Your New Stoic Role Models for a Stronger Life

Summary

The Daily Stoic – "Your New Stoic Role Models for a Stronger Life"

Date: December 24, 2025
Host: Ryan Holiday
Guests: Michelle "Mace" Curran, Nick Thompson, Rutger Bregman, Billy Oppenheimer

---

Episode Overview

In this special compilation episode, Ryan Holiday explores the four cardinal Stoic virtues—Courage, Discipline, Justice, and Wisdom—through candid conversations with four modern role models. Drawing on their life experiences, personal stories, and practical applications, the episode demonstrates how ancient Stoic principles remain urgent and actionable in everyday life. Each segment zooms in on a virtue through the lens of a remarkable guest:

• Fighter pilot Michelle Curran on Courage
• CEO and marathoner Nick Thompson on Discipline
• Historian and activist Rutger Bregman on Justice
• Writer and research assistant Billy Oppenheimer on Wisdom

Through real stories and honest discussions, listeners are invited to reflect on how these virtues can serve as guides and sources of strength in challenging moments.

---

Key Discussion Points & Insights

Introduction: Everyday Examples of the Virtues (05:10–08:55)

• Ryan shares a personal story: A tense encounter with a neighbor's car nearly clipping him while walking his dog. He reflects on how both his own and the driver's reactions illustrated aspects of the Stoic virtues—discipline in not escalating, courage in facing the situation, justice in the neighbor’s apology, and wisdom in learning restraint.
  • "A lack of restraint, lack of discipline on my part, that was like part of the inciting incident here. The willingness to make amends or admit error, right? That's what my neighbor illustrated there..." – Ryan Holiday [07:09]
• Framing: Virtue isn't only about grand acts—it's woven into small, everyday decisions.

---

Section 1: COURAGE with Michelle "Mace" Curran (08:55–21:21)

Michelle Curran: Former Air Force F-16 solo pilot, lead solo for the Thunderbirds, author of "The Flip Side"

Key Takeaways

• The Golden Mean and Real Courage:
  • Ryan: "Courage is not the opposite of cowardice. It's in the middle between recklessness and cowardice... Confidence is somewhere in the middle of those two extremes." [09:09–09:36]
  • Michelle illustrates the lesson with her "call sign" story—pushing herself nearly to black out on a training flight due to ego and the fear of looking weak.
    • "I was so worried about failing that. That was more important to me than my physical safety." – Michelle Curran [11:43]
    • "The irony of course is that you did look really stupid." – Ryan Holiday [11:54]
• Vulnerability and Asking for Help:
  • Ryan references Marcus Aurelius: "If you’re all storming a wall and someone falls, you're not like, you idiot. In fact, they're like, there's something beautiful about being able to help that person." [13:12]
  • Michelle: "When I was flying for the Thunderbirds... I'd be like, I'm not brave. Like, I've had so much self doubt. I've had so many moments of fear, I just forge ahead anyway. And it was never about what they thought I was being brave for..." [13:57]
  • Ryan: "But that is the definition of bravery though. If you're not afraid, then it's not brave." [14:17]
• The Unseen Side of High-Performance Careers:
  • Reality vs. pop culture myths (i.e., Top Gun): Long hours, discomfort, constant setbacks—real courage lies in enduring the grind, not just performing on "game day."
  • "If it was glamour, if the practice was fun, more people would do it." – Ryan Holiday [18:10]
• Process over Outcome:
  • Loving the process (writing, flying, training) rather than just the rewards or recognition is essential to long-term courage and continued growth.

---

Section 2: DISCIPLINE with Nick Thompson (22:39–28:02)

Nick Thompson: CEO of The Atlantic, elite marathoner, author of "The Running Ground"

Key Takeaways

• The Generational Loop of Discipline:
  • Nick reflects on how his complicated relationship with his father shaped his own drive and work habits.
  • "I try very hard not to let my discipline drop, in part because I don't want to be that." – Nick Thompson [23:29]
• Running as a Discipline Metaphor:
  • Running every day builds "cumulative" discipline, spills into other areas (work, writing).
  • "If you do a hard thing first thing in the morning, it's easy to do the next hard thing... the focus required for running helps you with everything else." – Nick Thompson [24:13–24:34]
• Incremental Progress Over Time:
  • "If you run every day and if you run hard from time to time, you get faster. It just happens." – Nick Thompson [25:22]
  • Often the improvements aren’t perceptible day-to-day, but accrue over time through consistent effort—a core Stoic lesson.
• Writing and Running Parallels:
  • Breaks down complex, long-term projects (like books or races) into manageable daily tasks.
  • "You just do it a little bit here, you do it a little bit there, and like, it gets done right. Eventually it's done right." – Nick Thompson [26:13]

---

Section 3: JUSTICE with Rutger Bregman (28:02–41:24)

Rutger Bregman: Dutch historian, co-founder of the School for Moral Ambition, author of "Moral Ambition"

Key Takeaways

• Justice Is Action, Not an Inheritance:
  • "You're not born as a good person. You become a good person by doing good things. So just get started." – Rutger Bregman [29:11]
• Inclusive Movements & Coalition Building:
  • Ryan highlights how the most powerful social movements (abolition, suffrage) succeeded through broad coalitions—not purity or exclusion.
    • "When you decline an alliance with someone, you are often forcing them to ally with your opponents." – Ryan Holiday [30:29]
    • "If someone agrees with you for like 70 to 80% of the time, that person is an ally, not your enemy." – Rutger Bregman [31:20]
• The Power of Perseverance and Legacy:
  • The long timeline of social change; most originators of major reforms died before seeing victory but inspired future movements.
  • "Knowing that you're part of something that's much bigger than you are, that gives me a lot of energy to work on that stuff." – Rutger Bregman [35:13]
• Justice as the Core Purpose of Strength and Virtue:
  • "All the other virtues are rendered meaningless if not directed at justice." – Ryan Holiday [40:23]
  • "So, yeah, justice has to be the thing that your life is." – Ryan Holiday [41:17]
  • Stoic justice is local and practical—how you pay, treat, and interact with those around you.

---

Section 4: WISDOM with Billy Oppenheimer (43:59–56:40)

Billy Oppenheimer: Writer, research assistant, author of the Six at Six newsletter

Key Takeaways

• Wisdom as a Process, Not a Destination:
  • Ryan discusses how writing each book in his Virtue series came at exactly the right moment to apply its teaching to his own life—wisdom, especially, is ever-relevant as life changes.
  • "Who I would be four, five years later, I would have more to say about it... some of the thoughts on education and setting up an education would be more relevant to me." – Ryan Holiday [45:11]
• No Shortcuts to Wisdom:
  • Seneca’s story of the Roman who employed slaves to memorize books for him as an early example of seeking shortcuts—an allegory for "outsourcing" wisdom, now echoed in modern AI and tech.
    • "Seneca is laughing about how, you know, it's not something anyone can do for you and there's no shortcuts. And he says, you know, no one was ever wise by chance. Like, no one's beaten the system, basically." – Ryan Holiday [48:01]
  • True wisdom is developed through effortful engagement, ongoing learning, and self-reflection—not by collecting facts or finding hacks.
• On Learning & Education:
  • The never-ending nature of education, both personal and for one's children—the "best way" is a perennial struggle.
    • "If you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit." – Ryan Holiday [56:23]
  • Timeless wisdom about education—principles over formats or systems, openness to new methods.

