Arthur Brooks’ Ultimate Philosophy Masterclass (PT. 1)

Summary

Podcast Summary: The Daily Stoic

Episode: Arthur Brooks’ Ultimate Philosophy Masterclass (PT. 1)

Date: March 26, 2026
Host: Ryan Holiday
Guest: Arthur Brooks

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Overview

In this rich and engaging episode, Ryan Holiday sits down with renowned author and philosopher Arthur Brooks for a wide-ranging “philosophy masterclass.” Together, they traverse the foundational schools of Western philosophy—Socrates, Plato, the Cynics, Nietzsche, Aristotle—and discuss how their ancient wisdom translates into practical guidance for finding purpose, happiness, and meaning in the messy, uncertain modern world. Brooks draws from his latest book, The Meaning of You: Finding Purpose in an Age of Emptiness, and intertwines philosophical theory with insights from psychology, neuroscience, and lived experience. The conversation is lively, full of humor and memorable anecdotes, making the history of ideas come alive for a contemporary audience.

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Key Discussion Points & Insights

1. Learning Across Philosophical Schools (03:48–08:31)

• Cross-Pollination of Ideas:

  • Ryan praises Brooks for synthesizing insights from many schools rather than staying in one philosophical “lane”:

    “People are like, I’m a Buddhist, I’m a Stoic, I’m a Christian…and you just stay in your lane, right? … What I like about the ancients is how familiar they were with all the other ancient schools.” (04:31)

  • Brooks notes that real wisdom emerges from “looking outside your tiny little worldview.”

    “There is an underlying objective reality, but you only get it by coming at it from many different perspectives…when you’re sitting only in your home, it’s through a glass too darkly.” (06:24)

• Universal Truths and Emergent Wisdom:

  • The two liken the convergence of philosophical truths to convergent evolution (Ryan) and emergent order in markets (Arthur):

    “You need lots and lots of people doing lots of different things…And then what’ll emerge is a wisdom.” (07:50)

2. Humility and the Socratic Method (09:24–12:44)

• Socratic Ignorance:

  • Brooks: “The average person can learn from Socrates the basic idea of humility. That your enlightenment will come when you’re not blocking that Truth with yourself…The only thing I know is that I don’t know anything.” (09:35, 09:48)

• Life in Turmoil:

  • Ryan reminds listeners that Socrates’ wisdom was forged during intense personal and social upheaval, not in academic comfort:

    “He lives in Athens as Athens is going through incredible turmoil…and we think of it as classical antiquity. To him it was the most advanced time in human history and it was scary and uncertain and not the past.” (11:04–11:33)

• Fading Affect Bias:

  • Brooks introduces this psychological concept as explaining why we romanticize the past and overlook its suffering:

    “Fading affect bias…you look back on prior times, strip out the discomfort from those times, and only enjoy the learning…” (11:33)

3. Plato: The Pursuit and Responsibility of Enlightenment (13:15–16:50)

• The Allegory of the Cave:

  • Plato’s allegory is explored as a timeless metaphor for human perception:

    “Most of us are looking at shadows. We’re chained in a cave…we see these shadows. We don’t know what they are…But there is this truth, unchanging truth.” (14:14–14:41)

• The Obligation to Share Wisdom:

  • Understanding obligates one to enlighten others:

    “The whole idea for you to find enlightenment is so that you can bring it to others.” (15:55, Arthur Brooks quoting the Dalai Lama to connect Plato and Buddhist thought)

• Role of the Public Intellectual:

  • They discuss whether philosophers or wise people should engage publicly or remain contemplative:

    “With insight and understanding and wisdom comes responsibility.” (15:59, Ryan Holiday)

4. Cynics, Skeptics, and Meaning Through Contrarianism (18:30–22:29)

• Cynics as Philosophical Rebels:

  • Ryan compares the Cynics to “punk rockers” for their radical critique of society:

    “They are, by taking it too far, actually providing us insights about sort of a moderate middle ground…” (19:04–19:42)

  • Brooks adds: “What they do is they can make you realize that life is hilarious.” (21:13)

• The Value of Extremes:

  • Skeptics and cynics, with their “anti-poses,” push boundaries, exposing the spectrum of philosophical possibility and humility.

• Philosophers’ Humor:

  • The episode delights in the underappreciated humor of figures like Diogenes and Nietzsche.

    “You read Diogenes the cynic, and you’re like, oh, this dude’s [expletive] hilarious. And he’s a badass.” (22:30, Ryan Holiday)

5. Nietzsche: Question All Assumptions (23:13–24:37)

• Essence and Existence:

  • Brooks: “The biggest problem, philosophically and…in terms of almost everything that we do, is an inability…to question our own assumptions…A lot of what Nietzsche is talking about is questioning this fundamental algorithm of life.” (23:17–24:07)

• The Contrast with Earlier Traditions:

  • Nietzsche is positioned as smashing not only religious and philosophical traditions but also assumptions about the purpose or legacy of one’s life.

6. Ancient Wisdom as a Living Tradition (24:48–32:02)

• Philosophical “Recycling”:

  • Ryan and Arthur stress that most progress comes from adapting and remixing ancient wisdom rather than inventing something wholly new:

    “You’re not going to be doing good work unless you’re mostly recycling. So the body of knowledge, when it’s actually useful, is like sourdough bread, right? The starter is the most important thing…” (30:20–30:38, Arthur Brooks)

• Dangers of Utopianism:

  • Brooks warns against philosophies without a history of rigorous, centuries-spanning testing:

    “…when somebody comes out of left field with a completely new way of seeing human nature, it’s always wrong and it’s actually destructive and dangerous.” (31:15–31:30)

7. Aristotle: Happiness, Virtue, and Change (32:06–38:18)

• Dynamism as Reality:

  • Brooks: “He [Aristotle] said that change isn’t a distraction from reality, it is reality. That’s a big deal…that dynamism is the essence of reality itself.” (32:16)

• Eudaimonia and Suffering:

  • Happiness is not a fleeting emotional state but a meaningful process full of struggle:

    “Feelings are evidence of happiness…If you’re actually looking for the feeling per se you’re searching for a vapor. Happiness is enjoyment and satisfaction and meaning. That’s what happiness is all about.” (34:37–35:54)

• The Arrival Fallacy:

  • The duo discusses how focusing on outcomes leads to disappointment; fulfillment resides in enjoying “the suffering” and struggle of pursuing goals.

