Make Stoicism Your Anchor in Chaos (Ryan Holiday Live at FreedomFest)

We should fight, as Marcus Aurelius says, to be the person philosophy tried to make us. In this episode, Ryan shares why deciding to live with virtue can completely transform your life. 🎟️ Come seeRyan Holiday LIVE https://www.dailystoiclive.com/: https://www.dailystoiclive.com/ Seattle, WA - December 3, 2025 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830976292379?aff=oddtdtcreatorSan Diego, CA - February 5, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1527497619499?aff=oddtdtcreatorPhoenix, AZ - February 27, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830981698549?aff=oddtdtcreator 📖Wisdom Takes Work https://store.dailystoic.com/pages/wisdom-takes-work by Ryan Holiday is out! Grab a copy here:https://store.dailystoic.com/pages/wisdom-takes-work 👉 Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ 🎥 Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast onInstagram https://www.instagram.com/dailystoicpodcast/?hl=en:https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://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 https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Ryan Holiday?

  Welcome to the Weekend Edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic, and other long-form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy, and most importantly, that you're able to apply it to your actual life. Thank you for listening.

• 0:43Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. America is a fascinating experiment, really, right? It is a country built around the idea of personal liberty. It is a free government, government of the people, by the people, for the people. It largely leaves up to the people how they want to live, what kind of life they want to have. Now, it's not a perfect system by any means, and liberty is a tricky concept. And it's tricky because where does one person's freedom begin and end? Where does it impede on someone else's freedom? But I think the interesting thing about this idea of a government

• 1:28Ryan Holiday?

  that largely allows you to live how you want to live, it was implicit and assumed by the founders, who were steeped in the ideas of classical virtue, that there were still things you wouldn't do, right? There were things that no honorable person would choose to do. The First Amendment allows you to say all sorts of horrendous horrible things. There's no law that says you can't be a dick, or a bully, or a liar. In many ways, it can't even prevent you from being a cheat or a manipulator, right? There's a... Pretty big line between a bunch of things that, you know, we all agree are wrong, but are not exactly illegal. So a couple of months ago, I was in Palm Springs,

• 2:11Ryan Holiday?

  and I talked at this event called Freedom Fest. Now, it's an independent, nonpartisan event. It's not really affiliated with any organization or think tank, but it's pretty clearly right-coded, right? It was definitely mostly libertarian folks. So I wanted to give a talk that I think challenged the folks in the audience. I wanted to see if they meant what they said when they talked about, you know, free expression and free thought. I disagreed with a number of the speakers that were there, not just like, hey, you think this policy is good, and I think that policy is good. As you'll hear in the talk, I think there were some people there who shouldn't have been platformed. One of them, I think, should be in jail, not for what he said, but for what he's actually

• 2:54Ryan Holiday?

  done. So this is all kind of a complicated milieu for me to be in, but I like challenges like that. And I was actually impressed that they seemed to be able to handle those challenges as well. So I gave a talk very different than what I normally talk about, but was actually much more philosophical than what I normally talk about. And I wanted to bring that to you today. So here is me talking some important Stoic ideas in Palm Springs. It is not overtly political, but it is about this paradox, right? This idea of, you know, freedom to and freedom from. Just because something is illegal doesn't mean it's right. And so with the incredible and obviously inalienable freedoms that we

• 3:38Ryan Holiday?

  have, what that means is the question falls to us about who we should be and how we should live. To me, the answer is we should live and act with virtue, not because we have to, but because it's the best way to live, right? We should fight, as Marx really says, to be the person philosophy tried to make us. That is what I'm talking about in today's episode. And thanks to the folks at Freedom Fest for having me out, for letting me spar with them a little bit. And I hope you enjoy this episode.

• 4:13Ryan Holiday?

  Hey, it's Ryan. I'm doing a bunch of live dates, including one coming up soon. I'm gonna be in Seattle, Washington on December 3rd, San Diego, California on February 5th, and Phoenix, Arizona on February 27th. The talk I just did in Austin sold out, so this will almost certainly sell out too. I would love to see you there. Go grab tickets at DailyStoicLive.com.

• 4:44Ryan Holiday?

