The Bitter Pill with Kirk Sheppard

Kirk Sheppard
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  • MENTAL HEALTH

Join Kirk Sheppard he talks about self-improvement - with a pro wrestling overlay. Happy Monday with Kirk Sheppard is for educational and entertainment purposes only. While Kirk Sheppard is a licensed therapist, none of the information provided should be considered clinical advice. To find a therapist, go to PsychologyToday.com Go to ⁠⁠kirksheppard.com⁠⁠ for more information and Kirk Sheppard, his books, and more.

  1. 12/15/2025

    The FINAL Bitter Pill - 12.15.25

    This may be the final episode of The Bitter Pill. In this episode, Kirk Sheppard reflects on closing one chapter and stepping into another—through wrestling, writing, Disney, burnout, kindness, and the idea of alignment. We start by honoring John Cena’s final match and what it means to “leave the business better than you found it.” From there, Kirk revisits the core themes of Soul Audit: values, authenticity, boundaries, and becoming the best version of yourself as an ongoing process. The episode also includes stories from a recent Disney World trip—unexpected kindness, the limits of roller coasters, hypervigilance, and what exhaustion is really made of. Finally, Kirk shares what’s next: retiring The Bitter Pill, rebranding Happy Monday as 50, choosing threshold as the word for 2026, and introducing what’s coming with This Is 50. 👉 Read the full show notes and transcript on Substack.

    28 min

  2. 11/27/2025

    The Bitter Pill - 11.27.25 - Happy Thanksgiving!

    Today, Kirk talks about cultural and occupational alignment. This content for is educational and entertainment purposes only. Go to kirksheppard.com for more info.

    24 min

  3. 11/14/2025

    The Bitter Pill - 11.14.25

    Today, Kirk talks about FORGIVENESS and how that relates to soul alignment. This content for is educational and entertainment purposes only. Go to kirksheppard.com for more info.

    21 min

  4. 11/07/2025

    The Bitter Pill - 11.7.25

    This week, Kirk talks about Chapter 12 of "Soul Audit," all about grief and loss. He also talks about heel turns in pro wrestling and dicussses why those stories work. THIS CONTENT IS FOR EDUCATIONAL AND ENTERTAINMENT PURPOSES ONLY.

    17 min

  5. 10/31/2025

    The Bitter Pill - 10.31.25

    Happy Halloween! This week, Kirk talks about Chapters 9 & 10 of "Soul Audit," all about shame and vulnerability. He also teaches us a little bit about wrestling psychology and why the babyface in peril works as a storytelling - and connection - device. Here's a link to the TEDTalk Kirk referenced from Brene Brown: https://www.ted.com/talks/brene_brown_the_power_of_vulnerability?language=en THIS CONTENT IS FOR EDUCATIONAL AND ENTERTAINMENT PURPOSES ONLY.

    19 min

  6. 10/25/2025

    The Bitter Pill - 10.25.25

    This week, Kirk talks about Chapters 6 & 7 of "Soul Audit," all about spiritual alignment - what it is and what it is not. THIS CONTENT IS FOR EDUCATIONAL AND ENTERTAINMENT PURPOSES ONLY.

    15 min

  7. 10/17/2025

    The Bitter Pill - 10.17.25

    This week, Kirk talks about Chapter 5 of "Soul Audit," all about being present. THIS CONTENT IS FOR EDUCATIONAL AND ENTERTAINMENT PURPOSES ONLY.

    16 min

  8. 10/10/2025

    The Bitter Pill - 10.10.25

    This week, Kirk talks about "What's Paaapin!," his appearance tomorrow at the Lousiville Book Festival, and Chapter 4 of "Soul Audit: Relational Alignment & Boundaries!" THIS CONTENT IS FOR EDUCATIONAL AND ENTERTAINMENT PURPOSES ONLY.

    20 min
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Join Kirk Sheppard he talks about self-improvement - with a pro wrestling overlay. Happy Monday with Kirk Sheppard is for educational and entertainment purposes only. While Kirk Sheppard is a licensed therapist, none of the information provided should be considered clinical advice. To find a therapist, go to PsychologyToday.com Go to ⁠⁠kirksheppard.com⁠⁠ for more information and Kirk Sheppard, his books, and more.

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