Most people work hard to improve their lives, optimize routines, plan for every outcome, and try to stay in control. But what if the constant chase for control is exactly what's holding us back? In this episode, I'm joined by best-selling author Ryan Holiday to explore Stoicism, an ancient philosophy that's helped everyone from emperors to entrepreneurs focus on what really matters and perform at their best.

As Ryan puts it: We spend a good chunk of that focused on the parts of it that are not up to us, and then we wonder why we don't get the things that are up to us as good as they can be. We'll talk about how to use discipline without over-optimizing, why defining success for yourself can be a competitive advantage, and what it takes to stay grounded when the world feels chaotic.

If you're trying to improve how you think, work, parent, or lead, this episode is packed with ideas and tactics to help you level up. I'm Chris Hutchins. If you enjoy this episode and you want to keep upgrading your money, points, and life, click follow or subscribe. Ryan, how do you explain Stoicism to people who aren't familiar?

That's probably the question I get the most, or I get, "Oh, you're right about that." Usually I try to tell people Stoicism is not what you think that word means. When people hear the word Stoicism or hear the word Stoic, they think sort of unfeeling or invulnerable or repressed, which the Stoics in practice were not.

I think what I say is Stoicism is this idea that we don't control the world, but we control how we respond to the world, right? We don't control what happens, we control how we respond to what happens. And it's an ancient philosophy built around that pretty basic, but very difficult premise.

And for 2,500 or so years, it's been this secret weapon of very successful people, people who've been through a lot of adversity and difficulty. That's the basic idea. That's what I read about. And what makes it so hard? Well, it's easy to say you don't control what happens, you control how you respond to what happens.

And then stuff that you don't like happens and you want to focus on whose fault it is, or you want to complain about it, or it really throws you for a loop and you're upset and frustrated and disappointed and sad and scared. And all these emotional things that get in the way between you acknowledging it and then doing something about it.

I've said before, I think Stoicism is simple, but it's not easy. And that's, I think a good, pretty good rule of life. Also, most of the things that are important are pretty simple and straightforward, but putting them into practice, that's where the problems start. And I know a lot of the philosophies here are very old.

It's not something that you just created six months ago. Do you think it's as relevant or maybe even more relevant in today's world than when it was first written about? The interesting thing is that in the ancient world, philosophy was this kind of front and center thing. They were the musicians and the influencers and the celebrities of their time.

They're kind of the first people to stand out as these people who could tell you how you ought to live your life or could have the secrets to life figured out. So the one hand philosophy was much more popular in ancient Athens. Like you can't imagine people getting together to put a philosopher to death today because nobody gives a shit.

No philosopher would be seen as transgressive enough to sort of bring up on trumped up charges as they did with Socrates. Right. It's just sort of irrelevant. So on the one hand, it was more relevant in the ancient world. On the other hand, there are more Stoics alive today.

There are more Stoics that get the daily Stoic email that I send out every day than have probably ever existed before in human history. So why is that? Philosophy itself is not a mainstream pursuit. People think about it for academics and university professors and what have you. And yet there are more Stoics, more people thinking and talking about Stoicism than probably has ever existed.

And I do think that's because Stoicism as a philosophy built around dealing with what we don't control, being a philosophy around regulating your emotions in a dysregulated world, making sense of things that don't make sense. All of that remains as relevant as it ever was. And Stoicism has a 2400 year track record of people going, hey, this works.

Maybe you should check it out. So it's an interesting thing. On the one hand, when I went to my publisher and I was like, I want to write about an obscure school of ancient philosophy, that probably seems like a bad bet. On the other hand, if you're going to write something in this sort of self-help, self-improvement genre, it helps that you know that it works because it's been tried and tested over 20 plus centuries.

If you look at that journey, I think for anyone trying to stop controlling the things you can't control, trying to craft your perfect world is hard. Is our ego where that journey starts? Or how does someone kind of begin to think about being a Stoic? In 12 steps, right?

The fourth step is about accepting a higher power. And a lot of people struggle with that. They go, I don't believe in God. I don't believe in a higher power. They think that there's something fundamentally religious about it. And there is for a lot of people. But I think the genius of the fourth step has been making profoundly selfish and self-absorbed people accept that they are not God, that they are not the center of the universe.

And I think what Stoicism is trying to do when it says, look, there's some stuff that's up to you and there's some stuff that's not up to you. This is what Epictetus 2000 years ago said is basically the starting point of Stoic philosophy. What he's trying to get you to understand is that weighing them out, there's some stuff up to you, some stuff not up to you.

The stuff that's not up to you vastly outweighs the stuff that is up to you. What is up to you is a relatively small bucket of things. Other people is not up to you. The weather is not up to you. The economy is not up to you. The laws of the government, for the most part, not up to you.

The political situation is not up to you, whether there's a pandemic or a plague or a war, or you get murdered for the money in your wallet. These are all just timeless realities of the human experience that come upon us randomly. And there's not really anything we can do about them per se.

I think the first part of Stoic philosophy is just kind of putting these things in these two categories and then going, okay, yes, a lot of things are not up to me. But as we were saying, the stuff that is up to me, my own thoughts, my own actions, the story I'm telling myself, where I'm choosing to put my attention, the good that I'm going to do, all of that is actually plenty to keep you very, very, very busy.