---

Notable Quotes & Memorable Moments

• On Courage

  • "If you're not afraid, then it's not brave." – Ryan Holiday [14:17]
  • "I was so worried about failing that that was more important to me than my physical safety." – Michelle Curran [11:43]

• On Discipline

  • "If you do a hard thing first thing in the morning, it’s easy to do the next hard thing." – Nick Thompson [24:13]
  • "It’s this cumulative gain... block by block." – Ryan Holiday [25:30]

• On Justice

  • "You're not born as a good person. You become a good person by doing good things." – Rutger Bregman [29:11]
  • "All the other virtues are rendered meaningless if not directed at justice." – Ryan Holiday [40:23]

• On Wisdom

  • "No one was ever wise by chance." – Seneca (quoted by Ryan Holiday) [48:10]
  • "If you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit." – Ryan Holiday [56:23]

---

Important Timestamps

| Timestamp | Segment / Topic | Speaker(s) | |-----------|------------------------------------------|-----------------------------| | 05:10 | Introduction & Everyday Virtue | Ryan Holiday | | 08:55 | COURAGE | Michelle Curran, Ryan Holiday | | 22:39 | DISCIPLINE | Nick Thompson, Ryan Holiday | | 28:02 | JUSTICE | Rutger Bregman, Ryan Holiday| | 43:59 | WISDOM | Billy Oppenheimer, Ryan Holiday | | 56:40 | Conclusion, reflections on education | Ryan Holiday |

---

Final Thoughts

Throughout the episode, Ryan Holiday and his guests illustrate that Stoic virtue is less about attaining a singular heroic status and more about how we respond, adapt, and persist in ordinary and extraordinary circumstances alike. Their lived experiences highlight that courage, discipline, justice, and wisdom are forged and revealed through daily trials, tough questions, and a willingness to learn and grow.

For listeners seeking practical, relatable inspiration to build a "stronger life," these new role models, and the virtues they embody, offer a clear and actionable path forward.

---

Podcast: The Daily Stoic – "Your New Stoic Role Models for a Stronger Life" – December 24, 2025

Transcript

[Ryan Holiday]

The world is full of tours, but.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

You don't choose a Toyota truck to follow the beaten path. You choose it to find the places.

[Michelle Mace Curran]

In between.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

The detours, where each adventure pulls you toward the next, and wrong turns turn out right. So why would you ever take a tour when you could take a detour? Toyota Trucks.

[Ryan Holiday]

My family owns a 2023 Toyota 4Runner, and honestly, it's my favorite vehicle that I've ever owned around town. It's smooth and reliable, but where it really shines is on our trips into the backcountry. We've taken it on backpacking adventures to Colorado and New Mexico, loaded up with gear and never had to think twice about whether it could handle the terrain. That's what Toyota trucks are built for. Off road confidence, rugged durability and the freedom to explore. Toyota has a long history with the outdoor community and they're committed to helping more people get out there and experience what nature has to offer. From remote trails to scenic byways, Toyota Trucks empowers you to take the detour, roam freely and discover places that still feel wild and untouched. And they're not just making great trucks. They're working to expand access to adventure so more people can connect with the outdoors and pass that passion on to the next generation. Discover your uncharted territory. Learn [e-mail] trucks adventure detours that's toyota.com trucks adventure detours I'm picking my kids up from school today and then doing our weekly routine, which is I take them over to Whole Foods and we get all our groceries for the week. Then we have dinner. It's one of their favorite things to do. It's one of my favorite things to do. And then my wife loves it because she doesn't have to take care of it. This holiday season, whether you're a guest or hosting the big dinner, Whole Foods Market has what you need to delight everyone at your table. They even have heat and eat sides from the prepared foods department. You can make Whole Foods your one stop shop. Everything follows Whole Foods Market's strict ingredient standards. Know it will be delicious and good for you. You can also order online for pickup and even delivery in select zip codes to skip the crowds. Shop everything you need at Whole Foods Market, your holiday headquarters. Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the Ancient Stoics, a short passage of of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays we talk to some of our fellow students of ancient philosophy, well known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their lives. Foreign. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. So I was walking my dog last night, walking down the dirt road we live on, and it's not exactly night. It's like dusk. It's starting to get dark. I have, like, a little flashing light I put on her collar. I have a flashlight, like a running flashlight that I have. It's actually this cool to kind of like. It's like kind of like an L shape. You sort of hold it. It's almost like a. You grip it. Anyways, this has nothing to do with what I'm saying. I'm walking the dog, and I'm listening to music, and this car kind of comes up behind me. It's a pretty small, contained little rural area we're in. So it's someone down towards the end of the road, and they're coming up behind me, and I can hear them, and I get over to the side, and then they come, like, insanely close to me in their car, and I have the dog on the left side, and they're coming up behind me, so they're on my right side. And I'm like, whoa, what is this? I kind of like, throw my hands up, you know, like in a. In a shrug, like, what the hell, man? And the car continues on, you know, maybe five yards. And then, like, I see the brake lights come on and I go, oh, no. I'm saying, oh, no, not. Cause, like, I'm afraid. Exactly. Cause I'm not. But it's more just like, they shouldn't have done this. I don't like that they did it. I'm fine, you know, but did I need to express my frustration with the situation and now have to have a confrontation with the person? I remember I was younger in New Orleans, and something similar had happened. Like, a car whipped out, and I was, you know, threw up my arm like this. The person got out. And I don't remember the details exactly, but I was, like, physically menaced as a result. And then I was like, okay, like, you're obviously in the right. The pedestrian is right here. But it's not something you need to die over. And so I generally try to. As exasperated and frustrated as I can get, with people who are not endangering me or doing dumb things in their car, I generally try to be chill about it because, you know, it's not worth it. That's what I'm saying. So the car not only slows down, but then like I see like they come to a stop and then that like they reverse a little bit. And so I'm like, ah, great. And then I remember, oh, I'm actually I'm. Because there's wild dogs in our neighborhood and sometimes hogs and stuff. I don't open carry. I guess I could again, not a, not a big gun person if I don't have to be, but I do carry like a collapsible police baton. I've had to raise it over my head, let's just say. So I realized, oh, I've got this thing on me. So. So I'm like feeling a little more not sure myself, but I'm feeling a little like, all right, they don't know what's going on. And so as I sort of walk up to the car and half dreading, half just sort of going, I hope this goes good because it doesn't need to be bad, but I'm not as vulnerable as I initially thought, right? I approached the car, they roll down the window and it's. There's this sort of a bunch of people live way down on the road and I know they don't speak English. And guy rolls down the window, I don't think I've seen him before. And he goes, sorry, amigo. And then I go, oh, don't worry about it. And he rolls up the window. I was relieved, right? I was relieved in a couple of ways. It went from a negative situation. Then I was like, is this going to be the worst of people to a thing where I'm like, this is the best of people, right? Like I was mad at myself for a little bit of lack of restraint that incited potentially a conflict. And then I was like impressed and pleased with this person who was in the wrong, by the way. Like they almost clipped me with their car to de escalate like he de escalated first, even though he had no idea whether I was going to be upset or not. Right. What does this have to do with today's episode? Well, we're going to be talking about virtue in today's episode and we tend to think of virtue as this big high minded thing. But I actually think these cardinal virtues, courage, discipline, justice, wisdom, they apply to situations like this, right? A lack of restraint, lack of discipline on my part, that was like part of the inciting incident here. The willingness to make amends or admit error, right? That's what my neighbor illustrated there. But also the courage to not run away from a situation. Like, just the, hey, I know how to handle myself in this situation. I'm not going to needlessly back down from a situation I'm gonna. I'm gonna go in. And I'm confident in my ability to handle this. Like, I wasn't confident in my ability to have to do something. I was just confident in my ability that I didn't need to be afraid here because I knew I could handle myself. Right. And then wisdom. When you're younger, you tend to fly off the handle. You tend to. You just don't know how bad things can get. And you don't always take things seriously that you should take seriously. Is this really the perfect illustration of courage, discipline, justice, and wisdom? No. But it is just a little minor example that I was thinking about that tees up what we're going to talk about in today's little compilation episode. Obviously, these are themes I talk to our various guests on the podcast about. And so I'm going to run you four sections on four of the different virtues. And I think there's going to be a lot to learn here at the beginning, we're talking with someone who I'm incredibly impressed with. This is former Air Force fighter pilot Michelle Mace Curran. She wrote a wonderful new book, the flip side, how to invert your perspective and turn fear into your superpower. She has nearly 2000 hours of flight in an F16. She flew combat missions in Afghanistan. She was also a lead solo pilot for the theater Thunderbirds. When it comes to courage, when it comes to sort of conquering fear, she knows what she's talking about. You know Aristotle's concept of the golden mean?

