The Daily Stoic

We should pride ourselves on our ability to put up with these people, to be able to be nice to people who are not nice, to be able to turn the other cheek and not be made bitter and cynical.

Day to day, it’s only our individual actions that are up to us: How we treat people, how we run our businesses, what we think about.

The Stoics knew that wanting less increases gratitude, just as wanting more obliterates it. "Freedom isn't secured by filling up on your heart's desire but by removing your desire." - Epictetus

It’s not that you should never speak up. It’s not that you should never speak truth to power. It’s just that you should never do it while you’re angry. Do it after you’ve calmed down. Do it after you’ve had time to think about it. Do it after you’ve slept on it.

All that we see must be illuminated by the calm light of mild philosophy. So we can see what it really is. So we don’t do anything we regret. 

Most people don’t read that many books, maybe a few a year at most. So if you’re only going to read a couple books this year, the decision of which ones you choose becomes really important.In today’s episode, Ryan shares a handful of books he’s confident are worth your time. They’ve changed him, made him better, and he believes they’ll make you better too in a lot of different areas of your life.

Love isn’t just an emotion. It’s not just a feeling that hits you out of nowhere. It’s an action, something you can practice and something you can get better at. And while philosophy might not seem like a guide to a great love life, especially Stoicism, it actually has a lot to teach us.

Marcus Aurelius said that if you ever found anything better in life than courage, discipline, justice, and wisdom—the four virtues—it must be an extraordinary thing indeed. Which raises the question: is there anything better?

Life has a way of stripping all our reasons bare, of humbling our plans and assumptions. We must live, as Marcus Aurelius said, as if death hangs over us. Because it does.

Why do the same patterns keep showing up in completely different centuries? In this episode, Pulitzer Prize–winning historian Stephen Greenblatt joins Ryan to discuss how power, fear, ego, and insecurity keep producing the same patterns. They talk about why dangerous leaders do not look dangerous at first, how great thinkers learned to survive unstable rulers, and why some of the most important ideas in history had to be hidden inside art, literature, and fiction just to stay alive. Stephen Greenblatt is Cogan University Professor of the Humanities at Harvard University. He has written extensively on English Renaissance literature and acts as general editor of The Norton Anthology of English Literature and The Norton Shakespeare. He is the author of fourteen books, including The Swerve, winner of the Pulitzer Prize and National Book Award, and Will in the World, a Pulitzer Prize finalist.

It can feel like everything is falling to pieces. It can feel like you’re lost. It can feel like there’s no hope, no way forward, nothing to do. But that’s just because you’ve gotten rattled.

It would be wonderful if the world was naturally just, if people were automatically good, always doing the right thing. But of course, they don’t. 

At the core of Stoicism is the idea that our emotions are our responsibility. No one can make us frustrated. No one can offend us either, Epictetus said, not without us being complicit in the taking of offense.

After recording their episode, Ryan and Bert Kreischer stopped by The Painted Porch, where Ryan shared some must-read books with Bert.Watch this episode on Ryan Holiday's YouTube Channel: https://www.youtube.com/watch?v=6VH7tzlzRwY

The most fearless philosopher in the ancient world didn’t rule an empire or write books. He lived on the street and begged for food. And yet, he was bold enough to challenge Alexander the Great to his face. In today’s episode, we’re talking about Diogenes, the philosopher who rejected status, comfort, and approval and may have understood freedom better than anyone who came after him.

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.

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.

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

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.

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?