I think maybe from an investing standpoint, right? You could spend a lot of time theorizing about how the market should be, why it's this way, historically what's happened, blah, blah, blah, blah, blah. But for the most part, what you need to be doing is like saving and investing and holding for the long term.

And if you do these three things, you're going to be pretty good. The problem is those three things, as simple as they are, seem to be pretty bedeviling to a lot of people and they don't actually do them. And perhaps part of the reason we focus on the things that are outside of our control is so we have an excuse for why we didn't do the things that are in our control.

I'm trying to think about an application of that, but is that a human desire to not do the hard things? Well, I'll give you an example. Like I'm writing a book, right? And I have one that comes out in a few weeks. Now, what the reviewers say about it is not in my control.

How many copies it sells is not in my control? Whether somebody sends me a mean email about it is not in my control? What part of it was in my control? The part where I showed up every day and wrote, the writing of it day to day, that was the main part of it that was up to me.

And then my definition of success is up to me. So is my definition of success that I got better as a writer? Is my definition of success that I put on the page? What I set out to write is my definition of success that I feel grateful and privileged that I get to do my dream as my job and that I had a good time doing it.

So there's that bucket of things that that I can focus on or I can spend the next three weeks miserably anticipating, anxiously awaiting the results of which I have some ability to influence, but don't control. Like I'm doing a podcast because I understand marketing is kind of in the gray area between those two things.

But I've had to do a lot of work on myself over the years and go, hey, whatever satisfaction you think you're going to get, hoping and praying that other people do things the way you want them to do. As far as your profession goes, you're not only unlikely to get it when you do get it, how does it actually make you feel?

Like I remember the first time I hit number one, I thought it was going to be, you know, the heavens parted and I heard it was going to be this amazing thing. And it didn't feel like fucking anything because no external thing feels like anything, which is what the Stoics sort of say over and over again.

As far as the application goes, it's where are you going to put your energy? You have a finite amount of energy and focus and brainpower and willpower. And the problem is we spend a good chunk of that focused on the parts of it that are not up to us.

And then we wonder why we don't get the things that are up to us as good as they can be. And then we also get very disappointed and frustrated that it didn't go our way. I've done it before where I objectively sold enough books to debut at number one on a bestseller list.

And I open up the paper and it's five. Nobody's going to explain to me why that was the case. That's the case because that's how lists work and because that's how the world works. And if nobody actually cares that you have the receipts, it's its own criteria. I am not an editor, the New York Times or the Wall Street Journal.

I don't get to decide. It's their list. And so a big chunk of Stoicism is deciding, hey, I'm not going to put my happiness or my sense of meaning or purpose or value on this thing that doesn't play by the quote unquote rules and is totally actually indifferent to your feelings entirely.

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And I know you know Sahil Bloom and one of my favorite things I saw him write once was he's like, I don't understand complaining. If you can't change it, like why are you talking about it? And if you can go fix it and don't complain about it. Yes. Yet it seems so easy and so commonplace for people to want to project their frustration on others and outcomes instead of thinking about it.

What makes it so hard? And you know, how do you cross the chasm to the point that you just kind of let it brush off? Well, look, I think culturally, obviously we encourage that. And then I think you think about the algorithm, you think about social media, they're never like, hey, keep your opinions to yourself.

The whole machine functions on you saying the first thought that pops into your head because the less filtered you are, the more raw and real it's going to feel, the more it's going to provoke other reactions and other people. And I think stoicism is really the idea of like, hey, Epictetus said like, look, you have the feelings, you have the opinions, you have the thought.

The stoics call these impressions, right? So you have an impression of something, right? That this thing happened and it sucks and it's bad that you were just insulted. You were just hurt that you just got screwed over. You just lost everything, right? You have an impression that person's a jerk.

They meant to hurt me, et cetera. You have this impression. And stoicism, he says, is the idea that you put every impression to the test. So you stop and you go, is this actually true? Like he talks about how in the ancient world, obviously when all the money was silver and copper and bronze coins, he was talking about how a skilled money changer could bang a coin on the table and tell from the sound of it, if it was pure or not, that they had a good sense of what was counterfeit and what was real.

And the stoics believe that that was what you're trying to cultivate in life. The ability to separate a sort of emotional in the moment or perhaps irrational impression from a true impression as to what was really valuable, important, meaningful, up to you, et cetera. So stoicism is this idea of like, look, my first instinct is, hey, it would be cool to be, I don't know, nominated for X, Y, or Z.

And then you go, doesn't Harvey Weinstein have a lot of those? Is that really so valuable? Or you go, aren't most of those awards the result of very expensive campaigns and they're effectively purchased? And then you go, and who are the people deciding these things? Do I respect them?

Does my favorite work, did it win these awards, right? And then you start to go, oh no, it's actually not what I thought it was. And it's not as important as my initial impression led me to believe. Therefore, I'm going to alter my goal or my definition of success here.

And I'm going to put it more towards something that is both reasonable and achievable by me. And this is something the stoics talk a lot about, the idea that if you only run races where winning is up to you, you'll win all the time. And that might seem like a cop-out, but again, am I trying to be the best-selling writer on the planet or am I trying to be the best writer that I am capable of being?

