Olivia Nuzzi Knows She Messed Up

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

12 Nov 1h

You don’t have to accept being treated this way. You should stand up. You should speak out. But you know what you shouldn’t do?👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

12 Nov 2min

Was Marcus Aurelius a bad father? How did he not manage to pass his Stoicism—to say nothing of his kindness and sense of responsibility—to his son?🎟️ 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👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

11 Nov 9min

Ulysses S. Grant knew what the Stoics knew—that outside circumstances don’t say anything about us, that it didn’t matter, as Epictetus said, what we bear, only how we bear it. 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

10 Nov 10min

What is the "Tortoise Method" and how can it help us build habits for happiness? Look no further than this excerpt from Chapter 9 of the audiobook of Aristotle’s Guide to Self-Persuasion: How Ancient Rhetoric, Taylor Swift, and Your Own Soul Can Help You Change Your Life by Jay Heinrichs (last week's guest on The Daily Stoic Podcast!). Jay Heinrichs is a New York Times bestselling author of Thank You For Arguing and is a persuasion and conflict consultant. Middlebury College has named him a Professor of the Practice in Rhetoric and Oratory. Jay has conducted influence strategy and training for clients as varied as Kaiser Permanente, Harvard, the European Speechwriters Association, Southwest Airlines, and NASA. He has overseen the remake and staff recruiting of more than a dozen magazines. Pick up a copy of Jay’s latest book Aristotle’s Guide to Self-Persuasion: How Ancient Rhetoric, Taylor Swift, and Your Own Soul Can Help You Change Your Life Follow Jay on Instagram @JayHeinrichs and check out more of his work at www.jayheinrichs.comThanks to Penguin Random House Audio for granting us permission to run this excerpt from Aristotle’s Guide to Self-Persuasion.🏛 The 2025 LIVE session of Stoicism 101: Ancient Philosophy For Your Actual Life starts November 10th. Don’t miss your chance to join us! Read on for more about the unique opportunities you get from joining the LIVE course.📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

9 Nov 14min

It takes a trained mind to see wonder and awe in the middle of everyday struggles. In today’s PT. 2 episode, Ryan and persuasion expert Jay Heinrichs dive deeper into discipline, the power of our inner dialogue, and what it really means to have agency. Jay shares the story of having breakfast with the Dalai Lama and how the Stoics, Buddhists, Aristotle, and even Taylor Swift all point to the same truth about how we see and respond to life. Jay Heinrichs is a New York Times bestselling author of Thank You For Arguing and is a persuasion and conflict consultant. Middlebury College has named him a Professor of the Practice in Rhetoric and Oratory. Jay has conducted influence strategy and training for clients as varied as Kaiser Permanente, Harvard, the European Speechwriters Association, Southwest Airlines, and NASA. He has overseen the remake and staff recruiting of more than a dozen magazines. Pick up a copy of Jay’s latest book Aristotle’s Guide to Self-Persuasion: How Ancient Rhetoric, Taylor Swift, and Your Own Soul Can Help You Change Your Life Follow Jay on Instagram @JayHeinrichs and check out more of his work at www.jayheinrichs.com🏛 The 2025 LIVE session of Stoicism 101: Ancient Philosophy For Your Actual Life starts November 10th. Don’t miss your chance to join us! Read on for more about the unique opportunities you get from joining the LIVE course.📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

8 Nov 44min

What’s the point? What is philosophy for?🏛 The 2025 LIVE session of Stoicism 101: Ancient Philosophy For Your Actual Life starts November 10th. Don’t miss your chance to join us! Read on for more about the unique opportunities you get from joining the LIVE course. | https://dailystoic.com/101👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/📖 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

7 Nov 9min

After their interview, Ryan and Nick Thompson, CEO of The Atlantic and author of The Running Ground, headed into The Painted Porch to talk about their favorite books and swap recommendations. 🎥 You can watch this episode on Ryan Holiday's YouTube channel: https://www.youtube.com/watch?v=XHT1krHB6Wg🎙️ Listen to Nick Thompson's episode on The Daily Stoic Podcast | Apple Podcasts, Spotify 📚 Full list of books that Ryan gave to Nick: Tunnel 29: The True Story of an Extraordinary Escape Beneath the Berlin Wall by Helena MerrimanDying Every Day: Seneca at the Court of Nero by James RommThe Pursuit of Happiness: How Classical Writers on Virtue Inspired the Lives of the Founders and Defined America by Jeffrey RosenNotes to John by Joan DidionNecessary Trouble by Drew Gilpin FaustMeditations by Marcus Aurelius (Gregory Hays Translation)Novelist as a Vocation by Haruki MurakamiLetter to the Father by Franz KafkaWhat I Talk about When I Talk about Running: A Memoir by Haruki MurakamiEverything Is Tuberculosis by John Green Death Be Not Proud by John GuntherCheck out Nick’s new book The Running Ground: A Father, a Son, and the Simplest of SportsFollow Nick on Instagram and X @NXThompson📚 Sign up for Ryan’s free monthly reading list newsletter: https://ryanholiday.net/the-reading-list/📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

6 Nov 28min