Joe: I'm excited to welcome our guest today, Ryan Holiday. Ryan is the host of The Daily Stoic Podcast and the best selling author of Courage Is Calling, The Daily Stoic, The Obstacle Is the Way, and other books about marketing, culture, Stoicism and the human condition which have sold more than 2 million copies in 30 languages. His work has directly influenced Super Bowl winning teams like the New England Patriots, NBA champions like the San Antonio Spurs and Olympic gold medalists, as well as sitting senators and military leaders. Ryan has also written for The New York Times, USA TODAY and The New York Observer.
Ryan had a successful marketing career at American Apparel, and then founded a creative agency called Brass Check which has advised clients such as Google, as well as many prominent bestselling authors, including Tim Ferris and Arianna Huffington. Brass Check is also the creator of the incredibly popular email newsletters, Daily Stoic, Daily Philosopher, and Daily Dad.
Welcome, Ryan. I'm so thrilled to have you here. I have been enjoying your books and I thought maybe just to start things off: can you tell us what Stoicism is and how you personally first became interested in it?
Ryan: So my working definition of Stoicism ... I like to define it as a philosophy that says we don't control what happens to us in life, but we control how we respond to what happens to us in life. And so it's really a philosophy focused on one's emotions, one's attitudes, one's mental models for seeing and understanding things and then it focuses — as far as one's actions go — less on trying to do things at the enormity of the global stage [but instead it] tries to focus on what we can do as individuals in the world.
My introduction to Stoicism came as a teenager. I was 19 years old and someone handed me Marcus Aurelius's Meditations, which is of all the works, not just of Stoic philosophy, but of ancient philosophy, it's not an explanation of the universe, it's not a bunch of philosophical theories, it's not even arguments about what Stoicism is. You know, the word “Stoic” never appears in it. It's the most powerful man in the world writing notes to himself about trying to be better. He's the emperor of Rome. He's the head of its armies. And he's trying to keep his temper in check. He's trying to face his mortalities, dealing with a plague. He's dealing with temptation and the corruption that happens when one is quite powerful and well known. And so what I love about Stoicism is that it's this individual journey of self-improvement that I think we'd all like to go on, but we don't exactly assume that philosophy is the roadmap for that.
Joe: And why do you think that is, Ryan? Why do you think that we normally think of philosophy as something other than practically useful for figuring out how to live our lives?
Ryan: I was talking yesterday at a bank in Oklahoma and I put up the famous picture of Plato's academy. And, you know, I was saying that when you look at all these old white guys in their robes, it doesn't exactly scream “modern solutions to modern problems.”
Ryan: And then when you get into these names that you can't pronounce, asking questions to which there's no answer: The Trolley Problem, or “How do we know if we live in a computer simulation?” or something. These are all intellectually interesting ... “How do you know that good and bad exists?” “What happens after you die?” These are all, again, interesting questions. Take “How do we know if we live in a computer simulation?” we could talk about that, but let's say you could definitively prove that we do, what am I supposed to do with this information? It doesn't change the fact that my kid was up late last night, it doesn't change the fact that I have a stressful job. You know, it doesn't change any of this stuff. It's still there. Our questions about whether [life] has meaning, how to be good at it, what happens after, you know, all those questions nevertheless remain. And so I think as philosophy became more specialized, more ensconced in academia, it became less and less applicable to real people with real problems, which is so ironic. Because again, Marcus Aurelius is not a professional philosopher. Marcus Aurelius is a professional emperor. The Stoics had jobs and philosophy was this thing that helped them with their jobs, as opposed to being their primary profession.
Joe: There are a couple of other pretty famous Stoics that you identify in your books that have very different jobs. Could you say a little more about some of the other roles people had that still use Stoicism for their life?
Ryan: Yeah. In my circles, we refer to them as the big three. There's Marcus Aurelius, the emperor, there's Seneca, who is a senator, a playwright, and Rome's most powerful political advisor [or] consigliere at the time. He becomes the tutor to the future emperor who becomes Nero. And Seneca is trying to prevent Nero from spinning off the planet. And then there's Epictetus. Epictetus, not having written anything down, but actually being a slave in Nero's court. So it's really remarkable: I think if one was to only look at two Stoics, I think Epictetus and Marcus Aurelius captures the full spectrum, not just of Roman life, but the full spectrum of adversity and privilege that exists even to this day.
I would argue that one of the places that the Stoic tries to get to is a place of freedom: freedom from disturbances; freedom from want; freedom from fear; freedom from all the things that make us unhappy or enslave us. And so if you can think then about Epictetus and Marcus Aurelius being on the same journey but facing very different circumstances, it gives you a sense of what Stoicism can do. So Epictetus is literally enslaved, literally in chains, and trying to find freedom inside himself.