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

So the golden mean is that all virtues sit between two vices. So, like, courage is not the opposite of cowardice. It's in the middle between recklessness and cowardice. And so I think there's something about confidence that sits between that sort of ego that we all recognize as the obvious ego, the sort of narcissistic, better than everyone ego, and then the sort of the quiet, well, I don't want to ask because I'll look stupid or, you know, the game is rigged against me. Imposter syndrome. Ego, which we don't typically think of as ego, but I think those are the two vices. And then confidence is somewhere in the middle of those two extremes.

[Michelle Mace Curran]

100. And I have a little story from in the jet that actually is how I got my call sign. Oh, which call signs come from a mistake you made? Yeah, everyone Thinks you get to pick them like Maverick's. Like that sounds cool. Let me be Maverick.

[Ryan Holiday]

Like soup because you ate a lot of soup one night.

[Michelle Mace Curran]

Yeah. Sometimes they're as benign as that. Mine is like a kind of a cool flying story, but essentially second flight in Japan, mock dog fighting. So dog fighting training, obviously flying safe guns. We're not actually shooting bullets at our instructors. So my instructor and I going up and I'm supposed to point at him, shoot him with the gun, call the kill, celebrate all the things. Right. And I really want to do well because I'm so worried about what everyone thinks of me. So I light the afterburner, wait a few seconds, roll, pull back on the stick. The F16 pulls nine GS. No problem. So nine times the force of gravity.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

So I am experiencing that. Which very easy to go unconscious from that G induced loss of consciousness. Blood gets forced out of your head. So I am doing that. I'm pulling, I'm just pulling and pulling and not able to point at him and my experienced self later or logically would be like, oh, so I need to change what I'm doing to adjust. Something's not right.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

I've done this like twice before in training. I'm just super young, but my ego is like, you must win, you must gun him. And I just keep pulling and I'm not giving up. And I don't touch my throttle. So just max a battle and I get to full light loss. So I am just blacked out as far as seeing nothing.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

But I am not quite G locked, I'm not quite unconscious cuz I can still hear. And my instructor ends up making a radio call to knock the fight off. Cuz he's like, something's not right.

[Ryan Holiday]

Right.

[Michelle Mace Curran]

And so I was pushing that so far where I was like the closest I've ever been to G locking in my whole life.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

If you G lock in a single seat aircraft, people have hit the ground and died.

[Ryan Holiday]

Right.

[Michelle Mace Curran]

Like it is the highest repercussion.

[Ryan Holiday]

Yes.

[Michelle Mace Curran]

This is a training flight. My second one ever in my new squadron. There was zero reason for me to push it that far.

[Ryan Holiday]

Yes.

[Michelle Mace Curran]

But I was so worried about failing that. That was more important to me than my physical safety.

[Ryan Holiday]

Yes.

[Michelle Mace Curran]

Like so illogical.

[Rutger Bregman]

Yeah.

[Ryan Holiday]

It's insane. But that's the appearances mattering more than reality.

[Michelle Mace Curran]

Yep.

[Ryan Holiday]

Yeah. And then the irony of course is that you did look really stupid. Right?

[Nick Thompson]

Yes.

[Ryan Holiday]

Everyone is. You're afraid of being judged and you end up doing this thing that causes you to be Judged so much more.

[Michelle Mace Curran]

Yes.

[Ryan Holiday]

And that. Yeah. Your call sign. Even that. Your call sign comes from it.

[Michelle Mace Curran]

Yeah. And so people ask, otherwise, I accidentally went supersonic when I first lit the afterburner before I rolled and pulled. Which is why I could pull so many GS for so long and why I could never shoot my instructor because I couldn't turn tight enough.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

Imagine you're driving 60 miles an hour and you need to be driving 30 to make the turn.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

That was essentially me. And so they named me Mock at Circle Entry, which is just the turn. Circle entry for Dog Fight. It gets into pilot jargon, but people are always like, how'd you get your call sign? Did you pepper spray a guy in a bar?

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

Like, not yet, but yeah.

[Ryan Holiday]

Like, this thing is this thing where you were like, well, I don't want to look bad in this one single encounter.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

Now follows you literally your entire career. And that's what we can't really think about in the moment. For sure. It's funny, too. You talked about asking for help. There's something about that too, where it's like, when other people ask us for help, we're like, oh, here, let me help you. We're not like, what a fucking moron. A loser. Right. Like, we're actually, like, excited or it doesn't even register. And then the next day we're like, well, if I ask for help, it's so crazy. Like, the thing we get in our head about it and then even though we have objective evidence that no one cares.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

There's actually a famous Marcus Aurelius quote where he says, we're like soldiers storming a wall. He says, you've fallen and you have to ask a comrade for help. So what? And I love the so what of it because it really does pierce this kind of insane chain of assumptions we make up in our head where, like, if you're all storming a wall and someone falls, you're not like, I told you not to do, like, you idiot. Yeah. That's not occurring to anyone. And in fact, they're like, there's something beautiful about being able to help that person. And yet we're so reluctant to possibly ask for the help that we need to get better.

[Michelle Mace Curran]

When I was flying for the Thunderbirds, people would be like, you're so brave. I could never do that. And I'd be like. I would be like, what a weird thing to say to me. I'm not brave. Like, I've had so much self doubt. I've had so Many moments of fear, I just forge ahead anyway. And it was never about what they thought I was being brave for the physical danger of the maneuvers was not the problem.

[Ryan Holiday]

But it's interesting you said that, because that is the definition of bravery, though. Like, if you're not afraid, then it's not brave.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

Like, if there was some pill you could give someone and it just suppresses all fear and doubt, first off, you wouldn't do that. It'd become extremely dangerous. Right. And that's why recklessness is the sort of vice that Aristotle holds up as the extreme end in that cold and mean. But it's also like, it would make the thing less impressive in a way, just in the sense that. In the same way that steroids make the accomplishment less impressive, because you're like, oh, it's not really you. I mean, there's part of you in there. But it changes how we understand what you really did for sure.

