Stoicism (ft. Ryan Holiday), Solved

0:00Welcome back, everybody, to the Solve Podcast. I am your host, Mark Manson, number one New York Times bestselling author. I'm here with my producer, lead researcher, intrepid failed acrobat, Drew Burney. Intellectual, failed intellectual acrobat. I don't even know what that means. And we are recording a very special episode this week. It's the first time that we've brought in a guest expert to tolerate this madness. I am here with my friend, Ryan Holiday, stoicism expert. I know you are a big endurance athlete. You do a lot of long-distance running.

0:39Have you ever done long distance podcasting? Well, you know, when, when I don't know about you, but like when I started doing books, they'd be like, can you come on this show and do a five minute interview? Or can you come to this 15 minute radio spot? And then it was like, no, no, there's this thing called podcasting. And then those were an hour. And then those became two hours. And now there's whatever this is. Well, now you're stuck. Yeah. It's just like, it just became bigger and bigger, bigger commitment. Yes, exactly. Um, You are known for many things, but I think the thing you're best known for... Yes. For those of you who are listening and can't see, I put a stack of books on the table that are threatening to collapse the table. Ryan is the author of, by my count...

1:2411 stoicism book nine stoicism book i don't even know do you know uh i don't i guess you could include the journal which has like 20 000 words in it too uh so but yeah those are those are all those are all the stoicism yeah we'll round up to uh what is that we'll round up to 10 okay um and your new one coming out wisdom takes work it's coming out i believe the week after this podcast is going live um Pleasure to have you, dude. Yeah, thanks. This is going to be fun. So as listeners know, as Ryan knows, our goal with these episodes is to be as comprehensive as possible. The whole shtick behind Solved is that if you listen to – if you actually get through a full episode of Solved, this is the last thing you will ever have to listen to on the topic. So for Ryan's sake, I hope that's not true.

2:16please go read his books. But if you don't want to read any books, then stick with us because we will get through as much stoicism as possible. Also, a quick reminder, we do have a PDF guide to this episode as we do with every episode. So if you want to look up our citations, check our work, and get a full summary of everything that we talk about in the show, go to solvepodcast.com slash stoicism. With that, shall we get into it? Okay, my plan here, and we'll see how this goes. Okay. Because you know a lot more ancient history than I do. But I'd like to just kind of set the scene for people. Yes. And like kind of set the context in which Stoicism emerges. I just want to talk through like what was the state of ancient Greece around this time? So Alexander the Great, who had just conquered most of the known world at the time, dies in 323 BC. Yeah.

3:19It leaves everything, the entire empire in disarray. It was completely unexpected. Generals are politicking, vying for control. Territories getting divvied up. All sorts of mayhem and political chaos is ensuing. What's interesting is that – Up until this point, Greece had always just been kind of a network of city-states. Everything was kind of self-contained. And suddenly they found themselves being controlled or passed off between these large foreign powers. And so there's suddenly this international influence that's happening in Greek society and culture that had never really – happened before. On top of that, you have merchants coming from the East, you have soldiers coming back from the East. So there's like all this exposure to all these philosophies and ideas that the ancient Greeks had never really been exposed to before. And I guess you could say like maybe there was a little bit of a crisis of Yeah.

4:38I think crisis is the right word. I was thinking about this because I was just in Greece. But you tend to think of it as this kind of chill place. You're like, OK, obviously it was a long time ago and they wore togas and they didn't have the technology we did. But this was a relatively stable and cool place. That's how they built these huge buildings. You don't think of it as chaos and dysfunction and danger, which it was. So Alexander the Great dies. Then all of his sort of successors are vying and conquering. And then there's these series of – they just call them like different – they're just these different tyrants, right? These kings from here, here. They're ruling these different city-states and then the city-states are going to war with each other. Like even Socrates, you think of Socrates like, oh, it must have been – They had the luxury of just talking about these ideas. But like Socrates lives through this great power conflict between Athens and Sparta that lasts for like 30 years, the Peloponnesian War. At one point when Athens loses this war, Athens is ruled by like 30 tyrants.

5:39It must have been similar to the feeling that we have now, which is like, okay, there are these institutions that we've had for a long time. Like that's the other thing is you think of ancient philosophy as being this like period. But in fact, ancient philosophy existed for hundreds of years. And so – Socrates is looking back to Heraclitus and Democritus and other philosophers as being like what Socrates is to us, right? Like they're looking back hundreds of years to these ideas that people have been thinking about just as Zeno is thinking back to Socrates and then the Roman Stoics are looking back to – so there's – it's – Similar to this feeling we have now where you have these ancient institutions that seemed like at one point they worked and now they've stopped working and there is this thing happening and we don't know what's going to happen next. And I think a lot of the practical philosophy comes out of like how do you figure out how to live in that?

6:38And I think Epicureanism and Stoicism are the two – are two very different reactions to the same crazy world. Like the Epicureans go, let's retreat to this garden. Let's just focus on our own stuff. And then the Stoics are a little bit more engaged and muscular. But they're both going like, the world is very scary. What do I cling to? Yeah. Let's start with the story of Zeno. Yeah. Yeah. He's a Phoenician merchant. Yes. Shipwrecks, shows up in Athens. Tell us – so like it's interesting that an outsider is the one who kind of comes in and – Yes. He's not an Athenian. Yeah. And also, yeah, you don't really understand that Greece is huge and spread out and include – I mean, I think Greece is like a thousand islands. And each one of those islands was its own country and its own culture – And they didn't always like each other and didn't always agree with each other. So these were foreigners. But Athens was kind of the New York City of that world or the London of that world where if you had talent or you wanted to be at the center of where stuff was happening, you would end up in Athens. But he's a Phoenician merchant. He's a dealer in what's known as Tyrian purple, which is the purple dye that they make from the blood of shellfish. Yeah.

7:56So also we don't think of it as this sort of global commerce empire, but it was. And each one of the city-states tended to specialize in one thing like olive oil or this or that. And so he suffers this shipwreck. I think it's fitting that stoicism comes out of a disaster. Yeah, right. So he loses everything. He washes up penniless in Athens and he's walking in the agora, which is like the meeting place or the marketplace. And he hears someone reading this story that we hear from Socrates. It's the choice of Hercules, which is about Hercules coming to the crossroads and choosing between basically the easy way or the hard way, virtue or vice.

8:32And Zeno hears this story and he goes, like, what is this? And he's told that this is philosophy. And he says, well, where can I find a philosopher like Socrates? And as it happens, a man named Crates, who's a cynic philosopher, is walking by. And the bookseller points at him and he says, you know, follow that man. Crates is known as the door opener. That's his nickname as a teacher, which I also think is fitting. That's what great teachers do. But he's introduced to philosophy there at sort of rock bottom. He rebuilds his life. His joke is that he makes a great fortune when he suffers a shipwreck. He sets up this school of philosophy on the Stoa Pokile, the painted porch, the which is the porch itself is not painted. It has a large painting of the Battle of Marathon above it. It's a public sort of meeting place. And again, we think of it as this peaceful – the Battle of Marathon is an existential battle against the Persians who are attempting to conquer and subjugate Greece. So anyways, he starts this school out of this disaster.

9:37And that school, you know, then we talk about the Roman Stoics, which I'm sure we will. But it's like 500 years between this moment and the Roman Stoics. So that's how – that's the arc we're talking about. Oh, and we will cover all 500. I do want to back up really quickly because one thing that I wasn't aware of or maybe I had forgotten – until I was researching for this show is that Zeno actually spent a lot of time kind of being that inherent of different schools within. So he was kind of this like seeking character. You know, he spent a bunch of time with the cynics and studied with them. And then I believe he went to the academy and studied with them. And it's kind of this classic story of – of everywhere he went, he wasn't quite satisfied. Like there was something missing. And so he would go to the next place and he was even ridiculed by some as like just a dabbler in all these different schools. But that feels very modern to me, which is like you take a little bit from here, you take a little bit from here, you take a little bit from here, and then every once in a while, something new comes from this combination.

10:42and I think that's sort of what Zeno was doing. But yeah, we tend to see the schools as being sort of very distinct and discreet, but I think there wasn't that many people. So I think they're all just kind of talking and sharing with each other, and they're not that far apart from each other either. So yeah, I think he's just kind of exploring and experimenting, and I also think it's interesting the idea of him being sort of a dad. He doesn't – it's like the only school that's not named after the person.

11:11Or one of the few that's not – it's not xenoism. It's called stoicism from the porch. But there's something to me revealing about the idea of it's like, no, no, we just sit here and we talk about stuff. And I think that's kind of – that's probably how we spent 10 or 15 years, just sort of exploring and learning and talking. And then this school comes out of it. What were some of those other – so you mentioned Epicureanism. You mentioned cynicism. What were some of those other schools that he dabbled in? Well, obviously the Plato's school is there. Aristotle's school is there. I think what he's doing is trying to – and this is I think what we do today, which is like you get all the basics. You go this smart person said this and this smart person said this and this smart person said this and then you kind of go – They're all kind of dancing around the same things, but like, here's what I think is missing. And I got to imagine coming out of a disaster where you lose everything is maybe something that Aristotle and Plato and Socrates are not.

12:14You know what I mean? They didn't relate to it, yeah. Yeah. There's something about – because that's so central to what Stoic philosophy is, that like life happens to us and then we figure out what we're going to do about it. Yeah. And that life can be cruel and unfair and things can get really bad really quickly. I wonder if that's kind of what he saw in the same way that like – you might go listen to a bunch of academic philosophers and go, this is all great if you are a tenured Ivy League professor, but what about this? And I think he brings that to him. My favorite thing about Zeno, and I was – again, I was just there, is – so at some point in his journeys through the Mediterranean, he stops at the Temple of Apollo at Delphi, which is where the Oracle is.

13:00And we're told that he asks sort of what is the secret to a good life. And the oracle may or may not be huffing these fumes from like this sort of vein deep in the earth gets high and then says this sort of mythical thing. And then you're supposed to figure out what it means. And the oracle tells him you will begin to become wise when you start to have conversations with the dead. And so he doesn't know what this means. And then he goes about his journey. And it's not until he ends up in Athens and he suffers that shipwreck and he hears someone reading Socrates who is at this point dead that he realizes that that's what reading is. Reading is talking to the dead. And so it does seem like Zeno's journey was a long one. And it was kind of all these different threads coming together. Yeah.

13:55It was interesting putting together this episode. One of the things I did is I made a list of all kind of the popular stoic practices. You know, negative visualization and memento mori and amor fati and like all these things that you've written about and we've heard in these different places. And I basically went and tried to look where those originated. And interestingly, most of them originated – prior to Stoicism. Like they were these threads that he pulled from all these different places. The exception is there is one Stoic philosopher who did originate a number of practices, which surprised me who the one it was. It was not Zeno who originated a lot of the practices that we associate with Stoicism, but most of them actually came from either Plato or the Cynics or Aristotle. The other thing that I uncovered is that And I don't know. I didn't go deep on this, so I don't know how true this was. But one of the things I read was that Plato and Aristotle were dead at this point. And so there was a little bit of a leadership vacuum that was going on. And what I read was that the academy, Plato's academy –

15:08at this point was kind of obsessed with metaphysical truth and like logical proofs of what the ideal, you know, what the form of the universe was and all this stuff. And it was like completely detached from any sort of practical usable advice that anybody would use. And then meanwhile, like the pair of pathetics, which is the Aristotelian school, they had kind of this obsession of like documenting and cataloging things. They were like the Google of ancient Greece. They wanted to catalog every species of fish and they wanted to document how every plant grew in every environment. Also completely detached from people's everyday concerns. So I – To your point about Epicureanism and Stoicism arising in this period, it's like you have all this strife in the background. And then it's like the schools that were kind of filling that void, I guess, for the previous centuries were a little bit checked out. Like they were nerding out. Was that elitism yet? Was there like a problem with elitism at the time? That's kind of what I had my reading of it anyway. I think you can kind of just end up living in your own head. And I think a school –

16:20just naturally kind of goes that way. It becomes obscure. It becomes specialized. And then it sort of becomes irrelevant. And there's something I do think that felt refreshing and urgent about stoicism when it's sort of being originated. And there's something – you're right. It's taking a lot from the other schools and kind of paring them down. It's like Aristotle has, what, like seven or eight virtues? Yeah. And then Zeno's like, oh, let's just four. Let's just put them in the subcathetic. So there's this kind of refining process that's happening, I think.

