Chapter X: Steering Men Through Rocky Transitions to Retirement

An older man in a hat smiles as he holds a trumpet. The image is mostly in gray-scale and the vibe is very cool.

Soon after author Michael Kay sold his New Jersey financial advisory business in 2020, he created Chapter X, a blog and monthly Zoom sessions for professional men like him transitioning into retirement. "They were talking about feeling lost, challenged, frightened and disconnected," says Kay. (His initiative is men-only because Kay doesn’t think he has the standing to speak to women about their retirement transitions.)

About five months after launching Chapter X, however, something strange happened.

"I hit the wall and was really depressed," Kay recalls. Then 68, he didn’t want to get out of bed in the morning and wasn’t sure why. "Here I am trying to write affirming things to be positive and supportive and I was feeling like I was eviscerated," he says.

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That crushing experience led Kay, a certified life coach, to devise a variety of Chapter X strategies to help men navigate this new life stage. They’re the heart of his new book, Craft Your Chapter X: A Guide for High-Performing Men to Discover Meaning (and Fun) in Retirement, which is filled with exercises and worksheets. The strategies also appear in his weekly Chapter X podcast.

"I want people to recognize that they’ve been through so many transitions in their lives, this is just one more," Kay says. "This chapter can be something amazing and meaningful even though it doesn’t revolve around how we made our success in life."

Kay chose the name "Chapter X" because he was inspired by middle-school algebra’s directive to "solve for X" when seeking the solution to problems. For men, solving for X is about defining their identity and purpose in retirement.

Before men can determine how to find meaning and joy in retirement, Kay says, they need to feel financially secure.

"It’s important to have your financial life in order, so you have peace of mind and clarity," says Kay. ‘Because if you always have this doubt in your head about finances, you’re never going to have the clarity to be able to go forth and experiment in retirement."

Kay believes men who feel financially shaky entering retirement should meet with a fee-only financial adviser to assess their assets, spending, income, and debt. They can tell the adviser what they hope to do in retirement — say, travel or buy a new home — and the adviser can run the numbers to see if it’s doable.

In Craft Your Chapter X, Kay offers a series of lessons for men wrestling with the transition to retirement.

Adopt a growth mindset

Once men have their finances in order for retirement, Kay says, they can begin the process of realigning themselves by adopting a growth mindset. "Think about ‘How can I bring a sense of energy to my life?’" he says.

It’s about determining who you are when you’re no longer your job. Kay concedes that jumping out of full-time work and into retirement can be frightening, destabilizing, and intimidating. The antidote, he believes, is figuring out what could be interesting and fun for you and trying it.

Kay did this by writing a short story that has now been published in a literary magazine. He’s currently working on a novel and plans to take a college class in German, Spanish or Italian.

The men in his Chapter X Zoom meetings often talk about ways they’re adopting growth mindsets. "A physician who’s retiring said he wants to take classes in physics. That’s what really turns him on," says Kay.

If something new you try isn't working for you, move on

Kay speaks from experience. He returned to the trumpet after a 50-year hiatus and joined a big-band group, thinking it would excite him. But he didn’t care for the band’s members or music.

"I walked away," Kay says. He has since found another band that he enjoys much more.

Find ways to add meaning to your life in retirement

"A lot of high-performing men feel like if they’re not curing cancer or solving world hunger, it’s not meaningful," says Kay. "That’s nonsense. Let’s create small wins. How can you use your time and expertise to help others?"

He suggests mentoring young people coming up in the field that you formerly worked in.

Leave a legacy for your children and grandchildren

That doesn’t necessarily mean a financial one, though, Kay says.

"You can leave someone a pile of money, and they can buy a house or a car, and that’s nice," he says. But Kay suggests retirees leave a legacy for younger family members by being kind and staying connected. Kay’s legacy to his two adult children and three granddaughters is his focus on being present and listening to them.

Retiring is a long-term process best taken in phases

Over time, expect to alter things you can, or want to, do.

"As we get older, we might have a diminishment of eyesight or mobility. Then we need to think about what we can do based on these new facts and circumstances," Kay says.

Similarly, your priorities may change in later phases of retirement. For example, you may find less of a craving to travel because it could become too taxing or expensive.

Tools you’ve sharpened over your life, like resilience, can be helpful in retirement

Kay calls resilience the most important tool in navigating retirement. "In this chapter of life, we’re going to get knocked down," he says. "But we can take what we’ve learned and apply that to our life now."

In retirement, Kay says, you need a Plan B, and maybe even a Plan C in case life throws you curveballs.

Lean into change

One of Kay’s worksheets asks readers to reflect on how they handle discomfort and find ways to bolster their courage and resolve. Another exercise is to write down your "possibilities list" to explore new opportunities.

"I understand that change can be uncomfortable," Kay says. "Just know that this change is a challenge and you’ve been through a million changes before."

Richard Eisenberg is an "unretired" personal finance writer, editor and podcaster. He writes a column for Dow Jones' MarketWatch; freelances for outlets including Kiplinger, AARP The Magazine, PBS' Next Avenue, The Stanford Center on Longevity Magazine and People magazine; and is co-host of the Friends Talk Money podcast for people over 50.

Previously, he was managing editor at Next Avenue, executive editor at Money magazine, special projects director/money editor at Good Housekeeping and director of NYU Summer Publishing Institute's Digital Media Strategies Program. He is the author of "How to Avoid a Midlife Financial Crisis" and "The Money Book of Personal Finance." Eisenberg graduated from Northwestern University's Medill School of Journalism and lives in New Jersey.