Kiplinger interviewed Kelly Ottman, a retirement coach and business professor at the Milwaukee School of Engineering, shared opinions about retirement from a host of executives.
Question: You recently surveyed nearly 120 executives who were within five years of retiring or who stopped working less than five years ago. What did you learn that applies to people who aren’t top corporate leaders?
Answer: Before retiring, the executives wondered: “What am I going to call myself in retirement? What is it that I do besides work?” I think those questions about finding your purpose are transferable, whether you have ever been a CEO or not.
Most of the preretirees and retirees in the study hadn’t thought much about what they’d do in retirement. That’s probably true for people who aren’t corporate executives, too.
Question: What did the retired executives think of the word retirement?
Answer: Only two liked the word; the rest almost despised it. They said the images of retirement they see and the messages they got on Facebook — such as, “Oh, you’re going to just be on the golf course” — didn’t fit them. They said: “Retirement is so much more than that.” But the retired executives didn’t have hobbies. They saw their job as their hobby — and that can be a problem.
One 2025 study found that hobby engagement may help slow declines in certain cognitive abilities. Another revealed that having a hobby is associated with fewer depressive symptoms, better self-reported health and higher life satisfaction. Bringing established interests into retirement can ease the transition and provide continuity and purpose.
Question: Most of the retired executives likely didn’t have big money worries. But did they struggle with anything financially?
Answer: Getting comfortable with spending in retirement was huge for them, even though they recognized they had enough money. One top executive I interviewed was lamenting over whether she could buy a new pair of shoes. She met with her financial adviser, who said, “Please buy new shoes. And while you’re at it, buy that car you’re looking at, too.”
From studies I’ve seen and my research, one of the strongest needs for a successful retirement is explicit permission to spend. I recommend seeking trusted advisers who can help you feel comfortable spending.
Question: What were the biggest gains for executives in retirement?
Answer: One was stress reduction. They slept better. Many reported health gains due to weight loss. Also, they said retirement gave them the ability to rekindle joy or find new joys. One woman said she took French in college and was now taking a French class and planning to live in France for a month. Somebody else picked up a musical instrument and is now in two bands. I think you need to let yourself be curious in retirement and explore things.
Question: What surprised the executives about retirement?
Answer: Loss of friendships. They didn’t anticipate that after they retired, people would stop calling them. Work friendships in their positions were more transactional. That loss of friendships was sometimes profound, particularly for men. Some people worked on this before they retired. One executive did not like chitchatting, but she recognized that it’s important for developing friends. So, prior to retirement, she’d get on the phone and chitchat. One recommendation I have from this research is to cultivate friendships before you retire.
Question: Some of the executives compensated for a lack of structure in their lives by finding ways to stay busy all the time. What’s your advice?
Answer: Don’t overschedule yourself. Many of the retired executives advised other retirees to take six months to a year before committing to a lot. That said, it’s not what they did — 80% were on nonprofit or for-profit boards.
Question: What’s your main takeaway from your research?
Answer: You need to look at retirement as more than just a financial equation. How do you pull forward your purpose and values so they shine in retirement and you’re the person you want to be? If you can talk with others about what retirement will be, and develop friendships, one to three years before retiring, things become a lot easier.
Richard Eisenberg is a contributing writer at Kiplinger Personal Finance magazine. For more on this and similar money topics, visit Kiplinger.com.
©2026 The Kiplinger Washington Editors, Inc. Distributed by Tribune Content Agency, LLC.
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