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

About this episode

<p>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 (<a href="https://www.thepaintedporch.com/products/selfhelp21?_pos=2&amp;_sid=786011f83&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Tiny Beautiful Things</em></a>,&nbsp;<a href="https://www.thepaintedporch.com/products/rhmoo14?_pos=1&amp;_sid=9a7257c39&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Wild</em></a><em>)</em>&nbsp;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.&nbsp;</p><br><p>Cheryl Strayed is the author of the #1 New York Times bestseller&nbsp;<a href="https://www.thepaintedporch.com/products/rhmoo14?_pos=1&amp;_sid=9a7257c39&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Wild: From Lost to Found on the Pacific Crest Trail</em></a>, which was made into an Oscar-nominated film. Her bestselling collection of Dear Sugar columns,&nbsp;<a href="https://www.thepaintedporch.com/products/selfhelp21?_pos=2&amp;_sid=9a7257c39&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Tiny Beautiful Things</em></a><em>,</em>&nbsp;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,&nbsp;<a href="https://www.amazon.com/Torch-Vintage-Contemporaries-Cheryl-Strayed/dp/0345805615" rel="noopener noreferrer" target="_blank"><em>Torch</em></a>, and the bestselling collection&nbsp;<a href="https://www.amazon.com/s?k=brave+enough+cheryl+strayed&amp;adgrpid=183606418062&amp;hvadid=779578903384&amp;hvdev=c&amp;hvexpln=0&amp;hvlocphy=9028217&amp;hvnetw=g&amp;hvocijid=4533830827821936126--&amp;hvqmt=e&amp;hvrand=4533830827821936126&amp;hvtargid=kwd-301924234297&amp;hydadcr=22127_13323349_14209&amp;mcid=103eaf315860327fa6e8c75a37630c06&amp;tag=googhydr-20&amp;ref=pd_sl_66q3ex0wfg_e" rel="noopener noreferrer" target="_blank"><em>Brave Enough</em></a>, 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</p><br><p>You can grab copies of&nbsp;<a href="https://www.thepaintedporch.com/products/rhmoo14?_pos=1&amp;_sid=9a7257c39&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Wild</em></a>&nbsp;and&nbsp;<a href="https://www.thepaintedporch.com/products/selfhelp21?_pos=2&amp;_sid=9a7257c39&amp;_ss=r" rel="noopener noreferrer" target="_blank"><em>Tiny Beautiful Things</em></a><em>&nbsp;</em>by Cheryl Strayed at The Painted Porch:&nbsp;<a href="https://www.thepaintedporch.com/" rel="noopener noreferrer" target="_blank">https://www.thepaintedporch.com/</a></p><br><p>Follow Cheryl Strayed on&nbsp;<a href="https://www.instagram.com/cherylstrayed/?hl=en" rel="noopener noreferrer" target="_blank">Instagram @CherylStrayed</a>&nbsp;and check out more of her work at her website&nbsp;<a href="http://cherylstrayed.com/" rel="noopener noreferrer" target="_blank">CherylStrayed.com</a></p><br><p><br></p><p>🎟️ Come see<a href="https://www.dailystoiclive.com/" rel="noopener noreferrer" target="_blank">&nbsp;Ryan Holiday LIVE</a>:&nbsp;<a href="https://www.dailystoiclive.com/" rel="noopener noreferrer" target="_blank">https://www.dailystoiclive.com/</a></p><ul><li><a href="https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830976292379?aff=oddtdtcreator" rel="noopener noreferrer" target="_blank">Seattle, WA&nbsp;- December 3, 2025&nbsp;</a></li><li><a href="https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1527497619499?aff=oddtdtcreator" rel="noopener noreferrer" target="_blank">San Diego, CA - February 5, 2026&nbsp;</a></li><li><a href="https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830981698549?aff=oddtdtcreator" rel="noopener noreferrer" target="_blank">Phoenix, AZ - February 27, 2026&nbsp;</a></li></ul><p><br></p><p>📖<a href="https://store.dailystoic.com/pages/wisdom-takes-work" rel="noopener noreferrer" target="_blank">&nbsp;<em>Wisdom Takes Work</em></a>&nbsp;by Ryan Holiday is out NOW! 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