The Emotional Cost of Providing for Your Family
Chapter X with Michael Kay
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...
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The Caregiving Chapter No One Prepares You For
Chapter X with Michael Kay
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...
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Why Experience Still Matters After Retirement
Chapter X with Michael Kay
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...
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How a Walk Changed His Relationship With His Son
Chapter X with Michael Kay
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...
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The First Months After Leaving Your Business
Chapter X with Michael Kay
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...
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Why Relationships Change After Retirement
Chapter X with Michael Kay
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...
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How to Stop Running on Autopilot After a Major Life Transition
Chapter X with Michael Kay
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...
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When Work Is Your Only Social Life
Chapter X with Michael Kay
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...
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Why Successful Men Feel Stuck Even When Life Looks Good
Chapter X with Michael Kay
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...
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Why Health Doesn’t Have to Decline With Age
Chapter X with Michael Kay
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...
info_outlineSome 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