[Michelle Mace Curran]

And that's what makes it impressive, right? Yes. If we were just fearless and not in danger and not afraid of that at all.

[Ryan Holiday]

Yes.

[Michelle Mace Curran]

Anyone would do it.

[Ryan Holiday]

Yeah. If you're not getting over something, it could still be impressive. It's just. We're just not talking about courage as the virtue that's there. Maybe it's discipline or some other thing. You're doing something that's hard, that's no question. But it's just you're not being brave. It's only because it's scary to you and you don't know if someone could say, hey, the outcome is a foregone conclusion, you are definitely going to succeed. Well, obviously a lot more people would do it, but then also doing it wouldn't be impressive in the same way. And it wouldn't require courage as we understand it.

[Michelle Mace Curran]

Yeah, if it was easy, everyone would do it.

[Ryan Holiday]

And that's a hard thing to remember while you're doing it. Like, when it's really fucking hard to go like, oh, this is keeping people out. But it is. Like, if, again, if there wasn't this sort of trough of despair in the middle, if there wasn't this valley that you had to go through, then everyone would do it because the rewards are obvious. Like, why people would want to be on the other side of it. Very clear. It's just when you get in the shit of it that you can lose your bearings there. And so what those difficulties do is separate the people who really want it from the people who just kind of think it would be nice to have for sure.

[Michelle Mace Curran]

And I think it's One of those careers that people think is sexy. Again, not to reference Top Gun for the third time, but that is such a pop culture phenom that has informed a lot of people's reality of the fighter pilot culture. So much of the job is so unsexy. Right. It is stuck in a tiny cockpit for eight hours and going to the bathroom in there and sometimes messing that up. And like where do I put my snacks to not have those two things overlap. And like it's just that kind of stuff. And it's like sleep deprivation and sun's in your eye and trying to air refuel. And it's hard in the skill set, but it's also a grind just in like the work that has to happen.

[Ryan Holiday]

It's behind the scenes bureaucratic shit and the fact that not everyone's nice and that you're not paid that much. Like there's. If it was all green lights, everyone would do it. The point is there's a bunch of red lights and detours and obstacles and that's why not that many people make it all the way there.

[Michelle Mace Curran]

Yeah. I always laugh when people are like, what's like the behind the scenes of being a Thunderbird pilot because they see very tight flight suit aviators, you know, locked in precision. And I'm like, the number of interviews I did for local media where you land, you fly cross country. So you fly four or five hour flight, you land from Las Vegas to Florida.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

You get out and there's like local ABC station there. Whatever. It's like, tell us about the air show. And I'm standing there talking on camera and I'm not going to turn around because I've had a piddle pack mishap halfway there and I'm a 35 year old expert in my field on this pedestal that has pee pants.

[Ryan Holiday]

Yes.

[Michelle Mace Curran]

I always think of like Adam Sandler. Like all the cool kids pee their pants. Like if they only knew.

[Ryan Holiday]

If it was glamour, if the practice was fun, more people would do it. Right. Like game day. You get the rush why people want to be a professional athlete or whatever. But it's all the parts that are not fun that you have to in a way learn to love and enjoy. Otherwise you just won't do it. The amount of shit you have to go through to be in the position to do the fun part, that's I think the ratio of it that people, people don't really understand. Like publishing a book is pretty fun.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

You know, but writing is not that fun. Having written is great.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

But it actually is fun to me. Like, I. I've had to get to a place where that I understand. That's. That's the part of it that I control. That's the part of it that's not going away. That's the part of it that, you know, separates the amateurs from the. I have to go like, no, no. I like writing books, not having books. I like writing books. I don't. Like. Like, being an author is actually now, like, my least favorite part. I like doing the thing. And the more you like doing the thing, the more you're gonna fucking do the thing.

[Michelle Mace Curran]

Yeah. I feel like that's why most authors don't have. I mean, 14, 15. How many books do you have?

[Ryan Holiday]

This?

[Michelle Mace Curran]

A lot.

[Ryan Holiday]

Yeah.

[Michelle Mace Curran]

Cause you enjoy it.

[Ryan Holiday]

Yeah, I just. I spend a lot of time doing the thing.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

And then, like, when people ask you. They're like when people ask for shortcuts. Like, there's this famous story. A samurai wants to attach himself to this sort of young master or to this famous master, and he says, you know, how long does it take? And he Sundays, it takes 10 years. And he goes, no, no, no. I'm going to, like, work really hard. I want to do it. Like, I'm really excited about this. And he goes, okay, 20 years. And he's like, what? You know, no, no, no. You don't understand. He's like, I want to get. I got to get this done now. And he's like, okay, 30 years. And the point is, like, if you're trying to rush through it, you're missing the whole point. Like, whenever people are like, do you have any tips for speed reading? And it's like, no. The point is that it takes a long time, and you do a lot of it that you're trying, that you're looking for. The shortcut is what is going to make it take a long time for you.

[Nick Thompson]

Yeah.

[Michelle Mace Curran]

No, some of it is just lived experience, too. It's the reps.

[Ryan Holiday]

Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked. It walked the rest of the way home, borrowed my wife's car, drove into Austin, and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation. It was getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were Places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn [e-mail] Trucks Adventure detours the world is full of tours.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

But you don't choose a Toyota truck to follow the beaten path. You choose it to find the places.

[Michelle Mace Curran]

In between.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

The detours, where each adventure pulls you toward the next. And wrong turns turn out right. So why would you ever take a tour when you could take a detour? Toyota trucks.

[Ryan Holiday]

And then next up, we have discipline. This is something I talked about with Nick Thompson, the CEO of the Atlantic. He's also an elite runner and marathoner. He talked a lot about his complicated past with his father and how that's helped him cultivate discipline in his own work and running life. Obviously, that's something I practice in my life. I'd run earlier yesterday morning, and then I was doing my sort of nightly dog walk in the afternoon. Nick also has an amazing book called the Running Ground. A Father, a Son, and the Simplest of Sports. There's a famous quote about Tiger Boy is another Stanford person and says one of the after all the stuff had happened, someone who knew him and his father, he said, mirror, mirror on the wall, we become like Daddy, after all.

[Nick Thompson]

Yeah, it's true.

[Ryan Holiday]

Yeah.

[Nick Thompson]

And I try, like, so I try very hard not to let my discipline drop, in part because I don't want to be that.

[Ryan Holiday]

Do you feel like running was maybe for you, an outlet? Like, running is a place you're in control. It's simple. I always say, like, I've never left for a run and not like, gotten back. You know, like, I've walked back, but, like, every time I've left my house, I've come back. So it's like, it's this win baked into your, into your life, into your day.

[Nick Thompson]

It's definitely that. So I get, you know, I run a little bit when I was like five or six years old with my dad, and then I get back into high school where I, you know, get cut from the basketball team, join the track team, and then like suddenly I'm very good.

[Michelle Mace Curran]

Right.

[Nick Thompson]

And that creates this like self confidence cycle that then helps me do better work, help makes me cool at school as opposed to kind of a loser. So it plays that role in life. I then, you know, go to college. I'm not quite good enough. I leave the team after the, after my first year. I take it back up in my 20s. And I definitely think that what you're talking about kind of the daily practice, like I believe discipline is cumulative. I think if you do a hard thing first thing in the morning, it's easy to do the next hard thing. Right. I also believe that the focus required for running helps you with everything else. Like, if you can go run two hours at a focused pace, you're gonna have a better time at your hard meeting at work. Right. Like, I absolutely believe that it creates these habits. And so part of why I do it is this like daily practice of I'm gonna do this hard thing and I'm gonna do it again tomorrow. And I think it's gonna make everything else in my life work a little better.

