Feeling Stuck When Life Looks Fine
Chapter X with Michael Kay
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 us to talk about those needs and why getting unstuck might start with feeling a little worse before you feel better. You'll hear about: Why people can feel stuck even when life...
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Why Health Doesn’t Have to Decline With Age
Chapter X with Michael Kay
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 different path. His work centers on lifestyle, education, and helping people stay healthy in the first place. We’ll hear how his perspective evolved over time, what he’s learned...
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How to Thrive in the Next Chapter of Life with Rand Selig
Chapter X with Michael Kay
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 narrated as an audiobook. Rand spent much of his career running his own investment banking firm. Now he's turned his attention to the questions that tend to matter most in life's later...
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Rethinking Success at 52
Chapter X with Michael Kay
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 volunteer trip in Aspen and a later time in rural Uganda made him question the life he had built. Over time, he realized that chasing success was different from living with purpose....
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When Success Doesn’t Erase Fear with Guru Yogi Shivan
Chapter X with Michael Kay
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 they were truly happy. That question sent him on a very different path. In this episode, we explore his journey from athlete to monk... and what his search for truth might mean for men...
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A Wake-Up Call at 51 with Howard Rosenberg
Chapter X with Michael Kay
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 questions about identity, purpose, creativity… and what really sustains us in the second half of life. We talked about: How a health wake-up call led to a complete identity shift Why...
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Why Retiring Early Didn’t Work for Randy Gage
Chapter X with Michael Kay
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 wasn’t done. That instinct to question what comes next started much earlier. At 15, Randy was sitting in a jail cell, facing the consequences of a life that had gone off track....
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Why Your Brain Predicts Pain When You Try to Change (And How to Rewire It)
Chapter X with Michael Kay
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-doubt and disorientation often show up during major transitions. We look at how long-standing emotional patterns can surface after work ends. Brian offers a way to see these reactions...
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Why Americans Struggle With Aging More Than They Should
Chapter X with Michael Kay
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 aging and retirement more than people in other countries… and what we get wrong about life after work. In this episode, we discuss: Why aging in America often leads to isolation after work What...
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What Comes After Work Ends
Chapter X with Michael Kay
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 life after work. Over time, those observations became the foundation for his book The AfterWork, which explores how people find meaning, connection, and direction beyond their careers. We cover:...
info_outlineMany 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 in New York City.
Over time, he shifted into teaching and storytelling in a way that opened a new path for him. In this conversation, Doug shares how the stories we hold can keep us stuck and how new ones can help us move into the next chapter.
We talk about:
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How Doug transitioned from a life in music to helping people change
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The moment that shifted how he viewed what is possible
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Why career identity becomes so difficult for many men to release
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The simple question that reveals who we are beneath our titles
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How storytelling helps reshape belief and create room for what comes next
Resources:
https://www.essentialcoachingskills.com
https://dougobrienhypnosis.com