Why Life After Retirement Depressed These CEOs

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After years of hard work, these three CEOs were nearing their retirement.  They should have been jumping for joy, but instead they felt like it was the end of the world.  Yet they soon discovered there is life after retirement, provided you take the time to plan.

In another conversation with Paul Cronin of the Strategic Transition Planning Institute (here’s our link to the first chat we had with him), we talked about these three CEOs, including how they pulled themselves out of a retirement funk that affects many owners.  (We’ve changed the CEO names for the article.)


Tale #1 - The CEO Who Feared for His Clients

Bill was a CPA with a successful business.  He was nearing the retirement age, and he knew that he had to think about grooming a successor.  But he never did it.  He kept worrying that the person he would pick wouldn’t have the skills to handle his client base.  

He was eventually forced to complete his succession plan, but not on his timeline.  A health issue forced Bill’s hand, and he had to bring in a successor.  As much as he worried about his clients not being treated in the proper manner, now Bill had to be concerned about them being helped at all.

To his credit, he moved fast.  He put together a wonderful plan, and hired someone to take over the business. And then a funny thing happened.

As Bill recovered, he was able to get back to work and spend some time with his successor.  They attended networking events, and Bill found that instead of people asking for him, they were starting to ask for his newfound partner.

“They used to want to talk to me.  Now they want to talk to the guy who’s taking over.  I had to laugh, because that’s what I wanted,” he said.  He also had to grin, because it was truly great for him to see.


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Tale #2 – The CEO Whose Wife Could See the Future

Paul also talked about Phil, CEO #2.  Phil attended a lecture from the STPI on how to transition into a meaningful retirement.  He approached STPI afterward, and said he needed to talk.  The reason?  His wife had told him to attend the presentation out of concern for his future.  

Call her a common-sense psychic, but Phil’s wife could see the moment he retired, he would be in trouble.  Phil just sold his business, and he had six months before his consulting contract with the new owners ran out.  

His wife was worried because in six months, he would have no activities to fill his time.  That would be the first time in the forty years she had known him that he would have absolutely nothing to do.

Phil knew he needed a structure for his new life, and so he worked through STPI’s program.  

Six months later, Paul received an email.  The subject line read:  “A day in the life of a retired guy with a plan.”  It was from Phil, and he detailed his daily, extremely pleasurable, and incredibly active day.  

He was up at 6 am for yoga.  Then he would walk the dog, meet friends for coffee, and attend a woodworking class.  His entire schedule was laid out like a workday, and Phil was enjoying every minute of it.  “I’m so busy, I wouldn’t have time to work even if I could,” he told Paul.

Phil had turned “nothing” into the most fun he had in years.  It was all because he had a plan, as well as a wife who could see the future.


Tale #3 – The CEO Who Retired Wrong

For many of you, this next tale sounds like fun – at least from the get-go.  

CEO #3 is Tom.  Like all business owners, he built a solid company, but he knew that the industry was changing and he didn’t want to be a part of it.  So he sold out, and decided that it was time for a change of his own.


Tom had always loved visiting Las Vegas, and he thought retiring there would be an absolute blast.  Somehow, he convinced his wife that would be the case, and they left their home and friends and headed to Vegas.

Six months later, Tom’s wife had an announcement.  While he was out golfing, gambling and having fun, she was miserable.  She had two friends in Vegas in similar situations, and both of them had announced they were returning to their homes.  “I’m going home, too,” she said, and she did, leaving him alone in Vegas.

You can imagine what happened next.  In short order, Tom did a lot of bad things, and his retirement and his life was turning into a very ugly train wreck.

Somehow, Tom had the wherewithal to pull himself out of his funk.  After getting some professional help for the issues that were driving him downward, he worked on constructing a retirement plan – one that would allow him to return to a more productive lifestyle.

First, he reconciled with his wife.  Then, because he so enjoyed working face-to-face with customers, he started a business where he wouldn’t have to worry about employees or tremendous overhead:  He opened a hot dog stand.  

Ironically, when he was a little kid, Tom had always wanted to own a hot dog stand.  So here, in his retirement, he pursued his true lifelong dream.  And the guy was happy as a clam.

* * *

At one time, all three CEOs felt true anxiety regarding their retirement.  The key to overcoming their fears was to develop a vision for life after retirement.  When they did that, they added gleam to their golden years.  

These are all stories with a happy ending.  If that has some appeal to you, click on the button below to receive a free first chapter of STPI’s book, Finding Your New Owners: For Your Business, For Your Life.  We’ll also provide you with a link to their “What’s Next? Self-Assessment.”


Finding Your New Owner

Topics: Succession Planning, M&A