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

EPISODE · Mar 19, 2026 · 32 MIN

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

from Dare On with Jodi · host Jodi Silverman

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 teacherThe unexpected connection between fear and joy (backed by neuroscience!)How to hold space — for yourself and others — during hard transitionsThe 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.Send me a quick note/message- what stood out in this episode! 🎙️ You've been listening to me—now I want to meet YOU.  Join me on Substack, where Dare On goes beyond the podcast. We're having real conversations about midlife, what's next, the things we're struggling with, and the lives we still want to create. You'll find live gatherings, connection, encouragement. Subscribe for FREE and come introduce yourself HEREI can't wait to meet Subscribe to my Substack HEREStep into the Dare On Circle HERE

Episode metadata supplied by the publisher feed · Published Mar 19, 2026

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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 ...

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

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