16:49It did feel like Zeno was a regular dude. He's coming to philosophy from business. So Zeno is actually where this concept of indifference or detachment comes from in Stoicism, which is really about just not trying to worry about things that don't matter. It's not necessarily being robotic. It's not about numbing your feelings. It's just simply being good at letting go of the things that don't actually matter. And with Zeno, this really originated with this idea of acting in accordance of one's nature. He saw the universe itself as a rational order, and so he saw each individual's actions and behavior as part of that rational order. And so his whole point was just, don't fuck it up.

17:40But the interesting thing about Zeno is that we actually don't have a lot of what he wrote. Like we don't really know exactly what he said. Basically nothing he wrote or said survives. We have like five quotes. Diogenes Laertes who wrote this biography of most of the philosophers – I forget when he's writing. But he's basically cataloging a list of everything we know about the major philosophers from this time – He gives us these sort of tantalizing lists of the names of the essays and books that people like Zeno wrote. Like Zeno wrote his own version of the Republic. Oh, wow. But like that's all that we know. And like this could change because right now like at Pompeii – I don't know if you know about this. But like at Pompeii, they have this – Yeah.

18:48Stuff from the later Greek and Roman Stoics who were quoting them in their works. So almost nothing we have directly from Zeno survives. How did the painted porch actually function? Like what did it look like? Like was he – barbecuing like way. Yeah. It's a long patio with, you know, Greek columns along it. And it was like a public meeting space. It's now, so apparently they just built shops over it and like they've only recently begun excavating it. And so you can see just a very small fraction of it, but there's another stoa in on the other side. There's like, they also put a train through it at some point. Yeah.

19:35But it's just – it's like your big classic Greek building or if you've been to like even DC, which is sort of neoclassical architecture. There's just kind of big, long hallways lined with columns. And so I think it's just a public space and they kind of just hung out there and talked. I don't even think – It wasn't even like the Lyceum or Plato's Academy where it was like a very formal academic setting that we might like recognize today. It's funny. David Mamet has talked about this a couple of times and he's like, they're just porch guys. And that's like an interesting read on it. I think it is. I think they're just sitting there talking in the way that you might sit and talk at a – general store or like at the cafeteria at a university. Like it's not this sort of formal academic setting where they're engaged in this sort of very specific research. It's just kind of talking about things. And so a lot of what we have from the Stoics even later is kind of like just snippets of conversation. Mm-hmm.

20:38But at some point, he starts to see students there or maybe he's walking like Aristotle did and he starts to teach. And I think these other spaces, you know, there's probably, you know, we're going to have a big class today. We're going to go over here. So I think it's just it's a little more informal than I think we would think about these things today. Well, and that becomes a little bit of an issue down the line, I believe. But we'll get to that in a minute.

21:03I want to talk about Zeno's framework itself. Yes. So he has this tripartite framework, the logic, the physics, and the ethics. Can you break down each of those? The physics part is nuts. Okay. Because it is very weird to be reading a 2,500-year-old text and, And then they're talking about atoms. And it's like, what the fuck is happening? Because you're like, I thought this was like very recent. Yes. And obviously they didn't know what an atom was. They couldn't see an atom. But they had some sense that life is made up of these tiny things that we can't see. So I think physics is basically their explanation for why we're here and how the world works today.

21:49And a good chunk of it is like obviously nonsense. And I'm pretty quick to just kind of toss all that aside. Even the logic side of things. I mean there was obviously a big emphasis educationally on like sort of how logic works. And you can see these kind of proofs and it kind of connects sometimes to the physics where they're like – If this is true, then this is true, then this is true. I find that stuff holds up the least well and is – even when it does hold up, you're like, what am I supposed to do with this information? That's never been what I've been super excited about when it comes to any of the ancient philosophies. But it is surreal. Like these people were – obviously geniuses in the sense that they had this whole sense of how the universe worked. And they were immensely curious. You talked about Aristotle too. You know, the scientific work that these guys were doing with the rudimentary tools that they had, it's pretty remarkable. I think sometimes people go like, well, I could have come up with this idea if I was alive 2,000 years ago or 2,500 years ago. And then you read some of the stuff –

23:00And you're like, oh, no, no, they were obviously also just all-around Renaissance geniuses because they were like deducing things about the universe that we weren't able to verify and prove until many centuries later. And then also – I think the psychological underpinnings of the ideas in the ethics and the philosophical component that they were just intuiting but had not actually like studied in any kind of experimental way is pretty mind-blowing to me.

23:33Towards the end of this podcast, we will get into the influence that stoicism has had on modern clinical psychology and therapy. And it's remarkable how much things like cognitive behavioral therapy owe to stoic practices that are over 2,000 years old. Yeah, so I mean I'd be curious what your read on it is like was it just – were they just seeing so much further than everyone else? Was the world so much – obviously we know it's not quieter but like were they just – more focused. It's remarkable that they were able to deduce these things, again, not from reams of prior research that they're just kind of going, I think this works because of this. And then they were pretty close. They're in the ballpark with these kind of guesses about how the world works or why animals do what they do or why the universe does this. There's something just kind of mind-blowing that someone could do this.

24:37I feel this way about a few schools of thought. Stoicism is one. Buddhism is another one that I'm just like, how the hell did a guy figure this out? Yes. Like 2,500 years ago. Just a lot of sitting and thinking. Sitting under a tree, right? You know, it is pretty remarkable. But I also realized too that there's a little bit of a perceptual bias going on because – there were probably hundreds, if not thousands of schools of thought that were invented throughout this time. Sure. And all of the ones that gave terrible advice or were not verifiable or were not replicable were lost to the annals of time. Selection bias there, yeah. Yeah, so there's a little bit of a survivorship bias aspect to this of which like, yeah, of course the true ones are probably gonna survive or the useful ones are probably gonna survive. But it is like, Even so, it is pretty incredible to think that it's just a bunch of smart dudes sitting on a porch. Yes. Hashing out like – you know, oh, your mind does this. My mind does that too. Like maybe we shouldn't do it that way anymore. You know, it turns out they're right. No, I do think there is this survivorship bias. And some even, like I said, we're pretty kind in what we edit out, you know, the nonsense that they believed. And some of the police were like sort of preposterous.

26:00But yeah, they were just able – they were able to think and work out a framework for the world that has held up remarkably well. And then it's been subsequently verified either scientifically or psychologically. Like you read these scientific studies and you're like – Oh, yeah, that's here in this epigram from this philosopher. Yeah. And they didn't need to pay 200 grad students to jump through these weird hoops to verify, but they just kind of intuit it. So there must have been just a lot of observation of human behavior. And I wonder if that kind of connects to the porch thing too.

26:40What blows my mind, honestly, is that so much of this happened in such a condensed area. Yes. It was centuries, but a relatively condensed period of time as well, right? It's the fact that so many of these thinkers and philosophers were contemporaries in many cases. Yes. Yes. that's the part that boggles my mind. Yeah, like Plato has, like one of my favorite anecdotes is Diogenes goes over to Plato's house and he thinks Plato is like sort of stuck up and annoying. And Diogenes, for people that know Diogenes is a cynic and he's kind of like, He's the rebellious transgressor. He's like the punk philosopher. He lives in a barrel. He rejects many of society's conventions. And so he starts like tracking mud into Plato's house and he's stomping on his carpets like to be like, you don't need this. And he says, I am stomping on Plato's vanity.

27:38And Plato goes, but how vain you are in acting like you're better than me. And so it's like they were not just friends but also kind of like frenemies. And just to survive 25 – just to have one person have ideas survive too long and then they're just like two people that had dinner together is fucking crazy. And so it was a very small world. Like Greece is both bigger than you think it is and the empire contained way more people and way more stuff happening than you think. And at the same time, it was much smaller than you think.

28:16Wasn't it also, though, too, I mean, doesn't the Stoic – these Stoic ideas get to something a little bit more fundamental at this point, too? Because you're saying they're sitting around and they're thinking – sitting under trees like the Buddhists and the Stoics and whatever. They're actually not, though. It's actually a very, very practical philosophy that comes out of this, Xeno and a shipwreck and adversity and all of this. I do think what the Stoics do, somewhat of a reaction against the cynics who were sort of like closer to the Buddhists or they were more monkish in their approach of like, hey, like dropout.

29:01man you know like there's something to like that with the cynics and i think zeno coming from like had a job ran a company seems to understand and and it gets very quickly to uh the world where where philosophy isn't this thing you do by itself as an end to itself but as part of the toolkit for whatever it is you're doing and so there is that i think zeno is close zeno being immediately descended from the cynics is still part of that kind of early Socratic cynic school where the philosopher is this kind of weird guy that you would go to for advice. And actually, Creti's wife, whose name is escaping, is also a famous cynic philosopher. So it's not just dudes. I think that's worth pointing out. But – Very quickly, the philosophers cease to be these kind of figures outside society and the Stoics pretty quickly become leaders of society who happen to subscribe to this school of thinking and living. I think that's why it has to be practical because they have day jobs and they need help with the job.

30:16I do want to comment very quickly before we move on. One of the things that I liked, I appreciated about Zeno's framework, because I've read quite a bit of Plato's work. I've read the Nicomachean ethics. And on this podcast, Aristotle generally comes up as being the guy who was right about everything. Pretty much, yeah. I really appreciated the elegance of the framework. Because reading Plato and Aristotle, there's a lot of brilliant ideas, but it doesn't...

30:44they never seem to have like kind of this cohesive worldview that fit and make sense with everything. Whereas, um, you know, this, this three part framework, it's kind of like the physics is the, the rational order, the predictive, predictable order of all existence. Logic is your faculty to understand that predictable order. And then virtue is your adherence to living out through the reason and logic that you're able to perceive. And like, that's just, um, I don't know. There's a part of me that just loves brevity and simplicity and elegance. In Lives of the Stokes, I have the metaphor they have, which is escaping me. But it's like there's the fence around the field and then there's like the crops in the field. It's like – The idea of them being these kind of interlocking ideas, I think, and then there's one where it's like ethics is the yolk, and then there's the egg, and then the shell. And so they did kind of think about them as these kind of interlocking, interdependent things. So you couldn't just be a philosopher. You also had to have some understanding of the scientific basis, and you had to have

31:52Obviously, like this sort of strong logical mind that could help you understand how things work. So yeah, it was kind of this framework, which again, because of what survives to us from the Stokes, we don't have the same – If you think about the famous Stoic works, and obviously we'll get into this later, but it's worth pointing out. We don't have, like, here's Zeno's explanation of the universe. We have a couple quotes. And then we have meditations, which is like a handful of aphorisms. And then we have Seneca's letters. Like, we just have these smattering of texts. Pieces, yeah. So we kind of only get people telling us how the Stoics thought about things as opposed to, like, the definitive Stoic text that goes, like, this is what we think. This is how it works.