And the more I focus on the latter, not only the happier I am, but I think the better that I get. And also I try to go, hey, if you're really judging yourself on whether you're selling the best out of everyone, why did you choose ancient philosophy in the first place?

That seems like your first mistake, right? So a lot of what we do is we kind of choose these conflicting goals. And so again, the ability to kind of step back and go, what's actually in my control here? What's actually valuable to me? What's actually meaningful? Let me separate the kind of fact from the fiction and then proceed from there.

And is part of the reason why we see a lot of negativity just that it feels good in our society to feel like we have it better off than other people? Like I think back to ego because it's probably my first introduction to your writing and I'm thinking, gosh, this happened a couple of weeks ago.

I was racing go-karts, right? And I'm not a competitive go-kart racer at all, but we were the fifth group to go out and it started kind of raining. And all I could think in my head, like instinctively was like, well, there's no way I'm going to have the best track time on this go-kart race because it's raining and all the other people had dry.

And by the end, I was like, I got to a place where like, I just wanted to improve over the course and feel like I was doing better, but I couldn't help, but instinctively think, well, you know, it's the rain's fault. They didn't have the rain. Like, you know, I could be better than that.

And I didn't know how that plays into our own ego and wanting to be better and saying it's the rain's fault or someone else's fault or something outside of our control. I do think our focus on what the Stokes would call externals and our endless competition, our insatiability, our desire to be the best, to have the most, it makes complete sense from an evolutionary standpoint.

It makes sense why we're never satisfied. We'd still be wherever we started as a species if we didn't have this desire to, well, what's over there? And what if I do this? And what if I'm the number one guy? Or what if I have the coolest house? Or wouldn't it really impress other people if I did X, Y, or Z?

It makes sense why we have that. It's obviously a propulsive force. It's just also repulsive in the sense that it's not only ugly, but I think it pushes away from us the one thing we actually say we want, which is happiness. Like you didn't leave your house to go go-karts because you have to be the number one go-kart racer that day.

You left your house because you wanted to have fun. And then here you are in this experience and the frame you're looking at it with, its first sort of choice is actually taking you away from the thing that you would want. And again, this is all very common and very normal.

And I deal with it all the time. I'm not saying any of this stuff from a person who's never competitive, never driven, never complains. I do all those things all the time. What I'm saying is that the Stoics taught that there was a way out of that trap. It's not easy, but when you sort of do exactly what you said you're doing, which is you go, okay, what if there's a different way to think about this?

Is that actually better? And so this ability to kind of question your own thoughts and question your own default assumptions, or to just not do it the way that everyone else is doing it, that's their version of philosophy. Philosophy wasn't like debating these arcane questions or these preposterous hypotheticals.

It was putting yourself up for review and putting those impressions to the test. You've mentioned happiness a few times. Is the ultimate goal that per se we're optimizing for in the way we think and the way we react our own happiness? Is that it? It depends on your definition of happiness, right?

Are we talking about the sort of Western definition of happiness, which is like having a good time all the time, having everything you want, pleasure and ease? No, that's not what the Stoics are talking about. Would they have maybe co-signed with Aristotle's definition of happiness as human flourishing? I think yes.

To me, where the Stoics get really interesting is like, we're sort of talking about some first world stuff. Like I'm go-kart racing with my friends, but like my desire to compete is like causing me some low-grade anxiety or frustration. That's obviously a use case of Stoicism, but you know, the Stoics live through wars and disasters and plagues and political tyranny and technological disruption and personal loss, a health crisis, a bankruptcy, all the shit ends of the human experience.

And so what they were thinking is like, hey, is it possible to be happy or to flourish or to be okay even inside that? The list of the Stoics who were sent into exile or in prison is a very long one. And Stoicism was designed to be a philosophy that not just got you through that, but allowed you to perhaps even thrive within it, to have it be, you know, your greatest moment.

And so it is also, I wouldn't say primarily, but it is significantly a philosophy designed to help you with disaster. I mean, Zeno, the founder of Stoicism is an entrepreneur. He's traveling through the Mediterranean. He suffers this shipwreck. He loses everything. It's when he shows up in Athens penniless that he ends up coming to philosophy and he creates this school called Stoicism, which Stoicist means porch, the Stoa pochile in ancient Athens.

His point was that he didn't control that this thing happened, but he controlled what he took out of it. And he would joke that he made a great fortune when he suffered a shipwreck because the shipwreck is what drove him to philosophy. So sometimes the Stoics want us to understand that this thing that seems awful and shitty and unfair and that we would have never chosen at the time, just a few years down the road or a lifetime from now.

You might look back and go, everything good in my life is a result of that thing happening. That was the best thing that could have possibly happened to me in that moment. And so that Stoicism is the ability to kind of be philosophical in that sense to see the bigger picture.

When I think about the kind of disaster scenarios, you're talking about wars, health losses, those kinds of things. It's like, well, on one hand, many of them are outside of your control, but I have some friends in Israel. It's like, well, they could build more bunkers to go live in.