    “The real trick here, the real stoic trick is enjoying the suffering.” (38:55, Arthur Brooks)

• Human Duality:

  • Brooks: “Human beings have kind of two spaces…animal impulse and moral aspiration…Aristotle points out…that you can choose to stand up to Mother Nature, to stand up to your animal impulses and live in your moral aspirations. And when you’re making that choice, the suffering is free.” (39:16–40:28)

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Notable Quotes & Moments

• On Wisdom’s Universal Roots:
  “You just gave me, like, five people saying the same things.”
  – Ryan Holiday (06:20)

• On Humility and Learning:
  “Your enlightenment will come when you’re not blocking that Truth with yourself… The only thing I know is that I don’t know anything.”
  – Arthur Brooks (09:35–09:48)

• On the Purpose of Enlightenment:
  “The whole idea for you to find enlightenment is so that you can bring it to others.”
  – Arthur Brooks, referencing the Dalai Lama & Plato (15:55)

• On Philosophy’s Endurance:
  “You’re not going to be doing good work unless you’re mostly recycling. So the body of knowledge, when it’s actually useful, is like sourdough bread, right?”
  – Arthur Brooks (30:20)

• On Fulfillment and the Nature of Suffering:
  “The real trick here, the real stoic trick is enjoying the suffering.”
  – Arthur Brooks (38:55)

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Timestamps for Major Segments

• Philosophical Cross-Pollination: 03:48 – 08:31
• Socrates & Socratic Humility: 09:24 – 12:44
• Plato, the Cave, and Enlightenment: 13:15 – 16:50
• Cynics, Skeptics, Humor & Contrarianism: 18:30 – 22:29
• Nietzsche & Questioning Assumptions: 23:13 – 24:37
• Ancient Wisdom as Sourdough Metaphor / Dangers of Utopianism: 24:48 – 32:02
• Aristotle, Eudaimonia, and the Value of Suffering: 32:06 – 40:28

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Tone and Language

The conversation is intellectually playful, mixing academic rigor with humor and practical analogies. Both Holiday and Brooks are clearly passionate about the subject, frequently referencing writers from Seneca to Schopenhauer, Nietzsche to the Dalai Lama. The tone remains open, inquisitive, and often self-deprecating, with plenty of contemporary touchstones and relatable examples (e.g., writing books, running companies, or surviving family life).

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Why Listen?

This episode offers a lively crash course in ancient and modern philosophy, packed with insights applicable to finding meaning, embracing change, and harmonizing ambition with humility. Whether you’re seeking practical wisdom for daily life or inspiration to “bring enlightenment back to the cave,” Brooks and Holiday deliver timeless lessons in a fresh and entertaining format.

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End of Part 1:
Stay tuned for future segments diving deeper into Stoicism and connecting these philosophical themes to the art of living a meaningful life.

Transcript

[Ryan Holiday]

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[Ryan Holiday]

Welcome to the Daily Stoic podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice and wisdom, into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. Maybe you can hear that. I'm in my office and my kids are stomping around upstairs making quite a bit of noise. So I. I will keep today's episode short because I want to get right into it. It's with one of my Absolute favorite people to nerd out about philosophy. Someone who has done a whole hell of a lot to bring practical philosophy of all different types from all different schools to a huge audience, mostly through his column at the Atlantic and then through his bestselling books, including one he recently did with Oprah called Build the Life youe Want. Arthur Brooks came out to the Painted Porch here in Bastrop. I think he's been on the podcast more. Anyone else? Or at least close to, he's close to being inducted into what, the Four Timer Club or the Five Timer Club. I don't remember exactly, but I do remember this conversation because we talked about Socrates, we talked about Plato, we talked about the Cynics, we talked about Nietzsche, and what we can learn from these ancient philosophers about living a good life. Today, Arthur has a new book that comes out on March 31st. It's called the Meaning of youf Finding Purpose in an Age of Emptiness. And if you're feeling lost or struggling, you want to find purpose, which is what we're here to do. I think Arthur is a great resource in that regard. He's also going to be doing a free live workshop on March 27. You can listen to him talking with Rainn Wilson and Hoda Cobb, Chip Conley, Simon Sinek, Andrew Yang, Maria Shiver, Dan Buettner and Chris Williamson. And you can also grab his books here at the Painted Porch. From Strength to Build the Life youe Want and his new book, the Mean of your Life, Finding Purpose in an Age of Emptiness. Here is me, Arthur Brooks, digging in on ancient philosophy. What I'm noticing about your columns, tell me if I'm wrong, but I feel like you are going through the philosophical schools one by one and saying, like, here's something from each one, which I think people don't do enough, right? Because people are like, I'm a Buddhist, I'm a Stoic, I'm a Christian, and you're just. You kind of just stay in your lane, right? And obviously there's something about going really deep into one school philosophy. But what I like about the ancients is how familiar they were with all the other ancient schools. So I thought maybe we'd just kind of go through them. And one of my favorite lines from Seneca is he says he'll quote a bad author if the line is good. And he quotes Epicurus more than he quotes any of the Stoics, which I always thought was really interesting, that he was not just familiar with his quote unquote opponents, but he really liked their ideas. And he could engage with them. Yeah.

