Major General Dan Caine on Becoming a Great Leader
The Daily Stoic9 Okt 2021

Major General Dan Caine on Becoming a Great Leader

On today’s podcast, Ryan talks to Major General Dan Caine about the importance of defining success before you set out to try to solve a problem, the responsibility of leaders to be as prepared as possible, the ineffectiveness of holding others to the standards you hold yourself to, becoming a lifelong student of leadership, and more.

Maj. Gen. J. Daniel Caine is the Director of Special Programs and the Department of Defense Special Access Program Central Office (DoD SAPCO), the Pentagon, Arlington, Virginia. He has commanded a joint special operations air directorate, a joint task force and a group. Maj. Gen. Caine is a Command Pilot with more than 2,800 hours in the F-16 and has served as a Joint Terminal Attack Controller in a special mission unit assigned to the U.S. Special Operations Command.

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Persuasion Expert: "You Can Manipulate Yourself Into Doing Hard Things" | Jay Heinrichs (PT. 1)

Persuasion Expert: "You Can Manipulate Yourself Into Doing Hard Things" | Jay Heinrichs (PT. 1)

You’re not lazy, you’re just losing the debate in your own head. In today’s episode, Ryan talks with Jay Heinrichs, bestselling author of Thank You for Arguing and one of the world’s leading experts on rhetoric and persuasion. Jay has spent decades studying how we influence others, but in this conversation, he flips that lens inward to show how we can use the same tools to influence ourselves.Ryan and Jay talk about the fascinating overlap between Stoicism and rhetoric, how Marcus Aurelius used rhetoric to his advantage, and why self-persuasion might actually be more powerful than raw willpower. They discuss the rhetorical tricks Jay used on himself and what the best tools are for getting unstuck.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🎟️ 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 🏛 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🎥 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.

5 Nov 202538min

This Is Not What We Fight For

This Is Not What We Fight For

The Stoics were not passive. They did impressive things. They were impressive people. They were fighters. But you know what? They, like the rest of us, sometimes got carried away, sometimes hung on too long, went after the wrong things. 🏛 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.🎟️ 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.

5 Nov 20252min

When The Statues Still Had Paint On Them | The Real Power You Have

When The Statues Still Had Paint On Them | The Real Power You Have

History isn’t something that other people lived through and we get to read about. We all live through history and we all can make it if we choose.🏛 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📓 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/👉 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.

4 Nov 20259min

This is How To Be Smart (Or At Least Not Dumb) | Following The Doctor's Orders

This is How To Be Smart (Or At Least Not Dumb) | Following The Doctor's Orders

We can avoid being swept up in the newest fad or the oldest con. We can stop reliving the same mistake. 📖 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/📘 Grab the hardcover edition of The Daily Stoic here: https://store.dailystoic.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.

3 Nov 20257min

Everything (And I Really Mean Everything) Is A Chance To Do This

Everything (And I Really Mean Everything) Is A Chance To Do This

Will you be ​brave​ or afraid? Selfish or ​selfless​? ​Strong​ or weak? ​Wise​ or stupid? Will you cultivate a good habit or a bad one? Courage or cowardice? The bliss of ignorance or the challenge of a new idea? Stay the same…or grow? The easy way or the right way? Is it easy to make these choices? Of course not.📚 Get a signed copy of each of the books in the Stoic Virtues Series: Courage is Calling, Discipline is Destiny, Right Thing Right Now, and Wisdom Takes Work 🎙️ Listen Francis Ford Coppola's episode on The Daily Stoic Podcast: Apple Podcasts, Spotify, YouTube👉 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.

2 Nov 202516min

What Did The Stoics Get WRONG? | Nick Thompson (CEO of The Atlantic)

What Did The Stoics Get WRONG? | Nick Thompson (CEO of The Atlantic)

Running isn’t just good exercise, it’s Stoicism in motion. In part two of Ryan’s conversation with Nick Thompson, CEO of The Atlantic, they talk about how running mirrors the daily discipline of Stoic philosophy, the decline of expertise in modern life, the one decision Marcus Aurelius made that changed history, and what the Stoics might have gotten wrong.Nick Thompson is the CEO of The Atlantic, an American magazine founded in 1857, which earned the top honor for magazines, General Excellence, at the National Magazine Awards in both 2022 and 2023. In his time as CEO, the company has seen record subscriber growth. Before joining The Atlantic, he was the editor-in-chief of Wired magazine. He is also a former contributor for CBS News and has previously served as editor. He has long been a competitive runner; in 2021, he set the American record for men 45+ in the 50K race.Check out Nick’s new book The Running Ground: A Father, a Son, and the Simplest of SportsFollow Nick on Instagram and X @NXThompson🎟️ 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.

1 Nov 202550min

This is the Deads Day | Harsh Truths From The Stoics

This is the Deads Day | Harsh Truths From The Stoics

Today is Halloween here in America, a holiday of fun and mischief for children—masks, candy, and staying up late. But tomorrow, in Mexico, begins Día de los Muertos, a holiday more aimed at adults and with deeper philosophical roots. 🪙 Memento Mori | We have a collection of items in the Daily Stoic store to help you in your own memento mori practice, check them out here: https://store.dailystoic.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.

31 Okt 202521min

BONUS | Seeking External Validation is RUINING Your Life - Dr. Rangan Chatterjee

BONUS | Seeking External Validation is RUINING Your Life - Dr. Rangan Chatterjee

Every time you chase approval, you trade a piece of who you really are. Today's bonus episode is a clip from Dr. Rangan Chatterjee's episode on The Daily Stoic Podcast. Dr. Rangan Chatterjee is a physician, author, TV presenter and podcast host of Feel Better Live More where he talks with leading health experts who offer easy health life-hacks, expert advice and debunk common health myths. Be sure to check out Dr. Rangan Chatterjee’s latest book Make Change That Lasts and grab signed copies of his other books: Feel Better in 5, Feel Great Lose Weight, and Happy Mind, Happy Life at The Painted Porch. You can follow Dr. Rangan on Instagram @DrChatterjee, on X @Dr.ChatterjeeUK, and on YouTube @DrChatterjeeRangan🎥 Watch Dr. Rangan Chatterjee’s FULL episode here: https://www.youtube.com/watch?v=mMg8KgzD8DM📖 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.

30 Okt 20258min

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