And with health, you can get tested all the time, nonstop, get an MRI every month and try to catch everything. So I feel like in today's world, it feels like these things maybe are in more in our control than maybe they actually are. How do you approach a world where it feels like there's a way you can control things and probably sends you down this anxious spiral of like, do I send my children to school with bulletproof vests and like, you know, all kinds of stuff.

Yeah. And look, the ancient world feels very foreign and different than ours. And yet in many ways, it's exactly the same, right? The health example is a great one, right? So when the Stoics say there's some things that are in your control, some things are not. Are they saying that you're like a Christian scientist who doesn't believe in medicine?

I don't think so. I mean, Mark Surrealist, we know who his doctor was. His doctor was a guy named Galen, who was the most famous mind of the ancient world, who was also a Stoic philosopher. And so when Mark Surrealist goes, you know, memento mori, remember we're all mortal.

Presumably his doctor was still trying to keep him alive, though. If he got sick, he took medicine, he exercised, he tried to eat well. They're still doing all the things that we would do today. We just, I think your point is well taken that there are things that were previously outside of our control that are more in our control, right?

Like the weather's a great example. We have the ability to predict and anticipate weather in a way that wasn't possible in the past, but still fundamentally like the hurricane doesn't give a shit what your plans were, right? And it'll wipe out your house all the same. Does that mean you shouldn't put up storm shutters and you shouldn't follow the laws that are designed to make that less likely to happen?

No, of course you should. I think like a Stoic would still wear a motorcycle helmet. And I live in Texas where riding a motorcycle without a helmet is not illegal, which seems insane to me. The point is just because a lot of things aren't in your control doesn't mean you give up on the things that are in your control.

But your point that it's very easy to spiral when you have trouble drawing the line is well taken. There's even a passage in meditations. Mark Surrealist is a parent and he lives in a time where infant mortality is like unimaginably brutal. He buries half of his children. He has 11 children and six of them die at various ages.

And yet he's trying to tell himself at one passage in meditations, your child is sick, but not that they might die from it. Like he's trying to go like, you can imagine someone who's been through that kind of tragedy. Every time one of his kids coughs, he could catastrophize and go into a complete doom loop.

And he's trying to remind himself like, hey, you got to stay present here. You know, you don't actually know and it's not in your control either way. So how do you kind of find this balance between being the protective parent who does everything that you can, So how do you feel like this?

How do you feel like this? You don't even know what you're going to be doing. You know, you don't even know what you're going to be doing. You don't know what you're going to be doing. You don't know what you're going to be doing. You don't know what you're going to be doing to be doing.

You don't know what you're going to be doing. You don't know what you're going to be doing. So how do you feel like this is not a reduction in the anxiety and worry? What am I doing here? These are the kinds of timeless battles that a stoic is facing 2,500 years ago, and they'll probably be facing 2,000 years in the future.

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Sure. Look, there's even a passage in meditation. This might seem dark for people, but Mark's really, he's riffing on Epictetus. He says, "As you tuck your child in at night, say to yourself, they will not make it until the morning." And so you go, "Wait, is this the stoicism that I've been warned about the unfeeling, disconnected, unattached, monkish philosophy?" Maybe.

My read is that he's saying, as I think any parent with young kids can remember, "Don't rush through bedtime, you idiot. You only get to do this so many times." What's in your control is that you have bedtime right now. And how you choose to show up for that, and how you choose to experience it, that's the part that's up to you.

And that there may be a time in the future, even in the best case scenario, where you miss this. In the best case scenario, how many bedtimes do you get with your kids? At some point, it ends. In the worst case scenario, it ends sooner than that. But at some point, you don't get to tuck them in anymore, and they tell you to shut the door on your way out.

And so I think what Marcus Aurelius is saying there is that's not right now. So live in it and experience it. And that's what these kind of philosophical practices are. So stoicism is a lot of things like that. Stoicism isn't necessarily like Buddhism or whatever, where it's like meditate in this manner for 40 minutes a day and you have enlightenment.

I know I'm being reductionist there, but stoicism is to me a series of kind of little thought exercises or insights like that, that you get from reading them and you draw on them in the situations in life that need them. Journaling would obviously be a big stoic practice. That's what Marcus Aurelius is doing in meditations.

But to me, it's they're more like these kind of just little ways of flipping how you would ordinarily think about things. And that's where the insights come from. It seems like if I were trying to come up with a practice that would make this easier, it's almost just pausing more before you react, before you think, before you decide, just kind of start to question everything as you're doing it.

It seems like I personally struggle with the kind of over optimization of everything. Like how could we dial this in? How could we have a better experience here? How could this cost less? And in some points pausing and saying, is continuing the pursuit of this even helpful? No, that's exactly right.

And look, there was a stoic named Athena Doris, who was the advisor to the emperor Octavian, who became Augustus. He warns Octavian. He says, look, the most important thing, he says, never react out of anger until you have counted all 24 letters of the alphabet. The ancient Latin alphabet only had 24 letters, but he's saying basically count all the letters of the alphabet in your head before you do something.

Just like today, we might go count to 10, or we might say sleep on it before you hit send or before you make that call. And so, yeah, to me, stoicism is in many ways that pause. It's the pause and then it's the reflection. It's not pause and then do the thing you were going to do later.

