When You Come To The Crossroads… | Ask Ds

At the founding of Stoicism was a choice. Zeno hears the legend Hercules, a story about a young man who came to a crossroads one day in Greece, where the great hero had to choose between virtue and vice, the easy way and the hard way. It was inspired by this very story that Zeno rebuilt the wreckage of his life and founded the school of Stoicism. So we’ll leave you today by putting a challenge in front of you. For the last four years, we have been doing what we call the Daily Stoic New Year New You Challenge—a set of 21 actionable challenges, presented one per day, built around the best, most timeless wisdom in Stoic philosophy. These aren’t pie-in-the-sky, theoretical discussions but clear, immediate exercises and methods you can begin right now to spark the reinvention you’ve been trying for. We’ll tell you what to do, how to do it, and why it works. From these challenges, you will:✓ Learn to stop procrastinating and avoiding the change you truly desire✓ Build new habits that form a strong foundation for change✓ Abandon the harmful habits that are dragging you down✓ Strengthen your character, becoming a more virtuous version of yourselfAnd above all: You will find out just how much you are capable of. Every morning, the email arrives in your inbox, and it presents you with a choice. You can do the harder thing, you can do the challenge. Or you can follow the drift of least resistance—you can open the email and leave it at that. Or worse…you can ignore this call right now and not sign up at all. Which way will you go? In today's Ask Daily Stoic, Ryan talks stoics and answers questions for 60 students at The United States Military Academy (USMA), also known metonymically as West Point or simply as Army. West Point is a United States service academy in West Point, New York. It was originally established as a fort, since it sits on strategic high ground overlooking the Hudson River 50 miles (80 km) north of New York City. It is the oldest of the five American service academies and educates cadets for commissioning into the United States Army. The 2024 New Year New You Challenge officially begins on Monday, January 1st. Stop delaying. Head over to dailystoic.com/challenge and sign up NOW! Let’s go.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:07Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. While on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics. We're trying to apply this philosophy just as you are. Some of these come from my talks. Some of these come from Zoom sessions that we do with Daily Stoic Life members or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. But thank you for listening, and we hope this is of use to you.

• 0:50Ryan Holiday?

  When you come to the crossroads, each day, life presents us with these small crossroads, moments where we must decide how to approach tasks and what actions to take. Often, these choices boil down to a selection between the challenging path and the easier one. Should you make that difficult phone call or opt for the convenience of an email? Should you apologize and take responsibility or hope it goes unnoticed? Will you rise early or give in to the temptation of the snooze button? Do you choose to read a few pages of a book or mindlessly scroll through social media? Is it time for an overdue oil change or do you procrastinate once more? These competing options are what Stoicism is for. When faced with these small crossroads,

• 1:34Ryan Holiday?

  a Stoic knows precisely which direction to take, towards the choice that challenges them more. Stoicism aims to guide us away from the path of least resistance. Marcus Aurelius wrote in Meditations about holding the reins in his non-dominant hand as both an exercise to practice and a metaphor for doing the difficult thing. Seneca would say that he actually pitied people who had never experienced challenges. "You have passed through life without an opponent," he said. "No one can ever know what you are capable of, not even you." Epictetus said that when a challenge is put in front of you, "Think of yourself as an athlete getting paired with a tough competitor. You want to be Olympic class? This is going to take some sweat to accomplish," he said.

• 2:18Ryan Holiday?

  We must take this to heart today and every day. We should cultivate the habit of choosing the more demanding option, actively seeking out challenges and embracing discomfort. Remember, iron sharpens iron. You will not only benefit from the growth that comes from overcoming challenges, but also from the willpower you develop by intentionally selecting the more challenging path. So we will leave you today by putting a challenge in front of you. For the last several years, we've been doing this thing at the beginning of each year called the Daily Stoic New Year, New You Challenge. It's 21 Stoic challenges, one per day, for the first three weeks of the year. These are challenges that you get better at. It's helping you build the habit of doing the harder thing,

• 3:01Ryan Holiday?

  so that when you come to choices in life, you'll do the right and the Stoic thing. I'm really excited about it. I think this is going to be our best year yet. There's a bunch of live sessions with me. There's a 21-day calendar, so you can track your progress. You get access to that private Stoic community. Basically, a book's worth of content. And each morning, an email arrives in your inbox, and it's going to present you a choice. You can do the harder thing, the challenge. You can follow the path of least resistance. You can open the email and leave it at that. Or you can not sign up for the challenge at all, right? Which way will you go? The 2024 New Year, New You Challenge from Daily Stoic officially begins on Monday, January 1st. So stop delaying, don't procrastinate. Head on over to dailystoic.com/challenge and sign up now. I'll see you in there.