32:38This is what we teach people who are interested in stoicism. None of that really survives to us. It's also worth noting too – probably should have done this at the top of the show but like – Everything we're talking about here is like early Stoicism. Yes. This is 200, 300 years BC. A lot of this is undocumented. A lot of what we know of Stoicism today, Seneca, Epictetus, Marcus Aurelius, like that's three, four, 500 years after this. Yes. The names you've heard of are coming centuries after these people. Yes. And those are much more well-documented.

33:15a lot of the ideas are more refined by then. They've been battle tested in many cases, literally. That's kind of like the later stoic period, which we will get to. So Clianthes was the successor to Zeno, correct? Well, so in the Wisdom book, I tell this story. Zeno has basically two promising students. He has one named Aristo and one named Clianthes. And Aristo is the smart one, the brilliant one, the flashy one, the one everyone thinks will inherit the school, but is also much more interested in all the different schools. Yeah.

33:52And he studies at the Lyceum. He says this. But he was sort of notoriously brash and egotistical. And he and Zeno clash many times. He is probably the recipient of Zeno's famous line about how we have two ears and one mouth for a reason. He is talking more than he is listening. And then Cleanthes, who again, sort of coming to philosophy from an interesting perspective, is a manual laborer. He waters the gardens of the wealthiest Athenians and then he's a boxer. And he comes to the school probably later in life. And I think Zeno sees something in him. His nickname was like – the ath of chithos or something like that but like the donkey of of the town he's from and he says yeah i am like an ass in that i am strong enough to carry the load and so he's he's it's kind of there's there's an interesting parallel here you know it's like sort of your classic tortoise in the hair thing and ultimately it's cleanthes who takes the school and um how official this transition process we don't really know yeah probably um Probably not so much, but it's not like a university endowment that you're taking over or something. But yeah, there's this kind of split in the school and I think it goes much more to the everyday, to the practical, to the accessible when it gets handed to clientes. Yeah.

35:26So it's with Clientes and his, I guess, kind of salt of the earth personality that you do see a lot of this celebration of voluntary hardship emerge in Stoicism, this ethos of doing hard things and not complaining about it. seems to kind of emerge from him. And Clientes, despite not really being an intellectual, he did do some writing, but he's definitely not the person that we associate with a lot of the principles or concepts of Stoicism today. He stood out to me as just an interesting, like in all my knowledge about philosophical history, I can't think of another I don't want to say anti-intellectual, but non-intellectual person, like obviously un-intellectual person who has taken the reins of a major philosophical school or movement. And so I just see it as like, it's such a fascinating decision on Zeno's part to pick the unassuming guy who's like literally carrying jugs of water every day and has like no vanity, no money to his name, He's your classic disciple, right? Zeno is the prophet and he is the apostle. He is like this smart guy, smarter than me, said X, Y, and Z. And I'm going to do a good job explaining and evangelizing and keeping that flame alive.

36:55And he does write some interesting things, but he is – yeah, he is not sort of slashing and cutting and breaking new ground as a philosopher, which is maybe exactly what it needed to remain a viable school. Well, after him, we get Chrysippus. Yeah. Who wrote over 700 books. Yes. Yeah. systematizing stoic doctrine. And this is really the first time that we get, or at least of everything that we still have, like clear documentation of, you know, what are the belief sets? What are, you know, what did, what are we believing? What are we following? You know, is this true? Is that true? Here's the argument for this side versus that side. Tell us a little bit about Chrysippus. Yeah.

37:46Yeah, he's the guy that comes in and cleans stuff up, right? The founder is sort of messy. He passes it to his sort of, you know, his chosen disciple. And then, you know, now in the third generation, it needs someone to go like, okay, is this a real thing or not? And what do we believe and what's important for us? And I think when people hear 700 books, again, that probably seems like impossible. And maybe there's an exaggeration in there. I assume this is mostly like essays and little treaties on things. But again, none of the 700 survive. So we don't really know.

38:23We just know that he's incredibly prolific. He's a fighter. Ironically, Cleanthes is actually the boxer, but he's the fighter. Chrysippus, though, also practical, is a runner. And he competes in this Olympic event called the Dialikos or something. I'm always terrible at the pronunciation. But I thought this was remarkable, too. The Greeks didn't run in a circle. They, they, the, the Olympic running track is like about 200 meters long and they would run back and forth, back and forth. So he did this, he competed in this race that is about, um, three miles of wind sprints. Oh, wow. So again, I think there's something like his, one of his famous analogies, he's like, life is like a race. You want to beat the other people, but you don't want to beat the other people by cheating. Hmm.

39:11And like you're like, oh, he's using a sports metaphor from a sport that he competed in, not a person who occasionally watches it on TV or something. So again, there's this kind of practicality to the Greeks too that it's not this sort of distinction between mind and body. Yeah, is an interesting kind of combative guy who seemed rather difficult to get along with. Insufferable I would say from what I read of it. Come constantly arguing. He was late. He would be an internet troll for sure. Yes. Yeah. And then famously dies of laughter on his front porch. I read that he was laughing about a joke of a donkey drinking his own urine.

39:56No. So as I understand it, and this is what Diogenes Leritas says, he's sitting on his front porch and a donkey breaks loose, wanders up to the front porch and begins eating figs out of the garden. And Chrysippus says, when the owner rushes up, he says, you should get that donkey some wine to wash down those figs. And then he begins laughing at his own joke so hard that he dies. And I've asked many comedians like on the Daily Soap packets over the years if they have any idea what this joke means. And no one can even begin to crack it. But I do think it's not – because there is some sense of the Stoics as being humorless. And I think when you read about Chrysippus' life, you go like, this guy must have been insufferable. And then you go, oh, but he obviously also had a sense of humor. Yeah. And so I think this idea of the Stoics as having no emotion – We can only take little anecdotes here or there, but to me that's always been kind of something that undermines that stereotype. And then I think it says something that it was his own joke that he was laughing at. He was on the list of unusual deaths on Wikipedia, which is quite an accomplishment. That is – yeah. You got to work hard to get up there. I'll also add that – I mean he really did seem to be –

41:11a bit of an intellectual giant. Yes. He essentially invented propositional logic. A lot of early stoicism involved a study of paradoxes, which is super interesting. I actually didn't realize that before this episode. I always associated that with like a Zen thing. But he very much like was very focused on creating a technical philosophical framework. And also he – offered one of the first solutions on the free will problem in terms of answering like the issue of determinism. Like if the whole universe is predetermined, how can you argue that you have free will or that your free will matters? And apparently he was one of the first people to attempt to answer this.

41:57And that is a theme for the Stoics throughout, right? Because they did believe that we're sort of not in control and that the kind of the universe is in control. And so does that mean that everything is predetermined? Does that mean that it doesn't matter what you do? And I – Maybe it comes all the way from Zeno, but there is this sort of metaphor in the Stoics about that we're like a dog tied to a cart. Did you find this when you were reading? So basically the Stoic view is that we're like a dog tied to a cart. And the cart's going where it's going. And the dog has two choices. The dog can trot cheerfully alongside or it can lay down and be dragged. Yeah.

42:35And so the idea there is – I think it comes back to this even, you know, Xeno reacting to the shipwreck, which is like it happened. Your life blew up. You lost everything. No amount of being angry about this, no amount of pointing out whose fault it was or how preventable, nothing changes that it happens. Really, all you control is your attitude about that thing, right? Are you going to cheerfully keep going or are you going to lay down and be like, this is it for me?

43:07Now, obviously, there is a certain amount of agency and choice in that he decides to become a philosopher. Like he rebuilds his life in another direction after. But I don't think we have that free will about – we certainly don't have free will over what has happened, right? Because it did happen. It's done. And I think that is kind of the perennial debate in Stoic philosophy is like how much agency do we actually have? And there is – I think a reasonable knock against the Stoics, that like there is acceptance very quickly becomes resignation. And do you want to live in a world where everyone is resigned? And then how do you explain the fact that most of the changes that happened came from people who chose not to resign themselves to the status quo? Yeah.

43:56I will add that this is a paradox and a philosophical issue that infects almost every school of philosophy, not just Stoicism. And we're actually going to return to this later, especially with the Roman Stoics, because it becomes actually extremely relevant in terms of a lot of their decisions that they chose to make. I feel like this would be a good place to go through the four virtues, talk through each of them briefly, just get an understanding of like what are the kind of core recommendations of Stoic philosophy. And then from there, we'll move into kind of the later Stoic age. So the four virtues, courage, temperance, justice, and wisdom. Which one do you want to start with?

44:46This has been my life for the last six years as I've been working on this series on the virtues. And – oh, and then you got the – Yeah, we got it. So I should add that you – yeah, you have written a full book on all four of these virtues with the fourth and final one coming out next week. Yes. Wisdom takes work. So yeah, you're probably – Well, but like when you're like, which one do you want to start with? It's like, as I'm writing this series, which one do you start with? Right. And which one do you end with? Yeah. And then Zeno, who lays these four virtues down, you know, points out that the virtues are independent yet inseparable from each other.

45:28which I think is a really interesting way of thinking about it. So the challenge on the series and then the challenge on even defining the virtues is like, where does one begin and end and where does the other begin and end? Because, you know, courage, well, obviously you have to bring discipline to the courage. And then what is the courage in pursuit of? And then how do you know what to be courageous about? Yeah. So all of them are related. But I think courage is the simplest, not simplest, because it is very complex, but I'll say it's the one that they start with. Like when everyone lists the virtues, courage tends to be the one that they start with. And then I think it's also worth pointing out, these are also known as the cardinal virtues in Christianity, not because cardinal has any religious context, but it just means pivotal, or it's, cardos means hinge.

46:26Like C.S. Lewis writes an incredible essay on the cardinal virtues and Aquinas has written about the cardinal virtues. You've probably seen it in a Catholic church if you've ever been to Europe or something. It is – it's this sort of core framework for understanding the universe and what is obligated of a person. And then obviously underneath each of these virtues is a number of sub-virtues. So maybe you can start with courage. Yeah. How would you describe the cardinal virtue of courage? Like how is it different than what we think of as just kind of everyday courage? Well, when we say there's sub-virtues, right, I think we all understand there's moral courage and physical courage. So physical courage is running into a burning building. It's exploring, you know, distant land. It's running onto the battlefield. And then moral courage is, you know, speaking truth to power. And yet – Why is – does it require courage? It's because sure, saying something unpopular is difficult because you don't want to be looked at. But if you said something unpopular to a tyrant in ancient Rome or ancient Greece, you would – you were also risking your life. So they're all – it's very difficult to say where one begins and ends. But courage was the decision to be yourself, to think for yourself.

47:54to act alone if necessary. Many of the Stoics serve and fight in various wars. And also I would think you would just say like just being alive in the ancient world required a certain amount of courage. This is eventually a more dangerous place, right? But to me courage is, like if you're deducing it, it's like it's putting your ass on the line, right? Like what are you willing to put on the line? And there is almost certainly no good or honorable life in which you don't do that. Yeah. I guess the alternative to courage, I mean, typically we would think of it as cowardice. But from a more philosophical point of view, it's actually just kind of a lack of living in general, right? Yeah. Like you're just – Complacency to it, yeah. Yeah. Like you – the alternative is nothing. It's indecision. It's – Well, the interesting thing about how interrelated the virtues are is Aristotle uses – when he's talking about the virtue of temperance, uses courage as the metaphor. So obviously you're familiar with the golden mean but he's like, look, the opposite of courage is not cowardice. The opposite of courage is recklessness. Yes. And so the virtue is in the middle, right? There's too much courage, not enough courage.