It's pause and then using that time to go, hey, what are my values here? What's the best response? What am I actually feeling? Why am I feeling this way? And look, I think a lot of what we're talking about here boils down to one of the key Stoic virtues.

So the Stoic virtues are courage, self-discipline, justice, and wisdom. So when the Stoics talk about virtue, that's what they mean. One or all of those four things. And self-discipline is sort of the modern reading of the virtue. But in the ancient world, the word was sofrosine or temperance. It was the idea of like, what is the right amount?

And a lot of times, the default that people are at is not the right amount. They're lacking in discipline. They're lacking in self-control. They're lacking in action, activity, whatever. But just as often, especially among successful people, it's the opposite. Like taking a rest day or turning down an opportunity is actually the real opportunity for self-discipline for some people.

And I think once you have that part of your mind that can see the chance to optimize, that can see that the chance to do it better, it becomes hard to turn that off, especially when it's a adaptive trait that for the most part brings you good results. Anything taken too far becomes a vice.

I mean, the famous example of this, are you familiar with Aristotle's concept of the golden mean? No. So Aristotle said actually that all virtues sit between two vices. So he said like courage is actually the midpoint, not the highest point. So courage is between cowardice on the one hand, but recklessness on the other.

So the opposite of courage is not cowardice. Courage is between having basically too much courage where you're deliberately ignoring and disregarding any and all dangers. And then over here where you're obsessively paralyzed by them. Courage is in the middle. And I think optimization itself needs to be optimized sometimes.

You're like, okay, I'm trying to save and save and save. And yet at some point my savings are costing me more than they are saving me because my time has a value or my relationships have value or my attention has a value. And so we have to optimize even that, just like we have to be disciplined about our discipline.

I think you've said discipline. It's not about letting things go, but finding kind of the right balance for yourself. How do you apply that in your own life? I think I'm more in line with what we're talking about, which is that usually my problem is an excess of discipline.

I don't mean that in the like my worst quality is I just work too hard. But if you're someone who loves what they do and is driven and then is rewarded for doing that thing, it becomes hard for you to like say no, right? It becomes hard for you to go, I have enough or I don't need to do that right now or I can save that till later.

So I sometimes struggle with that. Discipline to me is it's got a physical component. You know, I went for a long run this morning. It's got a emotional component. I was stuck in traffic and someone was driving poorly. Is that going to make me mad or I pull up the news and I'm like, what the fuck is happening?

I have to decide, hey, am I going to let this ruin my day? And then, you know, there's a sort of a spiritual component too of like, you know, I've got two young kids. I've got a business where you're just kind of getting emotionally and physically exhausted. And do you have the sort of determination and perseverance to just continue to keep going, to keep it all together?

So I think discipline is not just this one thing. It's about getting to that complete form of discipline. There's a lot of extremely disciplined people, extremely disciplined athletes whose emotional life is a mess or their personal life is a mess. They might be making millions and millions of dollars a year, but they spend millions and millions of dollars.

Or, you know, a great example with athletes, they're the most driven, disciplined person in the world. And then they get a bad call or somebody trash talks them and then they just absolutely lose it. And they don't have the ability to sort of be what the Stoics say is the most important thing, like in command of themselves.

Like they can't go, hey, I'm going to let that go. I'm not going to let that provoke me. I'm not going to stew on that. Elon Musk is a great example. This is someone who works harder than and longer hours on more complicated problems than just about anyone alive.

And then if he has a thought, he can't not tweet it. And so where would he be if he had a little discipline there? Probably just as successful, but maybe not so widely loathed. Is stillness important here? I think you've said that, like our inability to sit quietly is a massive problem in this world.

And is it just about learning how to pause and learning how to not be reactionary, even if you ultimately do react, but that pause before you do, is that stillness? And is that the thing we need to start cultivating more as a I don't know if it's practice is the right word?

I do think stillness is sort of the key that unlocks most elite performance, also most personal happiness and contentment and self-awareness. Like stillness is the sort of the state that you want to get to, to get most of the things you want. Nobody's at their best when they're doing 20 things at the same time.

And nobody's happy when they're doing 20 things at the same time. And it's about having that ability to slow down and to be disciplined. Now, I think sometimes people think stillness is like, Oh, I'm going to go rent a cabin in the woods and spend a month there. Then I'll have stillness.

For some people that might be the exact opposite of stillness because their mind is now actually racing more and more because now they've got no excuse. They got. So to me, stillness is something you're trying to cultivate inside a busy and noisy world with the sort of decisions you make.

I do think discipline is a big feature of it, for sure. When you mentioned the news nowadays, I have the same problem. It's like you see the news and you're like, there's just so many things to feel. Yes. Like without getting political, like it would be hard for almost anyone to not scroll through the news in America today and not have strong emotional feelings in one direction.

And that's not an accident. Right. And I think your point that everyone feels that way is worth pointing out. It's not like conservatives pull up the news and they love the state of the world and liberals are the miserable ones or vice versa. The entire business of both television news and online news and then social media driven news is to provoke high valence emotions.

And the highest valence emotion is anger and frustration. So very rarely are you going to come across information that is going to be like all good here. Put down your phone and enjoy your life. Just think about it from a content standpoint. Very rarely are you ever going to get the complete story because then you're done.

