75% of Founders Regret Selling Their Business Within a Year — Here’s How to Walk Away With More Than Just Money

When I sold my first business — a wine bar and brokerage — I hated the thing. I was working retail hours, coordinating with customers on three different continents and the stress was unrelenting. On the day the deal closed, you would have expected me to be celebrating my escape.

Instead, I entered a period of grief I hadn’t planned for and couldn’t have predicted. That business had defined my days, my identity and my sense of purpose for years. And the moment it was gone, so was all of that.

That surprise is one of the most common — and least discussed — parts of a business exit. According to widely cited research from the Exit Planning Institute and PricewaterhouseCoopers, roughly 75% of business owners report feeling profound regret within a year of selling their company. And the Exit Planning Institute’s 2023 State of Owner Readiness Report found that only 44% of owners felt they had planned enough — not for financial reasons, but for emotional ones.

Life after exiting a business is like many other new chapters. Whether you’re facing an empty nest, a wide-open future after college or your new status as a former owner, grief is a real possibility. But the grief that follows a business sale has a specific shape. If you’ve owned your company for five years or 40, part of your identity has been running it and being close to your employees and customers. After you sell, many of those relationships change or disappear. Which is why, as you build the financial structure of your exit, you have to build for the emotional upheaval too.

How, then, should an owner plan for life after the sale?

Decide what success looks like

At Exit Factor, this is one of the first things we ask a client, because it’s different for every entrepreneur.

For some owners, it’s the money — getting as much profit out of the deal as possible. That’s an important goal, and for many owners it’s the critical one. For others, it’s making sure the employees they leave behind are taken care of. For others, it’s simply the joy of living without the mental fatigue of owning a business. Whatever your version of a successful ending is, if you achieve it, I count that as a successful exit.

If you don’t begin with a clear picture of success, you may end up with something else entirely.

Decide what your company should look like

Legacy is a real metric for many business owners, especially founders still at the helm or successors who worked hard to preserve what came before them. They want to know the buyer will maintain the character and culture they built and operate according to the values they established.

A recent, high-profile example: Mark Cuban, the celebrity entrepreneur and Shark Tank veteran, former majority owner of the Dallas Mavericks. Cuban was famously hands-on with the talent side of the team — close to the players, involved in recruitment and trades. But after he sold his majority stake, the new owners decided not to renew a contract with one of Cuban’s favorite players. He was publicly upset, and there was nothing he could do about it. He hadn’t carved out a role in player contract decisions before the sale, and he couldn’t renegotiate the deal after — just as he probably wouldn’t let a Shark Tank contestant back out of a handshake (at least not on camera).

If legacy, culture or specific decisions matter to you, negotiate for them before the papers are signed. Once the deal closes, those levers are gone.

Get inspired about your future

Free time sounds great. But when you’ve been working 40, 60 or 80 hours a week for the last 30 years, it isn’t an easy transition.

I remember a client who called us a few months after his exit and said, “I don’t know what the heck to do with my time. All my buddies are working, my wife and kids are busy and I’ve got nothing to do.” That call was the whole reason we now ask clients to design what we call an inspiring future — before the exit, not after.

What do you want your life to look like for the next six to twelve months once the sale closes? A trip you’ve put off? Deeper involvement in parenthood, or caring for aging parents? Writing a book, starting a charity, learning something new? The specifics matter less than the fact that they exist. An empty calendar after a sale is a much harder problem than most owners expect.

When you exit your company, you are exiting a phase of your life. You lose relationships. You lose a community. You may lose a whole sense of who you are. But something is waiting for you in the next chapter — and the sooner you start designing it, the better that next chapter will be. Start now. What comes next could be the most exciting stage yet.

When I sold my first business — a wine bar and brokerage — I hated the thing. I was working retail hours, coordinating with customers on three different continents and the stress was unrelenting. On the day the deal closed, you would have expected me to be celebrating my escape.

Instead, I entered a period of grief I hadn’t planned for and couldn’t have predicted. That business had defined my days, my identity and my sense of purpose for years. And the moment it was gone, so was all of that.

That surprise is one of the most common — and least discussed — parts of a business exit. According to widely cited research from the Exit Planning Institute and PricewaterhouseCoopers, roughly 75% of business owners report feeling profound regret within a year of selling their company. And the Exit Planning Institute’s 2023 State of Owner Readiness Report found that only 44% of owners felt they had planned enough — not for financial reasons, but for emotional ones.