49:16The virtue is in the middle. But yeah, the idea of – like there's a famous story about a Roman stoic named Agrippinus who lives in the time of Nero. And he's just – he thinks Nero is a clown. He thinks he's illegitimate. He doesn't want anything to do with him. He doesn't want anything to do with him. And so he just, he's like, I'm not going to kiss the ring, right? And he doesn't. And so someone comes up to him and says, you know, hey, you know, why don't you just kind of go along with these things? Like, what are you doing? And he says, look, that's fine for everyone else. But he's like, I prefer to be the red thread in the garment that makes the garment beautiful.

49:52He was just making, I think, a very stoic, but I think we can trace this back to the cynic school of like to be independent and to be yourself. Like the courage to just be you instead of being like everyone else. I think we see this in most of the great stoics is that they weren't followers. They were just independent people in a world that didn't always appreciate that. So courage is all those things. There's an interesting crossover as well. You know, there's kind of this idea of voluntary hardship, like intentionally putting yourself in difficult situations. And it's almost like that's like a training ground for courage, right? Like it's if you can do difficult, small transgressions in your day-to-day life – then you will be prepared both mentally and physically to do it when it really matters. One of the stories we have about Zeno when he's studying under Kratis is that he was supposedly kind of socially awkward and very self-conscious. And so one of the tasks that Kratis gives him is he tells him to carry this pot of lentils through the agora.

51:03which he is, and then he's doing this thing. He doesn't know why his teachers make him do it. And then all of a sudden, Kratis jumps out from behind a building and he smacks him with his staff and he spills the lentils all over himself. And Zeno, as any sort of self-conscious or embarrassed person would be, is kind of mortified. And he says, I need you to understand that nothing bad has happened to you. Like, this isn't anything you have to think about or take seriously. So there is this kind of active training in the indifference process.

51:32Yeah. is obviously a key philosophical value and virtue going back at least to Socrates. And I don't think it's something you're necessarily born with. Or if you are born with it, then it's not a virtue for you, right? It's a thing you have to train and develop. Where's the line though with recklessness? You talked about the golden mean there. Where's that line? Well, the line is probably Diogenes who's like an antisocial wacko, you know? Like he's masturbating in public and, you know, he lives in a barrel and doesn't have a job. Like even – you know, maybe even the line is Socrates, right? Like Socrates is so obnoxious that they kill him.

52:31And someone with a slightly more social acuity could have probably escaped that death sentence. Yeah. I don't know about you, but like I didn't become a writer because I wanted to like be in front of a camera a lot or give talks to people. That's like the opposite of why you become a writer. Totally. And then you realize, oh, first off, it could be lucrative if you do these things. But second, like if you care about your message, you have to figure this thing out.

52:55And so courage isn't always, you know, charging a machine gun nest. Yeah. It's just can you do a thing that is uncomfortable and scary to you? Because most of the things you want in life are on the other side of those reservations that you have. Yeah, absolutely. Yeah, let's move on to temperance. A very attractive word in the English language for sure. It's funny. Yeah. You renamed it discipline in your book or to the title of your book. Yeah. When I hear temperance, I just hear like stop drinking. Yeah. The temperance movement. It is interesting internationally. It doesn't have the same context. Interesting. Because it just – it didn't work. It didn't happen in other countries. Yeah. But yeah. And then it's funny. I call it discipline. But we're really talking about self-discipline. Mm-hmm.

53:46It's a big bucket virtue, right? It's self-control, self-command. It is restraint. It's moderation. It's the ability to push yourself, the ability to do uncomfortable things. It's the kind of willpower that you bring to the other virtues. Do you see a golden mean aspect here as well? Because it's especially this day and age, right? Like discipline, there's kind of two meanings of discipline. One is just like get off the couch and fucking do something. But then there's also like the hardcore hustle culture grind set, a grind mentality of, you know, you should be working 12 hours. You should be hitting the gym at five in the morning. You should be, you know, doing.

54:31taking 50 grams of creatine every day, you know, like whatever the new thing on Twitter is these days. Do you see that as a golden meme thing? Totally. Yeah. I think it was Confucius. You know, he tells this one student he needs to hurry up and do the thing he needs to do. And then he tells the student's brother that he needs to slow down and take his time. And then a third student says, but these contradict each other. And he says, yeah, well, he needs to speed up and he needs to slow down.

54:57And I think some people need the discipline period. And then other people very clearly need more of the restraint. And I think we're all on that spectrum in the sense that in some areas we need more discipline and in other areas we need more restraint. Yeah. So Epictetus, somebody – one of the ancients sums up all of Epictetus' teachings in two words. He says persist and resist. And I think that weirdly captures the tension in the idea of discipline. Like there's some things you need to just do and do and do and then there's other things you need to stop doing and stop doing and stop doing. Like for me, discipline was the easiest of the books to write because I think it's one of the virtues I'm better at.

55:49But you're one of the most productive people I know. But when I think about where I need to be more disciplined, it's usually in the areas of restraint or pausing or recovering or slowing down. And yeah, so it's like if you're a professional athlete, discipline is probably not like how do you squeeze more workouts in. It's like how do you slow down and pace yourself and work more sustainably. And then, yeah, if you're sitting on your couch, it's probably you've got to get off the couch and do your thing.

56:19There's a life balance aspect to it as well, right? Like it's – you can be extremely optimized, say, in your professional life. But if you're ignoring your wife and never seeing your parents and – Totally. You know, ditching all your friends, then that's intemperance in a certain capacity. Totally. Yeah. And it's just a more socially accepted or adaptive form of ill-discipline, but it doesn't mean that it's not. Yeah. Like the image on the front of Discipline is Destiny, which was a metaphor they used, is a chariot racer. And it's this idea of like, look, sometimes you're prodding the horses to go faster, but a lot of the times you're reining them in. And especially when you're going around a sharp turn or – You're navigating some sort of narrow path, right? It's about knowing how to control and command. And I do think it's also worth pointing out just like in courage with discipline, there's physical discipline and sort of mental or spiritual discipline, which I ended up spending a lot more time thinking about and I think is weirdly – more relevant today than ever and not talked about enough. Like we live in a world where often people who are very temperate or very disciplined professionally are just like all over the place with like social media or their emotions. And so just the idea of like,

57:54I have opinions and I don't express them, you know, or like, like I'm not going to hit send on this email until tomorrow. And I'm going to, I'm going to think about what I have to say, or I'm going to come back to this later. Or, you know what, this is enough for today. Those all take a certain amount of self-command that I think we don't celebrate enough in society. I would argue too, in like the, you know, the 21st century, yeah. the importance of physical discipline, I mean, physically speaking, life's pretty easy these days. Like it's pretty low stakes. You know, you're not being chased by a lion and there's no, people aren't gonna bayonet you. I would say the mental discipline, there are a lot, the stakes are probably higher than they've ever been before because everything lives permanently online, because, you know, one awful text message.

58:47We'll sit on that person's phone forever because things can be shared so easily and come back to bite you so easily. Like it does seem like – and because of how many – how much addictive stimulation we're exposed to on a daily basis. Like it makes sense to me that mental discipline, the stakes are probably higher than they've ever been. There's a really good clip where Tina Fey was on Bowen Yang's podcast. And this is right after he had like, he had been talking shit on the podcast about, I don't know, Jennifer Lopez or something or someone. And then she was like coming on SNL. And, and so it was like this whole controversy. And she, Tina Fey came on the podcast and she was like, you're too famous to be saying your real opinions off, you know, like off the cut. She's like, what are you doing? Like, you can't say this movie sucks. Yeah. You might want to work with that director three movies from now. And you are not think she's, she's not saying like, don't be yourself. She's just saying like, there's more at stake here and more that needs to be considered than your knee-jerk reaction to a thing that you have not studied fully, right? And that's something that you find out as you become more successful or more connected is you go, hey, like, as a regular person, I can just, like...

59:59Do whatever. But now these things are more interconnected than I would have thought. And there's more going on than I knew about. And you have to take the time and have the restraint to be able to go like, is this really my opinion? Do I really feel strongly about this? Is this – actually constructive or helpful in any way? How does it help me with what I'm trying to do? And that to me is like, as the Stoics cease to be these fringe figures and start to become mayors and advisors and then ultimately senators and generals and emperors, The game is changing and they don't get to be Diogenes stomping on Plato's carpets, right? Their words mean too much and the effect is too great to be that person.

1:00:48One of the things too with discipline, were you talking about the balance you're striking between persist, resist? One of the things that's helped me kind of navigate that though is thinking about the definition of discipline as correction, right? So if you discipline a child, you're correcting a child. Or self-discipline is you're correcting yourself. So it's an active process. No, no, that's I like that a lot. And and I think that's what sometimes people miss when they talk about discipline is they think about discipline in the sense of like a Marine Corps general screaming in your face. That's discipline. Self-discipline is when no one is watching and when you can do whatever you want.

1:01:25What do you do? And so when you think about the Stoics, like we'll talk about them later, but you think about a Marcus Aurelius, no one can tell Marcus Aurelius what to do. He is the most powerful person in the world. So this is where the virtue of self-discipline becomes so important. You can, but you shouldn't. And I would argue in today's world this is something we very much missed in a lot of our political discussions. It's a lot about like whether something is legal or not or allowed or not or what the Constitution says. It's like, yes, the First Amendment allows you to say more or less whatever you want. But there's a whole bunch of things you shouldn't say or you're a shitty person, right?

1:02:04Right? And again, should someone who does say them go to jail? No, that's a very – that is a legal and sort of social contract discussion. But should you be the kind of person that says mean things at people for the – sake of hurting their feelings. No, right? This is where restraint comes in. And so self-discipline is something you apply to yourself. And then the tension there is it is very hard as a self-disciplined person to accept and come to terms with the fact that other people have different definitions of self-discipline and that it's not your place, one, to enforce it on them, and then also do you have the self-command to be like, I'm not even going to judge them for doing it differently? This is, I think, a thing that – I mean certainly I struggle with it, but I think all disciplined people struggle with it. It's interesting. So we just recorded our episode on resilience. Yeah.

1:03:04last week. And at the end of all of our episodes, we do a section of trade-offs of like, okay, if you develop a lot of resilience in your life, what are actually like the hidden costs of that? What are the downsides of that? And we listed that as one of them, which is that the stronger and more resilient you become as a person, you can say this about discipline too, the more disciplined you are as a person, the more you're able to manage your thoughts and feelings and behaviors, the less empathetic you're going to be for people who don't or can't. And, um, and I've definitely run into that quite a bit in my own life. And it's, it's like, it is a hard trap to not fall into.

1:03:45You tend to see this in like the first woman to do X or the first man to do – like when someone's like a minority and then they break through, you would think they would be very sympathetic to the people who didn't break through. But actually they tend to more identify with the group that was just trying to exclude them and make their life harder. They have a – it's called the adversity paradox or something like that where you tend to go, if I did it, everyone can do it. Yes. Yes.

1:04:14And to some extent, that's inspiring and true. And that's what people who break glass ceilings and barriers do. But then also, it's hard for them to go like, well, maybe I broke through for flukish reasons, or maybe it shouldn't, it didn't need to be this hard and all this. And yeah, you can tend to be very unsympathetic to other people. And to me, that's That's a failure of both discipline but then it leads us to the next virtue which is justice. Yes. Again, people think is the legal system but no, it's your ability to put yourself in someone else's shoes and go, no, they're just having a hard time and I'm injudging them only making that harder. Yeah. Like what are the stoic precepts of justice? And I – I ask this totally understanding that any sort of ethical philosophical conversation is messy as fuck and gets gets very convoluted quickly. But I'm curious if you were to like summarize what is the stoic position on justice? How would you describe it?

