When Good People Lose Themselves to Tyrants | James Romm (PT. 2)
The Daily Stoic16 Aug 2025

When Good People Lose Themselves to Tyrants | James Romm (PT. 2)

History has a way of looking calmer than it really was. In this PT. 2 episode, Ryan sits down with historian and author James Romm to talk about the messy, dangerous, and often absurd reality of life in ancient Greece and Rome, especially for the philosophers who tried to “advise” the powerful. From Plato’s naïve trips to Syracuse, to Seneca’s complicated dance with Nero, to Marcus Aurelius resisting the pull of corruption, they discuss the timeless tension between access and integrity.

James Romm is an author, reviewer, and a Professor of Classics at Bard College in Annandale, NY. He specializes in ancient Greek and Roman culture and civilization. His reviews and essays have appeared in the New Yorker, the Wall Street Journal, the London Review of Books, the Daily Beast, and other venues. He has held the Guggenheim Fellowship (1999-2000), the Birkelund Fellowship at the Dorothy and Lewis B. Cullman Center for Writers and Scholars at the New York Public Library (2010-11), and a Biography Fellowship at the Leon Levy Center of the City University of New York (2014-15).


Follow James on Instagram @James.Romm and check out more of his work at his website, www.jamesromm.com


📚 Get signed copies of James' latest book Plato and the Tyrant, and his other books Dying Every Day, How To Die, and How To Give, at The Painted Porch | https://www.thepaintedporch.com/


📚 View the full list of books mentioned in this episode here: https://www.thepaintedporch.com/collections/james-romm


🎥 Head to Ryan Holiday’s YouTube Channel to watch him give James Romm book recommendations at The Painted Porch: https://www.youtube.com/watch?v=iUuxMfJRc2c


🎙️ Listen to James Romm’s first episode on The Daily Stoic Podcast: https://dailystoic.com/romm/


📖 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


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Episoder(2816)

Mark Manson: “I Didn’t Realize How Out of Control I Was.”

Mark Manson: “I Didn’t Realize How Out of Control I Was.”

What’s the point of achieving success if you’re burned out, lonely, or exhausted? In today’s episode, Ryan sits down with Mark Manson (bestselling author of The Subtle Art of Not Giving a F**k) to talk about how the habits that help you “make it” are usually the same ones that burn you out later. Mark talks about the moment he realized he couldn’t keep living like a maniac, the changes he had to make in his 30s and 40s, and why he no longer trusts himself around certain decisions.Mark Manson is a bestselling author best known for The Subtle Art of Not Giving a F**k. In it, Mark looks at self-improvement not through avoiding problems or always being happy, but rather through improving amidst problems and learning to accept the occasional unhappiness. Grab Mark’s books: The Subtle Art of Not Giving a F**k, The Subtle Art of Not Giving a F**k Journal, and Everything Is F***ked: A Book About Hope, at The Painted Porch | https://www.thepaintedporch.com/Watch Ryan's episode on the Solved Podcast: https://www.youtube.com/watch?v=HvEg37B4DU4Listen to the Solved Podcast with Mark Manson on Spotify, Apple Podcasts, and YouTube Follow Mark on YouTube, and check out more of his work at https://markmanson.net/🎟️ 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 👉 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.

15 Nov 202540min

This Is The Part To Love | "I Spent 6 Years Researching The Most Elusive Trait In The World"

This Is The Part To Love | "I Spent 6 Years Researching The Most Elusive Trait In The World"

It seems insensitive to even suggest that someone “love” their fate. How are you supposed to love a breakup? Love that you buried someone? Love that you lost your business?🎥 Watch this episode on The Daily Stoic YouTube Channel: https://www.youtube.com/watch?v=2fLpCRbQUs8📖 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/🎙️ 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.

14 Nov 202521min

BONUS | Where Service Meets Stoicism — U.S. Army Lieutenant Colonel Joe Byerly & Ryan Holiday

BONUS | Where Service Meets Stoicism — U.S. Army Lieutenant Colonel Joe Byerly & Ryan Holiday

In this bonus episode, Ryan sits down with his friend and collaborator, Joe Byerly, retired U.S. Army Lieutenant Colonel, writer, and host of From the Green Notebook. The two talk about the overlap between Stoicism and service, the discipline it takes to think clearly, and why wisdom isn’t something you’re born with. Joe Byerly is a recently retired U.S. Army Lieutenant Colonel with 20 years of service, including combat tours in Iraq and Afghanistan and command of a cavalry squadron in Europe. He’s earned multiple honors, including the Legion of Merit, Bronze Star, and the Purple Heart.In 2013, he founded From the Green Notebook, a platform that helps leaders reflect, grow, and share their experiences. Joe’s passionate about the power of reading, writing, and self-reflection—and he’s the author of The Leader’s 90-Day Notebook and co-author of My Green Notebook: “Know Thyself” Before Changing Jobs.Follow Joe on Instagram @FromTheGreenNotebook and on X @jbyerly81Check out Joe’s podcast From The Green Notebook on YouTube, Apple Podcast, and Spotify See more of Joe’s work on his website: https://fromthegreennotebook.com/📖 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.

13 Nov 20251h 8min

There’s No One Stupider Than An Angry Person | Ask Daily Stoic

There’s No One Stupider Than An Angry Person | Ask Daily Stoic

There’s even a famous old saying: Whom the gods wish to destroy, they first make angry.🎟️ 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 👉 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.

13 Nov 202518min

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

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 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 20251h

Don’t Let It Trouble Your Mind

Don’t Let It Trouble Your Mind

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 20252min

None of Us Are Perfect | Judge Yourself, Not Others

None of Us Are Perfect | Judge Yourself, Not Others

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 20259min

Failure Doesn’t Define You—Neither Does Success | Always The Same

Failure Doesn’t Define You—Neither Does Success | Always The Same

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 202510min

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