Chapter X with Michael Kay

At 68 years old, Rand Timmerman looked in the mirror and thought his life was over. A decorated Vietnam War veteran and successful attorney, he had been undone by alcoholism and the toll of PTSD. Yet what seemed like the end became the beginning of a new path.   Now more than a decade sober, Rand shares how recovery gave him the strength to take on an extraordinary challenge with his brother: hiking the Appalachian Trail in their seventies. Along the way, they faced storms, solitude, and moments of reckoning that reshaped how Rand understands resilience, purpose, and second chances.   In this episode, we covered:   How Rand faced down alcoholism after decades of success in his career The hidden weight of PTSD and how it shaped his story What it was like to hike more than 1,400 miles of the Appalachian Trail in his seventies The role of grit, faith, and humor in getting through difficult seasons How recovery and service to others gave Rand a renewed sense of purpose   Resources: Visit: Rand Timmerman’s website Email Rand: rand.timmerman@gmail.com

What happens when life as you know it is suddenly pulled out from under you? For Ray Martin, the unraveling of his marriage, the death of his father, and the collapse of his career all came within months of each other. Left with nothing familiar to hold onto, Ray made a choice to let go of clinging to the life he had built. What began as a six-month sabbatical turned into a 14-year journey across Asia. Along the way, Ray discovered mindfulness and a new definition of success that wasn’t tied to titles, possessions, or status. His experiences became the foundation of his book Life Without a Tie. In this conversation, Ray shares the lessons he learned from starting over and the six rules of happiness that guide him today.   We’ll cover: How Ray turned personal loss into a catalyst for growth The most common regret people share at the end of life What he discovered during a silent 10-day meditation retreat The framework Ray calls his six rules of happiness How to approach life transitions with greater clarity and purpose Resources:Life Without a TieLife Without a Tie on AmazonConnect with Ray on LinkedIn

  Life after work doesn’t come with a roadmap. But my guest today shows what can happen when you stay curious and keep saying “yes.”   David Danon has worn many hats: sailor, hair stylist, yoga teacher, Hollywood crew member, and musician. Now, in his seventies, he continues to surf, foil, and coach others on healthy aging. His journey is proof that reinvention can happen at any age.   In this episode, David shares:   How sailing and surfing shaped his outlook on life Why curiosity has opened unexpected doors throughout his journey The lessons yoga and meditation taught him about resilience and peace Why vigilance and resolve are essential for healthy aging The importance of creating purpose beyond career identity   Resources: Visit David’s website Self-Realization Fellowship

Some people step into retirement without a clear plan, while others see it as an open canvas. My guest today, Thom Barrett, retired at 55 after a successful career at PriceWaterhouseCoopers and chose to fill his canvas with adventure, creativity, and service. From kayaking off the coast of Antarctica to building furniture in his workshop, Thom has lived a life of bold exploration. Even as he faces stage four cancer, he continues to write, travel, and approach each day with intention. In this episode, we discuss: Why Thom chose to retire early and pursue adventure How travel and time in nature became both refuge and teacher The lessons he’s learned about acceptance, vulnerability, and mindfulness Why he began writing books and travel reflections during his illness How he continues to live with purpose and presence despite new limitations Resources: The Edge of Now by Thom Barrett Living While Dying, Chasing My Northern Lights, and more of Thom’s books Visit Thom’s website  

Most of my conversations on Chapter X explore purpose, meaning, and navigating life after a career. Today’s episode takes us in another direction. My guest is Dr. Elliot Justin, founder of FirmTech and an expert in men’s sexual health.   Today, we talk about why sexual health is often left out of the conversation in the doctor’s office. We also look at how technology and data can enhance the way men monitor and improve their performance.    Plus, Dr. Justin takes us on his journey from a career in emergency medicine to developing a smart “erection ring” that tracks vital signs most of us don’t think to measure.   We discussed:   How a horse-riding accident set Dr. Justin on a new path The surprising link between nocturnal erections and heart health Why most men who say “I don’t need that” are missing the point How data can help tailor treatments and improve sexual performance Why Dr. Justin says “put a ring on it” applies to more than relationships

What would it take to trust something you can’t explain? Aaron French didn’t plan to become a spiritual mentor. He began as a biologist, then built a successful corporate career. On the surface, everything seemed great. But underneath, he felt pulled in a different direction. In this episode, we talk about how that shift unfolded and what it’s like to follow moments that don’t always make sense, but still feel meaningful. You don’t need to believe in anything mystical to listen. You just need to be curious about what else might be possible, especially in this next phase of life. We discussed: Why a scientist started listening to something beyond the rational How nudges show up (and what happens when you ignore them) The difference between thinking and knowing Practices that help you tune in, even if you’re not “spiritual” Why gratitude opens more than it resolves   Connect with Aaron: Website: naturalheartalchemy.com Instagram: @naturalheartalchemy  