1:05:19Well, I do think it's – justice is a tricky – again, how we render these words can sort of preclude people from being interested in them. Like so it was very obvious to me that justice should not be in the title of the book on the virtue of justice because when people hear it, they think law. They think the legal system. They think politics. They think social justice warriors, which again, it says something about our society that that's like a bad thing to be – Yeah, when you can't put justice on the cover of your book. You can say it's an indictment of our society. The virtue of justice is really the ethics that we were talking about earlier. At the core of the sort of stoic big three is this idea of ethics. So what are the ethics? Look, it would be nice if some Ten Commandments from Zeno had been passed down to us.

1:06:07But they didn't. And again, we see the Stoics over almost a 500-year period. Even the norms of what's OK and not OK is changing over the course of this. So it's hard to be like, well, the Stoics say this is really important. You can see this from their actions. And they also own slaves, right? Once we get into the Roman period, this is going to get very messy. It's complicated. But there was this middle Stoic named Hierocles where… And he talked about this idea of the concentric circles. So he said, at the beginning is us. We're born as a baby. All we care about is surviving and all we care about is ourselves. And then we attach to mom and dad and we care a lot about them. Then we have siblings. Then we have an extended family. And these are rings, right? Then we have our neighbors. We have the citizens of our city-state. Then maybe we belong to an empire. Then it's – All of humanity. And then you could probably add some rings that they didn't explicitly talk about, but I think are obviously logical extensions here, which is like animals. And then you could put like people you've never met. You could put like people who've never been born, right? But the idea, Hierocles said, was that philosophically, how do you pull these outer rings inward? And he said there's a beautiful madness in doing this. Mm-hmm.

1:07:26And I think this is so important because it is very clearly a counterbalance to those first two Stoic virtues. And so much of the Stoic thinking, which is primarily about the individual orienting himself in opposition to a world that is indifferent to them. So to then have this other virtue that's saying, well, like other people may not give a shit about you, but you have to give a shit about other people, I think was kind of radically transgressive and really, really interesting.

1:07:55So I think fundamentally there is this idea that we were in stoicism, that we were made for other people, that we were made to treat them well, that we were made to – and that we degrade and harm ourselves when we act with dishonesty, when we act with cruelty, when we write people off. And so I do think there is – It's something pretty similar to the sort of Christian ethic in the love thy neighbor, be of service, be a person of honor and integrity. That to me is like what we would categorize under this virtue of justice. We're going to come back to justice a lot when we talk about the Romans. Yes.

1:08:39They've got some interesting ideas about it. Well, and there's a lot of interesting decisions that are made as well in consequences of decisions. All right. Let's finish up with Wisdom, which is the new book. It's coming out next week. It's funny because I didn't say anything because I would have just interrupted you like six times. But like as you were describing the context and the situations in which the other virtues are applicable or make sense – almost all of your explanations, I was like, oh yeah, that's wisdom. Yes. Yes. Totally. Well, the line I've been saying is that no one is born with wisdom, but all the virtues are born from it. So like wisdom is the work to understand history, to understand human nature, to understand the world, to understand other people, right? It's this sort of Getting all this shit in your brain and then that's how you know what to be courageous about. That's how you know what the right amount of something is. That's how you know what the right cause is. The thing about wisdom is there's a lot of definitions. It's many things. Again, I think we can say we know for certain it's not something you get for free. Right? Like you earn it. But it's really this idea of discernment. Like what is what?

1:09:57Like do you know how things work, why they work, what works? You know, it's this kind of – and this is why I think it's so often associated with old age is that it's in large part something you accumulate slowly over time, not just from experiences but – From exposure both in learning and in fact and then the interplay between these things. And that is a slow and steady accumulative process. You can be born smarter than other people and you can get off to a pretty good start. But I think wisdom is something that's much more of a slow burn. But it informs all the other virtues. Yeah. Yeah.

1:10:42I also feel like wisdom kind of unlocks or properly explains the stoic concept of indifference. Because the simplistic view of indifference is being robotic, is just being not giving a fuck about anything, right? I was waiting for it. I was waiting for it. We had to go there. But it's – Like the example with the lentils in Zeno, it's, you know, wisdom is that ability to differentiate between do I control this or do I not control it? Does this matter? Does it not matter? Is it worth getting upset about? Is it worth investing myself into? Or is it not? And I really think that stoic practice of indifference is that ability to understand where you're, attention and effort where that boundary should be, right? Of like understanding like, oh, okay, that is something that I have absolutely no control over and doesn't affect me. So I'm just not going to worry about it.

1:11:44Yeah, one of Mark Sreos' lines, he says, to be indifferent to the things that make no difference. And you're like, oh, that's the key. It's not indifference generally or universally. That's to totally miss the point. But you're being indifferent to the things that are outside of your control or that don't matter. Yeah. And that's where wisdom comes in to really know that and— the things you cared about when you were younger, some of them you continue to care about because they're really, really important. And then other things you're like, why did I make such a big deal about that? And it's both like, how do you know the difference? It's like some of it's experience, some of it's like studying the experiences of others. Some of it's like having great teachers like Kratis who are like forcing you in that process. And then you kind of figure it out as you go.

1:12:37Where do you feel like you've developed the most wisdom? I mean, you've been writing about stoicism for 15 years now. So like in what areas of your life do you feel like you've developed the most wisdom over the last decade plus? Yeah. Yeah, I mean, I do think your point about like discipline, like what are you doing and why are you doing it? And then to go like, hey, I'm going to pull this back. I think a lot of it for me has been dialing. It's like where do the dials go on these things? And I think I've gotten better at kind of finding those different dials over the years. I think I understand – people in history and the world better. And like, I'm reading this book right now about this sort of mid 20th century kind of political figure. And then I'm like, Oh, like, I understand what's happening right now, like so much better, because Mm hmm.

1:13:35This person who I knew existed and I thought was one thing was actually this other thing. And now it's unlocking all this stuff that I understand about now. And so I think just as I've slowly read more and then experienced more, it's the interplay between those things that you go, okay, I – I just kind of – I know what's happening. That's to me what wisdom is, is like the ability to – well, Epictetus as a wisdom is like how many arguments are you getting in? Like the sign of progress is you just don't get in as many arguments. But I think that's part of it too. You're just like, oh, no, no. I understand what's going on here and I understand what I actually should do in response to it.

1:14:16I'm thinking of it. I'm probably thinking about this just because I've been thinking about AI a lot lately. But, you know, when you're when you're prompting an AI, the more context you give it, the better the result is. And I feel like wisdom is that like what you're describing, right? Like reading books, having life experiences, getting in fights with people, seeing what's stupid, seeing what's not stupid, seeing what matters a year later, seeing what doesn't matter a year later.

1:14:41That's all context building. Totally. And yeah, it's funny. I just made that connection of like relating. Like wisdom is just – it's having context. Wisdom is having – what context are you bringing to this situation? And I've been thinking a lot about how – If you don't have a lot of context, if you don't have a lot of experience, you don't have a lot of wisdom, it's going to eat you alive because it's wrong so often or it's incomplete so often. And so like I just – I was just using AI. I needed some fact for this thing I was writing and I asked it this question. And it started to solve – The solution was – the logic was sound but it was starting from a faulty assumption at the beginning. Yeah. Which I spotted immediately but it didn't and I said, no, this is wrong for this reason. It says, oh, I'm sorry. It's like an approximation. And it's like, OK. But the approximation again flows from a flawed premise. And I guess the point is – To me, a big part of wisdom is not always knowing the answer, but knowing what's bullshit. Like I don't know – like I see this even in my business where it would be like I'll ask someone something and they'll be like – I'll be like, how big is that segment? And they'll be like, it's 1,000. And I go, it's not 1,000. And they go, well, how big is it? I go, I don't know how big it is. I just know that that number is wrong. And that's context because I have – I can't tell you the exact thing, but I can tell you what it's not.

1:16:12And so the ability to spot bullshit, to spot misinformation, to spot flawed thinking or whatever, that to me is a lot of what wisdom is. And it comes from experience and knowledge and understanding where you're just like, I can see this. And so I think people that don't have that are going to get – How do you know when it's giving you a totally flawed answer? Yeah. I think that's going to be really hard for people. There's an irony in which that like AI has all the knowledge and very little wisdom or its wisdom is dependent on the wisdom or the context you give it. Yes.

1:16:44I'll actually give you a really funny example from this morning. So I was doing some last minute prep and I went to Claude and I wrote in, I said, I'm doing a podcast. I need, give me some example questions with Seneca, Marcus Aurelius and Epictetus. And then it generated podcast questions as if I was interviewing Seneca and... Epictetus and Marcus. It was like, so you've been an emperor now for 12 years. Like, what do you think about? And I was just like, what the fuck, man? Right. This is, you know, no human would ever make this mistake. But it's. Well, there's a funny thing about how like knowledge is that tomato is a fruit. Yeah. And wisdom or wisdom is knowing that it doesn't belong in a fruit salad. Yes.

1:17:26I could very easily see Chachibiti giving me a tomato-based fruit salad thing because it doesn't actually understand. It's just grabbing different things and throwing them together. There's not this extra filter. And this is timeless. There's a story I tell in the intro of the Wisdom Book about Seneca and this wealthy Roman who just hires these slaves to give him the answers to all the questions that come up at dinner parties. And so one of his friends comes up to him after – to this Roman and he says, you know, this is a great party. He says, have you thought about becoming a wrestler? He goes, why would I become a wrestler? I'm an old man. And he goes, but your slaves are still young. And the point is like you can't have anyone do this stuff for you. Yeah.

1:18:08If you have your own knowledge and context and understanding, you can have people help you who give you information that you then filter, synthesize, and make decisions on. But you're never fully going to be able to outsource this stuff to anyone other than you. And that's – wisdom is the ability to do that. So there's a lot of pressure to not be wise right now, right? It's a lot of pressure to hop on the bandwagon of things that maybe you can't control, right? Okay. So Mark and I, we talk a lot about how we think a lot of people are under-indexed on the local and over-indexed on the global. Sure. So just global events you can't control, but everybody's like – And I talk to people about this and I tell them this and then I immediately get a lot of pushback. Well, you're super privileged because you don't have to think about that, right? And I'm like, no, you can focus on your local communities and environments and make more impact there and not be just beside yourself and out of your mind half of the other time. What do you say to that, I guess, when – No, I get that a lot. People will comment. They'll be like, oh, this is easy for you to say. You just think we should do nothing. And like what I've come to – this person was already doing nothing. Exactly. It's not like this person was running this major activist organization that's desperately trying to recruit people. And like by telling them to focus on equanimity and poise and restraint, you're depriving them of like valuable team members. Yeah.

1:19:37It's this classic thing of conflating emoting about a problem and thinking about a problem with making a difference about that problem. And so there is a stereotype that the Stoics are not active or engaged. But when you look at the lives of the Stoics – which I have done, every single one of them was active and engaged, like more so than your average person. And so what do they mean then when they say like, you don't have to have an opinion about everything, focus on what you control. They just mean exactly what you mean when you say that not giving a fuck is a subtle art. There's a bunch of things that you don't give a fuck about that you don't think about so that you can allocate those resources and energy towards the things that you And, yeah, this distinction between global and local is obviously a very big one. Like even – yeah, you look at what's happening in the Middle East. I think it's – everything people are saying it is. Is that – but me saying that or thinking it, is that changing it? No. But right now, a person of that personality type – that's doing that horrible thing overseas is running in a local election in your town. And you're not voting. And so obviously that's a simplified example. But you get my point, which is that like we are – it's not just that we're over-indexed on the global and the national. It's that we're actively neglecting the things that we have. Like how many people have a hard – have an opinion on like what the minimum wage should be?

