Chapter X with Michael Kay

Why Retiring Early Didn't Work for Randy Gage

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. That moment forced him to rethink his direction, and he's been asking those same questions about what comes next ever since. We talked about: How a stint in jail at 15 forced Randy to rethink his life Why early beliefs shape how we think about money, relationships, and health What Randy learned after retiring at 40 (and why he went back to work) The difference between a finite game and a life built around purpose How Randy defines prosperity beyond money What it means to age with intention and resilience Resources: https://www.randygage.com [https://www.randygage.com/] Breakthrough U [https://www.randygage.com/breakthroughu] Randy on X [https://x.com/Randy_Gage] Randy on LinkedIn [https://www.linkedin.com/in/randygage/]

Why Your Brain Predicts Pain When You Try to Change (And How to Rewire It)

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 not as personal failures, but as learned responses that can finally be brought into the open. In this episode, we covered: Why identity loss can feel more unsettling than we expect How early emotional learning shapes our response to change What anxiety is often trying to protect us from Why so many men struggle without the structure of a professional role The emotional barriers to forming new connections How awareness can create room for something new Resources www.briandesroches.com [http://www.briandesroches.com] Living a Trigger-free Life [https://www.amazon.com/Living-Trigger-Free-Life-Experience-Empowerment-ebook/dp/B0FYZSF1ZB]

Why Americans Struggle With Aging More Than They Should

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 other cultures get right about belonging later in life The surprising benefits of continuing some form of work Why staying busy isn't the same as living well What longevity research overlooks about human connection Resources: Healthy to 100 by Ken Stern [https://www.hachettebookgroup.com/titles/ken-stern/healthy-to-100/9781541705012/] The Longevity Project [https://www.longevity-project.com/]

What Comes After Work Ends

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: Why the loss of structure can be one of retirement's biggest surprises How identity shifts once work is no longer central What Don learned from listening to others' retirement stories Why resilience matters more than having a perfect plan How Don rebuilt structure after leaving work Resources: Visit Don's website [https://donakchin.com/] Follow Don on LinkedIn [https://www.linkedin.com/in/don-akchin-288599141/] The AfterWork on Amazon [https://www.amazon.com/dp/B0FLVP3HBY] Read The EndGame on Substack [https://theendgame.substack.com/]

Finding Direction Without a Map

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 service, David didn't step away from engagement. Instead, he found new ways to teach, mentor, and share what he's learned, proving that purpose doesn't end when a career does. In this episode, we covered: What first drew David toward languages and life abroad How curiosity shaped his path into the Foreign Service The realities of representing the U.S. in unfamiliar places One early experience that changed how he viewed diplomacy Why teaching became a natural next chapter after retirement David's advice for staying intellectually engaged later in life