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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Episoder(2843)

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

The Surprising Habit Hack from Aristotle

The Surprising Habit Hack from Aristotle

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 202514min

Persuasion Expert: "You Can TRAIN Your Mind to See the Positive" | Jay Heinrichs (PT. 2)

Persuasion Expert: "You Can TRAIN Your Mind to See the Positive" | Jay Heinrichs (PT. 2)

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 202544min

This Is The Point of Philosophy | You're Wasting Your Life

This Is The Point of Philosophy | You're Wasting Your Life

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 20259min

BONUS | Ryan Holiday Curates a Reading List for Nick Thompson

BONUS | Ryan Holiday Curates a Reading List for Nick Thompson

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 202528min

Take This Seriously | Ask Daily Stoic

Take This Seriously | Ask Daily Stoic

This is what Stoicism has done throughout history. It’s made people the best they could be.🏛 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.👉 Get Stoicism 101: Ancient Philosophy For Your Actual Life & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎟️ 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.

6 Nov 202514min

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