[Arthur Brooks]

There's a lot to take from all different ways of thinking.

[Ryan Holiday]

Yes.

[Arthur Brooks]

And when it comes to philosophy, by the way, it's the same thing with behavioral science. I can talk about the whole approach that I've taken to the study of happiness for the past seven years. I started off by figuring out what was wrong with it, and then I rebuilt it in a particular way that required that I have more than passing familiarity across a bunch of different disciplines and then within the different disciplines as well.

[Ryan Holiday]

Do you find that they're all saying really similar things, though, like, at the core, when they boil down that. That there are some essential truths that all the schools have?

[Arthur Brooks]

No doubt. I mean, no doubt that there is something behind it. There's a basic physics behind it.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

But it's funny. It's kind of like what. That's what Schopenhauer calls villa, which means will in English. And what that means is that's the ultimate truth that you can't actually see. And so you can get at it. You can get at it. That's the shadows on the cave wall for Plato, of course, that's what Hegel would call Geist, you know, that's the ultimate truth behind. Which means ghost. And for him, that was kind of God in its way. But you can only get it through a glass darkly, as St. Paul put it. And so this is all. This whole thing.

[Ryan Holiday]

You just did it. You just gave me, like, five people saying the same things.

[Arthur Brooks]

And we could look at Husserl or any of those guys or, you know, any of those subjectivists who would say that actually there isn't that, but that the reality comes to exist at the moment and at the point of your perception. Yeah, that's. I don't think that's right. I think there is an underlying objective reality, but you only get it by coming at it from many different perspectives. Because when you're sitting only in your home, it's through a grass, a glass too darkly.

[Ryan Holiday]

Well, I've kind of likened it to convergent evolution, where, like, different animals have similar adaptations. So you go, oh, it must have descended from a common ancestor.

[Arthur Brooks]

Right.

[Ryan Holiday]

And it's like, actually the common ancestor is just the need. Like, it's helpful to have an opposable thumb. Or flying is. Is a. Is a great way to escape from things that are trying to eat you. And so different species, bats and birds and, you know, apes and different animals have similar things, but you can't actually trace it back to, like, some one animal, one person figured it out and then everyone's a branch. Obviously. What's that line about where it's all table scraps from the feast of Plato or whatever? Sometimes it's that.

[Arthur Brooks]

Right.

[Ryan Holiday]

But a lot of times, like we actually don't have much evidence of the Buddhists and the Western philosophers overlapping. At least when the ideas were being formed later you're like, wow, it's very similar. And that's kind of the point.

[Arthur Brooks]

That's the point. So you just gave the biological metaphor for. Of the philosophical and the. Then there's of course the market metaphor. And the market metaphor is what Hayek talked about, which is called emergent order. Emergent order says you need lots and lots of people doing lots of different things in different ways in different places for different reasons. And then what'll emerge is a wisdom.

[Ryan Holiday]

Yes.

[Arthur Brooks]

The wisdom emerges from the micro decisions of people all over the place. The truth emerges as you see the similarities between different philosophers coming at it from different angles. The biology will actually produce certain phenomena on the basis of congruent need.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

And so it's the same basic idea. And that's why you have to be looking outside your tiny little worldview.

[Ryan Holiday]

Yeah. They're. They're trying to navigate ships at sea and they're figuring out different ways of doing it. But there's only so many ways to do it. And it turns out they come up with kind of similar.

[Arthur Brooks]

That's right.

[Ryan Holiday]

Innovations.

[Arthur Brooks]

And that's why academics are often so radically wrong while so unbelievably smart. Is because we are trained when we get our PhDs, not to do that. Precisely. To not do that. And so you can be just like as great as you could possibly be to try to be right but going in the wrong direction. You're getting better and better and better at walking 180 degrees off Truth.

[Ryan Holiday]

Sure, sure.

[Arthur Brooks]

And.

[Ryan Holiday]

And, but you're a specialist in X and so that's the fullness of your domain. You're not going, well, what if. What if there's something totally the opposite of X or in a totally different discipline or domain? You. You have tunnel vision.

[Arthur Brooks]

Exactly. That's why I started my career over on the basis of not doing that seven years ago.

[Ryan Holiday]

Let's start with some schools. Should we start with Socrates who brings the wisdom down from the heavens? What do you think Socrates has to teach your average person about life? Where. Where do we start?

[Arthur Brooks]

So the average person can learn from Socrates the basic idea of humility. That your knowledge that your enlightenment will come when you're not blocking that Truth with yourself.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

When you're not standing in the way with your own shadow of the truth. That's the Socratic idea that the only thing I know is that I don't know anything. That concept, yeah. Which is of course a contradiction in terms, but it's a beautiful contradiction in terms because when you basically say I don't know man, then what you're actually doing. So what Socrates would say, if you bring it forward to what a modern, semi modern psychologist would say, William James, the father of modern psychology, is that Socrates helps us go from the me self to the I self. The me self is that which I'm thinking about myself and my rightness. The I self is that in which I'm just looking at the world and learning.

[Ryan Holiday]

Right.

[Arthur Brooks]

And that's humility. The I self, he's just going around

[Ryan Holiday]

asking questions, not making statements, plus he's

[Arthur Brooks]

actually not reflecting on his own brilliance and rightness. It's sort of a non defensive understanding of the world. It's an openness to the rest of the world. It's a beautiful kind of outward focus on actually trying to learn things.

