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Chapter X with Michael Kay

Chapter X with Michael Kay

Written by: Michael F Kay
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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. Careers Economics Personal Success Self-Help Success
Episodes
  • How to Get Comfortable With Not Knowing
    Sep 30 2026

    We spend a lot of time thinking about the past or worrying about the future. What gets lost in between?

    For Dr. Evan Fishman, that question became more personal after he was laid off from Facebook in 2023. The experience forced him to rethink how much of his identity was tied to work, achievement, and what came next.

    Today, Evan helps others navigate similar questions around identity, uncertainty, and being present.

    In this episode, we cover:

    • How Evan's Facebook layoff changed the way he saw his life

    • What we use to avoid uncomfortable feelings

    • Why fear can create stories that feel true (even when they aren't)

    • How to become more comfortable with uncertainty

    • Why the present moment matters during times of change

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    Resources

    www.evanfishman.com

    https://www.linkedin.com/in/evanfishman

    https://www.instagram.com/dr.evanfishman

    https://x.com/evan_fishman

    https://belovedinstitute.substack.com

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    33 mins
  • What Happens After You Sell the Business
    Jul 15 2026

    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)

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    Resources

    Website: encorecareerlab.com

    Email: jack@encorecareerlab.com

    LinkedIn: https://www.linkedin.com/in/jack-calhoun-encore

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    45 mins
  • The Joy of Becoming a Beginner Again
    Jul 22 2026

    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



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    Resources

    Get free chapters at: https://richardsparks.com

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    41 mins
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