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

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 bestselling collection of Dear Sugar columns, Tiny Beautiful Things, was adapted for a Hulu television show and as a play that continues to be staged in theaters nationwide. Strayed's other books are the critically acclaimed novel, Torch, and the bestselling collection Brave Enough, which brings together more than one hundred of her inspiring quotes. Her books have sold more than 5 million copies around the world and have been translated into forty languages

You can grab copies of Wild and Tiny Beautiful Things by Cheryl Strayed at The Painted Porch: https://www.thepaintedporch.com/

Follow Cheryl Strayed on Instagram @CherylStrayed and check out more of her work at her website CherylStrayed.com

🎟️ Come see Ryan Holiday LIVE: https://www.dailystoiclive.com/

Seattle, WA - December 3, 2025 San Diego, CA - February 5, 2026 Phoenix, AZ - February 27, 2026

📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work

🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos

🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast

✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail

🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/

📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.