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

Summary

The Daily Stoic Podcast — Episode Summary

Episode Overview

Title: Do Not Delay | Dan Harris & Ryan Holiday on The Pursuit of Wisdom
Date: February 12, 2026
Host: Ryan Holiday (Daily Stoic)
Guest: Dan Harris (10% Happier podcast, author of "10% Happier")

In this episode of The Daily Stoic Podcast, host Ryan Holiday explores the Stoic approach to living urgently and wisely, drawing on the theme "Do Not Delay." He shares historical examples, personal reflections, and a rich conversation segment with Dan Harris centered on the nature, pursuit, and application of wisdom. The discussion weaves together lessons from history, philosophy, and personal growth, providing actionable insight for listeners interested in Stoicism and the broader quest for wisdom.

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Main Theme & Purpose

• Urgency of Living: The episode stresses the importance of not postponing meaningful actions, relationships, or experiences, echoing the Stoic principle of memento mori — the remembrance of death as a motivator for living well now.
• Nature of Wisdom: Ryan Holiday and Dan Harris dive deep into unpacking what wisdom truly means, why it’s difficult to define, and how one might pursue it intentionally.

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Key Discussion Points & Insights

1. The Power of Memento Mori & Not Delaying (00:00–02:44)

• Anecdote of Abraham Lincoln: Lincoln's final wish to visit Jerusalem, unfulfilled due to his untimely death, highlights the unpredictability of life and the need to act on our priorities.
  • Quote: “We must live, as Marcus Aurelius said, as if death hangs over us because it does. We cannot put off till tomorrow… what we can do today.” (01:12, Ryan Holiday)
• Stoic Teachings: Reflections from Seneca and Marcus Aurelius on the certainty of death and why that should drive us to action.
  • Quote: “All of the future is uncertainty, Seneca said. So live now, live immediately.” (02:29, Ryan Holiday)
• Personal Practices: Ryan shares how he uses a memento mori coin and a piece of a tombstone to remind himself to live with urgency and clarity.

2. Conversation with Dan Harris: Defining and Pursuing Wisdom (05:30–16:16)

• What is Wisdom? (06:29–08:47)
  • Wisdom is multifaceted—spanning age, experience, intelligence, wit, and creativity. The more one seeks a clear-cut definition, the less likely it is that one possesses it.
  • Quote: “My definition of wisdom is that 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.” (07:30, Ryan Holiday)
  • The paradox: The truly wise seldom describe themselves as wise, and their journey resists tidy explanation.
• Wisdom vs. Intelligence (09:25–12:41)
  • Historical philosophers (Seneca, Socrates) demonstrate the gulf between being learned or smart and being truly wise—particularly when lacking social intelligence or awareness.
  • Quote: “Socrates is one of the wisest people who ever lived, and yet he’s obnoxious… If you’re smart, but your intelligence leads you to get sentenced to death avoidably… maybe you’re lacking some element of wisdom.” (11:55–12:41, Ryan Holiday)
• Wisdom as the Parent Virtue (12:41–16:16)
  • Wisdom is the foundation from which courage, justice, and temperance flow. One cannot be courageous or just in a meaningful way without wisdom’s guidance.
  • Historical Case Studies: Thomas Clarkson and Abraham Lincoln’s deep study and deliberate actions in abolishing slavery illustrate wisdom as the combination of moral clarity, curiosity, and technical competence.
  • Quote: “All the other virtues descend from wisdom, because wisdom informs or instructs us on what they are. 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.” (13:10, Ryan Holiday)

3. Notable Examples & Paradoxes

• Seneca’s Blind Spots: Highly intelligent individuals can be drawn to the service of tyrants (Nero, in Seneca’s case), showing that wisdom isn’t just a product of smarts or learning.
• The Failure of Social Intelligence: Even the revered Socrates displayed a lack of practical wisdom, failing to read the room in his own trial.

