Chapter X with Michael Kay

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...

A lot of people say they want to stay active or do work that still matters to them after they retire.   But then they rest, travel, or wait for the right opportunity to show up. Over time, that can turn into long stretches without structure or direction in life.   I'm really glad to welcome Lynn Friesth back to the show. He left corporate life in 2015 and has spent the last ten years helping other...

Rusty Gardner realized he wasn't listening to his son during their phone calls. So he stopped what he was doing and went for a walk.   That new habit changed their conversations. Then it changed his mornings, and eventually it turned into something he couldn't ignore.   Rusty spends a lot of time reflecting on identity and the different "passages" we move through as we get older. Today, we explore...

Stepping away from a career that has defined you for decades is rarely a clean break.   For founders and professionals alike, retirement isn't just leaving the work behind. It means untangling identity, habits, and a sense of responsibility that doesn't simply turn off.   My guest today is Dave Yeske, co-founder of Yeske Buie. After more than 35 years in financial planning, he and his wife made th...

We don't spend much time thinking about how we listen.   ​But if you've ever felt misunderstood or struggled to connect with someone, you've probably felt its impact.   Today, I'm joined by David Joseph, MD, a psychiatrist and psychoanalyst with more than fifty years of experience listening to people at a very deep level. He's devoted his career to something most of us struggle with: actually unde...

We like to think we're making choices about how we live. But most of the time, we're just repeating patterns we've been running for years.   In this episode, I'm joined by Marcy Axelrod, who shares why those patterns are so hard to break and what it actually takes to start showing up differently in this next chapter.   Marcy's work explores how we show up in the world. Today, she introduces a 3-pa...

For a lot of men, their social life is their job. So what happens when that job goes away? In this conversation, Anthony Silard shares what he's learned studying loneliness and relationships—and why so many reach this stage of life without the connections they actually need. He introduces the "four PRs" framework and how those roles shape identity for decades. The problem is, they leave very littl...

Most people go looking for purpose when they feel lost. J.D. Pincus believes that's not where we should start.   JD is a social psychologist, researcher, and author of The Emotionally Agile Brain. He's spent decades studying what humans actually need and mapped it into a framework that helps explain why people can feel adrift, even after achieving everything they set out to do.   Today, he joins u...

We're often told that declining health is just part of getting older. But what if that's not actually true?   In this episode, I'm speaking with Dr. Darren Clair, a physician with over 40 years of experience who has spent the last 25 years helping people take a more proactive approach to their health.   After seeing the limits of a system focused on diagnosing and prescribing, Darren chose a diffe...

Most of us spend the first half of life building. The second half, if we're paying attention, is when we start asking whether we built the right things.   Rand Selig is back on the show and a lot has changed since his first appearance two years ago. What started as a few early conversations has since grown into 100+ interviews and the continued success of his book Thriving, which he recently narra...

Larry Kesslin spent much of his life chasing success. After leaving corporate America at 29, he built a successful career as an entrepreneur advising business owners across the country.   By most standards, he had freedom, financial stability, and the life he once thought he wanted. Yet something was still missing. In this episode, Larry shares the moments that changed how he sees success.    A vo...

At 25, Guru Yogishivan was surrounded by luxury in the Middle East. He had trained as a martial artist and become a boxing champion. By most standards, he had success.   But as he spent time around people who had money and influence, he noticed that no one seemed free from fear. Whether it was fear of loss, fear of death, or fear of not having enough.    So he began asking the people around him if...

Howard Rosenberg had done what many of us were taught to do. He got an education, built a career, and provided for his family. From the outside, it checked every box.   But in his early fifties, a diagnosis of advanced heart disease and emergency quintuple bypass surgery forced him to slow down and take a hard look at the life he had built.   That wake-up call led Howard to begin asking deeper que...

Not everyone feels finished when their career ends, especially people who are wired to build.   This week, I'm joined by Randy Gage, an entrepreneur, author, and speaker who retired at 40 and realized he wasn't done creating. Stepping away from work didn't bring the sense of completion he expected, so he returned to building businesses, writing, and teaching. Not because he had to, but because he...

For many men, leaving behind a career also means leaving behind a sense of identity. And much of our response to that change is shaped long before retirement ever enters the picture.   My guest today is Brian DesRoches, PhD. He's a psychotherapist, coach, and author whose work focuses on how the brain responds to change. With more than 30 years of experience, Brian helps people understand why self...

What does it really take to age well—and why do so many people struggle with this transition after work? Today's guest is Ken Stern, author of Healthy to 100 and a researcher focused on aging, longevity, and social connection. Ken has spent years studying why some people remain healthy and engaged later in life, while others face isolation and decline. Ken explains why Americans struggle with agin...

After decades of work, Don Akchin found himself with too much time and very little structure. That moment marked the beginning of a new kind of work for Don: paying attention to what happens when careers end and the familiar routines of life fall away. Don Akchin is a writer and researcher who retired at 66 and began reflecting on his own experience alongside conversations with others navigating l...

Some people move through life by following a plan. Others move forward by paying attention to what holds their interest.   Today's guest, David Litt, spent more than three decades in the U.S. Foreign Service, working and living around the world. Along the way, he built a life shaped by language, learning, and a deep interest in how people and cultures function.   After retiring from government ser...