Chapter X with Michael Kay
What happens after a successful career ends? This podcast explores how men navigate retirement, identity, and purpose beyond work. Each week, Michael and his guests look at the real challenges of life transition. the loss of structure, the shift in identity, and the search for meaning and purpose that follows. If you're a man rethinking what fulfillment looks like after decades of hard-charging work, you're in the right place.
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What Makes Retirement Different for Executives
08/05/2026
What Makes Retirement Different for Executives
Retirement isn't just the end of a career. For many executives, it's the first time they've had to redefine who they are without the title they've spent decades earning. So why do so many accomplished leaders struggle with this transition? And what can they do now to prepare for what's next? My guest today is Dr. Kelly Ottman, executive coach, researcher, and founder of Leadership Portals. After interviewing executives before and after retirement, she uncovered surprising patterns about identity, relationships, and the skills people need to thrive in the next chapter. In this episode, we covered: Why the word "retirement" makes executives flinch The surprising skills many leaders find out they're missing after leaving work Why "I'll just join a few boards" isn't as simple as it sounds Losing your prestige vs. losing your credibility (and why they're not the same thing) What Kelly encourages people to create instead of a bucket list What organizations overlook when preparing leaders for retirement -- Resources Email: Website: LinkedIn:
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You're More Creative Than You Think
07/29/2026
You're More Creative Than You Think
Creativity isn't reserved for artists. It's something we use every day to solve problems, adapt to change, and discover new possibilities. That becomes especially important in Chapter X. Retirement reimagines how we spend our time, where we find fulfillment, and what comes next. Today I'm speaking with James Walters, photographer, podcaster, and author. He shares why curiosity is at the heart of creativity, why success and fulfillment aren't always the same thing, and how a shift in perspective can open the door to new possibilities. We cover: Why James sees creativity as problem-solving in disguise Why imposter syndrome doesn't retire when you do What it means to rebel against inherited definitions of success Two brothers who waited until their 70s to hike the Appalachian Trail together 3 phases of retirement James has seen in the people he interviews -- Resources
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The Joy of Becoming a Beginner Again
07/22/2026
The Joy of Becoming a Beginner Again
We tend to avoid anything we won't be instantly good at. Richard Sparks has spent forty years proving that instinct is wrong. Richard is a writer who has spent 40 years bouncing between comedy sketches, TV scripts, opera translations, and now fantasy novels. He wrote for a young Rowan Atkinson before anyone knew his name, then somehow ended up translating operas with no background in the form. In this episode, Richard shares why he never expects a first draft to work and how that same patience helped him build a fantasy series after decades of writing scripts. We cover: The strange side job that taught Richard he could actually get paid to write What happened the first time he watched an actor perform a sketch he wrote The one thing Richard tells every young writer about a bad first draft Why he walked away from decades of scriptwriting for something he'd never done before A story structure mistake he says ruined the ending of a hit TV series The line from Mel Brooks that reframed how Richard thinks about comedy vs. tragedy -- Resources Get free chapters at:
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What Happens After You Sell the Business
07/15/2026
What Happens After You Sell the Business
We spend decades working toward the exit. But what happens once we actually get there? Today I'm speaking with Jack Calhoun, who sold his wealth management firm in his fifties expecting to finally relax and write. Instead he found himself restless, then stuck running a company he didn't even like after a bootstrapped venture went sideways. In this episode, Jack shares what that wrong turn taught him and how it led him to create Encore Career Lab, a program built to help high achievers figure out what comes next. We cover: The moment selling his firm turned from a lottery win into “what have I done?” Why the freedom of retirement gave way to isolation What his coach's “autopsy” exercise taught him about walking away Why ego is the real enemy of reinvention Jack's case for treating your next chapter like a series of sprints (instead of one big bet) — Resources Website: Email: LinkedIn:
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The Four Questions That Shape Retirement
07/01/2026
The Four Questions That Shape Retirement
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 and the same opportunities as they entered this next chapter. We discuss: 4 questions almost everyone wrestles with after leaving their career behind What surprised Andi after interviewing dozens of retirees Why "Saturday every day" isn't always as fulfilling as it sounds How friendships often change more than we expect after retirement What an anthropologist sees that the rest of us often miss about retirement — Resources: Website: Book:
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Retirement Is Not Leaving the Arena
06/24/2026
Retirement Is Not Leaving the Arena
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 what it means to stay engaged with life long after a career ends. We cover: Why retirement can trigger an unexpected identity crisis The challenge of separating who you are from what you do What it means to transition from achievement to eldership Why staying "in the arena" matters at every stage of life The fear of becoming irrelevant as we grow older Lessons from a woman who began her most meaningful work in her seventies -- Keep Exploring If you enjoyed this conversation, check out Jake's novel, The Men's Group: A Novel of Messy Friendships.