Ryan: Now Marcus Aurelius is in an enormous palace, commands enormous armies, can do essentially anything he wants, but anyone who's had fame or power or influence understands that this too is not exactly a walk in the park. There are temptations and also burdens that go along with that. And so I see them both being on very similar journeys, and I think this is why Epictetus speaks to Marcus so strongly when he first picks him up.
Joe: So you pick up Marcus Aurelius as a 19-year-old, and you're reading the private reflections of an emperor trying to be good at being an emperor.
Joe: And are you thinking about this the way some 19-year-old boys do, “Oh, good: preparation for when I'm emperor”?
Joe: What's hitting you about it? What was it that drew you in?
Ryan: I think … in the way that really great comedy is very specific, but thus universal … You could be listening to a comic on the way up and they're talking about, you know, ordinary humdrum life, and it's very relatable. And then this comedian becomes extremely successful, they're flying around the world in private jets and they're in movies, and still the comedy is very funny because the specificity of their experiences is touching something that is common to all of us, right?
And so what I found so lovely about Marcus Aurelius is he's really not saying, “You know, it really sucks when you're trying to tell the Roman legions to go invade a foreign land and they don't listen.” That's not what he's talking about. He's talking about ... for instance, he opens both Book II and Book V of Meditations with the feeling that you have when you wake up in the morning. Book V is about how you're tired “but it's warm under these covers.”
Ryan: And then he says to himself, “but is this what you were put here to do, to stay under the warm covers?” And so, you know, to me, that's very relatable, not just across the centuries, but a college kid in his dorm room and an emperor in his palace, they're both like, “Do I have to do anything today?”
Ryan: But in Book II, Marcus Aurelius is talking not just about waking up early, but he is like, "Here are the people you're gonna meet today. You're going to meet jealous people and stupid people and frustrating people and envious people and bitter people and silly people." And he says, "if that surprises you, that's on you. You've been around long enough to expect this." And then he talks about not just “the day is gonna suck: be ready for it.” He's saying that you can't let those people implicate you in their ugliness, and that you have to understand why they are the way that they are, and that you have to love them despite that.
And so again, I think what really struck me at 19, struck me in my twenties, what strikes me now even rereading Marcus Aurelius [in] the last couple of years, is realizing, “Oh, he was writing in the middle of the Antonine Plague.” A lot of these references to pestilences or disease or plagues, that wasn't figurative. He was talking about actual experiences. And so I think what made Marcus so relatable then and now is that he's talking about what it means to be a human being in the world, not what it means to be the head of the Roman empire.
“I think what made Marcus [Aurelius] so relatable then and now is that he's talking about what it means to be a human being in the world, not what it means to be the head of the Roman empire.”
— Ryan Holiday
Joe: Thanks for that. Thinking about the two of them, again, just for a moment, what is it that they both imagine they have control over? Because it seems like an emperor and a slave probably have different spheres of influence.
Joe: So yeah, what's the common thread there?
Ryan: Well, you know, it's funny. Epictetus, looking out over Nero's court, realizes that all these people who are very powerful and very rich are probably less free than he is.
Ryan: Right. He describes watching this very powerful man suck up to Nero's cobbler because he wants to get on Nero's good side. So he watches these people debase themselves because they're afraid, because they want something, and because they're prisoners to their ambition. And I think Epictetus realizes pretty quickly that obviously physical liberty is very important, right? Epictetus walks with a limp his whole life because his slave master breaks his leg at some point. So obviously he's not discounting physical freedom, but I think he understands that freedom from an unquenchable ambition; freedom from greed; a freedom from ego; a freedom from caring what other people think about you ... these are more accessible freedoms that a lot of people, even who have physical freedom, take completely for granted.
So I think at the core of it… actually Epictetus says this is the first job of the Stoic philosopher is to distinguish the things that are outside of our control from the things that are inside of our control. Even Marcus Aurelius can't control that six of his children die before adulthood. He can't control that an Antonine Plague happens. He can't control that Rome is invaded by tribes at its borders. He can't control the flood that happens. He can't control 99% of what happens, right?
Ryan: Even this all powerful person has relatively circumscribed power. Ultimately what he controls is what he thinks and the decisions that he makes.
“The first job of the Stoic philosopher is to distinguish the things that are outside of our control from the things that are inside of our control. Even Marcus Aurelius can't control that six of his children die before adulthood. … He can't control the flood that happens. … Even this all powerful person has relatively circumscribed power. Ultimately what he controls is what he thinks
and the decisions that he makes.” — Ryan Holiday
Joe: When they were talking about control over their decisions — or when you think about it now — what does that entail for you?
Ryan: Sure. I mean, obviously they had a somewhat more rudimentary understanding of how the mind works, so they were less aware of biases. You know, we don't get a lot of discussion of mental illness or things like that. But I think largely they understood the power of reason and that our mind is this superpower that we have. And, you know, how many of us just refuse to use it or fail to use it. Instead we react emotionally, instead we react instinctively. We focus our energy on stuff that's immovable, unchangeable, that already happened. As a result, we relinquish this power we have, which is: to change how we think about [situations] to change how we respond to [situations]. To me, that's what Stoicism is really about.