I’ve always been drawn to people who’ve done the hard work of figuring themselves out. Dr. Glenn Berger is one of those people.   At 17, he was working in one of the top recording studios alongside Bob Dylan and Frank Sinatra. By 37, he was writing jingles for toys, using drugs every day, and wondering how his life had gotten so far off track.   In this episode, Glenn shares how he felt lost in life and what helped him feel like himself again. It’s one of the most personal and thoughtful conversations I’ve had in a long time.   He tells the story of a trip to Ellis Island and a message from his grandfather that changed everything. We also talk about why so many people feel stuck, how shame holds us back, and what it means to live in a way that aligns with your values.   We talk about:   Glen’s early years in the music industry (and what it really taught him) The burnout that brought him to a breaking point Why so many high-achievers feel lost The six traits of stuckness (and the six attributes of the heart) What it looks like to grow, evolve, and stay true to yourself at any age Glen’s HeartFinders project and how it helps people reconnect with their purpose Connect with Glenn: Visit go.heartfinders.co for a free lesson or free consultation

When John Geraghty was 29, he looked at his life and realized the path he was on wasn’t leading anywhere he wanted to go. Struggling with alcohol, he decided to change everything. That choice set him on a journey of growth and helping others find what lights them up.   In this conversation, John shares what he’s learned about why the traditional idea of retirement often leaves people feeling lost, and how discovering your strengths and staying curious can bring meaning to every stage of life.    We talk about how small steps, honest self-reflection, and contribution to others can create a life you’re excited to live.   We discussed:   Why leisure doesn’t lead to lasting fulfillment How to discover your “zone of genius” to build a life that lights you up The importance of identity beliefs in shaping what’s possible  Why the idea of flow matters for purpose and happiness Why your most rewarding years may still lie ahead   Connect with John:   Visit John's website Follow John on LinkedIn The Prism of Perspective Podcast  

  Alex Potts helped thousands of people plan for retirement until it was his turn. And like so many of us, he found himself asking what now?   This episode is a special one. Alex isn’t just a respected leader and former CEO. He’s also a longtime friend. We’ve known each other since the ’90s, and I’ve had the privilege of watching him grow into an authentic, grounded, and service-minded leader.   Our conversation explores what it means to live with intention. We talk about resilience, identity, letting go, and how to step into your next chapter with curiosity and purpose.   We discussed:   The money lessons Alex learned when there wasn’t enough How caregiving redefined what legacy means to him What the first day after stepping down actually felt like Why our purpose changes—and how Alex learned to follow it What a simple “just thinking of you” text can really mean The movie line that’s guided him for 25 years  

Agi Keramidas made a major life shift when he left behind a stable but unfulfilling life in Greece to follow a calling he couldn’t quite explain. Today, he shares how a midlife awakening (his words) sparked a journey of personal growth. Eventually it would lead Agi to launch his podcast, Personal Development Mastery, and write his book, 88 Actionable Insights for Life.  He talks about listening to that quiet voice that says something needs to change. Even when it means starting over in a new country with no safety net. We explore the role of self-awareness, the discomfort that often comes with growth, and how small, deliberate actions can open the door to a more meaningful life. You’ll hear about: Leaving a life that looked “fine” but didn’t feel right How Agi moved to a new country with two suitcases and no real plan Why podcasting opened a door to something more meaningful Building a morning routine that shapes the rest of the day The gap between insight and action (and how to close it) A two-minute exercise for naming your purpose Resources Personal Development Mastery Follow Agi on LinkedIn

When Rich Alderton left his high-powered corporate role on a Friday, signing off millions and fielding nonstop calls, he expected Monday to bring more of the same. Instead, the phone was silent. That stark contrast was the wake-up call: people had been in love with his title, not with him.   What followed was a journey into reinvention. Rich stepped away from corporate leadership to help others become more adaptable in a rapidly changing world. Along the way, he discovered just how unprepared most of us are for life’s biggest transitions.   Today, Rich joins me to talk about how to shift your mindset in the face of uncertainty, reframe fear as opportunity, and rediscover purpose in Chapter X.   We discussed:   Why we resist change (and how to stop fighting it) The mental tool that makes uncertainty more manageable What personal purpose looks like in life after work How to move from fearing change to finding freedom in it Redefining success when there’s no one left to grade you   Resources High Performance Change  Follow Rich on LinkedIn 

