Dare On with Jodi

Fear, Joy and a Python Named Boots- Ep#143

Jodi Silverman Season 5 Episode 143

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0:00 | 32:13

What if your biggest fears were actually doorways to your greatest joy?

In this deeply moving episode of Dare On with Jodi, Sheryl Wright — founder of Dare to Detour — shares her powerful story of confronting fear head-on, from a breast cancer diagnosis to a 32-year relationship ending, and even skydiving and snake handling. Yep, she went there.

But the real magic? Sheryl discovered that joy, awe, and wonder live on the other side of fear — and she's here to show you how to get there too.

In this episode, you’ll learn:

  • How stillness can become your greatest teacher
  • The unexpected connection between fear and joy (backed by neuroscience!)
  • How to hold space — for yourself and others — during hard transitions
  • The 5 fears Cheryl dared to face (and the profound gifts they brought)
  • A simple joy practice you can start today

🎧 Don’t miss the end where Sheryl shares a powerful 30-day joy dare you’ll want to take right away.

🎯 Featured Free Resource: 30 Days of Doable Dares
If you’re ready to start small and build momentum toward joy, courage, and purpose, this free challenge is for you.

🌍 Want to travel with purpose?
 Explore Sheryl’s Dare Guides Community — where curated, meaningful travel experiences help midlife women reconnect with joy, self, and wonder.

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