• 3:55Speaker 01

  What do you mean by Stoicism?

• 3:59Ryan Holiday?

  I mean the ancient philosophy, which comes to us by way of Greece around 2,300 years ago, built around four cardinal virtues of courage, discipline, justice, and wisdom. And it's a philosophy that...

• 4:15Ryan Holiday?

  I think, obviously, has made its way into the sort of common parlance in the sense that we all know what the word "stoic" means. I think fewer of us know what the philosophy was and who the philosophers were. You know, maybe they've heard of Marcus Aurelius because they've seen the movie Gladiator, or maybe they've heard of Seneca. Usually, people who've been taught Latin in some sort of private school have some vague familiarity with some of these names. But other than that, it's sort of been lost to time. And I think that's a tragic occurrence for two reasons. One, these weren't abstract theoretical philosophers, but these were philosophers who did stuff in the real world. In some cases, the exact

• 5:00Ryan Holiday?

  job that many of you are hoping to one day have. The Stoics were in the armed forces in Rome. The Stoics held diplomatic positions. The Stoics held elected office. The Stoics were business people. The Stoics were participating in the polis, right? They weren't sort of withdrawn. They weren't retreating into the world of ideas, but they were bringing the world of ideas and the best thinking of the age, the best ethical thinking of the age, into public life, into government, into foreign service, into raising families, into running businesses. And then I think the other part that's interesting, and I really enjoy the fact that you're teaching it as part of a composition class, I think the Stoics are

• 5:44Ryan Holiday?

  underrated as writers generally. So if you take a work like Marcus Aurelius's Meditations, it's not just unique in the sense that it's the private thoughts of the most powerful man in the world, one of the only people to ever hold that position. But what's particularly interesting about Meditations is that Marcus Aurelius is writing it exclusively privately. He's writing to himself. He'd probably be mortified that we're talking about it 2,000 years later, right? These are the campaign diaries, but not even in a diary, because when we think about a diary, we think about someone documenting what they experience sort of word for word. What Marcus is doing is having a philosophical diary.

• 6:25Ryan Holiday?

  Dialogue with himself. So when Marcus says, for instance, in the opening of Book Five of Meditations, you know, "At dawn, when you awake and you have trouble getting out of bed", he's talking to you and I. I mean, I read it when I was the age of most of the people on this call and I was like, "I get it. I don't want to get up for my morning class", but primarily, and in fact exclusively, Marcus is talking to himself, right? It's him telling himself what to do, what he wants to live up to. And I think it's even more remarkable when you see just how beautiful some of those passages are. You know, Marcus is writing in far-flung locations, he's writing by hand,

• 7:06Ryan Holiday?

  and he's doing it in Greek, which is the language of philosophy, as opposed to Latin, which was the language of Rome and the state. But to himself privately, in his second language, Marcus is writing a series of passages that are so good that they come down to us 2,000 years later and they feel like they're written for you and I. Seneca is a similar example. Now, Seneca was a bit more public-facing in his writing, but it's worth noting, Seneca is also a playwright. And for most of the last 2,000 years, it was inconceivable to both historians and philosophers

• 7:46Ryan Holiday?

  that Seneca, the playwright, and Seneca, the political power broker slash philosopher, could be the same person. They just assumed it had to be two people with the same name, because no one could be so good at both things. And in fact, Seneca was immensely popular in his own time as a writer. There's a line of graffiti from one of Seneca's plays on the wall at Pompeii. Like, it's the last name that somebody wrote, right? And so if we really understand just how great a writers the Stoics were, and how integral writing and communication are to inward sort of philosophical thinking, I think we understand them at a deeper level.

• 8:30Speaker 01

  Yeah, actually, it's great that you mentioned Seneca's plays because I came across them less than a year ago and reading them is just, they're just as good or better than the Greek ones. Actually, one of my students, she wrote a paper comparing Seneca's philosophy to his play. I believe she did Hercules.

• 8:52Ryan Holiday?

