You Think You Want Autonomy. You Don’t. | David Epstein

You think you want more freedom, but too much of it can work against you. In this episode, Ryan talks with David Epstein about why constraints can actually make us better. They discuss how deadlines sharpen focus, why too much autonomy can become a trap, and why “freedom within a framework” may be more useful than total freedom.

David Epstein is the author of the #1 New York Times best seller Range: Why Generalists Triumph in a Specialized World. His third book, Inside the Box: How Constraints Make Us Better, is out now!

📚 Grab signed copies of David Epstein Books at The Painted Porch:

Connect with David Epstein 👉 Instagram, YouTube, X, Substack

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Jaksot(2987)

You’ll Be Called Worse…By Better

Marcus Aurelius was the public face of an empire. Seneca published plays and books. Cato and Cicero ran for office. Epictetus was a slave to a powerful Roman, at his whim and his mercy. In other words...

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Can a Billionaire Be a Stoic? | Robert Rosenkranz (PT. 1)

Wealth can free you—or consume you. Self-made billionaire Robert Rosenkranz joins Ryan to discuss how Stoicism can transform our approach to money, ambition, and identity. Robert shares how Stoicism h...

7 Touko 202549min

It’s Strange How Cowardly We Sometimes Are | We Are A Product of Our Habits

Courage calls us and what do we do? We ignore it. We let it ring.📓 Pick up a signed edition of The Daily Stoic Journal: 366 Days of Writing and Reflection on The Art of Living: https://store.dailysto...

6 Touko 20258min

Will They Forgive You? | You Are The Project

You could say something…you should say something. But…you don’t.📚 Books mentioned:The Daily Stoic by Ryan Holiday | Grab a signed copy here https://store.dailystoic.com/ Augustus by John Williams | h...

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BONUS: You Know, You Can Do Something

If it’s right, if it must be done….do it now.📕 Tomorrow is the LAST DAY you can grab the Right Thing, Right Now ebook for just $2.99! Or if you prefer reading hardcover books, we have signed copies a...

4 Touko 20253min

Moral Courage Isn’t Always So Simple

The call for courage keeps returning, over and over. What matters most isn’t what we chose before, but what we choose right now.Listen to the talk that Ryan was supposed to give at The Naval Academy: ...

4 Touko 202522min

What The Stoics Thought Made You Rich | Sahil Bloom

If wealth meant fulfillment instead of finances, how rich would you be? In today's episode, Sahil Bloom, entrepreneur and author of The 5 Types of Wealth, joins Ryan to unpack how they balance ambitio...

3 Touko 20251h 7min

If You Want A Reason To Live Pt. II | 12 Stoic Choices To LEVEL UP Your Life TODAY

As dark as life can get, there are lovely things out there to cheer you up. 🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Da...

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