[Ryan Holiday]

One of the things I've been taking pains to point out about Socrates though is it's easy to see him as this intellectual figure. Like he's your academic, he's living off the largesse of the success of Athens, he's walking around in his toga. Life must have been simpler and easier then. But I think you point out, no, he's in the middle of a great power conflict. He serves in a war. He lives through the time of the 30 tyrants. Not everyone likes him. He lives in Athens as Athens is going through incredible turmoil. And like we think of it as classical antiquity. To him it was the most advanced time in human history and it was scary and uncertain and not the past.

[Arthur Brooks]

Yeah, and that's because we way in after any one of these phenomena. We have what's called what you have in your own life. What we all have is something that psychologists call fading affect bias. Fading affect bias is that which you look back on prior times, strip out the discomfort from those times, and only enjoy the learning that one got. And so fading affect bias in your own life is for everybody watching us right now, is that they went to college when they were 18 years old and they were incredibly lonely and unhappy and calling mom every single day, I'm so come pick me up, I hate it. And then they go back for their 10 year reunion and 20 year reunion for college and they're seeing their friends that I met in their first semester of college.

[Ryan Holiday]

Best years of my life.

[Arthur Brooks]

Best years of my life. That's fading affect bias because they learned a lot and made great relationships. And the discomfort of the moment wasn't there. The discomfort that was. Socrates's own life is stripped away and is completely irrelevant. Even though it was the most important thing to him.

[Ryan Holiday]

He had a shitty marriage. Like, that's one of the things you hear him talk about all the time. And everyone knew. It's like Socrates did not make a great marriage choice. They did not get along. And part of what allowed him, he saw even that, though, as a kind of a philosophical practice. Right.

[Arthur Brooks]

And indeed there are things that each of us deal with all the time. You know, we have children and soon enough you're going to have teenagers. And let me tell you, it's super fun. And these are difficult things that occupy most of your brain space. The current difficulties. And you know, it's a mess, your life is an actual mess. But the things that you're doing that will be passed on are not the current mess. It's the salient truth that you'll be able to uncover from time to time. And that's what people remember about Ryan Holiday. And that's a lot about what you'll remember about these years for yourself as well.

[Ryan Holiday]

Yes. Okay, so Plato comes from Socrates. What do you think Plato's main teaching for people is?

[Arthur Brooks]

There's so much. I mean, there's so much. For me, as we were talking about a little bit earlier, this is the first time that we start to see there's a truth, there's a transcendent truth, but we're changing all the time. The changes are kind of a distraction from the ultimate truth, but there's an ultimate truth that underlies all of this stuff. And a lot of people, by the way, are true Platonists. They're true Platonists because they believe that change is extraneous and the unchanging is actually the reality. And that's a very, very Platonic ideal of what's going on. And that's the whole idea that came to all the way up to the 19th century Existentialist philosophers and even absurdists who said there's an underlying truth. I mean, Hegel, Schopenhauer, et cetera, they believed that too. And they were highly Platonist in this way.

[Ryan Holiday]

And you mentioned the cave. I think cave is the, the allegory of the cave is one of Plato's most interesting concepts, which is the idea that there is this truth. But Most of us are looking at shadows. We're chained in a cave, he said, and we can sort of see out on the outer parts of the cave, light being reflected. And we see these shadows. We don't know what they are.

[Arthur Brooks]

It is a reality. And all we get is the shadows. And we have to do the best that we can with the shadows to figure out what's going on.

[Ryan Holiday]

Yes.

[Arthur Brooks]

Right.

[Ryan Holiday]

And then we escape from the cave.

[Arthur Brooks]

Exactly right. But there is this truth, unchanging truth.

[Ryan Holiday]

Yes.

[Arthur Brooks]

And all we. The dynamics and things of it are what confuse us, and we have to sort of triangulate across the images as best we can.

[Ryan Holiday]

Yeah. And we discover what this truth is, having left the cave.

[Arthur Brooks]

Right. Our obligation.

[Ryan Holiday]

Yeah. What is what Cato says?

[Arthur Brooks]

Is it Plato's cave or Cato's play?

[Ryan Holiday]

Yeah, exactly. So. So Plato says, you escape from the cave, you get some sense that, oh, what I was looking at before are only shadows. As I understand it, he believes that then the role of the philosopher, the human being, is you're obligated to try to come back and communicate to the other people in the cave what those shadows were.

[Arthur Brooks]

Right. Your obligation is, once you actually have greater enlightenment, is to share that particular enlightenment, which goes forward into all sorts of schools that people aren't even aware of.

[Ryan Holiday]

Well, Buddha wrestles with this exact thing.

[Arthur Brooks]

Well, this is super important. And so, you know, I've worked at the Dalai Lama for the last 12 years, and the Dalai Lama says that you can't actually benefit from meditation until you stop trying to get the benefit from meditation. I say. He says, this is why I tell Westerners not to become Buddhist, because they're doing it for the wrong reason. I said, what's the wrong reason, your Holiness? And he says, you want to meditate so you feel better. You need to meditate so the whole world will feel better. That's an incredibly platonic idea.

[Ryan Holiday]

Yes.

[Arthur Brooks]

Right. The whole idea for you to find enlightenment is so that you can bring it to others.

[Ryan Holiday]

Yeah. Buddha wrestles with, should I just continue to pursue my own enlightenment or should I teach enlightenment? Should I take on students? And there are. Is this kind of obligation. And I think you could trace it to this idea in Plato, but in all the schools of thought, that with insight and understanding and wisdom comes responsibility.

[Arthur Brooks]

Right. And so the whole concept is, what does the monastic life mean under the circumstances? And that's a really interesting medieval Christian idea, actually, from the time of St. Benedict and the 6th, 7th, 8th centuries early on, but then into the Middle Ages of the Scholastics. What are you supposed to do if you're actually monastic and the whole idea is teach other. Other people, like St. Thomas Aquinas? Or are you supposed to actually just pray for other people?

