Just after 2 a.m. on April 11, the U.S. Senate confirmed retired Air Force Lieutenant General Dan Caine as the 22nd Chairman of the Joint Chiefs of Staff. As it turns out, Ryan had the opportunity to interview Gen. Caine a few years ago as part of The Daily Stoic Leadership Challenge.

In honor of his recent confirmation, today’s episode is Ryan and Gen. Caine's powerful conversation. Gen. Caine reflects on being one of the first pilots in the air on 9/11, the core traits every great leader must embody, and how to effectively inspire and guide a team toward a shared mission.

General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal.

💡 Want more insights from extraordinary leaders like General Caine? Check out The Daily Stoic Leadership Challenge at store.dailystoic.com.

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It was a dark world…and Marcus Aurelius desperately needed some light.

🎉 Celebrate Marcus Aurelius' Birthday this month by reading Meditations with us and the Daily Stoic community. On April 26th, 1905 years after the day of his birth, Ryan Holiday will host an invite-only LIVE Q&A to talk about all things Marcus Aurelius and Meditations.

Get 20% off with a Meditations BOOK & GUIDE bundle. Join the LIVE Meditations Q&A with Ryan Holiday by purchasing before April 26th!

Get all our Meditations offering and learn more at our official Meditations Collection at dailystoic.com/meditations today.

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Check out the previous lectures from Ryan Holiday at the U.S. Naval Academy here:

Courage: The Power Of Courage

Discipline: The Life Changing Art Of Self-Discipline

Justice: Stoic Habits To Help You Live And Be Better

🗞️ Read Ryan Holiday's opinion piece in The New York Times: https://www.nytimes.com/2025/04/19/opinion/naval-academy-speech-censorship.html

📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work

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The right book at the right time is a powerful thing. In fact, it can change the whole course of your life.

🎉 Celebrate Marcus Aurelius' Birthday this month by reading Meditations with us and the Daily Stoic community. On April 26th, 1905 years after the day of his birth, Ryan Holiday will host an invite-only LIVE Q&A to talk about all things Marcus Aurelius and Meditations.

Get 20% off with a Meditations BOOK & GUIDE bundle. Join the LIVE Meditations Q&A with Ryan Holiday by purchasing before April 26th!

Get all our Meditations offering and learn more at our official Meditations Collection at dailystoic.com/meditations today.

🎙️ 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

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We were born to work together like feet, hands, and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural.

🎉 Celebrate Marcus Aurelius' Birthday this month by reading Meditations with us and the Daily Stoic community. On April 26th, 1905 years after the day of his birth, Ryan Holiday will host an invite-only LIVE Q&A to talk about all things Marcus Aurelius and Meditations.

Get 20% off with a Meditations BOOK & GUIDE bundle. Join the LIVE Meditations Q&A with Ryan Holiday by purchasing before April 26th!

Get all our Meditations offering and learn more at our official Meditations Collection at dailystoic.com/meditations today.

👉 Check out the FULL interview with Troy Baker: Apple Podcasts, Spotify, YouTube

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✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail

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

We all have those days where we’d rather just not. The ancients knew days like this.

🎉 Celebrate Marcus Aurelius' Birthday this month by reading Meditations with us and the Daily Stoic community. On April 26th, 1905 years after the day of his birth, Ryan Holiday will host an invite-only LIVE Q&A to talk about all things Marcus Aurelius and Meditations.

Get 20% off with a Meditations BOOK & GUIDE bundle. Join the LIVE Meditations Q&A with Ryan Holiday by purchasing before April 26th!

Get all our Meditations offering and learn more at our official Meditations Collection at dailystoic.com/meditations today.

📓 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

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✉️ 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/

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Happy Earth Day! Let today be a reminder of how the Stoics looked to nature as a guide for living wisely and well.

🎥 Watch this episode on The Daily Stoic YouTube Channel: https://www.youtube.com/watch?v=COfKIzH5cXE

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✉️ 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/

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