“Many of us … focus our energy on stuff that's immovable, unchangeable, that already happened.
As a result, we relinquish this power we have, which is: to change how we think about [situations, and] to change how we respond to [situations]. To me, that's what Stoicism is really about.” — Ryan Holiday
Joe: It really strikes me as I read your work and their work … how much of it resonates with the findings of modern psychology, the work of Kahneman and Tversky, for example. This is system two thinking we're talking about, or Stanovich's interrupt. But even back almost a hundred years now, Viktor Frankl's work, it's the gap between what happens to you and how you choose to behave or respond. That's where all liberty lies.
Ryan: Yeah. And the Stoics are influencers through those different types of thinking. You know, cognitive behavioral therapy has some roots in Epictetus's distinction between what's in our control and what's not in our control. Viktor Frankl's logotherapy, the logos is the through line of Stoic philosophy. So I think all of these things are related. And I think that is a credit to the ancient philosophers that so much of what they were basically just guessing at has been slowly and steadily either codified or confirmed by some of these studies.
Where they fall short is, you know, they go, "You have power over your mind." Well, do you have power over your mind if you're a schizophrenic? Do you have power over your mind if you're in a manic phase because you have bipolar or because you're delirious from thirst? Obviously there's parts of this that are not in your control, and I don't think they fully understood the way in which, let's say, a childhood trauma could warp or change how we think, or that perhaps we make really good decisions in some conditions and not other ones.
Obviously I think it's a little more complicated than that. But what I love about the Stoics too, is I feel like if they were here today, or if somehow that line of thinking had been introduced to them, I'm fairly confident they would've incorporated it really quickly. We've just been talking about Marcus Aurelius and Epictetus. But what I love about Seneca, when you read Seneca's letters, when you read some of his essays, across all of Seneca's works the philosopher he cites the most is Epicurus, his rival.
Joe: Right! [Laughs]
Ryan: And he's not setting it up to disagree with Epicurus, right? Although he does, often. He's writing to his friend Lucilius, “Here's this great line from Epicurus,” or, “as Epicurus said ...” He is quoting as regularly from his “enemy” as he is from his allies. And I think that was because he was deeply familiar with things that challenged or buttressed what he was talking about. And so I'd like to think that the Stoics would've used the tools of some modern psychology and cognitive understanding and neuroscience, they just didn't have access to it.
Joe: Yeah. To that point, They seemed to be constantly looking for ways to update their beliefs and improve the accuracy of their map of the world. In Decision Education, we talk about these four different domains. One of them is exercising and applying rationality, or valuing rationality. And we mean that in the Stanovich and Toplak sense, of the two parts: epistemic and instrumental. Seeing the world more accurately, that's epistemic, and then instrumentally, behaving in ways that are consistent with your goals.
Joe: And again, I think there were three parts to Stoicism that you were talking about. One of them was just perceiving more accurately, trying to to get a better model of the world. I wonder if you could talk about that a little bit.
Ryan: Yeah. And in my book, The Obstacle Is the Way, I break Stoicism down into its three most well known disciplines, which would be the Discipline of Perception, the Discipline of Action and then the Discipline of Will. And in Meditations Marcus Aurelius says that all you need in life is: objective judgment, unselfish action, and willing acceptance.
And those correspond perfectly to those three domains. Discipline of Perception is of course how we see things: the viewpoint, the biases, the rationality, how we look at the problem or obstacle in front of us, for instance.
Then unselfish action is of course the ethics that we apply to a situation, the agency that we assert over a situation, what we do about it.
And then finally, the willing acceptance part, that's endurance, that's perseverance, that's putting up with the consequences of those actions, for instance. So I think these three disciplines kind of overlap and loop with each other, but that's the framework that I think you can look at pretty much anything with.
Joe: I was struck by the last one because I assume you saw that we unfortunately lost Thích Nhất Hạnh from the world a few weeks ago. It struck me that the will to acceptance was very much aligned with the idea of equanimity, this active state of acceptance and wellbeing and balance, not to be quite so troubled by the things that are outside of your control. I don't know if you ever looked at the connection?
Ryan: Yes, so Marcus Aurelius’ beloved mentor and father figure is this guy Antoninus Pius who's not really his father or stepfather. It's this sort of complicated arrangement in which Marcus Aurelius is set up to become emperor, but needs a regent, essentially. It was supposed to be a year or two and instead Pius ruled for 19 years. But Marcus doesn't resent this. He uses the 19 years as sort of an apprenticeship under this great leader. And Antoninus is not explicitly a Stoic or a philosopher in any way. He just embodies all the ideals, right?
Ryan: Everything that Marcus wants to be, Antoninus naturally is. And as Antoninus dies, his final words to Marcus as he passes the throne is “aequanimitas.” Equanimity. You can see why. I think we think of equanimity as this soft thing or this spiritual thing. That’s of course what a monk would value. But that's also exactly what you want in a leader, right?