[Ryan Holiday]

Yeah.

[Arthur Brooks]

And. Or are you just supposed to be a pure contemplative.

[Ryan Holiday]

Right.

[Arthur Brooks]

What is the right approach to that? And Plato would have a strong view.

[Ryan Holiday]

Well. And the Stoics and the Epicureans have this debate, too. Should we participate in public life or not?

[Arthur Brooks]

Right. And what does it mean to participate in public life? Of course, there's another wrinkle on that.

[Ryan Holiday]

Yes, of course. We'll get to them in a second.

[Arthur Brooks]

Because you are. Even though presumably you're not going to run for public office.

[Ryan Holiday]

Yeah, I do. I do think the ancients had a much more limited definition of public life because there were only so many ways to contribute. Running an enormous company that employs thousands of people might be making a far bigger difference than being a senator.

[Arthur Brooks]

And also, yet you're a lot more in public life, like Plato. You personally, you're doing the public intellectual gig. It's just that you have the means to disseminate these ideas way, way, way beyond anything he could have imagined.

[Ryan Holiday]

Yes. And although the irony is I had James Raman here, and he wrote this book, Plato and the Tyrant. Plato's forays into politics are a cautionary tale against thought leaders and intellectuals, sometimes participating in public life because you're. Well, he was an easy mark, which is interesting.

[Arthur Brooks]

Easy mark.

[Ryan Holiday]

For Dionysus the tyrant. He goes and he advises a king who is making pretensions about wanting to be a philosopher king, but really wants to be a tyrant with the propaganda and the reputation. Yeah, exactly. And Plato is complicit in it, in the way that, you know, a generation later, many generations later, Seneca and Nero fall into the same.

[Arthur Brooks]

And in other words, intellectuals are easy to roll.

[Ryan Holiday]

Yes, yes. Because you don't have the experience and you don't even. You don't necessarily even understand what you represent to the people in power and how you can be a tool for that.

[Arthur Brooks]

Yeah.

[Ryan Holiday]

Okay. So what about the cynics? I find the cynics to be fascinating, Diogenes being the most famous of them, but I feel like they have a lot to teach us in today's very materialistic world to begin with.

[Arthur Brooks]

We don't understand them.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

Because we cast aspersions of people who are cynical.

[Ryan Holiday]

Yes.

[Arthur Brooks]

I mean, the whole idea of the skeptics and the cynics, different schools, of course, that there's something that's kind of suspect about the character. You know, you don't want to be a cynical person because you're just negative all the time. And that's exactly getting it wrong. You characterize this, the school of cynicism.

[Ryan Holiday]

I say they're like the punk rockers of the philosopher world. They are transgressive and radical, and they are, by taking it too far, actually providing us insights about sort of a moderate middle ground. Like, if. If everyone lived as Diogenes lived, the world would be a horrible place. But if everyone lived according to ambition and trying to, you know, make as much money and get as much power and valued all the wrong things, you also get a really bad society. And he's the. Not the court gesture, because that's almost too dismissive. But. But in sort. He's like the hippie sort of like, none of this matters, man. You know, like.

[Arthur Brooks]

And in so doing that matters, he's saying, this is stupid.

[Ryan Holiday]

Yes.

[Arthur Brooks]

So it's worse than whatevs.

[Ryan Holiday]

Yeah. It's making fun of your suit. Yeah. And your tie and your fancy car. Right. And, I mean, the famous story about Diogenes that I love is, you know, he has very few possessions, but he. He walks up to the well and he gets a cup of water, and a young boy runs up and gets water from. With his hands. And Diogenes realizes that even here, having reduced what he thought his needs were to nothing, actually has one more that he can get rid of. And he smashes his cup on the ground.

[Arthur Brooks]

What a piece of work. Imagine me marrying that guy.

[Ryan Holiday]

Yes. I don't think you want to. Although, you know. So Zeno, the founder of socism, his philosophy teacher was named Crates. I'm forgetting Crates. Wife's name. But she was a famous cynic philosopher too, so we tend to think of it as this primarily male world. But there were fascinating cynical philosophers in marriages, which, you know, if they were totally abstaining and rejecting all convention, they would have rejected even that. Yeah. So.

[Arthur Brooks]

And then the skeptics who just knew nothing. Yeah, I just. I know nothing.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

Who. Who just. They banked on knowing nothing. So no matter what they said. I don't know.

[Ryan Holiday]

And sometimes the extreme cases tell us something like it's not exactly a defensible position or a scalable position, but in the extremeness of it, gives us color and another angle to understand ourselves.

[Arthur Brooks]

Right. And there's a humility to it. Yes, there's a real humility to it. So there's. There's a kind of a. A pose with the Cynics. And there's. There's an anti pose with the skeptics. And so they're quite different in this particular way. The cynics are interesting because what they do is they can make you realize that life is hilarious.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

By the way, you go fast forward in history and you find that a lot in Nietzsche. So the whole competitive set of ideas between what the Greeks were doing, which is that essence precedes existence, and then what the existentialists were doing in the 19th and 20th centuries, which is that existence precedes essence. In other words, meaning either comes before you're born or you're born and then you find your meaning. That's the big conflict between ancient philosophy and Christian philosophy and all the things that you and I are stocking, trade and what the modern existentialists do. And Nietzsche's like, no, no, no, no, no. There is no essence. There is no meaning. It's like, so how am I supposed to live just to have a good laugh, man. Just have a good laugh.

[Ryan Holiday]

Well, the humor of the philosophers is not something I think your average person is clued in on. Right. Like, because philosophy seems dry, philosophy seems academic, philosophy seems confusing. And then you read it's all of

[Arthur Brooks]

the above in many cases.