David Marlow is known as the Ikigai Guy. I didn’t know that when I first came across his writing. What I did know was that something in his work resonated deeply with me.   Today, we talk about what happens when your career comes to a close, and you're left facing the question: who am I now? David shares how he discovered the concept of ikigai, what it means to him, and how it shaped the way he moved through the end of his own career.   He offers a thoughtful process for reconnecting with purpose, and for paying attention to the parts of your life that make you feel most alive. We talk about identity, daily rituals, the power of reflection, and how a few small steps can open the door to something meaningful.   We also explore:   What ikigai means (and what it doesn’t) How to quiet the noise enough to hear what’s true for you Why a beginner’s mindset is key to moving forward What it looks like to create your own “ikiverse” How old memories and stories can point you back to what matters most   Resources: Follow David on LinkedIn  Subscribe to the Ikiquest Newsletter David’s website   Where to find The Ikigai Way:  Amazon   Barnes and Noble  Wiley Books   

Richard Eisenberg is back. And this time, we’re diving into what his unretirement looks like now.    If you don’t know Richard’s story, he’s an “unretired” journalist who writes a column for MarketWatch and freelances for Next Avenue, Fortune, AARP, and Fodor’s. Richard calls this chapter “unretirement” — living it with purpose and intention.   Before all that, he was an editor at Next Avenue and Money magazine, and held senior roles at Yahoo! and Good Housekeeping. He’s also the author of two personal finance books and a proud Northwestern grad.   In our conversation, Richard shares his latest stories on medical debt, telehealth access, and the renewed value of travel advisors. He also opens up about caring for his mom during her dementia journey and what it taught him about starting financial conversations early.   Listen in to hear what Richard’s been up to since the last time we spoke.   We discussed:   What “unretirement” really looks like in practice The importance of having early financial conversations with aging parents Why telehealth access matters—and what could happen if it’s rolled back A fresh look at travel advisors and how they’re evolving Richard’s book recommendations and resources for deeper learning The challenge of caregiving for aging parents with dementia Resources The View From Unretirement Next Avenue Fortune | Richard Eisenberg Fodor’s Travel    Friends Talk Money   The Friday Afternoon Club by Griffin Dunne The Purpose Code by Jordan Grumet Retirement Intelligence by Robert Laura  

What happens when the career you built your life around stops feeling like it fits? Today, I’m talking to Jordan Grummet about what it really looks like to wrestle with purpose—especially during big life transitions like retirement.   Jordan opens up about losing his father at a young age, pursuing medicine to honor his legacy, and eventually realizing that career wasn’t fulfilling him. We covered the struggle between societal expectations and our own authentic path, and how to find meaning after a life-altering shift.   Jordan, an author and host of the Earn & Invest podcast, brings a perspective shaped by both his work in hospice care and his own experience of stepping away from a path that no longer felt right.   It’s a conversation about what happens when we let go of old identities and start figuring out what comes next. In this episode, you’ll hear: Why purpose feels like such a monumental challenge in retirement Jordan’s story of legacy, loss, and what medicine couldn’t give him The slow burn of professional misalignment and how he woke up to it How powerful external voices influence our life choices The Purpose Code path forward into a more meaningful second act   Resources jordangrumet.com The Purpose Code  

Only 5% of homes in the U.S. are moderately accessible. Stairways, sunken living rooms, poorly designed bathrooms, and trip hazards are just the start.    Greg Cantore’s journey has spanned bicycle mechanics to defense work and leading nonprofit programs. But his mother-in-law’s experience living in a house that wasn’t designed for her needs opened his eyes to the bigger issue.   After modifying her home, and later adjusting to her needs in assisted living, Greg realized there was a larger need for accessible, supportive home solutions. Today, he runs Little Deeds, a company dedicated to making homes safer and more accessible for aging individuals.   Your home should support you as you age. Find out how Greg is helping make that a reality for so many. We discussed:   How universal design makes homes safer and more accessible as we age Greg’s career journey—and how it led him to create Little Deeds The challenges people face with aging in place  Simple ways to make your home safer and more accessible Why it’s important to plan ahead with home modifications   Resources   Little Deeds  