Ryan: When I think of the Cuban Missile Crisis, if I could give anything to the person in charge, it would be equanimity, poise, patience, clarity, not being rattled or rushed.
So equanimity is a thing that we need not just spiritually, but we need professionally. You want Tom Brady, down 28 to 3 in the Super Bowl, obviously he has to be very active, but he also needs a kind of equanimity and poise to be able to pull off a series of difficult things. You would want a leader in a crisis, you'd want a poker player ... It doesn't matter what it is, equanimity is this place that you want to get to to do whatever it is that you do, well.
Marcus Aurelius tends to use the word “stillness” which appears nine or 10 times in Meditations, I think that's what he's referring to. And when he talks of stillness he uses the image of a rock. He says to be like the rock that the waves crash over and eventually the water falls still around. I think that's a beautiful way of expressing what equanimity really is, which is [when] everything can be happening out here, but you have to get to a sturdy, steady place that allows you to do what you need to do inside of that chaos.
Joe: That's really fun. I think it was reading Lao Tzu, where I first came across the idea that almost the opposite direction, that you're the pond and someone tosses a pebble in, and of course there are going to be ripples, but eventually you just let the rock settle down to the bottom and you return to being calm.
Ryan: Epictetus uses that exact same metaphor as well. And I love the idea ... I wrote the book Stillness Is the Key, which is the third in my trilogy on Stoicism ... how beautiful it is that East and West would sort of independently come to the same conclusion, use the same imagery, the same understanding. To me, it's like convergent evolution. It's like independently chancing upon the same adaptations.
Joe: Yeah, not a surprise since we're all stuck with the same sort of hardware, in some of the same conditions that we're dealing with.
Can we go back for a second to the second topic, the one about living ethically or being of service to others. I'm thinking [about] values and about our wants and what we want to want. You know, second order preferences. I'm just wondering how have you gotten to a place or [do you] think about deciding what you actually want and organizing your life and making your decisions to line up with that?
Ryan: Yeah, so the virtue of justice is a key theme in Stoic philosophy. You know, it's really easy to focus on the stuff we're talking about that makes you more resilient, that makes you have more equanimity, that makes you more rational. There's also an argument that all of those things, I think, could be used to make you a better sociopath. Right?
Ryan: And I constantly have to push back on this in my writing and I think [with] just some of the people my work has attracted. That's not what this philosophy is about. Not just because the virtue of justice is there, but almost all of the Stoics were actively engaged in public and political life in some form. Almost all of them behaved in accordance with virtues or practices that today might not make sense but were relatively progressive in their own time as far as ethics go. I think that is important to point out.
But Marcus Aurelius speaks over and over again in Meditations about the common good [and] our obligations to each other. He saw himself as the emperor of Rome, but also as a human being with obligations to his fellow human beings. And so you'd say, what's good for the hive is good for the bee, right? As opposed to the other way around.
Ryan: And you know, I think he tried to do his best to be a good person. I mean, there were certainly abominable practices that the Stoics failed to question or question enough. But I sort of liken it to how we look at the Founding Fathers. You know, we can almost use their framework to get to a place that they personally couldn't get, but that we could get to.
Joe: Nicely put.
Ryan: I try to think about Stoicism as a philosophy that not just makes you better, but as a result of making you better comes with some obligations for how one ought to conduct oneself.
Joe: Related to that, I think you mentioned earlier, briefly [about] “love” for Marcus Aurelius. And I think that might strike some of us as surprising because that sounds an awful lot like an emotion. Aren't the stoics supposed to be logical, Spock type creatures? What's going on there?
Ryan: Yeah. We like to point out that there's a difference between lowercase stoicism and uppercase Stoicism.
Joe: Oh, okay.
Ryan: Lowercase stoicism being the English understanding of what it means to be stoic, to have no emotions. Just as being an epicurean is not the same as being an Epicurean philosopher, right?
Joe: Yes, right.
Ryan: You think of one as being a hedonist and the other being actually a very interesting philosophy. You know, at the beginning of Meditations, Marcus Aurelius talks about how one of his mentors taught him how to be “free of passion, but full of love,” which I think is a beautiful way to put it. So love is an emotion, love is a passion, but of all the passions, it's the best one.
Joe: So moving a little bit to the book you mentioned The Obstacle is the Way. We're obviously focused on decision-making and decision-making strategies that can be useful to our audience. One of the strategies you recommend is to take your situation and pretend it's not happening to you. Can you explain that and then maybe give us an example where you've used that strategy?
Ryan: Yeah. I think we're very good at giving other people advice because it's objective, we're not emotionally wrapped up in it. It just is what it is. But then when it's us, we add all this other stuff: it’s unfair, maybe we feel guilty, maybe we feel embarrassed. And so, you know, what would you advise someone in your situation to do?
