The Bitter Pill with Kirk Sheppard

The FINAL Bitter Pill - 12.15.25


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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.

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The Bitter Pill with Kirk SheppardBy Kirk Sheppard