1:21:17And then when they decide to hire someone, they're like, well, what's the minimum wage? You know what I mean? Like that's the great thing about being an entrepreneur, being a person is that you get to make your own decisions and you can do whatever you want. You know, yes, we should also band together and try to solve these problems and codify them in law. But you could also be a good person in your local sphere. And that's those concentric circles again.

1:21:44Where do you think you've gained the most wisdom, Drew, over your whole life? Where have I gained the most wisdom? I guess we might get into this a little bit more later, but just like the acceptance and the indifference part, I think as I get older, the more. I'm like, yes, the discernment that comes with that. I think it's – you go through enough iterations of that. You go through enough relationships. You go through enough – um enough people in your life and you're just like this does and does not matter and you're right it's an experience thing it's it's it's one of those things you can be born smart you can be smart about a lot of things gaining that wisdom yeah just having less opinions is like yes very much by itself is all the i used to be very very opinionated now i'm just like god i don't know anything yeah Have you heard that idea of not yucking someone's yum? Oh, yeah. I was like, oh, that's a great fucking expression. Don't yuck on my yum. Yeah, it's like, why do I give a shit? It's like you're right in that you like that. Yeah. You know? And like – but the inexperience says like, no, no, this is a statement about whether something is objectively good or not and that –

1:22:49my inability and then the irony is my inability to let you like something you like is actually making me like just the idea of being able to be like I don't you do you man you do you yeah what about you Mark were you fishing for us to ask you that question too is that No, I'm just thinking about this. I think Ryan and I are very similar in that we're both – I consider us both like all gas, no brakes guys. Yeah. But in very different ways. Like you're very regimented and like incredibly consistent, productive. I think mine is – Compulsive might be a word.

1:23:30Wow, you've come a long way. Yeah, there is some wisdom there. I think on my side, it was more – I would call it like a little bit more like – You know, like I was always, I wanted to try everything. I wanted to experience everything. I wanted to go everywhere. I wanted to do everything. And I think that served me very well when I was younger, but it led to a very chaotic life. And so I've really had to learn how to calm down, but I think in a different way than you. I've had to learn how to like calm my desires and my feelings.

1:24:13my impulses. Um, you know, just like, I have a lot of shiny object syndrome. Yeah. Um, I think I, I've, I've never heard about a trip that didn't sound cool. Um, so it's, it's, it's taken a lot of time and work to like, get me to step back and just be like, you know, it's okay to chill out and just, you know, do the same thing every day for a few weeks. Like that's not going to kill you. Actually, it might be really good for you. Yeah. Yeah. Yeah. My my eight year old one time I was like trying. I was like, come on, dude, this take forever. Let's go. And he's like, we got nothing to do and nowhere to be. You've been watching the Big Lebowski.

1:24:59But it's like it's a Saturday. Yeah. There's literally nothing we have to do. Not only do we not have to do it on Saturday, but also like we're good. Like I don't have a boss. I don't have to think about money. I can do whatever I want. Yeah. And here I am going like we need to get there 30 seconds faster. Yes. You know. And I think the wisdom of just like, again, understanding what's important, what's like what's real and not like what's actually serious and what isn't is a big part of it. Yeah.

1:25:25And I think it's interesting that all three of our examples were various forms of temperance. Yes. Right? It's like the temperance is the correction. I like that definition of like it's correction. And then obviously to know what to correct, you need to have an understanding of justice. So yeah, it does all tie together quite nicely. As we move from this early Stoic period into the later Stoic period, there's kind of two major historical shifts or transitions that I wanna talk through.

1:26:03The first one is the Roman conquest of ancient Greece, which happens in 146 BC. There's a political fallout from this and there's a – and this didn't just happen with the Stoics, but it's all of the major Greek schools of thought. Like suddenly now there are Roman patrons to impress, to entice, to I guess ingratiate yourself with. So I want to cover that. And then the second major historical transition I want to talk about is the kind of civil war period of the Roman Empire or the Roman Republic, which emerges with the Roman Empire. Because there's a lot of interesting Stoic intrigue that happens during that period as well. But let's start with the Roman conquest of Greece and the influence that it starts exerting on a lot of the Stoic thinkers of the time.

1:26:54Well, Rome conquers Greece militarily, but Greece conquers Rome culturally. And there's a famous diplomatic mission where Greece sends like three of its greatest philosophers to Rome to basically plead with their new overlords. They were used to being the deciders. It's Britain sending Churchill to America to meet with FDR during the early days of World War II because the balance of power has shifted. They send Diogenes, different guy, same name, Carneades, and somebody else I'm forgetting. But basically, it doesn't go over well at first. Rome is like instinctively averse to philosophy and they particularly take issue with the way that one of the Stoics – or one of the philosophers who's more of a sophist – argues one position one day in a presentation and then argues the other way the next day in the way that, you know, in a university context or a debate environment we respect. But for the Romans who are sort of much more literal, this was repulsive.

1:28:04And actually Cato the Elder is this famous Roman, wants to ban the philosophers altogether from Rome. He would have hated the fact that his great-great-grandson, Cato the Younger, becomes maybe the most famous Stoic of the age. But it's this sort of slow acculturation where the ideas from – ancient Greece, in the same way that we look to them and admire them and are blown away by them and we look at these buildings and we go, how do they do this? The Romans had the same reaction. And so culturally, the Romans raid the Greeks of all their ideas and they renamed some of the gods. They pick some of the philosophers, reject some of the others. But Greek remains like the philosophical language. Marcus Aurelius, again, hundreds of years later is writing meditations. He is writing in Greek.

1:28:54and not in Latin. And almost all of the Roman emperors visit the Greek schools. And Hadrian famously listens to Epictetus. But all the Greek emperors and thinkers and lovers of philosophy make their pilgrimages to Greece in the same way that we would today because it's where it happened. It's interesting because I think when I think about kind of the early Stoic period, It's very cerebral. Like it's a bunch of dudes on a porch debating the nature of existence and like what is virtue and what is the right thing to do in this situation. And I feel like the later stage of stoicism is you get a lot more of the practicality and the implementation. And I feel like there seems to be a little bit of a shift or at least – Like it's – there's more of a focus that it goes – gets a little bit away from the metaphysics and like resolving paradoxes and trying to understand the nature of the universe. Whereas like when you read kind of the Roman era Stoics, it's much more about – What's the most effective thing to do in this moment or how to act in each situation? The word here I would use is engaged. The Romans are engaged in the business of running the world and the empire and the levers of power in a way that the Greek philosophers were not so much.

1:30:24And so the philosophy becomes about these questions of like, what do you do? How do you do this? What is – what are the skills and attributes and virtues of a public man? Yeah. Right? A person who is ruling a province or leading troops in battle or is serving in the senate – Or is a wealthy businessman? Like what are the tools you need? And so they're engaged in life in a very sort of vital, essential way that the – again, I think the earlier Stoics were a bit more on the periphery. So you see it – it's not that it's a softening, but it is sort of – it's like an assimilation into the real world from the theoretical world that just wasn't as much a part of it before. Is there a clear through line of – how so many of the Roman elite became interested in this philosophy? Because once we get to the Civil War and Augustus and everything, there are senators, there are very prominent Romans who are avowed Stoics. So what does that bridge look like?

1:31:32Yeah, that's a good question. I mean, and to go to this point about being engaged, like, I think it's interesting that, like, Greece is trying to solve this political, geopolitical issue, right? And they're like, who should we send to Rome? They're not like, let's send our strongest guy, let's send our richest guy, let's send our, you know, most illustrious, but they're like, let's send our philosophers. So there is this kind of entry into the global affairs that philosophy has, which I think is interesting.

1:31:57One of the big things, there's this group called the Scipionic Circle. So Scipio Aemilianus, he's this famous Roman general who he becomes interested in Stoic philosophy and he sort of cultivates this scene of thinkers and doers. You know, some are in generals, some are politicians, some are historians. But they kind of just cultivate this club that talks about philosophy and then they all kind of go back to their thing. And I think that's kind of in the way that we might look at sort of like the lost generation in Europe post-World War I or Samuel Johnson's the club in Enlightenment England. It's just this like scene that is kind of – it's like the PayPal mafia of stoic philosophy. Like all these people go on to do these things and then each under them have their own coaching tree.

1:32:43Yeah. And Cicero was particularly enamored with this idea of a Scipionic circle, and he's who we hear about it from a lot. So from this period, once we get into, I guess, first century BC, we get into the Civil War era of the Roman Empire and all the turbulence with Julius Caesar and what eventually emerges as the empire itself. I guess we can start with Cato the Younger since he is the most prominent story, although there are other examples as well. Tell us about Cato the Younger. Tell us his story, and then we'll kind of dig into the significance of it and – So Cato has a – probably his great-grandfather is rolling over in his grave, but has a tutor who teaches him stoic philosophy. So he learns it at this early age. Again, we think of this as a stable, solid period, and it wasn't. There's a great book by Mike Duncan called The Storm Before the Storm that's about the 100 years leading up to Julius Caesar. He doesn't come out of nowhere. The Roman Republic is struggling and sort of creaking under its own weight. Again, kind of like we feel today where it's like – They can't pass laws. You're watching political violence and political dysfunction and the continual breakdown of norms. So Cato comes out of this kind of a throwback figure. Like he takes to Stoic philosophy with a kind of monkish devotion. And he doesn't write anything about it. We know him as a Stoic philosopher because of how he lived. Mm-hmm.

1:34:14scrupulously honest. There was a saying in ancient Rome, like a politician when they were asked to do something would be like, we can't all be Cato's. You know, he was like, he's, he's, he's like an old school, like conservative in the lower sea sense. So as the system sort of creaks and groans under its own weight, and then you have the introduction of Caesar, the two are kind of these mortal enemies, one representing not just change, but an attempt to overthrow the old order and what the Romans would call the mos maiorum or the old ways. Cicero, Caesar, etc., these are like new men in the sense that they're allegiant to a new order.

1:34:58And Cato is the thorn in their side. He's the break. And it sets up this clash ultimately leading to the Civil War, which Cato dies in and then famously commits suicide in protest parties. rather than submit to Caesar. He goes to his room, he pulls out a copy of Socrates, or Plato's recounting of Socrates' last days, reads it, and then stabs himself in the chest. And then as the doctor rushes in, they hear him fall on the clatter of the sword, they sew him back up, and then when he wakes up and realizes he hasn't died, he rips the wound open and disembowels himself.

1:35:46But it's this powerful example of sort of Stoic opposition to tyranny and power and change that sort of stands as the example that inspires like subsequent generations of Stoics. But long story short, Cato is a philosopher not for his writing but for his way of life. He lives the Stoic ideas. He's literally a Stoic martyr. Yes, yes. And he's the first of many. Because it's interesting over the following period and it's probably worth noting too, you know, once we get into the Roman Empire, each emperor kind of had a different disposition towards being challenged by the Roman Empire.

1:36:29Stoic philosophers, I mean, there was one under Domitian. Is it Domitian? Domitian, I say Domitian. Domitian. Under Domitian, even writing a biography, even writing about Stoics was illegal. Yeah. He blanket bans all philosophers from Rome. Yeah. Just because it feels weird to think – we don't think of philosophers as being transgressive today. But that word was inherently revolutionary at this period in Rome. Just one sort of Stoic after another is a thorn in the emperor's side. But it doesn't – there's a brief period where that's not the case. The first emperor, Augustus or Octavian, is taught by two Stoic philosophers, Athenodorus and Arius Didymus.

1:37:15So there is this interesting debate even amongst the Stoics of like, are we Cato's or do we accommodate and adapt? And so I imagine there's a split. Like you can persuasively argue it either way. But these two teachers not from Athens are the two main teachers of the emperor. And they have some interesting stuff. You know, they're suddenly – Now the power is vested in one person and it's really just the individual dilemma writ large. And so they're talking to him about what do you do when you get angry?