A friend of mine is in the middle of this sort of public relations crisis. And the irony is that he is in public relations! And he's overwhelmed by this situation that he helps people with every day. So I've tried to walk him through this: if one of your clients was as turned upside down by this, you'd be like, “You're completely overreacting, none of this matters.” You'd be focused on all the things that they could do about it and all the ways that it wasn't nearly as bad as they thought it was. But because it's you, you're paralyzed by it, and that's the idea: by stepping away — Annie talks about this — getting to the outside of a problem.
Ryan: The problem is that we're on the inside of our problems, or that the problems are on the inside of us! And so to be able to step out allows us to see it with a little bit more distance.
“We're very good at giving other people advice … [so it’s helpful to think about] what would you advise someone in your situation to do? … The problem is that we're on the inside of our problems, or that the problems are on the inside of us! And so to be able to step out[side of our problems] allows us to see it with a little bit more distance.” — Ryan Holiday
Joe: So do you have people then pretend — as you're doing with your friend — that it's not them and they're giving advice. Is that the main thing? Or is there something else happening internally that you're asking them to do?
Ryan: Yeah. So sometimes what I like to do ... if I'm thinking about doing something and I know why I want to do it I'll ask people to tell me why I shouldn't do it. I try to get people to give me the opposite of the perspective that I already have.
Ryan: Or I'll describe a situation and I'll ask them for advice but I won't say that it's me, or I won't say what I already think. What I'm just trying to do is get to the outside of it, to get a little distance from it. As an example, let's say you're in an argument with your spouse about this thing, and let's say you think you're totally right and they're really upset and now neither of you are getting along. If your friend came to you, you'd be like, “Just apologize. Who cares?” But you care, that's the whole thing!
And so you know that you would tell someone in your exact situation how little this matters and that it's a pyrrhic victory even if you win. I think it's about reminding myself of that, often, like, “Berating this person might make me feel cathartic in the interim. But it's still going to land me with the consequences.” So what would I tell another person? I’d tell another person “don't do that” [so] I try not to do that.
“If I'm thinking about doing something and I know why I want to do it I'll ask people to tell me why I shouldn't do it. … Or I'll describe a situation and I'll ask them for advice but I won't say that it's me,
or I won't say what I already think. What I'm just trying to do is get to the outside of it,
to get a little distance from it.” — Ryan Holiday
Joe: So you've got this override of your system two thinking or your reasonable mind, your rational mind, that you're doing in those situations where you're trying to get outside of your lived experience, your feeling in the moment.
So the override seems like one [option,] another [option] is to do this thing where you try to give yourself credit for the behaviors that you want as opposed to the thing that you might think you want or feel like you want.
What does it feel like inside of Ryan's head at this point, compared to when you started this journey? Does it feel any different? Do you still have the same emotional valence or has it gone down? Are the interrupts faster? What's the experience?
Ryan: I definitely think you get better at it, but one of the humbling things about reading Meditations [is when] Marcus Aurelius says this towards the end, he's like, “You're an old man. You've been doing this forever and you're still afraid of death and you're still wishing for this and whining about that.” So I don't think it ever goes away, because it is hardwired in us.
But I sometimes think about the thing about admitting you're wrong. What might have taken me six months before, maybe takes me six days or six hours or six minutes [now]. Any of those is an improvement.
I think about this with losing your temper: getting mad [and] being provoked by something, maybe that never goes away. But can I take fewer actions out of anger? So maybe I decide that I don't like something that someone said or someone did. Okay. But that's stayed within me, right? Obviously it'd be ideal that I got to this point of being a Stoic sage and I felt nothing despite the provocation. But I'm happy if I just don't take actions based on the anger. I don't try to get even. I don't say something cruel back. I don't nurse a grudge against this person. I don't think about them at all. I just move on. So I think just getting to a place of checking yourself before the action, I think that is improvement enough.
Joe: Yeah. I find that to be true. I've worked with I guess thousands of high school boys now, because I worked with boys schools. And getting to that place where there was at least the interrupt, where there was the pause, was the first big step.
Ryan: Well, I was just thinking ... Think of the market right now, we're in this weird point of the market, the market's down, it's behaving strangely. So you have this impulse like, should I sell everything?
Ryan: You shouldn't check the news, but you check the news, and then you have the fear. As long as you don't sell everything, it's good enough, right? And I think getting to that place where you're able to have the provocation or the thought or the question or the anxiety or whatever it is ... You have the impulse, but who's in charge? You or the impulse?
Joe: So, Ray Dalio in his book Principles talks about, “Try to write down your algorithms ahead of time, know what you're gonna do in those situations.” In Decision Science, we’d probably talk about it as a Ulysses contract, tie yourself to the mast so you don't get drawn in by the Sirens. But there's this other quality that I've noticed where if you just bring awareness to the provocation, to the impulse, it starts to lose its strength. Just staying with it ... And that sounded a little to me like the first part of the first three principles. It wasn't just perception about the world around you. It was about being the perceiver, and staying in that role a little bit, that you could also lessen the strength of your emotions or your motivations, the push of the world.
