Do Not Delay | Dan Harris & Ryan Holiday on The Pursuit of Wisdom

Life has a way of stripping all our reasons bare, of humbling our plans and assumptions. We must live, as Marcus Aurelius said, as if death hangs over us. Because it does.👉 Listen to the full conversation between Dan Harris and Ryan Holiday on Apple Podcasts, Spotify, or watch on YouTube📚 Buy a copy of 10% Happier by Dan Harris at The Painted Porch: https://www.thepaintedporch.com/🪙 We have a collection of items in the Daily Stoic store to help you in your own memento mori practice, check them out here: https://store.dailystoic.com/🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription

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

• 0:00Ryan 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.

• 0:15Ryan Holiday?

  Do you know what one of the last things Abraham Lincoln ever said was? As he sat in a box at Ford's Theater as he waited for the play to start, Lincoln turned to his wife and said, "Oh, how I should like to visit Jerusalem sometime." Within minutes, an assassin would fire a bullet into his brain. Within hours, he would be dead. Now, of course, there were many reasons why this great man never found time in life to visit Jerusalem. He had to teach himself to read. He had to work himself out of abject poverty. He had to conquer depression. And then the gravest threat to freedom yet known in the United States. He freed the slaves and made sure democracy would not perish from the earth. And these are all reasons why he had to put off that trip till a later date,

• 0:59Ryan Holiday?

  just as you have many reasons why you are waiting to do this or delaying doing that. And yet, life has a way of stripping all our reasons bare of humbling our plans and assumptions. "We must live," as Marcus really said, "as if death hangs over us." Because it does. "We cannot put off till tomorrow," he said, "what we can do today, whether that's being good, our highest priority, or telling people we love them, or going places we wish to go. No one knows what the future holds. No one knows how much time we have left. So do not delay. Do not wish. Do not wait. Do it now, while you still have time, while there still is a chance."

• 1:44Ryan Holiday?

  "All of the future is uncertainty," Seneca said. So live now, live immediately. Or as Marcus says in the challenge coin I carry with me everywhere, "You could leave life right now. Let that determine what you do and say and think." This exercise of memento mori from the Stoics, it's not about being morbid. It's about creating a sense of urgency and clarity and priority. That's why the Stoics practice memento mori. That's why I carry this challenge coin with me. I have a memento mori, a piece of a tombstone that I keep in my bathroom mirror that I look at on a daily basis. Memento mori, it's so powerful. It gives so much clarity. Find some way to practice that. If you want ours, you can check it out at store.dailystoic.com. But just find something that reminds you

• 2:28Ryan Holiday?

  That you should not delay, you cannot wait. Do it now.

• 2:50Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Back in December, I was talking about Stoic philosophy with my friend Dan Harris. He has the 10% Happier Podcast. I love his book 10% Happier. He's sort of doing for Buddhism what I've been trying to do for Stoicism. I've been on the podcast a while ago, but we just had another chat back in December. And since that episode just dropped, I think it dropped on the 11th, I wanted to bring you a little chunk of that conversation. You can head over to the 10% Happier Podcast to listen to the full episode. You should definitely read his book. I just did a YouTube video where I was raving about it as one of the books you should definitely read this year if you want to navigate these stressful, crazy times. Dan's story is incredible, and I think you will like this

• 3:35Ryan Holiday?

  episode and his books.

• 3:41Speaker 01

  Ryan Holiday, welcome back to the show.

• 3:43Ryan Holiday?

  Yeah, thanks for having me.

• 3:44Speaker 01

  It's a pleasure to have you back. All right. Well, let me start with some basic questions.

• 3:48Ryan Holiday?

  Deal.

• 3:49Speaker 01

  The book is called Wisdom Takes Work. What do you mean by wisdom? It's one of those words that like you say it and you picture it like Dumbledore.

• 3:59Ryan Holiday?

  Mm hmm.

• 4:00Speaker 01

  What do you mean specifically by wisdom?

• 4:03Ryan Holiday?

  Yeah, it's a tricky one, right? What is the definition of wisdom? I've come to understand that it is many things, right? So obviously, it's experiences, it is reading. I guess what I figured out doing this book, so I've been doing this series on the cardinal virtues, the four virtues for people who don't know of Stoicism are courage, temperance or self-discipline, justice and wisdom. So they're all kind of basic words that are pretty obvious. And then as soon as you start to drill down on them, you realize, oh, there are many things and there are sort of sub virtues underneath each one. And so my definition of wisdom is that

• 4:44Ryan Holiday?

  There is no definition. And to think that there is a clean, one-sentence definition is probably some sign that whatever wisdom is, you don't have it. It's a complicated thing comprising intelligence and creativity and experience and age. It's wit. It's all of these things and more. And yet, at some level, it is incredibly elusive and it's hard to point to any one person that has it. Which ultimately comes to the title of the book, which you mentioned. Seneca is saying, the one thing that we can all agree on as far as wisdom is that nobody gets it by chance. It's not something you're born with.

• 5:27Ryan Holiday?

  It's not something anyone can give you. It only comes, the Stoics say, as a result of a lot of work. And so that's basically the premise of the book, that it's sort of this byproduct of this kind of timeless methodology or process, these sort of basic practices. And it's probably better to focus more on doing those things than trying to ascertain whether you have it or don't, if that makes sense.

• 5:59Speaker 01

  Yeah, it's like, you do the work, wisdom is the emergent property, and it's somewhat ineffable, indescribable.

• 6:06Ryan Holiday?

  Yes.

• 6:07Speaker 01

  But you kind of know it when you see it or experience it.

• 6:10Ryan Holiday?

