The Business Transition Blog

Why Boomer Entrepreneurs Need a New Mission

Gail Sheehy, author of the ground-breaking book, Passages, said this about people in their sixties:

No matter what your record of external achievement, you will need an internal mission to fortify your resilience in meeting the obstacles and exit events ahead. The optimum goal is to find a pleasurable commitment that allows you to exercise parts of yourself that had to be ignored earlier. A mission can give this stage of life its own meaning and even guarantee you a sliver of immortality.

Mark, a very successful business owner in the Southwest sold his business in 2004. He’s lucky he did because his company built single family houses – 740 of them a year – and he got out just before the big meltdown in the US housing market. At the time, he was so fixated on his goal of selling the business that he didn’t look beyond that event to what he would be doing afterwards.

He said, “The day the deal went through and I looked at my bank account and saw how much money they had wired me, was the happiest day of my life. And it went downhill from there. I got sick. It was as if I had the flu all the time and I couldn’t shake it. I couldn’t get out of bed. I went to my doctor who ran a bunch of tests and couldn’t find anything wrong. He referred me to a psychologist who couldn’t find anything wrong. I was in bed for almost a year and it took me two years before I felt better.”

Now think about this for a moment. Here’s a guy who has all the money in the world; he’s very, very wealthy and he loses two years of his life ‘recovering’ from selling his business.

Aside from his doctors, his lawyer and his wife, I was the first person he had shared this with. He was embarrassed. He had been blind-sided by this illness which turned out to be a loss of serotonin or clinical depression – a diagnosis that was especially tough for an optimistic, macho, self-made man to accept. But if you plan ahead, have goals to work toward, and dreams to chase, you can choose to make this transition in your life a positive one.

When I spoke with him four years after the sale, he was feeling much better. He spent a lot of time at the gym and with his family making up for lost time. He was in better physical and mental shape than he had been ten years earlier. He and a couple buddies were talking about starting a bank. He needed a new challenge, a new purpose. Too bad he hadn’t figured that out before he sold his business.


[1] Sheehy, Understanding Men’s Passages, p. 223

Fifty Ways to Leave Your Business

I was listening to the radio today and heard Paul Simon’s classic song, Fifty Ways to Leave Your Lover and it struck me that in many ways, leaving your business engages very similar emotions to what one must go through to leave a lover. Not that I have much personal experience leaving lovers as I’ve been happily married for 35 years. But I have struggled with the emotional turmoil of leaving a business.

With apologies to Paul Simon, here are a few lines of the song:

“The problem is all inside your head”, she said to me
The answer is easy if you take it logically
I’d like to help you in your struggle to be free
There must be fifty ways to leave your lover

You just slip out the back, Jack
Make a new plan, Stan
You don’t need to be coy, Roy
Just get yourself free
Hop on the bus, Gus
You don’t need to discuss much
Just drop off the key, Lee
And get yourself free.”

Now, I would suggest that many of these are deceptive and not particularly moral. So I’m not going to recommend them, but they do get the conversation going. And that’s what we need to do. Start thinking about it. Start talking about it. Start doing something about it.

Two I do like are, make a new plan and get yourself free. Part of the planning piece is seeing how many ways you can come up with to leave your business and then choose the one that is right for you and your stakeholders.

Plan, choose, execute and set yourself free.

To get your smile for the day,  watch an amusing video of this song performed by the Muppets at: 50 Ways to Leave Your Lover