[Ryan Holiday]

Yeah. Like when you're 2/3 of the way into a manuscript and you're like, is this a fucking book? Like, this is taking longer than I thought. It's not coming together. I don't wanna do it. I hate this. You know, you're like, oh, I know this feeling. You just keep going, you just keep going, you keep going. And then at some point you finish and you're like, oh, that was better than I thought. Right.

[Nick Thompson]

And the thing you learn about running, like it's one of the best lessons, is that if you run every day and if you run hard from time to time, you get faster. It just happens.

[Ryan Holiday]

And it always happens, but imperceptibly so. There's not some magic day where you're like, oh, it's just this cumulative gain that you're getting block by block.

[Nick Thompson]

I had that feeling this morning. So I ran this race two and a half weeks ago, 100K. I haven't really run much since I went out and ran 13 miles this morning. I was like, God, I am so slow. I'm like, look at My heart rate. Look at my pace. What is going on? I'm like, every single time, right? Like, it's gonna take. It takes a little time to recover. Like, it's hard to recover from a race. Takes a while. But I guarantee you, like, I'm just gonna run every day for the next six weeks, I'm gonna run a bunch of workouts, and six weeks from now, I'm gonna be back in great shape, right? And it just happens. And so that was a lesson. Like when I was writing this book, which took me, like, I have a hard day job, right? CEO of the Atlantic. I gotta work all the time at the Atlantic, right? So I'm working on the book like 20 minutes this morning or like 30 minutes that night. But part of it was the self confidence from running that you just. You just do it a little bit here, you do it a little bit there, and like, it gets done right. Eventually it's done right.

[Ryan Holiday]

Well, at some point you have the capacity to do a thing that seems unimaginably difficult. So, like, you're running, you run 10 miles and you run 20 miles, and then you run 8 miles and you just do this day in and day out. And then when you go do a hard. Whether it's a marathon or an ultra marathon, and you go, where did my ability to do that thing came from? It came from these little things. And writing is. Is. Is in the sense of, like, you worked on it for 20 minutes. You worked on it for. You thought about it. You read these books. It's just all this stuff is going in. And then at some point you have like a editable manuscript. Like, where did all this go?

[Nick Thompson]

How did this happen?

[Ryan Holiday]

I was just sitting in here yesterday and I finished the audiobook for the book that I just did. And I'm like, oh, like I'm. It was almost. This thing was almost unrecognizable to me because I didn't ever do it as a thing, right? I did it as each of its component parts. Like, one day I showed up and I wrote this paragraph. And then another day I wrote these seven paragraphs. And then at some point I stuck them together and moved them around and edited them. But, like, I never at. There was never at any point, and maybe there are some writers this way, where I had the whole thing in my head and I went, I'm starting here and I'm ending here. It was. It's this cumulative project, this chipping away. And eventually, cumulatively, you have a thing, right?

[Nick Thompson]

And then when you have the Thing. The other hard question is, okay, when do you stop? Right? Because, like, if I made it better yesterday, that means I might be able to make it better tomorrow. So when do you call it off?

[Ryan Holiday]

Yeah, when is it done? And shipping, that is very difficult. Now, the next virtue is one that people tend to get confused about. This is justice. And as I was working on the virtue series, I was worried that this one wasn't going to resonate, right. That people think of justice as something you get from the law courts or from a judge or a jury or from politics. But no, it's also how we treat our neighbors, right? It's apologizing when you get it wrong. It's being your own referee. It's the standards you hold yourself. It's how you treat people. Well, I spoke with Rutger Bregman over the summer. We had a really great conversation about justice as a virtue. Not just how to embody it, but how to design our lives to bring more of it into the world. Rutger is a Dutch historian. He co founded the School for Moral Ambition. He has this great new book called Moral Ambition, which I've been raving about. You can grab that at the Painted Porch.

[Rutger Bregman]

In your justice book, you quote Aristotle, right? You don't become a harpist because you're born that way. You become a harpist by playing the harp. Right. You become builder by building.

[Ryan Holiday]

You do.

[Rutger Bregman]

Exactly.

[Ryan Holiday]

Yes.

[Rutger Bregman]

And that's, for me, such a fundamental insight. You're not born as a good person. You become a good person by doing good things. So just get started.

[Ryan Holiday]

What I would add to that then, because that's very groundbreaking to me, that it's about being asked, what great activists do is they don't write anyone or any segment of society off. They create inclusive movements. And like you look at Gandhi, you look at Martin Luther King, you look at Harvey Milk. What was almost frustrating to about them, to their followers was how uncynical they were in the sense that they were always trying to create alliances, collaboration. They didn't see anyone or anything as irredeemable. Right. They were trying to bring people into the tent, which is kind of the opposite of how activism works today. Right? Which is like, it's about purity. It's about exclusivity. It's about kicking people out of the movement for not being totally on board with it. This is why the left has almost no political power, because they have. They not just kicked all the people out of the big tent, but they were so egregious in doing so that they went to the other side. No one wants to exist in political no man's land. So when you decline an alliance with someone, you are often forcing them to ally with your opponents. Right? When you cancel someone from the left, it's not a coincidence. Most of them end up on the right, you know, and so the idea of, hey, everyone is capable of being good, of being on the right side of this, and we're not going to write you off for being currently on the wrong side of this. I think to go back to abolition, I'm forgetting the guy's name, but the guy that writes Amazing Grace, obviously a song about grace and redeemability, is a former slave trader. They don't prevent him from joining because he did horrible things to other human beings. They actually see him as a potential ally for the movement because he knows how it works. And so the idea of who are you asking to join and how are you bringing people along with you? That's what they say. Leaders create leaders, right? Great activists help make people who are not currently politically engaged decide that they should be engaged and capable of making a contribution.

[Rutger Bregman]

Every great movement throughout history, it was a coalition of people who very often didn't agree with one another. So my rule of thumb is always, like, if someone agrees with you for like 70 to 80% of the time, that person is an ally, not your enemy.

[Ryan Holiday]

Yes.

[Rutger Bregman]

And indeed, you see it when, again, the abolitionists, the Quakers initially didn't get much done because they were this very weird Protestant radical sect who deeply believed in their own dogmas. It's only once they started working together with the evangelicals that they started to galvanize a movement. And for us, it's difficult to fully wrap our head around how difficult that was for them. These were very, very religious people. And that's pretty important that they were able to overcome those differences to build that coalition.

[Ryan Holiday]

Well, I mean, even in the women's rights movement, right, there's all these debates about should we let Mormon women in who were at that point polygamous, Right. And so utterly foreign and objectionable to, you know, sort of conservative women in New York City or whatever. And then do we let black women in? Do we let, do we let poor women in? Right? And the women's rights movement succeeds when it is this sort of big, broad tent that covers, you know, not just a good swath of American society, but British society as well. Right? Like the multiracial, multiethnic, multi class, multi viewpoint coalition is ultimately like the one that succeeds. Insular movements tends not only do they tend not to get a lot of support, but they tend to implode and take, you know, sort of silly and so idiosyncratic stance, like they get themselves in trouble because there's not enough ideological diversity inside the movement.