  I want to talk about virtue today, and I am not talking about virtue signaling, if we can get this on the screen here, but actual virtue, classical virtue. Specifically, I want to talk about the cardinal virtues of Stoicism: courage, discipline, justice, and wisdom. The four virtues that we get down from the Stoic philosopher Zeno that resound to us through Christianity, and then, of course, through today. But my argument is that philosophy is not riddles and abstractions. It is here to tell us what to do: how to govern,

• 5:26Ryan Holiday?

  how to govern ourselves, how to be, how to live, how to deal with the problems of life, which include travel delays and stress, and annoying coworkers, and health problems, and successes and failures, and pandemics, and parenting, and politics. And that this kind of philosophy, that virtue is not academic, it's not theoretical, but it is essential for individuals and for nations. Because without virtue, we're lost. And the founders knew this more than anyone. John Adams would say that a country without virtue in the people, that ambition and avarice and revenge and...

• 6:05Ryan Holiday?

  All the vices of humankind break through the strongest cords of the Constitution like a whale goes through the net. So let's start with courage, which has always been in short supply but feels like it's even rarer today. I think we sometimes underestimate the raw courage that the founders had, not just on the battlefield, but to take the stand that they did. There's a famous letter between Benjamin Rush and John Adams, where he says, "Do you recollect the pensive and awful silence which pervaded the house when we were called up, one after another, to sign what we thought might be our own death warrant?" And it's shocking when you really look at it just how young many of the founders were too.

• 6:50Ryan Holiday?

  The average age is late 30s, early 40s. There are some as young as their early 20s. These are people who are putting it all on the line, who are betting that they can do something better than it has ever been done. And they have a certain gallows humor about this. One jokes to another that he's not as scared as being hung because he knows his neck will break faster than the other. But they understood they were taking their lives in their hands when they formed this nation. And so where did they get this courage? What were they drawing on? Well, they were largely drawing on their understanding of classical ideas, classical virtue, and classical heroes. The most famous play of the 18th century was a play called Cato.

• 7:35Ryan Holiday?

  You could argue it was the Hamilton of its day. All the founders see it multiple times. It's about the defender of the Roman Republic, the great Stoic philosopher. And many of the famous lines in the American Revolution are actually, if you had seen this play, you would have understood they were lines or allusions to that play. Washington actually puts on Joseph Addison's Cato at Valley Forge, the lowest point of the American Revolution. He is turning to Cato to give himself and his men courage. My point is that the Stoics were not passive. They were not academic philosophers in the 18th century or 2000. 1000 years earlier, they were not resigned.

• 8:18Ryan Holiday?

  They were literally revolutionaries. Portia Cato, Cato's daughter, is totally undersold. Her role in the assassination of Caesar, it's actually she who gives Brutus the spine to do what he needs to do. There's a whole generation of Stoics known as the Stoic Opposition, who stand up to the tyrannical emperors that come after Caesar. In fact, there's a blanket ban on philosophers in Rome, because to be a Stoic philosopher was to be synonymous with being part of the opposition, or today, we might call the Resistance. Many of them die as a result of this resistance, a result of this adherence to principle,

• 9:03Ryan Holiday?

  this courage. And so my argument is courage is, yes, sometimes it's life or death thing. But it's also just the courage to put yourself out there, to try new things, to be weird, to speak up, to try things that haven't been done before, to think for yourself. One of my favorite Stoic philosophers is a guy named Agrippinus. He stands out in Nero's Rome, which you can imagine is not a safe thing to do. And a friend asked him, you know, why don't you try to blend in? Why don't you come to the parties? Why don't you pay your respects? And he says, I'm not going to do that. In fact, my whole personality is about not doing that. And he gives him this metaphor. He says that the world is a white sweater. Most of the threads are white.

• 9:46Ryan Holiday?

  He says, but it is the red thread that runs through the garment that makes it beautiful. And he says, I am that red thread, right? This idea of if not you, then who? And if not now, then when? This is by standing up, by speaking out, by being the person we are meant to be thinking for ourselves, being our unique selves. This is courage. Sometimes it's life or death courage, and sometimes it's just the courage to be criticized, to look askance at. And then that leads us to the next virtue, which would be the virtue of discipline. And yeah, it's temperance, moderation in eating and drinking. It's the temperance of working out. And pushing yourself physically, whether it's running, or biking, or swimming, or lifting weights, or a cold plunge.

• 10:31Ryan Holiday?

  The idea Seneca says is that we treat the body rigorously so that it is not disobedient to the mind. It is in our physical practice that we cultivate the self-command necessary for those moments of courage. There's a famous passage in Marcus Aurelius's Meditations, the most powerful man in the world, and he's having a dialogue with himself about why he needs to get up out of bed early, even though it's warmer under the covers. And he says, "Is this what you were put here to do, to huddle under the covers and stay warm?" Obviously, it is not. But there's another form of discipline that the Stoics practice, and I think it's even more relevant in today's world, and it is the sort of mental and emotional discipline.