The whole point is like developing tonight. And then they give you the news because like they want you to check back in tomorrow and then the day after and the day after. So I think most people's information diet is setting them up to be much more unhappy and frustrated than they need to be.

Now, I'm not saying that the world is in a great place and that you should tune out from it. I'm just saying that real time information is not what most of us, especially if we're not running a hedge fund or running for public office, probably not what most of us should be consuming.

Most people can get most of what they need from history. The irony is like a magazine that you would get once a week is probably like the ideal format for your average person to find out about what's happening in the world. Like something that's well edited, well curated and giving you a pretty balanced point of view that, by the way, you're paying for as opposed to getting for free and not understanding that you get what you pay for.

So I think most people's information diet is designed for maximum misery slash engagement. Is there a place for other media that maybe has no productive value, right? Like watching TV, watching movies, playing video games. I feel like a criticism I've heard that is probably a misconception of stoicism. It's like you got to be perfect.

You got to do all these things right. And you can't have fun. You look like a guy that has fun. I try. Yeah, look, I was just in Athens. I watched a concert at Michael Kiwanoka, the British singer. He's singing in a theater that was built by Marcus Aurelius, his rhetoric teacher.

Like it's still giving concerts. For 2000 years, this venue has been there. Now look to us, like mostly what they would have absorbed there would have been plays. Now to us, ancient Greek literature is the highest of the highbrow. It's the oldest, most celebrated, if not indecipherable form of literature.

But to them, it was popular entertainment. That isn't to say it didn't have all sorts of moral themes. Of course it did. But it was designed to entertain the masses. So was Shakespeare. Like they also did bear baiting in the same theater that Shakespeare would put on his plays, right?

And you have the elites in their boxes. And in the pit, so to speak, you have the poorest of the most ordinary citizens. So these things seem fancy and important to us now, but they were pretty ordinary then. So I don't know, would Seneca have watched The Office? I think it's pretty funny.

Why wouldn't he have? So honestly, like my view is I try to read a lot of philosophy. I try to read a lot of history. I try to consume a lot of important stuff. And then understanding that television is not a particularly serious medium. That's where I sort of decompress and relax.

What I like about watching reruns of my favorite shows is I know that I'm not fooling myself, that I'm staying informed. Like I know that it's an escape and escape is totally fine. We talked a lot about discipline. We skipped over courage, which is where you started. Do the virtues have any kind of order or ranking or importance?

So I've been doing this series. I started a series on the cardinal virtues in 2019. I wrote courage first, then discipline, then justice. And then this last one is wisdom. That's just the order that I happened to go in because it made the most sense to me. I don't think there's an order necessarily.

Zeno himself said they're basically separate but inseparable, which is an interesting way of thinking about it. Courage is sure running into a burning building or running out onto the battlefield. But what is the cause of the battle that you're fighting? Now we get justice and we also get wisdom.

The ability to see through, I don't know, perhaps the propaganda or the logic of your times to get on the right side of it. So all the virtues are interrelated with each other. I don't necessarily think there's an order. The idea is that they're all informing and shaping each other.

And you mentioned courage in the context of battle and burning buildings. But how does it probably show up more frequently in people's daily lives? And how can they improve that or work on it? You're Jeff Bezos and you're making a killing as a consultant. And you have an idea to start a company that sells books over the internet.

And your most trusted mentor goes, "This seems like a bad idea. You shouldn't do it." Courage is the decision to walk away from a sure thing for a not sure thing. Courage is the decision to be vulnerable and real in a artistic work. You know, I live in Austin, right?

Keep Austin weird. Like it's the desire to be your weird self, you know, as opposed to what other people want you to be. So there's a physical component to courage, like discipline. And then there's a moral component we call sort of moral courage. But the desire to do something new or difficult or unpredictable.

I mean, this is what motivates an entrepreneur. And we would be in a much worse place if we didn't have courageous people who were willing to question the status quo or to take a leap into the unknown. This episode is brought to you by Built. Most people think that rent is just money out the door every month, but it doesn't have to be.

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They're all brands I love and use, so please consider supporting those who support us. You say take a leap into the unknown and I was talking to my wife this weekend, our daughter went to a birthday party at like a parkour gym. So she climbed on top of this thing and she really wanted to jump for this bar.

It was literally a leap forward, fall down, missed three or four times and kept going. And I don't particularly take any credit for that courage, but I think it feels like in today's world, especially with kids, like there's a lot more risk adversity. I remember running around in the woods, you know, doing nothing and who knows where I even am, which seems crazy as a parent today to be like, oh, I don't know where my children are.

How do you develop courage in younger people? You have kids in a world where it feels like everyone's wants to be safer, wants to protect them. Yeah. And that is the balance, right? What are the parts of it that are reasonable precautions to take? And then where are you going to give them the chance to let them struggle and fail and figure out who they are?

And most importantly, develop the capacity and the sense of self that allows them to think, hey, I can do hard things. I've taken risks before and it's worked out. The child and the parent is fundamentally at odds in this way. Their job is to keep you safe. And the kid's job is to live their own life.

