Chapter X with Michael Kay

There's a whole industry devoted to helping us find ourselves. Samuel Strauch discovered that the search itself can become a trap.   We spend so much of our lives striving for success, solving problems, and looking for ways to improve. But sometimes, the constant need to do more gets in the way of finding fulfillment.   My guest today is Samuel Strauch, a real estate entrepreneur and author of Dea...

The most meaningful advice can take years to fully understand. Just two weeks before his death, Gary Coulton's father asked him a question about who would attend his funeral. It took Gary ten years to understand the wisdom behind it. My guest today is Dr. Gary Coulton, a former biomedical scientist and executive coach turned writer and poet. Gary describes himself as a "successful misfit" and a wo...

Sometimes finding purpose in retirement is as simple as picking up the phone and calling an old friend.   After decades of chasing success, it can be hard to imagine that something so small could make a difference. We're used to measuring our accomplishments by the size of the impact we make.   My guest today is Jonathan Logan, a coach who's reinvented himself several times throughout his life. Al...

Retirement is filled with decisions, and the choices we make today can have a lasting impact on our lives. With so much conflicting advice out there, how do we know we're making the right ones? My guest today is Dan Goldie, a former professional tennis player, financial advisor, and author of The Retirement Answer: The Six Key Decisions Every Retiree Needs to Make. In this episode, Dan shares the...

The first six months of retirement may be the easy part.   At first, there may be travel, projects, and long-awaited plans to fill the time. But once the dust settles, retirement can begin to feel very different.   Psychotherapist Austin Dowling joins me again on Chapter X to talk about what can surface after the initial transition. We explore loneliness, identity, self-reliance, and the challenge...

We spend a lot of time thinking about the past or worrying about the future. What gets lost in between?   For Dr. Evan Fishman, that question became more personal after he was laid off from Facebook in 2023. The experience forced him to rethink how much of his identity was tied to work, achievement, and what came next.   Today, Evan helps others navigate similar questions around identity, uncertai...

For people who've spent decades succeeding at work, life comes with a scoreboard. There are goals to hit, problems to solve, and clear ways to know when you're succeeding.   Then comes a stage of life when those measurements don't work quite as well. My guest today is psychologist Brent Beam, who works with executives and men navigating major life transitions.   We talk about what happens when the...

How long can you keep doing what you're supposed to do before you realize it isn't working anymore?   Ted Kopecko built a successful architecture practice, worked 16-hour days, and kept pushing forward until the life he created became one he no longer wanted to live.   Today, Ted is the author of Finding Joy: The Journey of You. In this episode, we talk about breaking old patterns, questioning the...

One partner's retirement dream may look very different from the other's.   Maybe one of you imagines traveling and spending every day together. The other likes the life, friendships, and routines they already have. If you haven't talked about what retirement will actually look like, you may be planning two very different futures.   My guest today is therapist, coach, and author Dorian Mintzer. Dor...

What happens when you love your work too much to retire from it?   David Fiala has spent more than 35 years helping people better understand themselves. When someone once asked him about retirement, his response was: "How can I retire from what I am?"   David is a clinical social worker and author of *The Courageous Seeker*. His own path has taken him from working in casinos to exploring monastic...

You're never too old to learn something new.   Ed Friedman didn't grow up around the arts. In fact, he didn't see his first stage play until his late 20s. But as an adult, creativity became a big part of his life.   Ed went on to act, write plays, and co-found Lifetime Arts, a nonprofit that helps older adults learn and create through the arts. Today, he's retired from the organization but still w...

Life has a way of telling us when something needs to change, even when we aren't ready to listen.   My guest today, Mark Feinberg, spent years building companies, serving on boards, and chasing success. From the outside, everything looked right. But internally, Mark knew something was missing.   After the sudden loss of his business partner and close friend forced him to stop, Mark began letting g...

