The Daily Stoic

You’re tough. You’re firm. You don’t get bothered by things. You keep yourself under control. Good. But you’re missing something else just as important and perhaps more impressive.

📚 Books Mentioned:
You Have to Be Prepared to Die Before You Can Begin to Live: Ten Weeks in Birmingham That Changed America by Paul Kix
The Obstacle Is the Way by Ryan Holiday
Meditations by Marcus Aurelius
It’s Better To Be Feared by Seth Wickersham
American Kings: A Biography of the Quarterback by Seth Wickersham

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If your New Year motivation didn’t make it to February, this episode is for you. Ryan and his business partner and longtime friend, Brent Underwood, talk about how waiting for permission, perfect conditions, or external validation quietly turns into procrastination, even for high performers. They discuss why open-ended ambitions are harder than deadlines, how success can actually make starting new things scarier, and the trap of telling yourself, “I’ll get to it later.”

Let’s not write the year off just yet. The Daily Stoic New Year New You challenge is opening back up for a limited time. Learn more and sign up today at dailystoic.com/challenge.

👉 Get The Daily Stoic New Year New You & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life

Brent Underwood is the owner of Cerro Gordo, an original boomtown silver mine, established in 1865. Check out Brent's book Ghost Town Living: Mining for Purpose and Chasing Dreams at the Edge of Death Valley at The Painted Porch.

Youtube: @GhostTownLiving
IG: @BrentWUnderwood

🎙️ 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

✉️ 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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From corruption to tyranny, the Stoics refused to sit on the sidelines. They tried to change things.

👉 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

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It’s always been a dilemma: Why should I be honest when no one else seems to be? Why should I play by the rules when others are so visibly breaking them? Why should I be respectful or kind or fair when nobody else is?

📕 Grab a signed copy of Right Thing, Right Now by Ryan Holiday | 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/

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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.

Few writers understand American culture like Chuck Klosterman, which is why he joins Ryan ahead of the Super Bowl to talk about how football reshaped American culture.

In this episode, Chuck and Ryan discuss what football really reveals about American culture, power, and the stories we tell ourselves about expertise and control. Chuck shares his observations, strange historical parallels, and personal stories that connect sports to technology, identity, and how monocultures form and eventually fade.

🏈 Pick up a copy of Football by Chuck Klosterman

📚 Chuck is the author of Sex, Drugs, and Cocoa Puffs, But What If We’re Wrong?, The Nineties, and now his latest book Football.

📱Follow Chuck on X @CKlosterman

🎟️ Come see Ryan Holiday LIVE: https://www.dailystoiclive.com/
San Diego, CA - February 5, 2026
Phoenix, AZ - February 27, 2026

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