[Ryan Holiday]

But you read Diogenes the cynic, and you're like, oh, this dude's fucking hilarious. And he's a badass. Like, he goes up to Alexander or Alexander the Great, comes up to him as he's sunbathing, and Alexander the Great says, I'm the most powerful man in the world. What can I do for you? And Diogenes looks at him, having reduced his needs to nothing, and says, you can stop blocking the sun. Get out of my way. And you know, that's like, that's not just funny, but it's. It's badass.

[Arthur Brooks]

Yeah. And Nietzsche's hilarious too, by the way, and probably the best writer of all of the. All the 19th century absurdists and existentialists.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

He's a beautiful writer. Incredible writer. It's really, really worth reading Nietzsche, even in English.

[Ryan Holiday]

Well, let's fast forward. What do you think Nietzsche has to teach people? Where would you go?

[Arthur Brooks]

You truly question your understanding of essence and existence.

[Ryan Holiday]

Okay.

[Arthur Brooks]

And it's really, really worth understanding it because the biggest problem, philosophically and by the way, scientifically and in terms of almost everything that we do, is an inability or unwillingness or just an ignorance about our own assumptions going in. That's a huge problem because it's garbage in, garbage out effectively. But that doesn't mean that your assumptions are garbage, but if you don't question them, it's very, very hard to grow because you're constrained to the philosophical outline that you've been given, your assumptions. And a lot of what Nietzsche is talking about is questioning this fundamental algorithm of life, which is, did your life have meaning before you were born or were you born and have to go find your life's meaning? And he breaks it all apart like smashing his cup.

[Ryan Holiday]

And he has a lot more to question. Socrates has a couple hundred years of philosophy to question. Nietzsche has 2,500 years and 2,500 years of, you know, Christian teachings too. So he's inherited a stabler world, sort of.

[Arthur Brooks]

Although I strongly suspect that Socrates was relying on a lot that simply wasn't written down.

[Ryan Holiday]

Yeah. The pre Socratic philosophers and who are

[Arthur Brooks]

very sophisticated, but we don't know. And what Nietzsche had was a lot of stuff that had been written down.

[Ryan Holiday]

Yes.

[Arthur Brooks]

And so the Socratic tradition was writing stuff down that had been preserved in the oral tradition.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

And who knows what's a bigger library. That's true.

[Ryan Holiday]

That is the interesting thing about the ancient world is we tend to compress it down into this period. We go, Socrates, Aristotle, Plato, they're all kind of around the same time. Diogenes is in there. And you're like, Zeno to Marcus Aurelius is like 600 years.

[Arthur Brooks]

It's like 300 BC to 300 AD

[Ryan Holiday]

or something like that swath of time. They would have been like, Marcus. The Roman philosophers would have come to Greece as tourists and said, look at these ancient ruins.

[Arthur Brooks]

I know, I know.

[Ryan Holiday]

You know, And. And it's like going.

[Arthur Brooks]

Looking to the Liberty Bell in Philadelphia or something.

[Ryan Holiday]

Yeah, yeah, yeah. But much older in many cases. Right. Like it would have gone through. It would have been built and rebuilt and then destroyed by an earthquake and then ravaged by the Persians and then rebuilt. They would have just seen generation after generation and generation. They would have experienced it differently. They would have been still polished and shiny in some cases, like they would have. They would have come and gone. The smartest people who ever lived centuries ago walked where I'm walking and it's like we're all tourists. Going back to this period is kind of a beautiful.

[Arthur Brooks]

It is. And the thing, however that's worth, I think it's always worth remembering is that, no doubt, in the time of Socrates, he was looking back to philosophies that have been. That he could chart back to the ancient Egyptians.

[Ryan Holiday]

Yes.

[Arthur Brooks]

And so Socrates was as far ago from us. Us as the Egyptians were to him. And that's a long time ago. And if we move over to India, for example, I mean Hinduism is a 6000 year old religion. Lord Krishna lived in Mathura in the Hindi heartland 6,000 years ago. And there's a little bit written, but the whole point is that the idea has reached us and for us to say knowledge is limited to what's been written down in books is like for our kids to say knowledge is limited to what's on the Internet.

[Ryan Holiday]

Internet, yeah.

[Arthur Brooks]

It's the same basic idea and that's actually obviously not true for all sorts of reasons.

[Ryan Holiday]

Look, I like home cooked meals. I just don't like the process of getting all the stuff to then cook at home. I don't like having to think about dinner and I like when it's time for dinner. I want the dinner pretty fast but then I also want to eat well and I like stuff that tastes good. That's like a pretty complicated set of needs there. And it actually fits perfectly with today's sponsor. And it's why we love HelloFresh. They take the mental load of what's for dinner off your to do list. HelloFresh makes it easy to do more home cooking with recipes that feel good and taste delicious night after night. They have more than a hundred recipes every week. It doesn't matter what your allergies or preferences are, you can make something work. They've got three times the seafood with no upcharge and you can even have guests over. Make them grass fed steak ribeyes or serve seasonal produce like pears and apples and asparagus. We love HelloFresh and I think you'll love it too. Just go to hellofresh.com stoic10fm to get 10 free meals and a free Zwilling knife which is $145 value on your third box. Offer is valid while supplies last. Free meals applied as a discount on first box. New subscribers only varies by plan. We've got an employee here at Daily Stoke. I won't say who because it's kind of private, but they've been using Monarch, Today's sponsor, to track their progress as they try to pay off their student loan debts. I'm a college dropout so I don't have any debt, thankfully, but I can only imagine how overwhelming it would be to have this thing hanging over you. And she's been using the app to budget and save and it's bringing her a little bit closer every day to being debt free, which I can only imagine would be a huge relief. Monarch shows you exactly, exactly where your money is going. It helps you redirect it towards what matters. With automated tracking and clear projections, you can actually see yourself getting closer to being debt free or hitting your savings milestone instead of just hoping it happens. Unlike most other personal finance apps, Monarch is built to help make you proactive and not just reactive. And Monarch helped users save over $200 per month on average after joining. You can set yourself up for financial success in 2026 with Monarch, the all in one tool that makes proactive money management simple all year long. And you can use code stoiconarch.com for half off your first year. That's 50% off your first [e-mail] code stoic. Yeah, that this is a thing that goes way back and sometimes we'll read, yeah, we read something from Socrates or you read something in Meditations and you go, that's a beautiful idea. And you don't realize that that is them riffing on things. Like, what I love is there's this play by Joseph Addison called Cato that was popular in the 18th century. And once you read it, you go, oh, like 80% of what the founders were saying was just them quoting this play. Like we might say immigrants. You get the job done. Or like you quote the Godfather or something.

