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Chapter X with Michael Kay

Chapter X with Michael Kay

By: Michael F Kay
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About this listen

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. Career Success Economics Personal Development Personal Success
Episodes
  • How a Walk Changed His Relationship With His Son
    Apr 29 2026

    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: https://justwalking.com

    TikTok: www.tiktok.com/@justwalking.com

    Instagram: https://www.instagram.com/justwalkingwithrusty

    Email:

    rusty@justwalking.com

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    41 mins
  • The First Months After Leaving Your Business
    Apr 22 2026

    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)

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    47 mins
  • Why Relationships Change After Retirement
    Apr 15 2026

    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

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    47 mins
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