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The Daily Stoic

The Daily Stoic

Cheryl Strayed: “I Had to Lose EVERYTHING to Find Myself”

Nov 12, 2025 · 1h 0m

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About this episode

At some point, you realize courage isn’t something you are born with, it’s something you build. In this episode, Ryan sits down with bestselling author Cheryl Strayed ( Tiny Beautiful Things , Wild ) to talk about what it really means to be brave. They discuss how fear and courage always show up together, why you can’t wait to “feel ready,” and the difference between saying you’ll change and actually doing it. Cheryl shares what hiking alone on the Pacific Crest Trail taught her about courage, loss, and starting over. Cheryl Strayed is the author of the #1 New York Times bestseller Wild: From Lost to Found on the Pacific Crest Trail , which was made into an Oscar-nominated film. Her…