Commentary by crisis management expert Edward Segal, author of Crisis Ahead: 101 Ways to Prepare for and Bounce Back from Disasters, Scandals, and Other Emergencies (published by Nicholas Brealey)

Some CEOs might nod their heads in agreement to one of the lyrics in My Way, a song popularized by Frank Sinatra, when he sang "Regrets, I've had a few, but then again, too few to mention."

Unlike most Americans who, according to a new Bankrate survey, have a financially-related regret about retiring, the CEOs I heard from had a different set of retirement remorses.

They were sorry that they left too soon, and some did not realize until later what they had lost.

Loss Of Leadership Role

Facing New Challenges

"I built and sold a company in my 30s, with enough to retire comfortably. But within a year, I missed guiding a team and facing new problems. I started another company to remedy boredom and feel productive again. For CEOs, work is life— losing that purpose prematurely leads to regret," Craig Lewis, founder and CEO of Gig Wage, a financial technology company, warned in an email interview.

Successors

A CEO who designates a successor and then retires could have second thoughts about the person who took the helm. That appears to be the case, as recounted today by the New York Times, when Bob Iger, who chose Bob Chapek to succeed him as CEO of The Walt Disney Company, later took steps to get his old job back.

Lose Of Daily Interactions

What CEOs once took for granted because of the nature of their positions can quickly disappear in retirement.

"What really surprised me… was the extent to which my identity had been wrapped up in the relationships I formed in becoming a CEO. The daily interaction with my executive team, board members, and partners wasn't business; it was life. When I stepped down, that network disappeared in short order. I felt disengaged from the very conversations and decisions that had fueled me. It wasn't the missing work; it was the feeling of not being in the loop in a world I'd once helped to mold and shape,"James White,, CEO of amazingmoves.co.uk, a house and furniture removal company in the UK, recalled in an email message.

Boredom

Being bored in retirement, combined with family and health issues, can trigger regret for leaving a top job too early.

One example is Tammy Sons. She is the founder and CEO of Tennessee Wholesale Nursery and a horticultural expert. Sons retired when she was 50 years old.

It was a short-lived retirement.

"I had planned to retire at 50. After all, I had made enough money to live comfortably for the rest of my life and had everything I wanted. I dreamed of traveling, fishing, and living a life of pure solitude and enjoyment. After spending most of my life working and getting educated, I wanted to retire early to enjoy life. Well, things didn't work out like I had planned at all," she recalled in an email.

"After some major health issues, losing a father, and having two children that almost drove me insane with drug habits, plus pure boredom, I was happy to go back to work a year later," Sone recalled.

She pointed to singer Dolly Parton who said she'd never stop working. "I'll just hopefully drop dead in the middle of a song on stage someday, hopefully, one I've written." 

For her part, Sons said she hopes to "fall over on the job and never retire."

Stagnation

Lack of opportunities to interact and engage with others that also trigger remorse for having left too early.

"The CEO role demands constant learning and growth. Stepping away means stagnating your mind and skills. I've found hobbies and community work can't replace the thrill of building a business. CEOs should find ways to stay engaged, through board seats, consulting, or new ventures. Total retirement often seems appealing but rarely satisfies in reality," Lewis recommended.

'I Felt A Void'

To help counter their regret about no longer being a CEO, former executives will often find other ways to replace what was missing in their lives.

"Two years ago, I began seriously planning my retirement by developing a strong management team and successor to lead the company into the future. Still, when I officially retired last year, I felt a void from no longer being involved in the day-to-day challenges. To fill that, I joined the board of a local non-profit to stay active in the community," Ben Klesinger, founder and CEO of Helping Hand Financial, recounted via email.

Struggling With The Decision

For CEOs who founded their companies, the decision to retire can be a difficult one.

"As a CEO and wealth advisor for over 20 years, I've seen many executives struggle with the decision to retire. The most common regret is leaving before ensuring a smooth transition. Founders often underestimate the time required to hand over control and responsibility. Because of this, some CEOs find themselves adrift after stepping down, causing distress for both themselves and the company," David Blain, CEO and founder of Blue Sky Wealth Advisors, observed in an email interview.

Proper Planning Needed

It is possible, of course, to have an engaging and fulfilling retirement. But it often requires advance planning.

"The keys for CEOs are planning financially, finding purpose outside of work, and ensuring a strong succession plan. Do that, and retirement can be the rewarding next chapter rather than a regretted premature ending," Rob Macoviak, president of the Oyer, Macoviak and Associates insurance firm, advised via an email interview.

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