[Rutger Bregman]

So that's one thing we need the coalition building. The other thing that we can really learn here is the importance of perseverance.

[Ryan Holiday]

Yes.

[Rutger Bregman]

So I already said that only one of the founders of the British Society for the Abolition of the Slave Trade was still alive when they finally accomplished their goals. We'll take the women's right movement. Of the 68 women who came together at Seneca Falls in 1848, you know, the first women's rights convention in the United States, only one was still alive in 1920 when finally, what is it, the 20th Amendment was passed and, you know, the federal right to vote was there and she was sick on the day of elections.

[Ryan Holiday]

This is Carrie Chapman Cat, who wasn't even born until after Seneca Falls.

[Rutger Bregman]

I know which quote. Yeah, this is a very.

[Ryan Holiday]

To get the word male in effect out of the Constitution, it cost the women of the country 52 years of pauseless campaign. During that time, they were forced to conduct 56 campaigns of referenda to male voters. 480 campaigns to get legislatures to submit suffrage amendments. 47 campaigns to get state constitutional conventions to write women's suffrage into state constitutions. 277 campaigns to get state party conventions to include women's suffrage blanks. 30 campaigns to get presidential party conventions to adopt women's suffrage blanks. And 19 campaigns with 19 successive congresses.

[Rutger Bregman]

And this is again, the thing, like, we only. We study history and we know the end of the story. Like, we know, oh, all's well that ends well. You know, women got the right to vote.

[Ryan Holiday]

Yes.

[Rutger Bregman]

But Susan B. Anthony, you know, she was dead before that amendment was passed. Elizabeth Cady Stanton, she didn't get to see it. Like, so many of these, These great pioneers, they never saw.

[Ryan Holiday]

Yeah.

[Rutger Bregman]

What we know, what happened in the end.

[Ryan Holiday]

And.

[Rutger Bregman]

Yeah, that realization that. That perseverance to be part of something that's much bigger than you, that just inspired in me an emotion that I like to describe as moral envy.

[Ryan Holiday]

Yes.

[Rutger Bregman]

Like, I studied these great moral pioneers of the past. I'm like, this is what it means to live a great life. To be able to. How do you say that? Follow in the footsteps of those who came before you.

[Ryan Holiday]

Yes.

[Rutger Bregman]

It's almost a form of transcendence. Like, I'm not a super religious guy myself. My father is a Protestant Minister, but I never caught the bug in that way. I don't go to church often, but for me, this is almost a kind of religion. This is how I believe in the afterlife. Right. Is just this feeling that you can follow in those footsteps. And that, like I mentioned factory farming. I don't think I'm going to see the end of that, like, or. I think it's going to take a lot. A lot of time, at least. But knowing that you're part of something that's much bigger than you are, that gives me a lot of energy to work on that stuff.

[Ryan Holiday]

There's a line from a Longfellow poem which I'll probably butcher, but I think about it all the time. He says, the lives of great men all remind us we can make our lives sublime and. And leave footprints behind us in the sands of time. He says footprints that some other person struggling difficulty can take solace and inspiration from that. That's the meaning of life, is that somebody did something that inspired you to do something, and you, in doing something, can leave something behind that inspires some other person. And that's. It's this idea of a procession of torches. And we don't study the abolition movement enough. Thomas Clarkson, but Thomas Clarkson puts in motion this movement, which leads to the women's rights movement, which leads to the civil rights movement, which leads to the gay rights movement, which leads to the environmental movement, which leads to everything that's happening right now. And that. That if you see it as this sort of one movement, learning and teaching and inspiring and, by the way, building up mailing lists and, you know, constituencies and experience and tactics and strategies that then the next group is inheriting and building on and adding on. That's really how you make a difference, is like, how have you left? In that same Longfellow poem, he says, you know, like, tomorrow should find you further than today. It's weird to be talking about moral ambition, but then also shrink it down to just that, which is like, how are you making progress on these things? That's the goal.

[Rutger Bregman]

This is, for me, the form of immortality we can all believe in. No matter if you believe in God, yes or no. It's like building monuments in time. And no one can take that away from you. Right. If you've done something, achieved something, created something that will inspire people who come after you. I mean, Thomas Clarkson is dead for two centuries now, and here we're fanboy about, you know, someone who's been so inspirational to us, and I read his memoirs and speaking through me, you know, through the centuries. And it's like, indeed, this is what it means to live a great life. It's almost like as if he's reaching out through the pages and asking me that question, like, do you want to do this as well? I'm like, yeah.

[Ryan Holiday]

Yes.

[Rutger Bregman]

So, yeah, it's been super influential in me. It's like with this book, for example, I thought, you know, I spent a decade now in the quote unquote awareness industry writing articles and books, which is powerful, which is important, sharing ideas. But learning more about these abolitionists really made me want to build something. So I became the co founder of the School for Moral Ambition. We're helping as many people as possible to pivot their careers towards more socially meaningful jobs. And again, I never thought if you would have asked me this a couple of years ago, I would have said, look, I'm just a writer, I live in my little cave and I write books and that's what I do. I'm like, I'm not entrepreneurial at all. And reading about these people helped me to discover that, again, being entrepreneurial, this is not something you're born with. You can really get stuck in a kind of self image. That's not who I am. No, you become someone by just doing it.

[Ryan Holiday]

Yes, yes.

[Rutger Bregman]

It's such a simple lesson, but very powerful.

[Ryan Holiday]

Well, so the cardinal virtues of stoicism are courage. I think people know what that is. Discipline. People know what that is. Wisdom, they know what that is. And then justice is the one that we kind of skip over or we think we have a strange sense of, like, too many people think justice is a thing that you get, right? Like, you get justice from the legal system. You get justice from a judge or a jury. You get justice because the law says this is how things are supposed to be. What I've tried to do in my writings, and this is what I did in the justice book and what I tried to build this series around is the idea that, no, no, no, all the virtues but justice perhaps most of all is a thing that you do. Like, justice is a thing that you give. Justice is not like, hey, here's how I think society should be. Like, in the. Like, I'd like people to treat other people well. No, justice is how you treat people. Justice is not, hey, what I want those politicians in Brussels or D.C. to be doing. Justice is like, you run a small business, right? Do you give your employees health insurance? Like, justice is not, hey, what should the minimum wage law be? It is. But justice is also like, what do you Pay the person who cleans your house. Right. Like, justice is both smaller and bigger than I think we. Unfortunately, it's the most important one of all.

[Rutger Bregman]

Right.

[Ryan Holiday]

Of course.

[Rutger Bregman]

I read this piece the other day about, I think the author called it Modern Monks. You know, these men who spend a lot of time going to the gym, you know, getting the right vitamins, taking care of their body, I don't know, meditating a lot. And I think all of that is powerful. But the most important question is, like, what for? Like, what's the purpose if you're so healthy, if you're so powerful, like, what are you going to do with all those talents? And the answer is, I would say justice.

[Ryan Holiday]

Yeah, Right.

[Rutger Bregman]

So I think it's important all the.

