Chapter X with Michael Kay

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...

Doug Fleener woke up on an airplane with no idea how he got there. That was the moment his life began to change.   Today, Doug shares the story of hitting bottom and rebuilding his life one decision at a time. He reflects on addiction, recovery, and the importance of learning how to pause before reacting.   Today, Doug is an author and speaker whose work centers on a simple but powerful question:...

As we move into the later chapters of life, many of us begin to think differently about health. Not just how long we'll live, but how well we'll live. What if the symptoms we accept as "normal aging" are actually signals pointing to something deeper?   In this episode, I'm joined by Reed Davis, a double board-certified holistic health practitioner and founder of Functional Diagnostic Nutrition. Re...

Why is it often easier to know what we don't want than to ask for what we do?   In this episode, I'm joined by Paul Quinn, author of The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests. Paul began his career as an actor before moving into corporate training and writing, where he became fascinated by the moments that spark real change.   Today, we explore how...

Many men feel caught between the identity they built at work and the person they hope to become. Today's guest helps us explore that space.   Doug O'Brien has spent his career studying how our stories shape the way we live and the way we move through change. Before entering this work, Doug lived an entirely different life as a classical pianist, a Carnegie Hall performer, and a punk rock musician...

Modern medicine can treat almost anything. Yet it often misses the root of what makes us sick.   Dr. Ravi Kumar is a neurosurgeon who trained at the Mayo Clinic and spent years in operating rooms before realizing he needed to step away. He sold everything and moved his family to India, where he worked in mission hospitals under the most basic conditions.   Those experiences changed the way he view...

What happens when life forces us to confront the unexplainable?   Today's guest, Dr. Gregg Korbon, is a retired anesthesiologist whose life took an extraordinary turn after the loss of his nine-year-old son, Brian.    A lifelong man of science, Gregg was suddenly faced with experiences that defied logic and ultimately changed the course of his life. In this deeply moving conversation, Gregg shares...

For nearly 30 years, Peter Haskell's voice was a familiar one across New York. As a reporter for WCBS Newsradio 880, he covered some of the region's most defining moments.   When a rare vocal disorder forced Peter to step away from the microphone, it brought an unexpected crossroads. What followed was a shift toward gratitude, purpose, and a renewed belief in the power of stories and kindness.   T...

At 68 years old, Rand Timmerman looked in the mirror and thought his life was over. A decorated Vietnam War veteran and successful attorney, he had been undone by alcoholism and the toll of PTSD. Yet what seemed like the end became the beginning of a new path.   Now more than a decade sober, Rand shares how recovery gave him the strength to take on an extraordinary challenge with his brother: hiki...