And I remember when I dropped out of college, my parents freaked out and couldn't wrap their heads around it. And it was this huge conflict. And I obviously have come to understand that their main thing was not, is this going to lead to Ryan's fulfillment and contentment and happiness?

That's not what the job is. The job is to make sure that I didn't throw my life away before it had started, right? They were like worried I would end up under a bridge somewhere. And so understanding that there is a fundamental tension here is a big part of it.

And that their job is to sort of jockey for freedom. And your job is to worry about the dangers of every one of those freedoms, but that you can't protect them from everything and that you have to give them the opportunity to go out and do those things. Or inevitably, when they do find themselves in dangerous or unfamiliar or risky territory, you don't want that to be the first time they've ever dealt with that.

We're dealing with that with our kids now. Like, do we let them walk down the street to the store by themselves? And it's not a huge inconvenience for me to go with them. But if I escort them everywhere in life, where does that leave them? And that sort of tension is always there.

Yeah. And you've probably seen the documentaries about Japan where kids are doing this at like age four. Yeah. It's like there's a TV show about it, right? Yeah. Yeah. It's crazy. And I look at that. I'm like, oh, my gosh, like, could my daughter make it to the park?

There's a lot different things about American roads and safety and whatnot that make it even more daunting. But looking at other cultures and how they treat some of these things is kind of both inspiring and makes me question a lot of what I've done. Yes. Yes. I don't have a good answer because I struggle with it very much myself.

And then, you know, it's hard because I remember it hit me about six months ago. I was in, I was at the beach and I'm watching these parents let their kid play in the water next to a sign that is saying there's a rip current right there. And you're like, okay, great.

Obviously, I care about that kid. I'm like, this is insane. You shouldn't do this. But I also go, my kid lives in the world with these people, you know, and that stresses me out. Yeah, it's rough. Nothing challenges your stoicism quite like having this little person who you love more than yourself, who's quite frankly, stupid and bad at most things out in a dangerous world.

It's emotionally and physically exhausting. And we didn't talk much about justice. My instinct prior to a lot of learning about stoicism would say, well, and especially in a world that isn't just where things aren't fair. But I think you think of justice and the Stoics would more as an action than just a state.

Yes. It says something about our society that when we think justice, we think the legal system, that we think of justice as something we get and not as something that we give. So justice obviously does have to do with laws and politics and all of that. But first and foremost, it's like, how do you as a person go through the world?

What are the standards you hold yourself to? So probably a better translation would just be ethics. And what you realize, especially in America where the founders were very much informed by the Stoics, the foundation of a government built on liberty was the idea that it would be counterbalanced with strong personal ethics.

And just because you can do something doesn't mean you should. I think it's interesting. We've kind of lost this in some of our debates about the first amendment, just because someone should be allowed to say something doesn't mean that they should say it. And it doesn't mean that they don't suck for saying it.

The idea isn't that you should be thrown in jail for slurring people or spreading misinformation or generally being a jerk. But that doesn't mean that that should be celebrated either. The consequences should be social. And I don't mean cancel culture. I just mean we should condemn things that suck.

The Stoics would also argue, of course, that most of the punishment itself inflicted like you have to be that person. But look, we live in a world where you could run a company that chews its people up and spits them out. There's no law against that. But it's not only in your self-interest, but I think it's in your basket of responsibilities as a decent human being to treat people decently well.

I think Whole Foods is a great example of this, right? Like John Mackey is about as libertarian as you get. And yet with that freedom, he has chosen to run his company along a pretty firm set of values and ethics about what ingredients, what their pricing is, how the animals are treated, what its standards are, what it pays its employees, what it gives them access to, how success is shared.

If we're looking for a place of agreement, that's where we should talk about justice, not contentious political issues necessarily. And so you rounded off the Virtue series with wisdom. And the title "Wisdom Takes Work" kind of really pushed back because I've always thought of wisdom as this thing that's like, well, as you work, as you learn, you know, you mentioned children early on, they don't know what they're doing.

They don't know what's going on. They just have to kind of learn that over time. But I guess the Stoic virtue of wisdom is not something that just comes to you. You just experience life and then it shows up and now you can use it when you're older and be better.

Well, look, I do think growing up and just being a person, that is work, right? Because life is constantly kicking you around. The problem is the result is not always wisdom. Churchill had this line about one of his political opponents. He said on the occasion that he stumbled over the truth, he quickly picked himself up and carried on as if nothing had happened.

And so there's a lot of people that have had a lot of experiences and have not taken wisdom from that. At the same time, the idea that wisdom is only the result of experiences in life strikes me as insufficient also. Wisdom is mentorship, wisdom is reading, wisdom is travel, wisdom is trying things, wisdom is teachers, wisdom is school, wisdom is teaching.

We tend to think mentorship is this top down thing as if the person doing the mentoring isn't also learning from the process of teaching. So I wanted to present wisdom as I think it actually is, which is a method, a process, a set of sort of timeless strategies of which insight and understanding and truth and all the things that comprise wisdom is a byproduct.

You're not born with wisdom and no one can give it to you. It is hard won. So the question is like, what do you do to get it? Are there a few strategies to kind of help someone understand how they might gain more wisdom? Well, you know, it's funny.

