The Emotional Side of Selling Your Business
Nobody Prepares You For

William worked for years with an attorney at a law firm in the DC area that handled M&A work. When the firm went under during the 2008 financial crisis, this client landed on his feet quickly. The M&A team he was part of got picked up by a much larger firm almost immediately. And his compensation did not just change. It tripled.

What was already a good salary became an extraordinary one overnight.

For years William and this client had been working through retirement projections together. The plan was clear. Move down to the South Carolina coast, retire comfortably, enjoy the next chapter. They were close to the finish line. Everything was modeled, visualized, and mapped out.

And then the money got bigger. And walking away got harder.

The client sat at his kitchen table one day and said something William has never forgotten. If my dad knew what I was making now and knew I was walking away from it, I don’t think he’d talk to me.

The Statistic That Should Stop Every Business Owner

Somewhere between 70 and 80 percent of business owners regret selling their business within a year of doing it. That number is not an accident. And William argues the reason behind it is almost always the same.

They knew what they were walking away from. They did not have a clear enough picture of what they were walking into.

The financial plan was done. The projections were modeled. The exit was structured correctly. But the emotional side of selling your business, the part that asks who you are when the business is no longer yours, rarely gets the same level of attention.

Why Letting Go Is So Hard

Part of what makes pulling the trigger so difficult is the irreversibility of it. Once you sell, you almost certainly cannot buy that business back. Once you leave a lucrative position, your replacement has already been hired. The door closes behind you and it stays closed.

That reality, even when you know it intellectually, hits differently when you are standing at the edge of it. The attorney client knew the math. He had run the projections. He understood that retirement made financial sense. But the emotional weight of walking away from income his father would have marveled at was something no spreadsheet could fully address.

What Actually Helps

The planning, the modeling, the retirement projections, all of it matters. But what matters just as much is having something on the other side that pulls you forward.

Not just a plan for what you are leaving behind. A vision for what you are walking into. A reason to look ahead rather than back. Whether that is travel, a new venture, time with family, or something you have always wanted to pursue but never had the space for, that draw toward the next chapter is one of the most important and most underappreciated components of a successful exit.

If you are getting closer to a sale and finding it harder than you expected to pull the trigger, that is not weakness. It is completely normal. The key is to start working on the emotional side of the transition with the same intentionality you bring to the financial side.

Because the financial plan gets you to the finish line. The vision for what comes next is what carries you across it.

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We had a client, had a client that I worked with years ago, haven’t worked with him since I left my previous firm in Baltimore, was an attorney and worked for a smaller M&A shop up in the, in the DC area. And unfortunately, in the 2008 financial crisis, that M&A shop, uh, the M&A firm, the law firm I should say, it wasn’t an M&A shop, it was a law firm.

The law firm ended up going under, and there were a number of law firms that went under in 2008, 2009, just as the way they were structured and hiring decisions, et cetera, et cetera. Fortunately for this firm, the M&A team within that firm got picked up and moved to a, a much larger firm, and instantly [00:01:00] compensation changed, and it didn’t change for the worse.

It changed for the better. Probably 3X’d, um, what was already a good salary. And we’d been going through retirement iterations with the attorney and his wife, um, for, for many years. Um, awesome set of retirement projections, right? Wanted to move down to the coast along South Carolina, retire. And as As he spent time with the acquisition firm and his compensation was higher and higher, it made it more and more difficult, right?

Prior to that s- we were close to the finish line. He knew that, you know, retirement was coming up. They’d planned for it. They had this set aside. This is how it was gonna happen. This is w- what was gonna unfold, and all of these different things. But as, as time got closer now and he looked at what was coming in on a monthly [00:02:00] basis, he said, “I’m having a hard time walking away from this.

If my…” And he said this once at their kitchen table. He said, “If my dad knew what I was making now and knew that I was walking away from it, I don’t think he’d talk to me.” So anyways, it’s just a, a reminder, like so many other things, that knowing what you intend to do next, having that thing to walk into, planning for it, right?

The more you model it, the more comfortable you get with it. And but even, even doing all those things, even having conversations around it, visualizing it, modeling it, having an understanding of what’s that draw that’s gonna pull you into the next thing, pulling that trigger’s hard because, um, if you’re selling a business, you…

The likelihood that you can go back and, and buy that business or, or restart or do whatever is, is really low. [00:03:00] And if you’re, you know, in, if you’re in a lucrative job, it’s the same thing, right? Like walking away from it and realizing, “Oh, shoot, I can’t, I can’t go back s- they’ve already hired my replacement.”

You know, those things are hard to unwind, like when you’ve made that decision, when you’ve made that commitment. And you know that when you’re, when you’re getting close to it. You know that I can’t undo this, and so that’s the reality, and I think that’s why you see so many statistics out there about business owners that regret selling their business, right?

70, 70 to 80% of business owners regret selling their business within a year of doing it. And I think a lot of it is the same conversations that our attorney client was having, which is that, what am I walking away from? And am I really ready to walk away from it? And, you know, having that draw, having that component that pulls you through to the next side so that you’re not thinking about what was behind, you’re thinking about what’s [00:04:00] ahead, is such an important component of that visualization, preparing yourself to get ready to exit and retire.

So think about that as you get towards and closer towards that moment.

ORIGINAL MEDIA SOURCE(S):

William Bissett: Why 70% of Business Owners Regret Selling Within a Year | Portus Perspectives

Originally Recorded on July 13, 2026

Portus Perspectives: Episode 32

By /Published On: August 18, 2026/