[Arthur Brooks]

It was a cultural touchstone at the time.

[Ryan Holiday]

You lose the illusions that they're riffing on. And in some cases, if you really go in, you go, oh, actually, okay, the footnote is telling me comes from a play, from a line from a play by Euripides or whatever. But if most of it was oral, we wouldn't know that. Actually. Socrates is a recycler.

[Arthur Brooks]

Yeah, yeah, of course he's a recycler. That's the point. And that's exactly sort of the whole point of what we're discussing here. You're not going to be doing good work unless you're mostly recycling. So the body of knowledge, when it's actually useful, is like sourdough bread, right?

[Ryan Holiday]

Sure.

[Arthur Brooks]

And that means it has this old thing in it.

[Ryan Holiday]

It. Yeah.

[Arthur Brooks]

And that, yeah, the starter is the most important thing in sourdough. That's the most important thing. And it can be really old or, you know, the yeast and bread can go back literally the ancient Egyptians is what it comes down to. And if you don't have it, you don't have bread. And, you know, the truth is that. And it's probably, you know, you know, as, you know, you and I, we Do a lot of talks on the outside is kind of what we do for a living. And you know, 20% of a. Has got to be some old stuff that you've been working on and the jokes that you know that work and the big ideas. And that's the spine of your talk, of your new talk. Yes, if it's 100% new, it sucks.

[Ryan Holiday]

Yeah. Because you're doing it by trial and error with a new audience.

[Arthur Brooks]

And this is a profoundly conservative worldview, by the way, but I think it has the virtue of being largely correct, is that when somebody comes out of left field with a completely new way of seeing human nature, it's always wrong and it's actually destructive and dangerous.

[Ryan Holiday]

Well, it hasn't been tested in actual human experience yet and it hasn't been through boom times and depressions, wars and. And like, yeah, if you came up with some totally new philosophy, it might sound really great, it might work great in a TikTok, but does it have a thousand years of human.

[Arthur Brooks]

That's the problem with utopianism. That's the problem with utopianisms all throughout history is that they've always been a failure and led to, you know, large scale destruction, death and suffering precisely because they're not sourdough.

[Ryan Holiday]

Yeah, you gotta take something. Old wine and new skins, as they say.

[Arthur Brooks]

Yeah, I mean, the problem with that is that. That of course is from the gospels and it says that old wine and new skins breaks the new skins.

[Ryan Holiday]

Well, we skipped Aristotle. Give me something from Aristotle.

[Arthur Brooks]

So of course Aristotle was almost forgotten until the Middle Ages and considered, you know, and also ran to Plato because everybody was a Neoplatonist in the Middle Ages. So by the time you get to the 12th and 13th centuries, you know, you have Averroes and you have Maimonides and of course Thomas, Aquinas from the three great southern European and Abrahamic traditions. And they were all Platonists. They were all Platonists, but especially Aquinas. He rediscovered Aristotle and brought Aristotle to what at the time was a modern audience. And he said, this is the guy. This is the guy. I mean, Plato's okay, but Aristotle, he's the guy. Why? Because he was a full spectrum scientist. But there was also this one weird thing that he did that Plato didn't do. He said that change isn't a distraction from reality, it is reality. That's a big deal. That's the whole idea that dynamism is the essence of reality itself. And so you as a person are different than who you were and who you're going to be. And that change, that first derivative of Ryan Ness is the essence of Ryan Ness. And that's a pretty big deal when you think about it, because that's just the dynamic understanding of oneself and to be celebrating the change. And that has a lot to do with how we understand modern behavioral science. We, I mean, the, the underlying unchanging essence of ourselves is not very interesting to us. What we want to make is progress.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

We're just like progress, progress. That's the essence of what a good life is really all about.

[Ryan Holiday]

When his point that virtue is something not that you have as an essence, but is something you are doing and getting better at doing.

[Arthur Brooks]

That has been super, super influential in my own work.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

Which is this one third philosophy, 1/3 neuroscience, 1/3 behavioral science.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

Is kind of the, the three PI, the parts of the pie, as I'm putting it in there, that I started off doing this work years ago saying I want to find the secret to happiness. And that's wrong because you can't be happy. What you can be is happier, which is an Aristotelian notion as opposed to a Platonic notion. You can get happier. And the goal is putting yourself, your life, on a jagged, messy path toward happierness.

[Ryan Holiday]

And his definition of happiness, Eudaimonia, maybe give us that definition. Because it's not, I think when people think happy, they think grinning from ear to ear, living your best life. And it's not quite that.

