Men Can Have a Terrible Time Transitioning to Retirement

An online support community aims to help professional men who have been knocked off the career ladder.

By Richard Eisenberg

Stepping out of the world of full-time work and into the world of retirement can feel like losing your footing to quicksand. Loss of identity. Loss of income. Loss of colleagues. Perhaps the loss of a spouse or partner. Michael F. Kay, managing partner of Financial Life Focus in Livingston, N.J., thinks the transition can be especially rough on high-achieving men.

That’s why he started Chapter X, a new online sharing, supportive community that currently has roughly 30 recently retired professional men, mostly in the New York area and California. Kay also writes a Chapter X blog for men about this stage in life, read by several hundred men, and hosts the weekly Chapter X With Michael Kay podcast.

“All of a sudden, for some [retired men], the rug’s been pulled out from them,” says Kay, who’s 66 and not yet retired. “They’re out of a job. They’re left bereft of meaning and purpose in their life because they no longer have this ladder to climb. It becomes a terrible time for a lot of men.”

“It’s more than just managing your money. It’s managing what’s your life after your retirement.”

Why The Retirement Group Is Called ‘Chapter X’

And the name “Chapter X?” Kay chose that after recalling his frustrating days of eighth-grade algebra, where his teacher said “you’ve got to solve for X.” The phrase stuck in his head. For retired men, Kay says, “you’ve got to solve for what retirement is for you. What is it that lights you up?”

The men who meet with him at Chapter X’s Zoom support meetings and read his blog are trying to figure it out. I sat in on a recent Chapter X session and talked with a few of the X men afterwards.

“It’s more than just managing your money. It’s managing what’s your life after your retirement,” says one of them — Marty Kanengiser, a kindergarten friend of Kay who retired at 64 in 2019 from his 35-year managing procurement at PepsiCo in Westchester County, N.Y. “It’s like you’re no longer what you were. And you have to kind of almost reinvent yourself.”

That raises a whole lot of questions, says Kanengiser, who’s been married for 27 years and is a grandfather. A big one: What does reinvention mean? “And what do you think of that? And what does that mean for your family?” says Kanengiser.

Failing to Plan Much for Retirement Life

At PepsiCo, Kanengiser says, he planned a lot as part of his job. But “I didn’t really plan so much about what am I going to do for myself personally, and for my family, after I finish work,” Kanengiser notes.

Carl Schecter, another Chapter X member, is asking himself a lot of questions, too. A Wall Street arbitrageur for 34 years, Schecter found himself out of a job and newly divorced at 56 a few years ago. “My reality turned upside down,” he says.

A self-professed math geek, Schecter calls this time of his life “a jump discontinuity.” (That’s a function whose side limits don’t coincide and are finite. But you knew that.)

Schecter says many men have an “almost willful blindness to this unpleasant reality that there’s going to be a period where, at some point, you’re not going to be

Until Chapter X, Schecter didn’t know who to talk to about his new, unmoored life. Although he has “two wonderful daughters” and “wonderful friends,” he didn’t think they’d fully understand what he was going through.

At Chapter X, they do.

When the men Zoom together, Kay says, they help each other find out what they really care about; what gives them meaning and purpose (or could) and how to avoid the landmines of retired life. Says Kanengiser: “It’s interesting to hear about others and what are they concerned about.”

Kay, the holistic author of “The Feel Rich Project” and “The Business of Life,” explains the genesis of Chapter X this way: “I’ve had so many men who said to me, ‘Oh, when I retire, I’m going to play golf.’ And I go, ‘Okay. You’re going to play golf once or twice a week. What are you going to do the other five days? ‘ And most of them have no idea. So that really became the foundation for Chapter X, because they needed an answer.”

Finding Answers to The Big Questions of Retirement

Some Chapter X members have begun finding those answers.

Kanengiser, for instance, now offers advice to entrepreneurs and wannabes as a mentor for SCORE, the nonprofit affiliated with the Small Business Administration; volunteers as a New York State COVID-19 contact tracer and for the Red Cross. Lately, he and Buddy — his calm Black Lab rescue dog — have been offering dog therapy sessions with residents of retirement communities. On Zoom, of course.

Schecter’s doing dog therapy, too, with his Goldendoodle, coaching chess in schools and is on an advisory board for cancer research.

But why aren’t women allowed in Chapter X?

Why Chapter X Is For Men Only

He felt he could be useful by offering a “safe space” just for newly retired men to talk with each other.

“I really wrestled with this,” Kay says. Ultimately, he decided, “women are so much better” at community building than men. “I think women are far more socialized and know how to relate in ways that have nothing to do with competition,” says Kay.

Kay notes that a 2018 TD Ameritrade survey of women showed that they tended to look to retirement optimistically, as a liberating phase of their lives. He felt he could be useful by offering a “safe space” just for newly retired men to talk with each other.

Schecter thinks the men-only rule for Chapter X makes sense because men “have in our DNA a different set of shame of failure — or the trappings of feelings of failure — for not having done X, Y or Z, that are very different from what a woman would have.”

The pandemic, Kay says, has made the need for Chapter X even greater.

“There are a lot of men who might’ve thought before the pandemic, ‘Well, what I’ll do in retirement is I am going to travel somewhere.’ And now they can’t go very many places. So, in some ways, it’s narrowed what they can think of as their transition to retirement.”

At the Chapter X meeting I attended, I noticed that all the men were white. Kay’s working on that. “My hope is that [Chapter X] will be as widely diverse as can absolutely happen,” he says.

Kay hopes to grow Chapter X in multiple ways, starting with adding a resource page to his group’s site. He’s also getting certified as a coach so he can then launch a formalized coaching program. It’s all about continually solving for X.

©Next Avenue. Richard Eisenberg is the author of “How to Avoid a Mid-Life Financial Crisis” and has been a personal finance editor at Money, Yahoo, Good Housekeeping, and CBS MoneyWatch. This article was first published by

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