“I have a love-hate relationship with my retirement. I love not having to worry about employees, cranky customers, or fickle vendors. But I hate the absence of purpose in my life, the sense that I don’t have anything to do that matters to anyone.”

Marvin (not his real name) has been a good friend for years. We went to law school together, were in each other’s weddings, and have traveled together with our families over the years. I hadn’t seen him since before Covid, so I was particularly excited to meet him and his wife Linda (not her real name) for a long weekend at their lake cottage in the Midwest.

“Covid was the final straw in my decision to retire,” Marvin told me as we chatted by an outdoor fireplace overlooking the lake. “But I might have misread the writing on the wall telling me it was time to stop working. Linda warned me that it might be too early.”

Millions of aging baby boomers are wrestling with the decision of when to retire. Once we reach a certain age, we begin to hear and see signs all around us telling us “it’s time.” But, as in Marvin’s case, it’s easy to misread those signs. 

A week doesn’t go by that I don’t get a call from a baby boomer business owner asking if I think he/she should sell their business. While they might want my execution help once they decide to sell, they are usually calling just to talk through the decision, almost like they want a thoughtful second opinion from a peer. 

There is a lot of noise around the decision to retire, but it is an especially complicated decision for a business owner who has to sell their business before retirement can be a reality. Moreover, since the owner is usually involved in a post-sale period of transition, the actual retirement is usually two or more years away from the decision to retire.

I have no formula to help an owner decide the right time to sell their business, but one thing is for certain, the decision to retire and the actual retirement are two very different things.

Had my friend Marvin been a business owner, he would have had more time between the decision to sell and the actual retirement. This might have mitigated his concern that he retired too soon. He walked out the door perhaps too early, but for the business owner, be prepared for a long and arduous process. Selling a business is not an easy or quick process.

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Tennessee Valley Group

Jim is an attorney (non-resident status with the Missouri Bar) and though he no longer practices law, he has read and negotiated enough legal documents to fill a cargo tanker. He has an MBA from Harvard Business School and knows how Wall Street and private equity operates. Jim is a Tennessee Supreme Court Rule 31 listed general civil mediator with tons of experience helping business owners (large and small) work through sensitive problems to achieve winning results. He is the author of "Home Run, A Pro's Guide to Selling Your Business, Seven Principles to Make Your Company Irresistible."

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