[Arthur Brooks]

Well, it's not that at all, actually. So the biggest mistake that the moderns make is thinking that happiness is an emotion. Happiness is a feeling. It's not. It's not even one of the basic emotions. According to behaviorists who do work on emotions, the basic emotions researchers, happiness has feelings associated with it like, like Thanksgiving dinner has a smell. So feelings are evidence of happiness, which is really, really important thing to keep in mind. Because if you're actually looking for the feeling per se that you're searching for a vapor, you're going to be about as nourished as if you were trying to get the ultimate smell experience on Thanksgiving Day. Happiness is enjoyment and satisfaction and meaning. That's what happiness is all about. And that experience of going from pleasure to enjoyment, which is what it means to grow up, up and be a responsible person, but also to be a happier person, to derive satisfaction, which is joy that comes from accomplishment after struggle and meaning, finding the meaning of your life, the why of your existence. There's tons of suffering in that, tons of suffering in all three of those Bins, which is, you know, and that's very Aristotelian. Eudaimonia means a good life, well lived. There's actually. There's not an adequate translation. I mean, everybody. We all struggle with, actually. What does eudaimonia mean? It's the good life. And the good life has lots of suffering in it.

[Sponsor/Ad Voice]

It.

[Arthur Brooks]

And so therefore, the modern eliminationist strategy, which is to say that if you're feeling sad and anxious, you're broken and you need therapy, that is profoundly anti Aristotelian, but it's also an exercise in futility because you can't get enjoyment, satisfaction and meaning unless you're like, suffering. Bring it on. Which is stoic, by the way, of course.

[Ryan Holiday]

Yeah. He's saying that you have to be doing the things that humans were meant to do, and specifically, what were you meant to do? So it's a lot of. Like when people say, I gotta find my purpose, like, that's what Aristotle is saying. When you get there, you're a lot closer to happiness than anything else.

[Arthur Brooks]

Which is why, you know, Aristotle was a great theorist. And the Stoics are very practical. I mean, they're working out Eudaimonia. That's the Stoic philosophy is like, how do we do this thing? How do we get this Eudaimonia? And, you know, a lot of it is like, get the hell out of bed.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

You know. Yeah. Which is this. And is extremely Aristotelian. And it's.

[Ryan Holiday]

Yeah. I think that, like, this is more stoic than Aristotelian, but it's like, what are the things that I'm glad I did after that I hated while I was doing it? Like, going for a run, you feel great after. It's not that fun. While you're doing jumping in a cold plunge. You're not. You don't love the period of jumping in. You don't love as you come up for it, but you love 20 minutes after.

[Arthur Brooks]

Yeah. Let me ask you a question. Do you love writing books or having written books?

[Ryan Holiday]

Well, they said that's the joke, that painters like painting and writers like having written.

[Arthur Brooks]

Yeah.

[Ryan Holiday]

I try to make a distinction between writing and publishing. Writing is in my control. Publishing is not. So, like, sure, am I glad to be done with a book? And is there something about that? Because books involve suffering and as all projects do. So I get that. I do make a distinction, though. Like, I actually try to work on enjoying doing the thing because it's the only part of it that's up to me.

[Arthur Brooks]

Yeah. And that's a really important thing to keep in mind because there is a lot of suffering. But in the dynamics of the whole thing, if there's nothing good for you in the journey, then you'll find fault prey. Sure. As we're sitting here to the arrival fallacy, a very well known phenomenon that says when I get to the end, then I will feel pure bliss.

[Ryan Holiday]

Yes.

[Arthur Brooks]

Which is. It's axiomatically wrong.

[Ryan Holiday]

If the whole thing is suffering, then you need external results to make it worth the suffering. You have to figure out how actually you enjoy practice like you enjoy the doing of the thing.

[Arthur Brooks]

And then the question becomes, which is a very stoic and both Aristotelian kind of a stoic.

[Ryan Holiday]

Yeah.

[Arthur Brooks]

You know, he set the ships in motion, I guess.

[Ryan Holiday]

Yes.

[Arthur Brooks]

Is how much did you enjoy the suffering?

[Ryan Holiday]

Yeah.

[Arthur Brooks]

See, this is the thing people are like, they try to dichotomize and they say the process should have enjoyment, but it also has a lot of suffering. And if you only suffer so you can get to the enjoyment at the end, the arrival fallacy will hunt you down and kill you like a dog. Which means you'll be more. You'll win the Olympic gold and be depressed for six months because you're like, you feel like your life is over. The real trick here, the real stoic trick is enjoying the suffering.

[Ryan Holiday]

Yes.

[Arthur Brooks]

Do you enjoy the suffering?

[Ryan Holiday]

I do, I do. I've had to work on it. I don't think you're just naturally there because there's this part of you that wants to avert and avoid suffering wherever possible. But then I try to go, oh no, this is actually like a dream, like I get to do this, this is my job, I'm very lucky. And I try to enjoy it and then try not to rush through it also.

[Arthur Brooks]

And this is probably the most profound Aristotelian point of all, which is because he was, he was a good biologist as well as a philosopher. And he asserted in many, many places in the writings that human beings have kind of two spaces that they can live in. There's animal impulse and there's moral aspiration. Animal impulse and moral aspiration. And now we know why. The reason that we actually have a choice of living in one of these two spaces is because we have a prefrontal cortex that's astonishing in its complexity beyond any supercomputer that exists or will exist. I mean, it's one third of our brain by way weight. And you know, your dog's prefrontal cortex is wafer thin, which is why it has only animal impulse. But if you follow what Mother Nature is telling you, what your urges are, all you'll do is the things that will immediately slightly raise your odds of survival and passing on your genes. Aristotle points out, as do all the good philosophers and religious traditions, that you can actually choose to stand up to Mother Nature, to stand up to your animal impulses and live in your moral aspirations. And when you're making that choice, the suffering is free. Yes, that's the point. This is. This is. I mean, this is a key point of aerosol and everybody else. By the way,

[Ryan Holiday]

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

[Sponsor/Ad Voice]

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