What did you love before work and responsibility took over?   As kids, we followed our curiosity without worrying whether an interest was productive or impressive. Somewhere along the way, many of us leave those parts of ourselves behind.   My guest today, therapist and author Alexander Osterman, believes they're worth going back for. He even has Lego castles on his office wall simply because he a...

Retirement isn't just the end of a career. For many executives, it's the first time they've had to redefine who they are without the title they've spent decades earning.   So why do so many accomplished leaders struggle with this transition? And what can they do now to prepare for what's next?   My guest today is Dr. Kelly Ottman, executive coach, researcher, and founder of Leadership Portals. Aft...

Creativity isn't reserved for artists. It's something we use every day to solve problems, adapt to change, and discover new possibilities.   That becomes especially important in Chapter X. Retirement reimagines how we spend our time, where we find fulfillment, and what comes next.   Today I'm speaking with James Walters, photographer, podcaster, and author. He shares why curiosity is at the heart...

We tend to avoid anything we won't be instantly good at. Richard Sparks has spent forty years proving that instinct is wrong.   Richard is a writer who has spent 40 years bouncing between comedy sketches, TV scripts, opera translations, and now fantasy novels. He wrote for a young Rowan Atkinson before anyone knew his name, then somehow ended up translating operas with no background in the form.  ...

We spend decades working toward the exit. But what happens once we actually get there?   Today I'm speaking with Jack Calhoun, who sold his wealth management firm in his fifties expecting to finally relax and write. Instead he found himself restless, then stuck running a company he didn't even like after a bootstrapped venture went sideways.   In this episode, Jack shares what that wrong turn taug...

What can we learn from someone who spent weeks living in retirement communities and interviewing dozens of retirees?   That's exactly what today's guest set out to discover. Dr. Andi Simon is a corporate anthropologist whose curiosity about retirement led her to study how people navigate life after work.   Although every story was different, she found that many retirees shared the same struggles a...

Jake Fishbein joined his first men's group for research.   He was helping write a novel about men's groups and thought he should probably see one from the inside.   What he didn't expect was that the experience would change the course of his own life.   In this episode, we discuss why retirement can trigger an unexpected identity crisis, the challenge of separating who we are from what we do, and...

Loneliness isn't something we usually associate with successful people. When the career ends, where do purpose, connection, and belonging come from next?   My guest today is Carl Nassar. He's an engineer, teacher, businessman, and eventually, psychotherapist. After achieving everything his parents had hoped for, Carl realized the one thing he was still searching for was a sense of belonging.   So...

Larry Hagner was nine months old when his father left. For years, he searched for answers about the man he barely knew and the impact that absence had on his life.   Today, Larry is the founder of The Dad Edge podcast, where he has spent more than a decade helping men become better husbands, fathers, and leaders.   In this episode, Larry shares his story, from growing up without a father to raisin...

What if the goal isn't just to live longer, but to remain capable of doing the things you love for as long as possible? After decades as a physician, surgeon, and medical innovator, Dr. Arnon Krongrad believes we've been asking the wrong question. Rather than chasing longevity, he's focused on something he calls "functional supremacy." Today, Arnon challenges conventional thinking about health and...

What if the things you loved most as a kid still hold clues about the life you actually want now?   I still remember Yankees games crackling through a transistor radio tucked under my pillow long past bedtime. For Ben Orlando, it was realizing those moments were never really about baseball at all.   I'm talking with psychotherapist, writer, and Midnight Library of Baseball host Ben Orlando about m...

Many fathers spent their lives learning how to provide for their families. But emotional connection often became much harder to pass down.   My guest today is Marc Azoulay, therapist and founder of Men's Therapy Online. Marc works with men navigating relationships, identity, purpose, and emotional health across different stages of life.   In this episode, Marc shares his own journey through addict...

What happens when life forces you into a chapter you never planned for?   After decades building a successful career in technology, writing books, and growing a business, Jeffrey Ton suddenly found himself stepping away from work to become a full-time caregiver for his wife following a devastating diagnosis.   In this episode, Jeff shares how revisiting memories of traveling the Lewis and Clark Tr...