  Well, and just to nerd out about that a second, because this is the perfect audience for that. Seneca's plays are shockingly dark and twisted, and you might even say evil. And one of the lines of thought is that nowhere in Seneca's philosophical or political writings does he address working for Nero, does he address the brutality and evil of his time? And it's only when you read the plays that you see what Seneca is really doing there, I think, is processing his moral injury, processing the pain and guilt and horror that he feels about the violence and dysfunction and evil of his time. He just didn't have

• 9:34Ryan Holiday?

  the ability to communicate openly about what he saw or what he was doing, or in other cases, perhaps he was too ashamed, because he is, I think, in some ways complicit in Nero's regime. And so Seneca is channeling those feelings consciously or subconsciously into his plays where he's able to say, "I'm not talking about Nero and his repeated attempts to kill his family members. I'm talking about, you know, these ancient historical or mythological creatures, and so you can't get mad at me," which is, by the way, what Shakespeare was also doing. Shakespeare writes basically one overtly contemporaneous comment in all

• 10:15Ryan Holiday?

  of his plays, and it nearly ends in his death. So the reason Shakespeare is talking about Mark Antony and Caesar and all these historical figures is because you can't talk about what's happening now.

• 10:33Speaker 01

  And, you know, thinking of Seneca, because we read some of his letters as well.

• 10:40Speaker 01

  You know, it's interesting, sort of that when he's writing these letters to his friends, he doesn't really mention a whole lot of like the details or the gruesomeness. And I wonder, you know, because you've read the, you've read the ancient Stoics, just like our students have, and one, and we started out with Epictetus, and his discourse is on the idea that it's not the thing itself that's good or bad, it's, it's our perception of it.

• 11:10Ryan Holiday?

  Sure.

• 11:11Speaker 01

  And so, you know, you, you, you, you came up with the, or not came up, but you sort of described Stoicism as, as those four virtues. Besides, going back to like Marcus Aurelius's, his third book, where he has that line about, if you find anything more so than like, more, more than courage, justice, wisdom, and that, you know, think on those, how, how did you come to those, those specifically, as sort of like your way of presenting them?

• 11:43Ryan Holiday?

  So those, those four virtues trace their way, all the way back to Zeno, who's the, the first Stoic to mention them. Now, other philosophers had come up with sort of their list of cardinal virtues, there were usually more, you know, I think Aristotle's like seven virtues, or something like that. But I think what I like about the cardinal virtues of Stoicism is not just that they trace their way back to the founder of Stoicism, but they, they were clearly adopted by and integrated into Christian thought around the time of, of Seneca, and then Marcus Aurelius, and then beyond. So, there's a familiarity with those, right? People have heard them in a church service, or maybe they were visiting some old Catholic church, and they saw them kind of inscribed on a building or something.

• 12:28Ryan Holiday?

  There, there's a familiarity there, which I think is really important, because, you know, it wasn't like these were just ideas 2,000 plus years ago, that just fell off the face of the earth. They were just... Co-opted and remixed and reorganized and re-presented in many different ways and present essentially a continuous tradition. I mean, even Epictetus is interesting, you know, for you guys to be reading him in this English composition class. You know, Epictetus doesn't write anything. Epictetus survives to us through the writings of Arian, who, by the way, writes an incredible biography of Alexander the Great. One of the best sort of documentary pieces of evidence we have about the campaigns of Alexander.

• 13:10Ryan Holiday?

  If you haven't read The Anabasis, I would encourage everyone to read it, especially as conflict in the Middle East continues to present itself. But Arian is a student of Epictetus, and he captures some of what Epictetus writes down or what Epictetus is talking about. It's by no means exclusive. We think some of those books are also probably lost. But, but, you know, as you guys sit there and you write notes from, from what your professors are talking about, just imagine if that was the only records 2,000 years later of what that great man or woman had said in their brief time on earth.

• 13:51Ryan Holiday?

  And, and that those notes, you know, Epictetus is a slave and this sort of high-ranking, you know, politician or, you know, officer of the state writes them down and they survive to us. But, but shortly thereafter, those notes, either from Arian or perhaps Marcus's philosophy teacher, Junius Rusticus, has his own notes or his more extensive notes, we don't know exactly, but those make their way to the most powerful man in the world. And that's Marcus's entry point into the teachings of Epictetus, which he quotes repeatedly throughout Meditations. So again, you know, great speaking translates to great writing, which translates into influence

• 14:35Ryan Holiday?

  at the highest level, both politically and historically, that you could just about imagine. It's a pretty remarkable, you know, contrast of extreme powerlessness and incredible privilege and power coming together through the common ideas. And Marcus mentions this at the beginning of Meditations, where he says, you know, "Thanks to, uh, thanks to, to Junius Rusticus for lending me his copy of, of Epictetus." And, and, you know, he didn't just lend it to him, but Marcus then read it, right? And so that's also kind of a timeless process that I've, I've always loved.

