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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:   Retirement Plan (an Oscar nominated short film from The New Yorker)  

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:   Listening for a Life: The Artful Science of Psychotherapy  

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: www.ChooseToShowUp.com Instagram: @MarcyAxelrodArt Instagram: @MarcyAxelrod

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: theartoflivingfree.org/freehappinessandfriendshipbooks Available on Amazon: Love and Suffering: Break the Emotional Chains that Prevent You from Experiencing Love

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: The Emotionally Agile Brain  LinkedIn: J. David Pincus Website: AgileBrain   

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: Creating a Life of Vibrance  Facebook: facebook.com/VibranceHealth Instagram: instagram.com/vibrancehealth

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: www.randselig.com LinkedIn: Connect with Rand  

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: Larry on LinkedIn  5-Dots Joy Molecule

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: Book an Ask Yogi Session    YouTube: Indimasi Healing Village  Facebook: Indimas Healing Village  Instagram: Indimasi Healing Village  Whatsapp: +91 62386 00274

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 Howard Rosenberg's Life Coaching Howard on LinkedIn Creative Humanity Alliance  

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  

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

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  

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  

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