[Ryan Holiday]

Other virtues are rendered meaningless if not directed at justice. Right. So yeah, you're like incredibly self disciplined. You're working incredibly hard on your body and you just get really strong. This is vanity. Have you created a strong body that can then work long hours in pursuit of something meaningful? If you are. There were a lot of brave soldiers in the Confederacy, right? There were, I'm sure, brave captains who led convoys of slave ships and challenged the elements. But if it's in pursuit of something morally bankrupt, it is itself morally bankrupt. None of these things exist in isolation, right? Like the people who decided I'm not going to get a vaccine during the middle of a pandemic and then like lost their jobs over. There's a certain amount of courage in that. I guess it's just fucking stupid though, right? Like you've picked a dumb cause to go all in on, right? And so, yeah, justice has to be the thing that your life is.

[Rutger Bregman]

It's the most important question, what do you actually work on?

[Ryan Holiday]

Deciding what workout to do or how much weight to use. These are all roadblocks, ways that we sort of get in our own way. And that's where today's sponsor comes in. Tonal will pick the perfect weight, track your progress and suggest what to do next based on your muscle readiness. Taking the guesswork out of getting a great workout. Tonal provides the convenience of a full gym and the guidance of a personal trainer anytime at home with one sleep system system designed to reduce your mental load. Tonal is the ultimate strength training system, helping you focus less on workout planning and more on getting great results. You don't have to second guess your form because tonal is giving you real time coaching cues to dial in your form and help you lift safely and effectively. After a quick assessment, Tonal sets the optimal weight for every move and adjusts in 1 pound increments as you get stronger. So you're always challenged. And right now Tonal is offering our listeners 200 bucks off your first Tonal purchase with the promo code TDS. That's Tonal.com and use promo code TDS for 200 off your purchase Tonal.com promo code TDS for $200 off I got an amazing night's sleep last night. One because my six year old fell asleep in the car at like six o' clock and he transferred him from the car seat to the bed and it stuck, which is just magic. So he's in bed way earlier than normal. But I sleep really well every night because I have a Eight Sleep Pod 5 Ultra, which is Eight Sleep's best product. I've used Eight Sleep for many years now and it's just totally transformed how I sleep. Made me sleep better, made my wife sleep better. It's amazing. So basically eight Sleep is this topper that goes over your mattress. It can heat and cool both sides separately. It can raise and lower each side separately. So it helps you fall asleep faster, stay asleep and then wake up better. Eight Sleep buzzes me to wake gent morning as opposed to some loud blaring alarm and then I can check the app and it tells me my sleep score. It even helps me optimize my day based on how I slept. If you want to survive the holidays like a pro and just generally sleep better, head over to eightsleep.com dailystoic and use code Daily Stoic to get $350 off your very own Pod 5 Ultra. The best part is you still get 30 days to try it at home and return it if you don't like it.

[Michelle Mace Curran]

So.

[Ryan Holiday]

But I know you will. Trust me, your body will thank you for this investment in better sleep shipping to many countries worldwide. See [e-mail] Dailystoic and then lastly, for the Virtue of Wisdom. That's the fourth and final book in the Virtue series that came out back in October. Thanks to everyone who helped make it a New York Times bestseller. I've been loving signing all your copies. I sat down and talked with my friend and research assistant Billy Oppenheimer for just sort of what I mean when I talk about wisdom, how I see it as not so much a destination but as a byproduct of doing the right things the right way at the right time. And in this chunk he's sort of turning the tables and asking me some questions. Billy has a great weekly Newsletter that I get something out of each and every week that's called the six at six on Sunday. You can grab [e-mail].

[Ryan Holiday (voiceover for Toyota Trucks ad)]

You say in the Afterword to Justice that that book was a kind of ethical will.

[Ryan Holiday]

Yes.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Your kids. And I wondered if wisdom is sort of like the way you were thinking about education.

[Ryan Holiday]

Yes, a little bit. Although, you know, it's funny in the Taylor Branch series on Martin Luther King at the end of the last one, and these are like. That's like a. If you want to talk about a trilogy, that's like an epic trilogy. Is it four books? I think it's a trilogy. Anyways, at the. In the acknowledgments at the end of the Taylor Branch book, he talks about how his son, who was born as he was starting the first one, helped with the research of the final book, like his senior year of college or something. And you're like. So you're like. That's like an adult life, like, from infant to functioning member of society, like the arc of it. So I remember being struck by that. So this is just a much smaller version of that. But. Yeah. Well, one of the reasons I wanted to save the Wisdom book for last in the series is that I just thought who I would be four, five years later, I would have more to say about it. And then I also knew my kids were little, and so some of the thoughts on education and setting up an education would be more relevant to me. Weirdly, it's turned out every book in the Virtue series has been exactly the book that I needed to be thinking about in that moment. So courage during the depths of the pandemic, discipline during the other depths of the pandemic, that is sort of where you're stuck working from home, reimagining it just like, as it had dragged on. And then justice in the middle of a sort of social justice awakening, and then a political turbulence and turmoil, and then wisdom as my kids are, you know, sort of now fully in school and the mainstream integration of artificial intelligence and also, you know, a time of political misinformation and disinformation and making sense. Orwell talked about how to see what's right in front of your nose is the hardest thing to do in the world. That's the wisdom that I was interested in when I was writing the book. Not just knowledge for knowledge sake, but how do you make sense of the moment that you are in, which is both a timely and a timeless moment.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Yeah. If you had started with wisdom, like AI wasn't yet in the conversation.

[Ryan Holiday]

Sure.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

The way. And now this book opens with that great story of. Of Seneca.

[Ryan Holiday]

Yep.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Which is just like how ancient the.

[Ryan Holiday]

Desire for shortcuts is. Yes. Yeah, yeah. He's talking about this guy who hires these slaves to basically be his chat GPT.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Yeah.

[Ryan Holiday]

Like to just be the repository of knowledge that he could have at any moment and then he could. He could be smart without having to do the work to earn the knowledge that he was throwing around. Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Each slave is like an LLM for like.

[Ryan Holiday]

Yes, totally. Yes. And, you know, Seneca is laughing about how, you know, it's not something anyone can do for you and there's no shortcuts. And he says, you know, no one was ever wise by chance. Like, no one's beaten the system, basically. Yeah. That came very late in the book, I think. There was a different intro, which I don't remember what it was built around exactly, but that came later.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

I remember forwarding you an email somebody had sent me.

[Ryan Holiday]

Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And it made me think of the Seneca story.

[Ryan Holiday]

Oh, is that what happened?

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And I was like, probably a chapter on this.

[Ryan Holiday]

Yes.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And then when I saw the first galleys, it was in the intro.

[Ryan Holiday]

Well, credit where credit is due. That was a great find. And there's something. My relationship with the Stoics, having read them many times, is that it's all kind of there. And why you have to reread the Stoics. Is that the thing you're looking for? Or. That would explain the moment you're in. It kind of pops out at you. Right. And so that's why you have to have this kind of ongoing relationship with the text. Because when I first heard that story, however many years ago it was, I didn't go, oh, this will perfectly explain modern America's relationship with technology and wisdom in the year 2025. Obviously, that's insane. Yeah. So. But it makes an impression and then you. Comes back to you and you're like, oh, this would work perfectly here. I used to write very intentional intros for my books. Robert Greene is the opposite. Robert Green, if I remember correctly. Does the intro last? And I'm now kind of split the difference. Like, I do kind of a light intro or a basic. It's like a warm up. Like the intro is really just warming up the vibe and the tone that I want to. And then I understand that almost certainly the ideas that it's going to be built around are going to come later. So that was like. Oh, yeah. Because I do like. I do like it when the Intros have a story like discipline, I think is mostly built around Eisenhower, if I'm remembering correctly. Courage is Churchill and justice is. Who's the main person in Justice?