Ryan: I think that's right. And I think Eastern philosophy does a little better job of talking about this. To me, part of what mindfulness is, is you're sitting there and you're going, “I'm feeling jealous, I'm feeling restless, I'm feeling angry, I'm feeling afraid,” whatever it is. I'm feeling it, but it doesn't mean that I am that thing, right?
You can just let it take hold of you and then move on. You don't have to take hold of it back, right? I think it's a Stoic idea as well. It's more commonly expressed in the Eastern thought. Just this idea that you don't have to identify with the feeling, you don't have to choose to accept the feeling, and you certainly don't have to act on the feeling just because you have it. This seems so basic, but I'm not sure everyone is aware of that. I'm not sure everyone is aware that just because you want to do something doesn't mean that you have to do it, and it certainly doesn't mean that you should do it.
“I'm feeling jealous, I'm feeling restless, I'm feeling angry, I'm feeling afraid … You can just move on … You don't have to identify with the feeling, you don't have to choose to accept the feeling, and you certainly don't have to act on the feeling just because you have it. ” — Ryan Holiday
Ryan: One of the things I like from Epicurus [is that] he talks about: how are you going to feel after? So you want to have sex, or you want to gorge yourself at this dessert buffet, or you want do this drug or yell this thing — how are you going to feel after? Because you've done it before, so you know, right? You're going to feel disappointed, you always do.
Joe: Yeah. I mean, the idea that Epicurus is sitting there eating lentil soup, and somehow we walk away thinking he might be a hedonist, is hilarious. I think about him with the idea of maximizing lifetime expected value. Like it's not about the next moment or the next temptation or the next pleasure or the next enjoyment, it's: how do you get the maximal wellbeing out of your entire life?
Joe: [That] seems to be what they're going after. The Stoics, to your point, if they had access to what we now know about probabilistic thinking, they would probably have updated their models to include that kind of formulation. I don't know if you've given much thought to: where do you see the differences between Stoicism and Epicureanism? Where does it break down for you?
Ryan: Yeah. Seneca says that the big distinction between the Stoics and the Epicureans was that the Epicureans sort of retreat into private life and private satisfaction, which is important, but it's about individual personal enlightenment. And the Stoic is more civically engaged or involved. They're both trying to get to that same place of ataraxia or apatheia, the freedom from disturbances. But I think the Epicurean is more monkish, right? The Epicurean retreats to the garden, the Stoic is in the forum or on the battlefield or in the agora.
Ryan: Seneca says that an Epicurean will get involved in politics only if they have to and a Stoic will get involved in politics unless something prevents them. It's not politics in the sense that we see it. It's contributing to the common good, it's being involved. Whereas, Epicurus says "tarry in my garden,” hang out here. There's a childlikeness to that and naivete to that. Obviously, if everyone did that, it wouldn't work, right? It works because only some people do that. And Stoicism was a philosophy for running Rome.
Joe: To have the people who are most even-tempered and philosophical withdraw from society is a recipe for disaster in my mind. Who's going to be left controlling things?
Ryan: That's what the Stoics said. There's a lecture that survives to us from Musonius Rufus, he's speaking to a Syrian king and he says: should a king study philosophy? Who is better to study philosophy? Who do we need to have philosophical principles more than a king? And again, the Stoics don't do a great job questioning autocracy or what is the most just form of government. But yes, if the philosophers disengage, you are ceding the fields to the non philosophers, and I do think that's a problem.
Joe: I agree. One of the things we emphasized when we started the Alliance [for Decision Education] was that we understand that better decisions lead to better lives and a better society. That last part is critically important, that this is not a purely private pursuit. This is a public pursuit, it's a civic pursuit as well as being an individual and familial pursuit.
Your capacity for making skillful decisions has ramifications for your entire life and those around you.
I could talk to you about this stuff [laughs] I think forever, it seems, but I want to get to another topic that I know you're passionate about, and I don't think it gets enough public space right now, but maybe it'll create some more philosophers.
“One of the things we emphasized when we started the Alliance [for Decision Education] was that we understand that better decisions lead to better lives and a better society. That last part is critically important, that this is not a purely private pursuit. This is a public pursuit, it's a civic pursuit as well as being an individual and familial pursuit. Your capacity for making skillful decisions has ramifications for your entire life and those around you.” — Joe Sweeney
Joe: Can you talk about what a commonplace book is, and how you came across that idea?
Ryan: So it's funny, it's this rare thing now, but if you read basically any work of ancient philosophy or history, they have these commonplace books. Thomas Jefferson would have one, Montaigne would have one, Erasmus had one. Basically it was a collection of thoughts. You could argue that Meditations is a commonplace book because very little of what's in Meditations is wholly original. You know, it's a lot of quotes, a lot of rephrasing, a lot of riffing, a lot of remembrances.