• 15:09Speaker 01

  In thinking about the Stoicism now as you present, live by, do you think modern Stoicism includes some of the more philosophical foundations that like Epictetus and others talk about, like Seneca, living in accordance with nature? Or is modern Stoicism?

• 15:32Ryan Holiday?

  Yeah, Stoicism was a multi-part philosophy in the ancient world. It had physics and logic and ethics, essentially. And I think we can all understand why their physics have not stood the test of time, although it is incredible when you read the Stoics or the Epicureans and you have these people 2,000 years ago talking about atoms. And you're like, how did they know? They knew more than you'd think they would know. But yeah, some of these things have fallen away. I mean, the Stoics, Epictetus, probably more than, say, Marcus, seemed to be remarkably predeterministic. You know, there wasn't a sense of much in the way of personal agency or that things could change.

• 16:16Ryan Holiday?

  And I don't think that's an unforgivable sin. I mean, this is a guy who was born into brutal slavery and sees the worst unchangeable parts of human nature. He doesn't realize the things that are going to come along later and some of the breakthroughs we're going to have. So I think there are parts of the Stoic canon I think are interesting to read about and talk about, and certainly if I was an academic philosopher, maybe I would talk about these more. But I'm more interested in what's fallen to me is the idea of talking to a lay audience about these philosophical principles. So I tend to focus primarily on the ethical stuff, which is, by the way, when Marcus realist is talking to himself, almost entirely what he talks about.

• 17:00Speaker 01

  That's a great segue into one of the other questions I had was, you have a sort of a lay audience generally, but you have a lot of different ways in which you talk about that, like lectures like this, your books, podcasts. In terms of, so one thing my students have to do at the end of the semester is they have to define some virtue or virtue itself. To a non-academic audience. And so when you do that with Stoicism, how do you think about how you're gonna present those ideas?

• 17:37Ryan Holiday?

  It's really difficult. I mean, I think you have to accept and understand where the audience is, what their biases are, what their inhibitions are, you know, what their base level of knowledge is. So I'll give you an example. I'm in the middle of this series that I've been doing for the last four years on the cardinal virtues. So I did a book on courage. I did a book on discipline. I am just finished and turned in the third book in the series, which is about justice. And the fourth is going to be about wisdom. Now, these middle two were the toughest. I think courage, we all sort of universally agree what it is and why it matters. Wisdom, I think we all sort of universally agree what it is and why it matters. Now, what about discipline? I think discipline, we know is good. We all kind of wish we had more discipline. But the Stoics typically

• 18:21Ryan Holiday?

  talked about sophrassine as the virtue of temperance or moderation. Now, when I'm writing a book that I hope reaches people as diverse as NFL coaches, to military officers, to stay-at-home moms, and, you know, college students, I'm probably not going to sit down and write a book about temperance, particularly in America where temperance is so associated with the ill-fated prohibition movement, right? That's what temperance meant for, you know, it meant not drinking alcohol, not moderation, or balance, or disappointment, not drinking alcohol. So I think a lot in my books about what's the best way into

• 19:04Ryan Holiday?

  this idea? What's the word that most lines up with what the audience also identifies as the virtue? And once I get in, then I can talk about more expansive things. So at the same token, when I'm writing this book about justice, I think it says something about our society today, that when people hear justice, they think the legal system. Or when they hear the word justice, they think social justice warriors, which Which again says something that we think of that as an insult, right? But, but you know, most people are not roaring to read a book about justice. So that book is going to be called Right Thing Right Now. And it's going to be about doing the right thing, which is a form of justice, of course. And I think justice is, is integral to that.

• 19:48Ryan Holiday?

  But as I'm, even as I'm thinking about the subtitle, I've been going back with my publisher about, do we use the word justice at all in a book, in the packaging, in a book about justice? And again, I would love to live in a world where I could call it, you know, justice, the most important virtue, and, and people would line up to buy it, but they don't, right? Just like when I wrote a book several years ago about ego, I was really writing a book about humility, but I had to make it about ego to make it both interesting and accessible and sort of of the moment. So there's a lot you have to think about when you're trying to communicate seemingly old fashioned ideas to a modern audience.

• 20:47Ryan 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.