Chapter X with Michael Kay

Michael F Kay
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  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

Navigating your next chapter after traditional work requires a new kind of bravery—especially for men. Michael and his guests speak straight to how to overcome the conditioning of our hard-charging career years and explore what will bring us fulfillment.

  1. 1D AGO

    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 Breakthrough U   Randy on X Randy on LinkedIn

    43 min

  2. FEB 4

    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  Living a Trigger-free Life

    41 min

  3. JAN 28

    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 The Longevity Project

    47 min

  4. JAN 21

    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 Follow Don on LinkedIn The AfterWork on Amazon Read The EndGame on Substack

    29 min

  5. JAN 14

    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

    53 min

  6. JAN 7

    What If You Didn't React Right Away?

    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: What if? We talk about how that question creates space for perspective and action, especially during major life transitions. We discuss: The moment Doug realized his life needed to change Why hitting bottom didn't immediately lead to transformation How asking one simple question interrupts old patterns The role of identity and routine during life after career Why action matters more than insight alone   Resources Get a free book excerpt at StartWithWhatIf.com Visit DougFleener.com

    35 min

  7. 12/31/2025

    What Your Annual Physical Doesn't Tell You with Reed Davis

    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. Reed helps people understand what's really happening inside their bodies by looking beyond standard lab work and surface-level symptoms.   In this episode, we discuss:   Why standard blood work often misses early warning signs The difference between treating symptoms and addressing root causes How stress, diet, and lifestyle quietly shape long-term health What aging well really requires beyond diet and exercise Why having purpose may be one of the most overlooked health factors Resources Learn more and access Reed's free workshop at: fdntraining.com/kay  Visit Reed's website Follow Reed on Instagram Watch on Youtube Follow on LinkedIn

    41 min

  8. 12/17/2025

    Learning to Ask for What You Want with Paul Quinn

    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 identity, fear, and unspoken rules shape the choices we make. Paul also shares stories that show how a single, well-timed question can open doors we didn't know were there.   You'll hear about: How asking the right questions can help you reconnect with what you actually want Why redefining identity after work can feel so disorienting The trap of focusing on what we don't want (instead of naming what we do) How fear and perfectionism can limit what you're willing to try A simple question that can shift how we imagine what comes next   Mentioned Visit Paul's Website The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests Follow Paul on Facebook

    45 min
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Navigating your next chapter after traditional work requires a new kind of bravery—especially for men. Michael and his guests speak straight to how to overcome the conditioning of our hard-charging career years and explore what will bring us fulfillment.

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