1:37:55Can the emperor afford to lose – the emperor can lose his temper and do whatever he wants. But can the emperor afford to lose his temper? And how can this person who now possesses all this power learn the ideas of restraint and these virtues that we're talking about? So they're just – I think if you're sort of looking at the montage of this period, you're just noticing the Stoics moving forward. closer and closer to the levers of power and then moving, taking a resistance role when they lose the levers of power. Well, and it is interesting because there are examples of Stoics on both sides of that equation, right? There are some Stoics who quietly and try to subvert the power and resist maybe in a not-so-obvious way. And then there are like...

1:38:47people like Cato who just overtly challenge authority repeatedly. And it's, I don't know, like it does raise an interesting question, especially in, in times like these, like, you know, What is the most responsible thing to do? Totally. So Seneca is a senator, right? He's taught Stoke philosophy as a young man. He becomes a senator. So he gets to basically the peak of Roman life. And then based on these rumors that he's having an affair with the emperor's sister, which are probably not true, he is banished by the emperor Claudius, who was not a good emperor. And so he's banished to this rock in the middle of the ocean. Yeah.

1:39:28And he spends like a good chunk of a decade there. And at some point, he is given an opportunity to come by Nero's mother. And Nero is then just a young man who's being groomed to be emperor. And so Seneca obviously doesn't know who he's going to become. But for a guy who worships Cato, this is like an interesting question. Do you serve the emperor? Are you an oppositional resistance figure? And he decides it's better to be in the room where it's happening than in exile. So he comes back and he tutors Nero. Nero, when he takes power, actually people are pretty optimistic because And he has – there's a period they call it the Quinquineum Neuronium and it's the first five years, the golden years of Nero. And he mostly listens to Nero and his military advisor Burris. And then at some point, you know, they say power doesn't corrupt, it reveals. And power begins to reveal that Nero is deranged. And at one point, Seneca has to remind Nero that it's impossible to kill all of your successors. Yeah.

1:40:40The joke being that eventually somebody does it, right? And he writes a speech after Nero tries to kill his own mother. Seneca almost certainly is telling himself he is the adult in the room. He is containing the madness. And on the outside, the other Stoics, and there's a number of resistant Stoics like Thrasia who are senators who are like, no, no, no, you're enabling, you are complicit – And Seneca becomes enormously rich working for Nero. And so it is this – it's a fascinating and eminently modern debate. Is it better to be on the outside or be on the inside? And Seneca chooses the inside. A number of other Stokes in the same period choose the outside. And – Kind of depending on what side of the bed I'm on when I wake up, I can argue it either way. But Seneca is very, very fascinating in this regard because he is forced in a number of incredibly morally compromising positions.

1:41:42Yeah, he's full of contradictions. Yes. Much more so than probably any Stoic thinker. You mentioned briefly the wealth thing. Yeah. That's another aspect of him that is— He's the second richest man in Rome. Which is mind-boggling. Yes, as a philosopher. And he has this—and he can never—he can't talk about any of this, right? So he does write a number of like really dark— really fucking dark plays that where he talks about depravity and paranoia and stuff. And it's, he's obviously subtweeting Nero as he's doing this, but, um, yeah, he becomes incredibly wealthy. And, and so he understood this was a charge against him even at this time. And one of his, uh, Essays are – it's an essay or letter. I forget. But he goes, you know, can a philosopher be rich? And he says, yes, a philosopher can absolutely be rich. He says, provided that their money is not stained in another man's blood. And – which is like an interesting – a very vivid and interesting point.

1:42:45Which doesn't give us any clarity as to his specific case, right? Like, because that's exactly why it's so complex, you know? Seneca is fascinating. He writes probably most beautifully of all the Stoics about Stoicism. I agree with that. And then also seems to be the most fun. Yeah. Yeah. and modern of them, and almost certainly the... He and Cicero are both better writers than practicing Stoics. He's definitely my favorite of the Stoics to read, and it was interesting. I mentioned earlier that I did a bit of a deep dive on...

1:43:21I think it was eight common stoic practices and just digging up where they came from. And I mentioned earlier that almost all of them came from Plato, Aristotle, or the cynics with the exception of one philosopher and it was him. So he is where negative visualization originates from, daily gratitude practices. Yeah. And then obviously he probably wasn't the first person to journal, but he was the first one who explicitly said that you should write down your thoughts every single day so that you can reflect upon them and think about them impartially. So for listeners who aren't familiar with what negative visualization is, basically – You know, when you're stressed about something or worried about something or afraid that something bad is going to happen, the conventional wisdom is visualize what success looks like. Visualize everything working out. Well, what Seneca actually said is to do the opposite. Visualize the worst case scenario. Visualize what it would mean if everything went wrong. And the point that he made, which is extremely profound, is that if you actually sit and visualize and think through the worst case scenario, you realize that.

1:44:29it's often not that bad. Like when you run through the mental examples of like all the horrible things that could potentially happen to you, you start to realize like, wait a second, I actually think I'd be okay. And so paradoxically, it makes you more confident to do the thing. And even if it doesn't, it at least gets you in the mental practice of preparing for the worst. He's such an interesting character because he is twisted up and tied up with all these. Like even the money thing, you could even make the same argument that – by being the second richest man in Rome, you have more opportunity to influence good. Sure. Than if you were, you know, like Diogenes the cynic, right? Totally. Living in a barrel or whatever. So, um, when here to, to go back to the period we're talking about first, right? So Cato is the moral enemy of Caesar. And then his daughter, Portia Cato is married to Brutus who assassinate Caesar. Right. And Brutus is, um, Stoic-ish. Shakespeare makes him more explicitly stoic than he was. But like the Romans have a very real counter example to why you don't get rid of the emperor. Like so they assassinate Caesar and then a civil war breaks out that ravages the – like – and then they end up with another emperor. It doesn't do anything. Yeah. And so I do think –

1:45:55Humility is the wrong word. There was a reticence for the later Stoics to go, hey, we would rather be a republic, but we don't know how to get from here to there. And we don't exactly have a playbook here. And the revolutionary attempts previously have been disastrous. So I think Stoicism as a – like what do you do about a flawed status quo is – a stoic dilemma. And it wasn't a theoretical dilemma to these people. It was, hey, last time, what happened? And there was, I think, a fear of that. Well, and I think this is a perfect example of...

1:46:39kind of that transition between early stoicism, which was still very intellectual, cerebral, still worried about like the free will problem and determinism and this later period, which is like, okay, you can either, you have an emperor who's fucking crazy and murdering everybody, but he listens to you. Yeah. So should you try to talk to him? Yeah, yeah, yeah. Right? And we can imagine Seneca being like, dude, you don't understand, I nixed nine out of the ten bad ideas, and then you're saying I'm complicit because one of the bad ideas happened. The Senecas of the world would say, you don't understand how much worse it would be without me. And then the outsiders, your Thrasias and Helvidiuses and Agrippinuses, the Stoics who are in this same period but on the outside, are saying, well, actually, you're complicit and you're enabling and we need to do something about this. Yeah.

1:47:36It's – these are no longer these kind of black and white philosophical issues. They are pragmatic policy choices between evil issues. Well, isn't there just too the stoic idea that you play the hand you're dealt, right? Like this is what it is, right? And so that is kind of the two sides of the warring camps there. Yeah. But it's still – like is this the hand that you're dealt? Like is this out of your – I think that's what's interesting. Right? Like we say that and then obviously if we said that all the time, nothing would ever change. And that is the trickiness of it.

1:48:18It reminds me of the Steve Jobs quote. It's the people who are crazy enough to think they can change the world who inevitably do, right? Yes. Seneca's letters are fantastic. Like I – that – between that and meditations, like to me, those are like the two entry points in the Stoicism. I don't know if you would agree with that, but for anybody listening – um other than Seneca's essays are also very good you know he has a he has an essay called on the shortness of life which is incredible he has one called on anger which is incredible he has one on on tranquility which is incredible and then he has a few on grief that I always recommend to people uh you know I just lost my father my mother yeah um He's not just a political philosopher. He's also writing these deeply moving essays and letters about just kind of practical human problems. And I would argue better than almost any philosopher in human history, which is what makes his story all that more compelling. So he was also – he also died by force suicide. Yes. Yeah.

1:49:26Yeah, Seneca and Jesus are born in the same year in different provinces of the Roman Empire. Both become enormously famous philosophers and then both die at the hands of the Roman state gruesomely. I've always been fascinated by that parallel. But yeah, at some point he does what everyone says he should do, which is he walks away from Nero – And you could say it's too late, but he walks away from Nero. He tries to give all the money back. And Nero goes, that's not how this works. He's like, I'll let you live in exile, but I decide what happens next.

1:50:00And we're told Nero tries to kill him a couple different times and then finally the sort of goons come. And in those days, they would give you – as a courtesy, they would allow you to commit suicide. And so, yeah, they allow Seneca to commit suicide and he tries to slit his wrists. It doesn't work. He tries to take hemlock. It doesn't work. It's this kind of gruesome thing where if he was the hypocrite and the charlatan that everyone wanted to make him out to be, I don't think he could have handled the scariest thing that happened to him in his life the way that he did. And he supposedly handles it with this sort of like almost good humor.

1:50:38And in the end, he's suffocated to death in a steam room. And yeah, he's killed by his prized pupil, right? And in one of his plays in Theistes, Seneca has a line that crimes return upon their teachers. And there's some poetic justice, I think, in being killed by the monster you helped create. Yeah. Honestly, his life story could be a Greek tragedy. It is. Yes, totally. It's one of those, if you didn't tell me this actually happened, I would think it was made up. Well, they thought it was made up for many years. Like, first off, what we thought Seneca looked like, we only found out he looked totally different like 10 years ago. Okay. Like, the famous sort of haggard picture of Seneca is now known as pseudo-Seneca because it's not a bust of Seneca. And we found Seneca was much— plumper and epicurean looking. Okay. But like Seneca the philosopher and Seneca the political power broker, then there's Seneca the playwright and it was – all the Romans had like the same names. Yeah. Yeah.

1:51:51For most of the last 2,000 years, people just – most historians assumed that was at least two if not three different people. And only more recently have they – did they really confirm that no, he also wrote these plits. So it's like – I don't know. It's just like think of the most powerful unelected political official – also your most famous self-help thinker, and then also writing blockbuster movies. There's a line from one of Seneca's plays on the wall in Pompeii. So he was famous that people knew his stuff, and he's just doing that on the side. So he's a genius. Did he do the plays before or after he got elected? No.

1:52:35During. Oh, during. So what they take it to mean is that this is where he is processing the moral injury and the trauma because all his plays are fucking dark. Yeah. And like incredibly dark. Like he was taking the Greek tragedies and adding a brutality and a viciousness to them that wasn't – it's not a stretch to be like, oh, this is this guy processing what he saw his boss do. Right, right. What are the biggest lessons that you take from Seneca that you think are the best takeaways? Well, Seneca writes a lot on mortality. And one of the ones I think about all the time, he says, you know, it's wrong to think that death is something that we are moving towards, that it happens at the end. His point was that we're actually dying every day. This is the time that passes belongs to death.

1:53:24And so Seneca writes a lot about, as I said, he has a session called On the Shortness of Life, but he thinks about how time is our most precious resource, but it's the thing we're worst at managing. Yeah. And he writes beautifully about what an active practice of meditating on our mortality gives us as far as perspective on how to manage our time. Nice. And then, yeah, he writes a lot about tranquility. He writes a lot about controlling your temper. His essay on anger is very interesting. Again, when you go, oh, this guy is Nero's advisor. He's like, yeah, you can't just kill everyone you get mad at. But he's talking about how you manage the passions, which a leader has to figure out. Right.