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Notable Quotes & Memorable Moments

• On Life’s Uncertainty:
  • “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…” (01:39, Ryan Holiday)
• On Wisdom’s Elusiveness:
  • “If you or I were to agree on someone that we both think is wise, and then we asked them…how did you get wise? They would almost certainly not describe themselves in that way…” (08:52, Ryan Holiday)
• On Socrates:
  • “He gives such a bad speech…he says, ‘Not only should I not have been convicted, you should give me a pension …’. He’s so annoying that a larger percentage of the jury votes to convict him to death, than voted for his guilt in the first place.” (11:38, Ryan Holiday)
• On Links Between Virtues:
  • “Courage in pursuit of a profoundly evil or selfish 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…” (13:01, Ryan Holiday)

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Important Timestamps

| Timestamp | Segment | Content/Theme | |-----------|-------------------------------------------|----------------------------------------------------| | 00:00 | Opening | Introduction, urgency of Stoic virtues | | 00:15 | Memento mori anecdote | Lincoln, impermanence, acting with urgency | | 01:12 | Stoic teachings on urgency | Quotes from Marcus Aurelius, Seneca | | 02:29 | Memento mori is not morbid | Live now, create clarity and priority | | 05:30 | Segment intro: Dan Harris conversation | Transition to discussion on wisdom | | 06:29 | Defining wisdom | Wisdom’s complexity and elusiveness | | 07:30 | “No definition” | Holiday’s take on defining wisdom | | 11:38 | Socrates and social intelligence | Intellectual blind spots in wise people | | 12:59 | Wisdom as parent virtue | Relationship between virtues | | 13:55 | Lincoln & Clarkson | Historical examples of wisdom-in-action |

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Overall Tone & Takeaways

• Language & Tone: The conversation is reflective, wise, and lightly humorous, often employing historical anecdotes and philosophical insight in accessible language.
• Practical Wisdom: Listeners are urged not only to contemplate the meaning of wisdom but to practice daily urgency—living out Stoic virtues with purpose, clarity, and a readiness not to delay what matters most.

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Suggested Actions for Listeners

• Practice Memento Mori: Find a personal reminder (coin, object, note) to recall life’s fragility and act with intention.
• Pursue Wisdom through Action: Focus on consistent self-examination, reading, and action rather than seeking to be recognized as “wise.”
• Integrate the Virtues: Recognize how justice, courage, discipline, and wisdom inform and support each other.

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Listen to the full conversation on the 10% Happier podcast for further insights.

Transcript

[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.

[Daily Stoic Narrator]

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. 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 Aurelius 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 or highest priority or telling people we love them, we're 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. 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 Stokes, 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 [e-mail] but just find something that reminds you that you should not delay. You cannot wait. Do it now.

[Guest Philosopher/Author]

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[Ryan Holiday]

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[Daily Stoic Narrator]

Hey, it's Ryan.

[Ryan Holiday]

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.

[Daily Stoic Narrator]

He's sort of doing for Buddhism what.

[Ryan Holiday]

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.

[Daily Stoic Narrator]

A little chunk of that conversation.

[Ryan Holiday]

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.

[Daily Stoic Narrator]

I was raving about it as one.

[Guest Philosopher/Author]

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.

[Ryan Holiday]

You will like this episode and his books.

[Podcast Host/Interviewer]

Ryan Holiday, welcome back to the show.

[Guest Philosopher/Author]

Yeah, thanks for having me.

[Podcast Host/Interviewer]

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

[Guest Philosopher/Author]

Deal.

[Podcast Host/Interviewer]

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, like Dumbledore. What do you mean specifically by wisdom?

[Guest Philosopher/Author]

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 or 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 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, 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. 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. Yeah.

[Podcast Host/Interviewer]

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

[Ryan Holiday]

Yes.

[Podcast Host/Interviewer]

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

[Guest Philosopher/Author]

It eludes your grasp.

[Daily Stoic Narrator]

Right.

[Guest Philosopher/Author]

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.

[Podcast Host/Interviewer]

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

[Guest Philosopher/Author]

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 message. One of the things I end up talking about in the book, actually, is this idea of why so often very smart people, academics or philosophers or gurus or whatever, 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.

[Podcast Host/Interviewer]

Yeah. I mean, you see, it was 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.

[Guest Philosopher/Author]

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

[Podcast Host/Interviewer]

Oh, wow.

[Guest Philosopher/Author]

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.

[Podcast Host/Interviewer]

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

[Guest Philosopher/Author]

Yeah.

[Podcast Host/Interviewer]

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

[Guest Philosopher/Author]

Yes.

[Podcast Host/Interviewer]

And you got him. 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?

[Guest Philosopher/Author]

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 injust 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. 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 the invention of most modern political activism, nonviolent activism. What both he and Lincoln do is they say, okay, 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. 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. 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 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.

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[Ryan Holiday]

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