  It eludes your grasp, right? Even if you, like, the paradoxical nature of it is that if you or I were to agree on someone that we both think is wise, and then we asked them, not just, "Are you wise?", but "How did you get wise?", they would almost certainly not describe themselves in that way. And there would be, as you said, a certain ineffability to how they got to wherever they got, because it's such a long and gradual process.

• 6:45Speaker 01

  You mentioned Seneca. For people who don't know who that is, can you just fill us in?

• 6:50Ryan Holiday?

  Yeah, Seneca is one of the wisest philosophers of the ancient world. He lives in the time of Nero. He's a Roman senator who becomes a Stoic philosopher. A complicated, fascinating guy who writes quite eloquently and persuasively about all these Stoic ideals and the pursuit of wisdom. And then I think to go to our point that even the wisest people have huge blind spots and make all sorts of mistakes. He is Nero's teacher, one of the worst emperors that ever lived. And he's sort of caught up in this political mess. One of the things I end up talking about in the book actually is this idea of like, why so often very smart people, academics, or philosophers, or gurus, or whatever,

• 7:34Ryan Holiday?

  find themselves drawn into the service or the orbit of profoundly bad people and seem to be genuinely bad at reading those people? Plato does the same thing. I'm fascinated with that as well.

• 7:50Speaker 01

  Yeah, I mean, you see it with Jeffrey Epstein. I mean, he had all these smart people in his orbit. I mean, maybe it speaks to the difference between intelligence or being smart and wisdom.

• 7:59Ryan Holiday?

  Yes. Also, though, like when we're talking about intelligence, social intelligence is such a underrated form of it. Like, one of my favorite stories in the book, and not everyone agrees with me on it, but I think it's fascinating. So Socrates, we hold up as this great, wise philosopher, this brave man who is brought up on these trumped up charges and goes bravely to his death. But to me, the illustrative thing about Socrates is, okay, so Socrates is brought up on trial for impiety and corrupting the youth. And he's only narrowly convicted by the jury, right? The juries in ancient Athens were hundreds of people, but he's like narrowly convicted of the crime. But then he's given the opportunity to suggest his own punishment, right?

• 8:43Ryan Holiday?

  He's allowed to address the court. And after Socrates addresses the court, he gives such a bad speech. Like, he reads the room so poorly and he's so obnoxious. He says, actually, not only should I not have been convicted, you should give me a pension. Like, my punishment should be a reward. And he's so annoying that a larger percentage of the jury votes to convict him.

• 9:09Ryan Holiday?

  To death, to sentence him to death, then voted for his guilt in the first place.

• 9:14Speaker 01

  Oh, wow.

• 9:15Ryan Holiday?

  So what this means is that some people who thought he was innocent still wanted him sentenced to death. My point is that Socrates is one of the wisest people who ever lived, and yet he's obnoxious. He's not just obnoxious, but he seems to poorly perceive how he comes off to people. Like, he would describe himself as the gadfly of Athens. But people hate flies, right? Like, that's a bad thing to be. So I think there is a tendency, and I think we see this in these extreme examples, and then we want to wonder where we're doing it. My point is just, if you're smart, but your intelligence leads you to get sentenced to death, avoidably so, maybe you're not so smart, right? Maybe you're lacking some element of wisdom.

• 10:01Speaker 01

  So you said earlier that wisdom is one of the four cardinal virtues.

• 10:05Ryan Holiday?

  Yeah.

• 10:06Speaker 01

  And then you walked us through what they were, and I can't remember the justice, temperance, courage, maybe?

• 10:11Ryan Holiday?

  Yes.

• 10:11Speaker 01

  And?

• 10:11Ryan Holiday?

  You got them.

• 10:12Speaker 01

  Thank you. You didn't say this, but you say it in the book, that wisdom is the mother of all of these virtues. So why is that?

• 10:18Ryan Holiday?

  What's the most important of the virtues? Obviously, at some level, they're inseparable and all interdependent on each other. A great example of this would be courage and justice. Courage in pursuit of a profoundly evil or selfish aim, like an unjust or an unjust aim, is obviously not an admirable or a virtuous form of courage. So I think we can say that all the other virtues descend from wisdom, because wisdom informs or instructs us on what they are. So the cause that you pick is not just informed by wisdom, but then your understanding of how to bring that justice into the world has to be shaped by wisdom.

• 11:03Ryan Holiday?

  Like, the example that I give in this, actually two fascinating examples, Thomas Clarkson and Abraham Lincoln, the two individuals most responsible for the eradication of slavery in the Western world, at some kind of moral, personal Level, they just instinctively believe that slavery is wrong. But what's fascinating about both of them, if you study their journey from just two individuals who disliked slavery to two crusading activists who bring about its demise. Thomas Clarkson, for people who don't know, is in England. He starts the abolitionist movement and leads to the invention of most modern political activism, nonviolent activism.

• 11:47Ryan Holiday?

  What both he and Lincoln do is they say, OK, I have this sense that this thing is wrong. But they do these multi-year deep dives into the history of the institution, both its legality, its philosophical roots, its economic underpinnings. Like, Lincoln goes to the Library of Congress and reads as much original documentation, debates amongst the founders, letters, bullet points from senatorial and congressional debates. Clarkson does the same thing. He goes and actually visits a slave ship, like that famous drawing of what a slave, the inside of a slave ship looks like, that comes from Clarkson.

• 12:29Ryan Holiday?

  So my point is that both the interest, like the curiosity, and then the technical competence to go wrap your arms around a subject or a topic is a part of wisdom. It's not, oh, I think this thing is wrong and therefore everyone should agree with me. What both of them do in their crusade is they go and understand the thing and figure out how to communicate it, and then also figure out its center of gravity that they're then able to attack courageously with discipline to make a more just world.

• 13:07Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please, spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say thank you.