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Key Takeaways Roughly three in four founders will regret selling their business within a year, even if they sell on their own terms at their target price.
Most founders face a feeling of loss after selling their business, and the journey of transition and reinvention can be emotionally complex.
When you run a company, being the founder is a bit part of who you are. When the business is sold, that part of your identity is gone, and you feel that loss regardless of how much money you made.
The importance of getting ready emotionally for the sale is as important as getting the finances and the legal work right, and it might take far longer.
I conducted research interviewing founders who had successful exits and uncovered something I did not expect at all.
One of the founders I interviewed had sold his company after 11 years of scaling it and preparing for the sale, made more money than he anticipated, and a few days after the deal finally closed, he sat at his kitchen table looking at multiple zeros in his bank account but felt nothing at all. Within a week, he could barely get out of bed. He had assumed the sale would be one of the best days of his life, and he could not understand why it was not.
I heard versions of this from almost every founder I interviewed as part of my research, and what they told me matches what we see in surveys of exited business owners.
Over the next decade, 73% of privately held businesses in the United States are expected to change hands, a $14 trillion transfer of wealth. Most of the people selling those companies expect it to be one of the happiest events of their lives, just as the people I interviewed did. And yet, roughly three in four of them will regret it within a year, even if they sell on their own terms at their target price.
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