These Are All The Ways Ryan Holiday Feels Poorer Than He Is

How does it happen? How does someone become great? 👉 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/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues📘 Grab the hardcover edition of The Daily Stoic here: https://store.dailystoic.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

22 Sep 20259min

If you think you know what wisdom is, you probably don't. If you think you have wisdom, you almost certainly don't. 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": 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/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

21 Sep 202518min

Is ego a prerequisite for greatness as an NFL quarterback? In this episode, Ryan is joined by award-winning sports journalist, Seth Wickersham, to dig into the brutal realities of the position, from overbearing parents and sideline meltdowns to Tom Brady’s relationship with Bill Belichick. They talk about the psychology, pressure, and identity struggles that come with the glory of America’s most powerful position in sports. Seth Wickersham is a senior writer at ESPN and the New York Times bestselling author of It’s Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness. Focusing primarily on longform enterprise and investigative work on the National Football League, Wickersham has been a finalist for the National Magazine Award for Reporting, and his stories have been anthologized in the Best American Magazine Writing, the Best American Sports Writing, and Next Wave: America’s New Generation of Great Literary Journalists, among others. Released in 2021, It’s Better to Be Feared was named Nonfiction Book of the Year by Sports Illustrated and Best Sports Book by the National Sports Media Association. Follow Seth Wickersham: X & Instagram: @Seth.Wickersham📚 Grab signed copies of It’s Better to Be Feared and American Kings: A Biography of a Quarterback at The Painted Porch | https://www.thepaintedporch.com🎙️ Listen to Seth Wickersham's first interview on The Daily Stoic Podcast: https://dailystoic.com/seth-wickersham/👉 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/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

20 Sep 202547min

Each of us is sent on missions, each of us does our stint in this situation or that one. The question is, then, will we return with honor?👉 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/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

19 Sep 202523min

You may not have a lot of money. Or powerful connections. Or even superior genetics. Does this mean you’re at a disadvantage?👉 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/📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

18 Sep 202514min

“As long as you live,” Seneca said, “keep learning how to live.” As long as we’re alive, we must keep learning and wrestling with these ideas.📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": 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/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

17 Sep 20254min

In America, kings don’t wear crowns, they wear helmets. Being an NFL quarterback is the ultimate crown and it never comes free. Today, award-winning journalist Seth Wickersham joins Ryan to pull back the curtain on football’s most scrutinized position. They dive into why players can’t walk away, the intense loneliness at the top, and how the pressure can consume a player’s life.Seth Wickersham is a senior writer at ESPN and the New York Times bestselling author of It’s Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness. Focusing primarily on longform enterprise and investigative work on the National Football League, Wickersham has been a finalist for the National Magazine Award for Reporting, and his stories have been anthologized in the Best American Magazine Writing, the Best American Sports Writing, and Next Wave: America’s New Generation of Great Literary Journalists, among others. Released in 2021, It’s Better to Be Feared was named Nonfiction Book of the Year by Sports Illustrated and Best Sports Book by the National Sports Media Association. Follow Seth Wickersham: X & Instagram: @Seth.Wickersham📚 Grab signed copies of It’s Better to Be Feared and American Kings: A Biography of a Quarterback at The Painted Porch | https://www.thepaintedporch.com🎙️ Listen to Seth Wickersham's first interview on The Daily Stoic Podcast: https://dailystoic.com/seth-wickersham/👉 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/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

17 Sep 202534min

Anyone who has had a run of bad luck knows the feeling. It’s frustrating and annoying and sometimes deeply unfair, but there is also something freeing about 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/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work📓 Pick up a signed edition of The Daily Stoic Journal: 366 Days of Writing and Reflection on The Art of Living: https://store.dailystoic.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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.

16 Sep 20258min