no one seems “good enough.” These aren’t financial errors; they’re psychological ones. And they kill deals.
Or even worse still: there are many stories of sellers calling their business broker a week or so after the deal has closed, stating that it was a big mistake and they want to reverse the sale.
But the paradox is that the owners who manage this transition well often achieve not just higher sale prices, but smoother exits and healthier post-sale lives. Why? Because they understood the psychology early and built a plan around it.
Instead of feeling blindsided by the emotional rollercoaster, you anticipate it. You define what life after the business looks like, and you separate your self-worth from your P&L. You walk into negotiations clear-eyed, ready to maximize transferable value, not defend your ego. That’s when buyers lean in, and deals get done.
So, what’s the solution?
It starts with three mental shifts.
First, stop thinking of your business as an extension of yourself. Think of it as an asset you’ve stewarded. Your legacy isn’t the company itself—it’s the people you’ve developed, the customers you’ve served, and the value you’ve created.
Second, replace “What will I lose?” with “What am I gaining?” Time, freedom, new ventures, health, family—these are currencies too. When you weigh them honestly, the sale becomes an opportunity, not a death sentence.
Third, prepare emotionally as thoroughly as you prepare financially. Just as you’d clean up the books and optimize operations, clean up your mindset. Talk to peers who’ve sold. Work with advisors who understand the emotional side. Even simple rituals—like writing down what you want life to look like post-sale—can anchor you when doubts creep in.
Here’s the sentence I tell nearly every seller:
If you can’t picture life after the sale, we need to prepare you to sell.
I spoke to an owner who had built a manufacturing firm over three decades. His first instinct was to pass the business to his children. But after honest conversations, he realized none of them wanted it. That moment could have been devastating. Instead, we reframed it: his legacy wasn’t forcing them into his path, but giving them the freedom to pursue their own. He sold to a buyer who modernized the company, preserved jobs, and kept his name on the building. Today, he calls me from his boat a few times a year to tell me he’s living better than he ever imagined.
Selling a business is as much a psychological shift as a financial one. If you want to maximize both the value of your company and your personal fulfillment, you have to master the mental game as much as the numbers.
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.