• 11:13Ryan Holiday?

  The greatest empire, the Stoics would say, is command of oneself. "No one is fit to rule," they said, "who is not first master of themselves." Washington, again, he loves this play about Cato, and his favorite quote is, as I said, a line from this play. He would talk about looking at everything in the calm light of mild philosophy. In fact, he recites this exact quote at the scene of the Newburgh conspiracy, where he talks the group of disgruntled Continental soldiers out of overthrowing the government, "to look at everything not in the light of passion and anger and grievance, but in calmness, in rationality, in justice."

• 11:56Ryan Holiday?

  And this was not his natural disposition, it should be worth saying. He is not literally made of marble, he is flesh and blood. Stoicism is not something you are, it's something you do, right? It's a practice. John Adams would say that Washington had a great self-command, but that required a great amount of work. And Gouverneur Morris would say that underneath...

• 12:22Ryan Holiday?

  Washington's calm demeanor was in fact incredible passions. And that his first and perhaps his greatest victory was not on the battlefield, but over these very passions. And that's what discipline is, that's what this virtue is. Command of oneself, looking at things in the calm light of mild philosophy, not the heat of the moment. It is victory over ourselves, it's victory over the phone, it's victory over the news cycle that wants to distract us and anger us and get us bogged down in the details. It is the practice of journaling, which Stoicism is. Again, Marcus Aurelius's Meditations, which survives to us, is the private thoughts of the most powerful man in the world. It's about creating calm within the storm,

• 13:05Ryan Holiday?

  grabbing firm hold of ourselves as everyone else is losing their mind. Virtue of justice follows from discipline. Now, contrary to some of the resurgent popularity of what we now call "Broicism" and AI, Stoicism is not about getting super jacked and shredded, although it sometimes looks that way. Stoicism is not a formula for becoming a better sociopath. It is a ethical philosophy, a profoundly ethical philosophy. All the virtues circle around this idea of justice. A middle Stoic named Hierocles would say that, "Sure, we're all self-interested, we're all self-motivated,

• 13:50Ryan Holiday?

  we all want to preserve ourselves, this is natural, but we are surrounded," he said, "by concentric circles of concern." Our family, extended family, our community, fellow citizens, people we've never met in distant countries, people who haven't been born yet, the environment. And he said, "The beauty of Stoic philosophy," he said, "a beautiful madness even," "is the ability to pull these outer rings inward." That our fates are all bound up with each other, that we are part of a collective whole. I am convinced that people are better off when the whole city is flourishing than when certain citizens prosper but the community has gone off course. When someone is doing well but his country is falling to pieces.

• 14:34Ryan Holiday?

  He goes to pieces along with it. This is not Bernie Sanders or AOC. This is Pericles in the 4th century B.C. articulating this very idea. And look, I think it is important that we push back on the excesses of wokeness and virtue signaling is indeed insufferable and annoying. But there is something much worse than either of these things. And that is the open embrace of vice and awfulness that seems to have overwhelmed our society. I get why, I get why young boys are interested in what Andrew Tate has to say. What I do not understand is his embrace by the right as some sort of countercultural figure.

• 15:19Ryan Holiday?

  This is a guy who at best is a misogynist, at best is a bigot, at best is a pornographer. At worst, he is a sex trafficker and a serial rapist. So the fact that he is anti-PC strikes me as not being that consequential. I think about the war on drugs. Our war, our drug policy in this country is of course insane and unfair and unjust. This hasn't changed the fact that Ross Ulbricht helped flood this country with fentanyl and cocaine and heroin facilitated money laundering and all sorts of awful things. Things way worse than any illegal immigrant or gang member currently being rounded up

• 16:04Ryan Holiday?

  by ICE would ever even dream of doing. And yet, we celebrate him at this event like some sort of digital technology evangelist. It is baffling to me. And again, that is the best case scenario. The worst case scenario, which is pretty persuasive when you read the transcripts, is that he ordered the contract killings of like a half a dozen people. And we celebrate this. It is deranged.

• 16:31Ryan Holiday?