You don’t have to spend hours in the gym to stay strong and mobile as you age. My guest, Mark Firehammer, created myFeelness to help men remain functional without grueling workouts or fitness gimmicks.   At 43, Mark’s body started pushing back. There were aches, stiffness, and limits he couldn’t ignore. He knew something had to change but wasn’t willing to spend hours in the gym.   That led him to rethink movement entirely. Mark found a way to stay strong, mobile, and pain-free through small, mindful movements. Now, he’s helping other men do the same with a system that keeps you moving without intense workouts.   If you care about moving well, feeling good, and staying strong as you get older, you’ll want to hear this one.   In this episode, we discuss: Simple daily moves to check how well your body is working Why your nervous system is the key to better movement How paying attention to your body can improve your health The problem with mainstream fitness advice and what actually works What it really means to be "Out of Function" (and how to fix it) A small mindset shift that could help you avoid serious health problems   Resources: myFeelness Living Well Without Fitness on YouTube Mark Firehammer on Instagram Mark Firehammer on LinkedIn

If you had to make an important healthcare decision today, would you know what to do?   My guest, Dr. Corinne Auman, is an expert in aging. She helps people and families figure out senior healthcare, retirement planning, and life’s unexpected changes. She’s a psychologist, CEO of Choice Care Navigators, and author of Keenagers.   Most of us don’t think about aging until we have to, like when a parent falls or we realize our own home might not work for us as we get older. Suddenly, we’re faced with tough choices about Medicare, long-term care, and what it means to age well.   Today, Dr. Auman shares why planning ahead is so important, how to talk to loved ones about it, and what steps you can take now to have more options later. I think you’ll find this episode both eye-opening and helpful.   We discussed:   Start planning your future home in your 50s What we often get wrong about retirement communities How to bring your loved ones into the conversation The 3 main phases of retirement Who we can turn to for guidance on our next steps   Resources: Keenagers by Dr. Corinne Auman www.CorinneAuman.com

Today, we’re taking a different approach. Instead of focusing on men’s transitions, we’re diving into the journey women face in their next chapter.   My guest, T. Kari Mitchell (TK), is a transformational speaker, author, and integrative wellness coach who has dedicated her second half to helping women reclaim their health, confidence, purpose, and power after retirement so they can truly flourish in their golden years.   After 32 years as a teacher, she boldly transitioned into holistic coaching and motivational speaking at 62. Now, through her programs, TK helps boomers overcome challenges and rediscover their potential. We explore the transitions women face, including shifting identities, hormonal changes, and societal expectations.   Guys, this is the episode to share with the women in your life because growth is better when we do it together. TK’s energy is contagious, and I think you’ll walk away with a new perspective on how we can all grow into the next stage of life.   We covered:   The mindset shifts that help women step into their next chapter with confidence How past experiences can open the door to new passions and opportunities The societal challenges that women face as they age (and how to push back) Practical ways men can better support the women in their lives How women can start reclaiming their purpose today Resources https://www.lifestyle120.com

With freedom comes the risk of losing direction. When we’re younger, the world feels full of possibilities. But as we get older, our focus narrows—one job, one partner, one path. Over time, our routines can make it harder to see new opportunities.   In this episode, Paul Wilson explains how mental blocks can keep us stuck and shares how to break free and explore what’s still out there. After a bicycle accident and a broken arm in 2017, Paul found a new career path.   Now, Paul is a life coach, business coach, and hypnotherapist who helps people overcome feeling stuck through his practice, A Happy Head. He developed the Shift Process, a method that uses small mindset shifts to create big transformations.   Paul shares how to remove the mental “blinkers” that limit personal growth, especially as we navigate life transitions like retirement.   How a broken arm led to a new career When Paul realized he had found a superpower 3 ways to discover new hobbies or interests What hypnosis can do for you (and what it can’t) The difference one phone call can make for retirees Connect with Paul: A Happy Head Business Coaching with Paul

Willie Handler was born to Holocaust survivors. Though his home was loving, the trauma his parents endured left deep scars that shaped his life in ways he only came to understand much later.   During the pandemic, Willie began exploring his family’s history and the intergenerational trauma he carried. What started as a way to honor his parents became a transformative journey. It unearthed buried memories, led to tough therapy sessions, and inspired his powerful new book, Out From the Shadows.   Along the way, Willie interviewed nearly 100 others with similar stories. He brings their voices together in a book that sheds light on the resilience of generations shaped by unimaginable pain. My conversation with Willie left me in awe of his courage. His story is one of reinvention and hope—and I can’t wait for you to hear it.   We discussed: Why growing up with distant parents left Willie in survival mode How a HR consultant convinced Willie to retire When he realized it was time to unearth his survivor experience The challenges Willie faced in getting the memoir published His advice for aspiring authors in their Chapter X Resources: williehandler.com  Willie on Substack Willie on Instagram      Out From the Shadows Deep Into the Weeds The Road Ahead Loved Mars, Hated the Food