I told you Zeno comes to Stoicism in the Athenian Agora. Well, actually as a young man, he'd visited Oracle of Delphi, the Temple of Apollo in Delphi, and he gets this prophecy. And the prophecy is you will learn to become wise when you start to have conversations with the dead.

And he doesn't know what this means until he suffers that shipwreck and he ends up in Athens and he stumbles upon a bookseller. And it's there that he realizes that books are conversations with the dead, that philosophy is a conversation with the dead. In the same way that Socrates was dead to him, he is dead to us.

And yet when you read Plato's dialogues, there he is leaping off the page. And so obviously reading is a big one. Occasionally you'll meet someone who's wise, who's never read a book, but that's the exception to the rule. Like books are codifications of thousands of years of wisdom. And most people are like, I'll figure it out myself, which is insane.

Yeah. It's funny. When I think we talked about investing earlier and it seems so obvious to say, oh, let's just look at what hundreds of years of people have done and what data shows. And some people are like, great. So I'm just going to do those things and I'm not really going to think about it.

Yeah. And in the rest of our lives, it's like, no, I can figure it out. And for some people, investing is that area where they're like, no, I can do better. I can do better. But it seems like there's just encyclopedias and not specifically an encyclopedia, but there's just a ton of information about what has worked, what hasn't worked, how have people done things that myself, I even wonder like, am I not paying as much attention to that as I could?

And the ego of like, oh no, I know better. I know there's thousands of years of experience or hundreds of years of experience of some of the most successful people in the world, or there are pages and pages of reports that the companies are legally obligated to put out and analysis and whatever.

And people are like, I don't know. I like the name of that one. I think it's going to go up. The arrogance of wanting to just kind of trust your gut when you haven't actually done the work to develop that gut. No, I'm not saying there's not a place for intuition.

I'm just saying like, have you actually earned the right to defer to your intuition? In some areas in our lives, we have in other areas, maybe not so much. The self-awareness to know the difference is pretty key too. When I quickly reflect on the entire conversation, I think about Stoicism becoming this kind of emotional shell that you could say, you know, let's not overreact to all the stuff happening in the world.

Are part of those feelings, those emotions about things that are outside of your control, part of the human experience? Yeah, I think so. And I try to urge people to look at the lives of the Stoics. They got married, they had kids, they made works of art, they traveled, they ran for public office, they told jokes, they had friends, they were full human beings.

It's just when you look on the page, you can kind of get this sense that this is some sort of monk who's only telling themselves not to do this and not to do that. And it's no, no, no. These are people who, because they are operating at the highest levels.

I mean, Marcus Julius is the emperor of Rome. It's really important that he talked to himself about not making emotional decisions because millions of people are going to be affected by those decisions. He's not writing in meditations, like, hey, just a reminder, like food tastes good and make sure you spend time with your kid.

Like, maybe he just didn't need a reminder of those things, but he did need a reminder of these things. And that's what survives to us in meditation. It's not that he didn't want to have emotions. It's that he didn't want his emotions to control his actions. That's right. Right.

He still probably felt a lot of things. He could be upset with injustice or sad about loss, but wouldn't act necessarily because of those in isolation. Well, and look, I think that's one of the problems that we have today, which is that people think that being upset about an injustice is itself some kind of accomplishment or important thing.

Now, look, I'd rather you be upset about the injustice than indifferent to the injustice. But what matters is, do you participate in the attempt to address said injustice? The idea is, is this feeling addressing what needs to be addressed? Or am I just feeling sorry for myself? Or am I just being outraged about something and then I'm leaving it there?

We confuse emoting about a problem with contributing to the solution of the problem. I think a lot of people probably heard you talk and I think it's helpful to know that you still struggle with these things. Of course. This isn't, you're not this perfect Stoic being that just has no issues in the world.

For people who want to try to apply this to their life, what's a good next step place to start? The Stoics are a group of writers and thinkers that you should be reading, not that you have read. They are people you're supposed to sort of dip in and dip out of over the course of your life.

Marx really is someone that should be on your bedside table. Or the reason I do the daily Stoic email every day is that it's like one little insight from Stoic philosophy every day. Philosophy was supposed to be this day-to-day thing to help us with the actual problems of life.

It wasn't something you got a degree in and then you're like a jujitsu black belt or something. No, what matters is are you going and training every day? That's what it's about. So I would urge people to start with one of the Stoics or daily Stoic and then understand that it's this ongoing thing.

It's not a thing that you did. The last book in the Virtue series, Wisdom Takes Work, is by the time this is out, will be out. Congratulations. Thank you. I'm sure people can find it anywhere they look for books. Yes. Where do you want to send people that want more?

Yeah, just go to dailystoic.com. We do a free daily email every day. There's a bunch of articles, there's a podcast, there's YouTube videos. I just try to take these ideas from the ancients and, you know, every day put out something that makes them applicable and practical to modern life.

That's what sort of gets me out of bed every day. Yeah, I appreciate you doing it. That's why I reached out to you and we've been trying to make this happen. I know. I'm glad we finally did it. Thank you so much for coming. Yeah. Thanks, man. Hopefully I'll run into you at an airport again one of these days.