  Del Bigtree is protected by the First Amendment. The First Amendment protects your right to think and say what you want. That is spectacular. That's what it is there for. It doesn't change the fact that it's wrong. You're free to be wrong, but it is wrong. And it is also profoundly antisocial. It is a violation in every way of what the Stoics talked about. It is a violation of every reading of Christianity as well, which, by the way, like all religious zealots, he believes he is the messenger of. I don't understand why we would celebrate someone

• 17:14Ryan Holiday?

  who is responsible for a measles outbreak across North America, in Texas, where I live, who is directly and indirectly responsible for the deaths of tens of thousands of people. The consequences of this message will resound through this country for decades. It is undermining our most essential invention, which is to say, "public health." We invented this. Marcus Aurelius lived through the Antonine Plague. If you want to live in a country that does not have public health, I would urge you to look at the death toll of the Antonine Plague. Why is an anti-vaccine activist giving a talk of the Capitol on January 6th?

• 17:57Ryan Holiday?

  It is because, as the founders would recognize, this is what demagogues do. This is what a catalene is. Someone who works up grievances and turns people on each other, preys on people who don't know better. So, my point is, look, this is what kind of person you decide to be. And in fact, if you believe in liberty, which I do, deeply believe in liberty, these things become all the more essential because it becomes an individual choice. Hyman Rickover, the founder of the Nuclear Navy, would say that when we say, "I'm not responsible," say, "It's not my fault," we are right because we are irresponsible when we declaim responsibility, the consequences of our actions.

• 18:42Ryan Holiday?

  It's about good character, right? This is the virtue of justice. Who you are, not what you're allowed to do, but what you choose to do. And this final virtue, then, the virtue of wisdom, not galaxy-brain wisdom, but real wisdom.

• 18:56Ryan Holiday?

  I have a podcast, I love podcasts, I listen to podcasts. This does not count as doing your research. We should all be listening to a lot less chatter. We should all be chattering a lot less. We should be putting our phones down. We should be doing the real work of learning and understanding. And by the way, that's the foundation of Stoicism. Zeno, a merchant of Tyrian purple, suffers a shipwreck. He washes up in Athens penniless. He hears a bookseller reading aloud the works of Socrates. It's his introduction to wisdom. And there, a prophecy that he received as a young man from the oracle of Delphi comes back to him. "You will begin to become wise when you have conversations with the dead." Reading is a way to have conversations with the dead,

• 19:38Ryan Holiday?

  to bring back into our life the ancient wisdom of the past. And this wisdom takes work, a lot of work. Seneca tells us a story about an ancient Roman who tries to acquire a bunch of slaves to whisper smart things in his ear so people can think he's smart. And then when a friend comes to him and says, "Oh, you are so smart. Have you thought of taking up wrestling?" The man says, "What do you mean? I'm old." And he says, "But your slaves are still young." And Seneca's point was that you cannot become wise without work. No one ever became wise by chance. It is the result of work. Here is Seneca advising Nero. "If you have a teenager, you might recognize this body language. You cannot learn that which you think you already know," Epictetus reminds us. And I get it. Look, nobody likes to feel stupid.

• 20:22Ryan Holiday?

  Complexity is uncomfortable. History is painful. Ideas can be scary, and the truth can hurt. And that's why we can't be sensitive little snowflakes if we want to become wise, if we want to learn. I was supposed to give a talk at the Naval Academy in April, and it was canceled an hour before I was supposed to go on because I was going to mention that I think it's a bad idea to ban books from college libraries as they had just done a few hundred yards away from where I'm speaking. These are people we expect to trust with nuclear submarines and fighter jets and aircraft carriers, but we think that they're too fragile to read. And indeed, we make them more fragile as a result. And you might well dislike some of the things that I have said today.

• 21:07Ryan Holiday?

  I understand that. I respect that you listened to me. My point is, as I wrap up here, that we live in tumultuous times. So much is outside of our control. I would argue we live in deranged times. And it doesn't matter where you sit on the political spectrum. I don't think that's a controversial statement. We live in deranged times. We live in times reminiscent of the Stoics. But the Stoics believe that this is actually the opportunity. This is what calls forth virtue from each and every one of us. We can't necessarily control what the government does. We can't even control who our leaders are necessarily. But we can control who we are. As Marx really said, "They can kill you and cut you with knives and shower you with curses." How does that cut you off from four virtues?

• 21:52Ryan Holiday?

  From the four virtues? From courage and discipline and justice and wisdom? It doesn't. In fact, it is the opportunity. Nothing can stop us from doing good. Nothing can stop us from doing the right thing. And in fact, in a world where the freedoms that you want become more commonplace, this virtue becomes all the more essential. Thank you all very much.

• 22:19Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.