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What Success Can't Give You
06/17/2026
What Success Can't Give You
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 he walked away from a tenured professorship, started over, and spent the next twenty-five years helping people find their way back to each other. In this episode, we covered: Why Carl walked away from a tenured professorship to start over The childhood lesson that fueled his drive to achieve What thousands of therapy sessions taught him about loneliness Why consumer culture promises belonging but rarely delivers it How becoming a "lingerer" can lead to deeper relationships Practical ways to build community in the next chapter of life -- Resources Website:
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Becoming the Father You Needed
06/10/2026
Becoming the Father You Needed
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 raising four sons of his own. We discuss fatherhood, generational patterns, personal responsibility, and what it takes to be the father you didn't have. In this episode, we covered: How Larry's experiences growing up influenced the father he became Why repairing mistakes quickly is a critical parenting skill The messages our parents pass down (and how to decide which ones to keep) How to start breaking unhealthy generational patterns What Larry has learned from raising four sons Why good intentions are not enough and what to do instead -- Resources Podcast: Website:
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What Matters More Than Living Longer?
06/03/2026
What Matters More Than Living Longer?
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 aging. You’ll hear why he believes physical, cognitive, and emotional function may matter far more than simply adding years to our lives. We discuss: How to prepare for a life you still want to be living decades from now Why the best health goal may have nothing to do with a number on a chart The challenge of staying physically, mentally, and emotionally sharp as we age What becomes possible when you stop measuring success by lifespan alone How to build a future worth staying healthy for -- Resources Ezz: Learn more about Ezzpedition 2026:
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Why the Things We Loved as Kids Stay With Us
05/27/2026
Why the Things We Loved as Kids Stay With Us
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 masculinity, nostalgia, and what happens when men lose the thread back to themselves. We explore why the hobbies we dismiss as “not serious” often point to something much deeper, and why reconnecting with joy and authenticity matters even more as we get older. You’ll hear about: Why certain childhood memories stay with us for life How men lose themselves in careers and responsibilities The importance of reconnecting with joy and nostalgia Why hobbies and passions matter more than we think The emotional power of shared memories What older men regret most at the end of life Why it’s never too late to reconnect with yourself -- Resources Podcast: Website: Instagram: Therapy:
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The Emotional Cost of Providing for Your Family
05/20/2026
The Emotional Cost of Providing for Your Family
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 addiction, recovery, and self-discovery. We look at the emotional disconnect many men experience with themselves, their children, and each other. You’ll hear about: Why Marc believes many men were never taught emotional connection The frightening turning point that forced him to reevaluate his life How different generations of men struggle with identity, work, and purpose The reason why emotional openness between men still feels uncomfortable How curiosity can help parents strengthen relationships with adult children -- Resources:
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The Caregiving Chapter No One Prepares You For
05/13/2026
The Caregiving Chapter No One Prepares You For
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 Trail with his wife helped him process grief, rediscover meaning, and reconnect with the person she has always been beyond her illness. Their journey became the foundation for his newest book, Uncharted Moments: Love, Legacy, and the Lewis & Clark Trail. In this episode, we covered: Why becoming a caregiver forced Jeff to let go of a business and identity he loved What anticipatory grief taught him about navigating uncertainty and change The remarkable story behind retracing the Lewis and Clark Trail together How slowing down changed the way Jeff and his wife experienced life The powerful lesson Jeff learned about pausing during chaos How one simple phrase became a philosophy for navigating difficult seasons of life -- Resources Website: Amazon:
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Why Experience Still Matters After Retirement
05/06/2026
Why Experience Still Matters After Retirement
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 others turn their experience into coaching, consulting, or project-based work in the next chapter. We talk about: Why many people drift in retirement instead of designing what’s next The idea of a “portfolio life” and moving beyond your job title Lynn’s G.L.E.A.N. process for uncovering the value in your experience Why starting with identity matters more than starting with action The mindset shift from needing certainty to being willing to experiment How curiosity becomes an advantage as you move into something new Where AI fits in (and why experience still matters) -- Resources Podcast: “Creating Your Encore Life” - Website: LinkedIn:
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How a Walk Changed His Relationship With His Son
04/29/2026
How a Walk Changed His Relationship With His Son
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 what happens when you start paying attention to what actually feels different. We discuss: How Rusty built a completely new career without a clear plan The moment he realized he wasn’t fully present with his son How walking became a daily practice for connection and clarity What he’s learned about identity through life’s different decades His experience facing aging, mortality, and a major life “passage” Why following your energy can reveal what actually matters Resources: Just Walking: TikTok: Instagram: Email:
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The First Months After Leaving Your Business
04/22/2026
The First Months After Leaving Your Business
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 the intentional decision to step away from the firm they built together. As Dave shares, even a well-planned transition doesn’t remove the emotional weight of letting go. We explore what it means to build something you can eventually leave—and what unfolds after you do. In this episode, we covered: What makes it so difficult for founders to step away The gap between knowing everything will be fine (and actually feeling it) Why retirement can bring unexpected emotions How identity is often tied to professional roles more than we realize Why meaningful moments in this stage of life don’t have to be big to matter How joy can become a useful filter for deciding how to spend your time Resources:
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Why Relationships Change After Retirement
04/15/2026
Why Relationships Change After Retirement
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 understanding what someone is trying to say. And for many men, especially in retirement or approaching it, this becomes more important than ever. When the structure of work falls away and relationships shift, we’re left with more space to connect, or feel disconnected. We covered: Why listening is more than just hearing words What we miss when we focus only on what’s being said Why most of us aren’t as good at listening as we think How learning to listen to yourself changes everything What gets in the way of deeper conversations Why relationships can feel harder after leaving work What it means to really understand another person -- Resources:
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How to Stop Running on Autopilot After a Major Life Transition
04/08/2026
How to Stop Running on Autopilot After a Major Life Transition
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-part framework for understanding how we operate—and why most of us are only partially present in our lives. In this episode, we covered: -Why most people are operating on patterns they don’t even realize -How decades of routine shape the way we see ourselves -The difference between “just showing up” and being fully present -Why stress and fear keep us stuck in old ways of thinking -The idea that we’re always playing multiple roles (not just one identity) -A simple exercise to rethink who you are beyond your career Resources Website: Instagram: Instagram:
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When Work Is Your Only Social Life
04/01/2026
When Work Is Your Only Social Life
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 little room for friendships outside of work and family. Once that structure disappears, many men find themselves starting from scratch. You’ll hear about: -The moment a retired executive tried to go back to the office… and couldn’t get in -Why work relationships often don’t carry over after retirement -The “four PRs” that shape identity (and what they leave out) -Why men often rely on their partner as their entire social network -A striking stat on what happens to men vs. women after losing a spouse -Why some of the loneliest people are surrounded by others -What leaders do that builds real connection (and why it has nothing to do with confidence) Resources Download Anthony's free books: Available on Amazon:
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Why Successful Men Feel Stuck Even When Life Looks Good
03/25/2026
Why Successful Men Feel Stuck Even When Life Looks Good
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 looks fine -How loss of social connection impacts stability and direction -Why this transition can be especially challenging for men -JD’s framework of 12 core emotional needs -Why feeling stuck often comes from unmet needs -Why purpose doesn’t always come first Resources: Book: LinkedIn: Website:
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Why Health Doesn’t Have to Decline With Age
03/18/2026
Why Health Doesn’t Have to Decline With Age
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 along the way, and why it’s never too late to improve your health. • Why Darren moved away from traditional medicine • How the current system focuses on treating symptoms • The role lifestyle plays in long-term health outcomes • Why many people don’t take action until later in life • The difference between prevention and a proactive approach • Why better health often feels like gaining something (not giving something up) Resources: Dr. Clair's Book: Facebook: Instagram:
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How to Thrive in the Next Chapter of Life
03/11/2026
How to Thrive in the Next Chapter of Life
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 chapters: relationships, legacy, and what it looks like to truly live well. You’ll hear about: • How a simple habit made him a better listener (and changed everything) • The self-reflection practice he uses to actually measure his own growth • What finally pushed him to start writing Thriving • Why your purpose doesn't have to be big to be meaningful • The real difference between success and thriving • Why curiosity is one of the best predictors of a good later life Resources Website: LinkedIn:
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Rethinking Success at 52
03/04/2026
Rethinking Success at 52
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. In this episode: How financial insecurity in childhood shaped his drive to succeed The moment at GE that led him to leave corporate life What he learned about happiness while traveling in Africa The difference between success and significance How our belief systems are formed and why they can be unlearned Why aging gives us the chance to question identity Resources:
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When Success Doesn’t Erase Fear
02/25/2026
When Success Doesn’t Erase Fear
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 entering their next chapter of life. We discuss: What happens when success no longer feels like enough Why your identity is constantly changing Whether losing your career is actually losing yourself What 24 minutes a day of inward focus might change A disciplined daily practice for reconnecting with yourself Resources: YouTube: Facebook: Instagram: Whatsapp: +91 62386 00274
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The Wake-Up Call That Changed Everything at 51
02/18/2026
The Wake-Up Call That Changed Everything at 51
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 the way we finish the sentence “I am…” matters The difference between external success and internal fulfillment How creativity extends far beyond art What it really means to consciously create your next chapter Resources
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Why Retiring Early Didn’t Work for Randy Gage
02/11/2026
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:
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Why Your Brain Predicts Pain When You Try to Change (And How to Rewire It)
02/04/2026
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
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Why Americans Struggle With Aging More Than They Should
01/28/2026
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:
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What Comes After Work Ends
01/21/2026
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:
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Finding Direction Without a Map
01/14/2026
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
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What If You Didn’t React Right Away?
01/07/2026
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 Visit
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