[Ryan Holiday (voiceover for Toyota Trucks ad)]

I don't remember Florence Nightingale.

[Ryan Holiday]

No, no, in the intro. Oh, there's usually a story in the intros. Let me see. For this is more than you can have in your head. Oh, Hyman Rickover, do what you think is right. Slam down the phone. What was it like to have it? I mean, you have an actual copy there.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Yeah. So this is my experience on all of the books, which is that, you know, I see them in Google Docs as you're working on them.

[Ryan Holiday]

Yes.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And then my sort of role as sort of off ramp and you have a lot more work to do. And then I see the galleys and it's like.

[Ryan Holiday]

Right. Because it leaves. It leaves in my process. It leaves Google at some point and goes into Microsoft Word.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Yes.

[Ryan Holiday]

And then there's really no sort of research assistant tasks pertaining to the more or less complete manuscript and then all the edits and stuff.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And so when I get the physical book, like, I don't recognize. I don't recognize. It's like a new book to me.

[Ryan Holiday]

Yeah, yeah, I did. I did find that on Robert Greene's books. It was hard because, yeah, I would see all these different things or I'd read it as a galley, but then I would never actually sit down and read it as a finished physical book. And there was something sad about that to me that I didn't like. I loved the access and the appreciation, but the cost was that I didn't get to experience it like everyone else. Like you, like if you work on a movie, you don't get to watch it for the first time in the theater with everyone. That's never going to be your experience. And so there's a little bit of that with seeing a book get made.

[Michelle Mace Curran]

Yeah.

[Ryan Holiday]

But even, I mean, I sat here in this room to do the audiobook and there was like still changes I was making.

[Rutger Bregman]

Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

I also was going through the box of note cards and the section of where you're kind of kicking around different structure ideas and what ultimately became the structure of this book. There's like a note card and it was like on bike ride in like 2020 or something.

[Ryan Holiday]

Really?

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Yeah. I forget the date, but it was like. And there was, you know, you had one that was like internal and external.

[Ryan Holiday]

Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

So do you remember like nailing down? Because I know the importance for you of like cracking the structure.

[Ryan Holiday]

Yeah. We should find that note card. That's cool. I forgot about that. Yeah. And I'm trying to do better at saying when I found stuff because like it's cool to me going back to it. There's a lot of it, you just forget. But no, I do remember that for the three other books the three part structure was obvious and pretty clear. And for this one it was not. And actually when I talked to Rick Rubin, I was talking about doing the fourth book and he was like, have you thought about for the fourth one just like doing something totally different? Which I liked the idea. That's a very Rick Rubin thing. And I considered it and there just wasn't anything that like called to me that like really felt like that would be right and it wouldn't just be like sort of performative weirdness, you know, like there was. I had this fantasy like, what if I just did it like really short, you know, and then that was like one of the lessons, you know, and then I wouldn't have to do a long book, like. And so I thought about it a bunch of different ways and there was. It just didn't feel like it would come together. But, but the idea of. And that is an idea in the book. It's just like you respect precedence and tradition, but you question convention. And so I had done the same style in the same structure for the first three. And then you go to first principles and go, what is actually the best way to organize this book? Putting aside what has been done before, what is the best way to do it? And I think doing it as a three part structure, I eventually found the things that I wanted to say and I knew from the outset that I wanted Lincoln to be a main character. Lincoln was originally going to be at the beginning as the self education person because that's what he's so famous for. And then I found that actually I wanted to talk about him more in moral terms. So he became at the end. So then it was who's going to be at the beginning? And that's where Montaigne came in. And then it was sort of who's going to be in the middle? I guess all of which is to say the structure took a lot longer on this book and was a harder puzzle to crack. But the idea of sort of here's how you inform yourself. Basically. It's like that thing from the Office where Dwight says, like. What I figured out is I asked myself what would a stupid person do? And I don't do that. I wanted to spend a lot of time not just Just sort of talking about what wisdom is. But as I did in the Ego book, like, what is anti wisdom? Like, what is the opposite of wisdom? And. And how do we sort of lionize one and then steer clear of the others? So it took a while. Yeah. That's funny that it came together on a. On a bike ride. Yeah. I wonder when that was.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

Part one opens with Montaigne.

[Ryan Holiday]

Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

A most unusual education.

[Ryan Holiday]

Yeah.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

And in some ways, it's very relevant to education today.

[Ryan Holiday]

Like, sure.

[Ryan Holiday (voiceover for Toyota Trucks ad)]

His upbringing, his dad instills, like, a love of learning that almost gets snuffed out in the schooling system.

[Ryan Holiday]

Well, you know what's funny is his dad, like, travels. He was like a soldier or something. His dad had traveled around Europe and was, like, fascinated by, like, these breakthroughs that were happening in education. Like, he talked to all these educators in the 1500s, he talked to these experts on education, and then brought home these cutting edge strategies. So there's something kind of timeless and timely about, like, the old way is obviously not working. What's the new way? And it's like this New Way is 500 years old, but it also, when you're reading it, it feels radical. And this was actually something that my editor, Adrian, he was asking my wife, Samantha, he's asking her about what we were doing for education for our kids. And she was like, well, you know, we've tried this. We're wondering about this. We don't know about this. You know, do you do private? Do you do public? Do you do tutors? What do you do? And he was like, the one thing I know is that there's not anyone of any socioeconomic status, high or low, you know, that is, like, thinks that they're like, crushing. Like, no one's, like, we figured it out. It's perfect. We are totally happy with the option. And so I guess the idea is that people have been struggling since there have been people to try to figure out the best way to teach their kids.

[Rutger Bregman]

Yeah.

[Ryan Holiday]

The hard part about writing part one of the book is like, I didn't just want it to be about your kids, and I didn't just want it to be about how your education should have been. I wanted to think about the principles of learning generally, because, like, the epigraph of the book is like, if you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit, and it has to be seen as an ongoing pursuit. But like, with learning languages, like, younger is better. Obviously, these four virtues are the subject of the Four Virtues series, right Courage is Calling, Discipline is Destiny, Right Thing Right now, and Wisdom Takes Work. You can buy all four books as a set, or you can grab a signed copy of any of them. I'll link to that in today's show notes and I hope you are having a great holiday break. 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.

[Michelle Mace Curran]

VRBO makes it easy to claim your dream summer spot with early booking deals from homes with pools to poolside loungers.

[Ryan Holiday]

When you book a vrbo, you don't.

[Michelle Mace Curran]

Have to reserve any loungers.

[Ryan Holiday]

They're all yours.

[Michelle Mace Curran]

Get that early Booking [e-mail] Hey, it's Ryan.

[Ryan Holiday]

I try not to make too many puns on my last name because I've been hearing it my whole life. But if you want to give a holiday gift of me, Ryan Holiday and the Daily Stoic, well, you can. We have a special offer. If you want to give Daily Stoic Premium as a gift, you can do that. Your friends, your family members, coworkers, whoever you give it to can get ad free episodes, early access and exclusive bonus content. Plus we'll even throw in premium episodes of the Daily Dad Podcast. You can get both premium plans for together for 25% off. It's a limited offer, available now through the end of the holidays. That's through December 31st. You can click below to get it for them today. Happy Holidays.