1:54:08You do not need a degree in the classics to read Seneca. It is incredibly readable and accessible, and that's why he's so popular. And very applicable still. Like anybody can pick it up and relate to it. So really quick, there are a couple other concepts that are associated with Stoicism. Both of them are in Latin. One is memento mori, which literally means remember your death. And basically the Stoics argued that the more you think about your own death and your own mortality— The more you appreciate what's in front of you, the more you take advantage of the opportunities in front of you, and the more perspective you have on what actually matters in your life, on what to actually put your effort towards. And the other concept is amor fati, which literally means loving your fate. And this goes all the way back to Zeno and Chrysippus and the early Stoics. Amor fati basically says, love whatever happens to you.

1:55:02Find a way to appreciate and take advantage of any circumstance that comes your way. Basically, don't resist the things that happen to you. Don't try to fight the nature of the universe. Don't try to change the natural order of things. Instead, find something to be grateful for. Find some sort of opportunity in the hardship. And look at your struggle in a way that you can love it. Like find a way to love the hard things that you're going through.

1:55:32which is a very counterintuitive concept on the surface. And I think it's people's natural reaction is to kind of recoil to it. But if you can find a way to do it, it is incredibly powerful and profound. All right, let's move on to Epictetus. Yes. Tell us about Epictetus. So if Seneca is the privileged man in Nero's court, Epictetus is also in Nero's court, but on the exact opposite end of the spectrum. He's a Greek slave. Literally his name just means acquired one. And he is owned by one of Nero's top slaves.

1:56:13aides, secretaries, you know, sort of administrators. So Epictetus is there watching these same people, but from a very different vantage point. And I think Epictetus's main observation is contrasting his lack of freedom— which is legal, with the lack of freedom that these supposedly free and powerless people have. One of his most brilliant and I think vivid observations is he talks about seeing this man sucking up to Nero's cobbler. Like this guy is trying to get in good – be in the good graces of the guy that makes Nero's shoes because he's both afraid of Nero and wants something from Nero. And I think what Epictetus sees when he sees like these millionaires begging for favors or these people who are afraid to tell the emperor that he's wrong – I think he just kind of goes like, oh, I might be freer than they are because I know what's good and bad. I focus on what's up to me and I'm not hoping or wanting for anything. Yeah.

1:57:29And so he achieves this kind of freedom inside captivity that I think is a really important layer on top of stoicism that is the resilience layer that obviously Zeno begins coming out of a shipwreck but is the most – has a large degree to do with why stoicism is still popular to this day. And he is the originator of the idea of focusing only on what you control. Yeah. He says that most clearly. There's stuff that's up to you. There's stuff that's not up to you. Anything that's not up to you, don't think about. And, you know, he eventually goes on to be a philosophy teacher. Then he's banished when all the philosophers are banished.

1:58:10And then, you know, it's funny how the tables turn towards the end of his life. One day, you know, the Emperor Hadrian, who loves Greek thought, is just there in Nicopolis listening to Epictetus's lectures. And to me, I love the – again, the full circle-ness of like – Well, doesn't that make him the most powerful man in the world? If the emperor is coming to listen to you because you have so conquered yourself and found plenty in the midst of scarcity and all this, like, aren't you actually more impressive? And then it is the lectures of Epictetus – He doesn't write anything down recorded by this guy named Arian who's one of Hadrian's administrators that makes its way to Marcus Aurelius. So that's the – now you have the most powerful man in the world being directly influenced. Like the Epictetus is the philosophical Bible of Marcus Aurelius.

1:59:10Would I be overstating it too thinking that like Epictetus, that represents a huge shift in the morality of Western thought. Wouldn't you say? How so? Well, because he's saying it's not about like the power that you have. It's about the virtue, right? That morality or goodness or whatever you want to call it isn't derived from power. It's not derived from – whatever it is, success, power that all these emperors had or whatever. It's more about who you are as a person. So you have this slave. It's almost like a precursor to what Nietzsche ended up calling the slave morality. Am I overstating how much Epictetus had an influence in that? Well, Epictetus remarking on the idea back then that only the free were allowed to be educated makes this point that he's like, no, no, no. Only the wise are free.

2:00:01And I think his point is that, you know, it doesn't matter who you are. It doesn't matter where you come from. Like, it matters what you know and what you do with what you know. And so there is something kind of individualistic in a kind of corrupt, broken world that he's kind of turning around. And – Yeah, I think that's what's so – there's a reason he is so striking, not just to – Epictetus becomes obviously deeply influential in powerful people like Marcus Rios, but then also like other people who are later political prisoners or experience incredible adversity or deprivation. There's just something about Epictetus where you're like – this dude not only fucking said it right, but he gets it because he lived through it. Like, he has the least privilege of all the Stoics, right? And then, so you're like, okay, if he is saying this, like, it's been battle-tested.

2:00:59One thing I heard is that he would often use shocking language and harsh statements as a pedagogical tool. Yeah. I don't know what kind of fucking idiot would you do that? Yeah. He's a little bit more like – he's a little bit of a throwback to the cynics in that he's like – Like even that story about the cobbler, he's making fun of people and breaking them down and kind of – he's questioning your most basic bedrock assumptions, which is what great teachers do. You think this and then he shows you why you don't have any idea what the fuck you're talking about.

2:01:36What are the biggest or most important lessons you've taken from Epictetus? I mean obviously the dichotomy of control is like the core of Stoicism. I like his thing where he says it's not things that upset us. It's our opinion about things. That's like – that's the definition of Stoicism right there. Like the thing is – You see that all throughout Western thought. Of course. Since then. The thing is objective. The news is. And then we say it's a bear market. It's a bull market. We're saying it's good or bad, fair, unfair. Epictetus talks a lot about virtue and good and evil. So he's not saying there's no such thing as right and wrong. He's just saying there really is no such thing as positive or negative. It just is.

2:02:16And then his other one that I really like is it's impossible to learn that which you think you already know. And so he is as a teacher in the same way that we get some good insights from Zeno on this. I think very much about breaking you down first and disabusing you of your notions and your faulty assumptions. So then you can be remade in this sort of stoic mold. Mm-hmm. That's why the most powerful Romans sent their kids to him to be educated. It's mind-boggling that, yeah, that the most powerful Romans would send their family to a slave. Yeah. And then actually- To learn how to live. But also, you know, to go to the idea of justice, right? I think it's really interesting that his teacher, Musonius Rufus, not only teaches Epictetus, so he's teaching this former slave, or maybe he still was a slave, but he also writes this fascinating essay on, which survives to us on, you know, whether women should be taught philosophy. Mm-hmm.

2:03:19And he has another one about how whether virtue is the same in a man or a woman. And there is something really progressive about these people, you know, again, almost 2,000 years ago going like, oh, yeah, virtue is virtue. It doesn't have a genderedness. And obviously there's a lot of misogynistic things in all their writings. But they are starting to question some of the earlier ideas. And we're seeing, you know, threads that get picked up by other people later.

2:03:46So how does Epictetus' work reach Marcus Aurelius? Yeah. In Meditations, at the beginning of it, he thanks his philosophy teacher, Rusticus, he says, for loaning me his copy, The Discourses of Epictetus, from his own library. And so I just love that, you know, again, 20 centuries ago, like, hey, you might like this book. Yeah. And then it changes the course of Western civilization. Yeah. Yeah. And I think everyone's had a book like that, that someone was like, hey, this worked for me. It might work for you. And so you have this young man, probably in his early 20s, gets this thing. You know, he's not born to be the emperor. There's a series of Roman emperors who have to choose their heir. And Marcus is chosen by Hadrian, but he has to choose someone in between them. So he chooses Antoninus, who in turn has to choose Marcus. At some point in there, Marcus reads Epictetus.

2:04:36And then that's what sets in motion one of the only instances of a philosopher king in human history. And I think it's remarkable that you have in Marcus Rielus a guy who could do whatever he wants. And so the voice in his head saying, ah, that's not a good idea. That's not right. I don't think you should do that, is the voice of this slave. And how powerful that is. It's notable. The two things that kind of stand out to me within meditations is obviously the memento mori aspect of it, but also his idea of the view from above, right? Zooming out, zooming out across history and time and space and everything. And it makes sense considering…

2:05:27Where he's coming from, right? As you said, like he's the most powerful person in the world. There's literally not a single soul that can tell him no. Yes. So the only thing that can potentially give him perspective or challenge his perspective is history and time itself. And so he has to regularly develop, he has to develop a practice of regularly like zooming out and making himself feel insignificant. Yeah. To keep his head on straight. Imagine how even just like logistically that's actually pretty groundbreaking. Like we so take it for granted. It's like you get in an airplane and you look down or you drive a car up to the top of a mountain and you look down.

2:06:08Or you have a picture that they sent you from outer fucking space of this tiny blue marble that we look – like they didn't know any of this. So when he's talking about taking the bird's eye view, this is like – actually an imaginative exercise. And I was just at the Acropolis and I was thinking, it's like, no, he came here and he stood there and he looked down on this. And this would have been, he would have been looking down at the sum total of the ancient world that he so admired And it's like he wouldn't get that view very often. But you do. I was just talking to this astronaut and he was saying it's just incredible because the borders go away and time goes away and race goes away. And all you're left with is like this sense of like everyone's in this together. And that's not a perspective that people who find themselves the most powerful person in the world – are often naturally inclined to or get, you know? Right. So Meditations was written almost as a personal journal. Yeah. It wasn't ever meant to be published or seen by the world. You read it in college, I believe, and it had a profound impact on you. Yeah. Yeah.

2:07:28Tell us about that. What was that process like? Well, just like somebody gives Marx to realize Epictetus, someone was like, hey, you should read this book, Meditations, which I didn't know existed and I didn't know anything about it other than that's the old guy from the movie Gladiator. There's nothing like it in any language, in any philosophical tradition, like almost every book. And I think you and I as authors appreciate this. There's something inherently performative about a book. You are writing it to be read by someone else.

2:07:54And so that's not to say you're not being honest and you're not pushing yourself, but there is, you're performing. You're putting on your best outfit. Yes. You know, you're trying to make a good impression. Yeah. And so the idea that this guy who has a pretty busy day job is writing these notes to himself and he's doing it in his second language and he's doing it, never intending it to be published. And it's so good that we're still reading it 2000 years later is incredible. But there's a he says you. And when he goes like, you know, when you wake up in the morning and you want to stay in bed, you know, he's not thinking of you. He's thinking of him.

2:08:34but from the specificity came this timeless universality. And it's him talking about controlling his temper. It's him talking about his fear of death. It's him talking about fear of losing his children, which he did. You know, it's fear. It's him wondering about legacy and will he be remembered. It's him, you know, getting worked up about stuff. It's like just this very human book, but it's a human trying to not transcend their humanness, but trying to get from the lower self to the higher self.

2:09:14It does seem what is so remarkable about it is that you would – I don't know. I think this is just like a natural human bias. We do it all the time with celebrities and world leaders and historical figures. But we assume that there must be something different about them. Like, oh, clearly – Clearly, Steve Jobs didn't have the same amount of hours in the day or didn't worry about the same things I worry about. So it is wild to peer into the mind of a Roman emperor, not just any emperor, but like at the peak of the Roman Empire and its power. And yeah, see passages about not wanting to get out of bed and – And also though like it's easy to read like a – I don't know, a Buddhist monk being like power doesn't matter, fame doesn't matter, money doesn't matter. And it's like that's easy for you to say you've never had those things and you didn't have a shot at having those things. Mm-hmm.