The first chapter of Meditations is Marcus Aurelius just pointing out lessons that he learned from people who are influential in his life. So I was vaguely familiar with the idea of a commonplace book in that sense, and then I started as a writer, as a research assistant for a great writer named Robert Greene. And Robert does all the research for his books on four by six notecards. So instead of doing it in a book, which obviously has a beginning and an end and then is somewhat less modular, less easy to move stuff around, I just started doing it on index cards.
So my commonplace book ... every time I read a book, every time I find something I like, every time I have a thought that might be something, I put it down in a note card and I organize them by themes. And that's the basis for all my books and all my writing.
Joe: Have you tried any electronic versions?
Ryan: I have. And I don't have strong negative opinions about them, but I do have a very strong opinion about the benefits of doing it by hand. So for instance, I was doing this yesterday. I was going through three or four books that I'd read. I took notes while I was reading them, in the margins, I folded pages.
“So my commonplace book [is where] every time I read a book, every time I find something I like, every time I have a thought that might be something, I put it down in a note card and I organize them by themes. And that's the basis for all my books and all my writing.” — Ryan Holiday
Ryan: So then, you know, now I'm going back through it and I'm writing them down, the stuff I like by hand, so I'm now interacting with it for a second or a third time. Then all those are that I'm researching for my next book, so all those are just going in like a general box. And then when I sit down to start to get serious about that book, I'll go through all the cards again.
So now I've interacted with the material three or four or five times, then I'm moving it around and then, “Oh, okay. This story that I read in this book, it's on page 63. I think I want to tell that story.” So now I'm going back to the shelf and I'm getting the book. It's really that engagement and re-engagement and re-engagement and looking at it from different angles. That's the real benefit of doing it analog. And I tend to find that when I'm just highlighting stuff and it goes into a black hole, you know, as a file on my computer. I'm not getting that same familiarity.
Joe: So I appreciate that. It makes a lot of sense for a writer. I know that many of the more prolific writers in history, this is exactly how they produced so many works, is because they were constantly collecting and re-indexing and making connections. And every time they ended up with 50 or 60 quotes on friendship, then out comes the pamphlet on friendship, you know, that sort of thing.
Joe: For those of us who are maybe not public writers, do you still see value in this sort of thing, especially as related to developing our minds and developing our decision making effectiveness?
Ryan: I do. I think, look, whatever works for you, you should do. But to be able to engage with the text, you know, either highlighting it with your finger on an iPad or writing in the margins or putting it on a notecard, that is what's really important. To just have it go in one ear, I'm very suspicious that it's just going out the other.
Joe: Yeah. And to your point about the marginalia, that was a big transition point for me when I when I began to break the taboo of writing in books and just starting to consume them instead, underline, write in the sides, you know, come with my own notation for what's a question versus something I want to research versus a quote, just those sorts of behaviors. I don't think that it's a common practice, which is ironic in the name.
Have you spoken about it elsewhere? Do you try to promote the idea to people?
Ryan: Yeah, I've done a couple of videos on it and I have a course that I do for Daily Stoic on these sorts of Stoic practices as I think it's really important. It's funny, obviously it doesn't happen as much because of the pandemic, but you know, people will come up to you as an author, they'll be like, “I've read your book. It was my favorite book. I loved it." And they'll hand it to you and it's like, “I'm not sure you read this! It's pristine.”
Joe: Right [laughs].
Ryan: But then when you get a book and there's food on it, the spine's broken and there's pages folded and notes sticking out, I'm like, “All right, you did the work.” I love it. Every once in a while ... I read a lot of old books. And so, you'll get a book for a penny on Amazon because it was published 90 years ago. I got this one the other day and it was a pristine review copy.
Joe: Oh boy.
Ryan: So there was a part of me that was like, should I keep this?
Joe: Yeah. [Laughs].
Ryan: And I was like, “You know what, the highest compliment I can give to this book is to use it.” For people who think that it's disrespectful or whatever, the only way you can disrespect a book is by not reading it.
Joe: I totally agree.
Ryan: If you engage with it, if you put miles on it, that warms an author's heart. I could tell you that from experience.
Joe: Yeah. I think [it was] a very different thing when it was an enormously expensive illuminated volume when there was only one book in the town, but we're so fortunate that books are cheap, printing is cheap. Go ahead and get the book and tear it up!
Ryan: You look at those old family Bibles where they would write births. But I'm not sure anyone in the family has read this Bible, you know? Is it really the family Bible if it just sits on a shelf and no one reads it?
Even when books are rare, even when they're expensive ... Sometimes the book is a penny, sometimes this book I needed to get is $200 because they're not available and I just [tell myself] no, the job is to read the book, is to get the stuff out of it, right? And in Meditations Marcus Aurelius says that one of the things he learns from Rusticus is to never be satisfied just getting the gist of something, he has to really understand it. I try to read accordingly.
