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Key Takeaways Studies show there is an emotional toll and loss of purpose that entrepreneurs experience during business transition.
There are three important things to consider before selling: Is the timing right? Do you have the bandwidth? And last, do you know what you’re doing next?
It is a massive wave — one that is expected to peak by 2035. According to a McKinsey report about “The Great Ownership Transfer” from February 2026, this wave encompasses “6 million businesses involving roughly five trillion in assets transitioning as baby boomers retire.” The Great Ownership Transfer is one of the most significant movements for small to medium-sized businesses we have seen in some time.
I am acutely aware of this movement because I recently sold a business I started, grew and ran for over 39 years. I learned a lot, did some things well and made my fair share of missteps.
While the report focuses on a specific demographic, the truth is that whether you are a baby boomer or a young, enterprising entrepreneur, the personal impact of a business sale is real. I know from my own experience and the stories I have gathered from fellow business owners. As a mentor of young entrepreneurs through various programs, including the American Academy of Entrepreneurs, I was surprised by the hesitation they experience even when, from the outset, the goal was to grow the business quickly, sell it to a larger entity and move on.
The traditional advice for those considering a sale is to assemble a team of advisors, do valuations, find a broker and cut the deal. Advisors can help with tax and cash flow strategies for the exit. I would argue that it is fine, but there is much more to consider. In fact, studies show there is an emotional toll and loss of purpose that entrepreneurs experience during business transition. Here are three things to consider before you begin the sales effort.
Is the timing right?
Most people think about timing in the context of their personal needs and desires. In my book, Should You Stay or Should You Go? Navigating the emotional Crossroads of Business Ownership, I look at the signs that point to an exit. Are you burned out? Bored? Have you lost your passion? These are a few things to consider.
There are other signs that point to “staying.” The most important one might be that you still have passion for the work. For many years, I stayed at my business because I still had a passion for it. Over time, the signs that I should plan to go started to mount. I no longer wanted to manage employees. I had done everything I wanted to do at my company and knew that someone else needed to take it to the next level. I needed a new challenge. Timing is critical.
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