Joe: So since you mentioned that … You said you're working on a new book. What can we expect, what's coming?
Ryan: So I did this trilogy, it was sort of an accidental trilogy of: The Obstacle Is the Way, Ego Is the Enemy, Stillness Is the Key, which is loosely about Stoicism, or little ideas in Stoicism that I thought would be fun to explore. And then about two years ago, I had this idea to do a series on the Cardinal Virtues of Stoicism. So courage, temperance, justice, wisdom. So I sold a four book series, and the first book which is on courage came out in September. And so the way the timeline is, I'm just finishing the first draft of the second book, which is about temperance or self discipline. Then I've got a couple month break here and then I have to get started on what will be the third book, which is on justice.
Joe: All right, it sounds fantastic, I'm looking forward to reading them. We'll put links on our website for them.
Ryan: Oh, thank you.
Joe: So we're getting close to the end here so I have some regular questions that we like to ask.
Ryan: All right.
Joe: I'm wondering Ryan, in your perspective, what will look different in society when we succeed in our mission to ensure Decision Education is part of every middle and high school student's learning experience?
Ryan: Oh, that's a good question. I'd like to think that we'd make better decisions and then become more efficient. There's that Churchill quote about how you can trust America to do the right thing after it's tried everything else.
Joe: Right [Laughs]
Ryan: If you just think about the resources that that burns.
Joe: Oh yeah.
Ryan: And not at a political level, but just think about us as individuals, right? We learn so many things by experience that are in literally every book. I would hope that we could save some people some painful bumps on the head that they could learn from the experiences of others and make better decisions as a result.
Joe: All right, so here's your magic wand moment. What's the single decision-making tool or idea that you'd like to pass down to the next generation of decision makers?
Ryan: The big thing that I see people mess up, it's not that they make the wrong decision, it's that they make the wrong decision per their own goals or preferences or priorities. So someone will go, “My dream is to do X,” and then they'll make a bunch of individual decisions that are in direct contradiction of X because they lack the ability to be strategic.
So someone is like, “I'm writing this book because I really care about the ideas and I want to get them out in the world. I want to transition from what I'm doing to this.” And then, you know, then they'll make the publisher that they sign with … they'll make financial decisions. And it's like, but you already chose to not do a financial thing and then here you are making the individual decisions along the way based on a totally different frame.
And I just see that all the time, people lack the ability to consider downstream consequences or how decisions interrelate to each other. So if I had a magic wand, I'd give people the ability to see things in that context, some sort of strategic interconnectedness.
“The big thing that I see people mess up … [is] that they make the wrong decision per their own goals or preferences or priorities. So someone will go, ‘My dream is to do X,’ and then they'll make a bunch
of individual decisions that are in direct contradiction of X because they lack the ability to be strategic … people lack the ability to consider downstream consequences or how decisions interrelate
to each other.” — Ryan Holiday
Joe: Yeah, I do. That's a really good one. I haven't heard that one before and you can immediately see its utility. In a related sort of way, which single book would you recommend as priority reading for listeners to improve their decision making?
Ryan: That's a really good question. I mean, obviously Annie [Duke]'s stuff is incredible [How to Decide and Thinking In Bets]. I think Shane Parrish's book [The Great Mental Models] is really good. Robert Greene's books like The 48 Laws of Power or The 33 Strategies of War, The Laws of Human Nature.
Again, I think people lack not just the ability to be strategic in their own decision making, but they lack any understanding of the forces that are occurring in the world around them, inside other human beings. They go, “You know, I'm doing my absolute best and I'm crushing it at work and blah, and I can't figure out why my boss doesn't love it.”
And it's like, well, you're making your boss look bad, right? That's why. We often make the mistake of thinking that our decisions occur in a vacuum or that the right thing is what always works or is embraced with open arms and only to our peril and at much later juncture do we realize that there's other factors at play.
Joe: That sounds awfully pragmatic! [laughs]
Ryan: A little bit.
“We often make the mistake of thinking that our decisions occur in a vacuum or that the right thing is what always works or is embraced with open arms. Only to our peril and at much later juncture do we realize that there's other factors at play.” — Ryan Holiday
Joe: Ryan, I just want to thank you so much for coming on the show. If listeners want to go online and learn more about you, your newsletters and The Daily Stoic Podcast or follow you on social media, where should they start? Where would you like them to go first?
Ryan: Yeah, I do a free email about stoic philosophy every day at dailystoic.com. I do a parenting one at dailydad.com and then those social media handles are out there also.
Joe: For any books, articles mentioned today you can check out the show notes on the Alliance site, and you'll also be able to find a transcript of today's conversation. We'll put the links to those books that Ryan just mentioned, and the social media handles. Ryan, thank you so much for this. It was really a treat.
Ryan: Thanks for having me.
Published June 8, 2022