Lessons & Meditations from the Stoics — with Ryan Holiday

25:14You're trying to manage a bookstore. You're trying to build a business. You're at a point right now, Ryan, where you could sort of be that guy who had one book, or you could be a real influence on the world, right? And my guess is that you would really like to be the latter. And that involves enormous trade-offs and sacrifices. I just don't think you can have it all. And there's just there's a tension between wanting to achieve what you could achieve professionally. But at the same time, it's going to come at a cost. Your relationships with your partner, your relationship with your kids. Have you thought about managing that tension and where the fulcrum is and decisions you've made?

25:52Yeah, there's a great quote from Ursula Lequin. She's saying, you know, it's impossible for one person to do two jobs, which is your career and raising children. But two people can do three jobs. Right. And the idea, I think, of partnership. So I met my wife when I was 19 years old. We didn't get married until we were 27 or 28. We had kids afterwards. But I think it does, it starts with the relationship, right? The decision to not just find a person, but to decide to be with that person. Like when people ask me for advice on, you know, getting married or finding that person, like I've been with my wife now almost 20 years.

26:33And I go, they go, what's the secret? And I say, you know, the secret is not breaking up, right? That's the number one secret of being together a long time. It's not breaking up. And I think in a world of dating apps, in a world of potentially limitless options, I think a lot of people aren't willing to do the work that is a long-term, stable, not just relationship, but partnership, right? And so I think a lot of people are worried that being with someone, deciding to be with someone and building a life with someone is going to come at the expense of your career. and there are trade-offs, but you also get a certain amount of stability and strength and support that I feel like when I had my success in my early 20s, if I had been a single dude, if I hadn't been on a track towards buying a house, getting married, having kids, I think I would have spun off the planet.

27:32I don't think social media, dating apps, cheap airfare to anywhere in the world, Airbnb is on the beach. I don't think that would have channeled me towards being a mature, responsible, resilient adult, because it's so easy to run away from everything. It's so easy to live in a fantasy world, to live out of a suitcase or to hop from job to job, opportunity to opportunity, concert festival to concert festival. And there is something about, you know, making a decision, putting roots down and being a responsible adult that I think a lot of the things that people want later in life all stem from, but they don't make that decision earlier.

28:18And at a certain point, it becomes harder and harder to make that decision. Yeah, I did what you're describing for 20 years, and that is arrested adolescence. So in your book, you write, we can find lessons on how to control our temper in front of our kids from Plato. And you have a bunch of them, and I want to go through each of them. Tell us about figuring out how to control our temper in front of our kids from Plato. Yeah, there's a story about a young boy who goes to live and study under Plato, who's obviously one of the greatest philosophers of all time. Then after his sort of apprenticeship ends, he goes back home and he's living with his dad, and he watches his dad lose his temper at a servant or a server or something.

28:57And the boy says, wow, I never saw anyone act like that at Plato's house. And the idea of, you know, the model that we show our kids obviously is important. But one of the things I try to stop myself, whenever you're out in public, you're at the airport, you're at a restaurant, and you watch someone lose their temper at their kids, you know, you watch someone really lose it, you're never like, that's a great look. They are crushing it. Yeah, well done. Exactly. And then the idea, though, is that somehow we look differently when we do that, right? And so one of the big stoic exercises is just stepping back and going, you know, what does this look like to someone else?

29:38What does this look like with even a modicum of distance? And it gives us a little bit of perspective. There's a great quote from Seneca where he says, you know, getting angry is like returning a kick to a mule or a bite to a dog. You know, It doesn't make anything, it doesn't teach that animal a lesson. It just makes you look like an animal. And so when I get mad that my toddler is throwing a temper tantrum, I go, but now I'm throwing a temper tantrum in response to the temper tantrum. And what is this teaching them? It's that when you're upset, when you don't like what's happening, a temper tantrum is appropriate response.

30:13I'm torn on this one because I can see that raising your kids, being a role model, controlling your emotions is a fantastic, sets a great example for your kids. At the same time, occasionally when I've lost my shit with one of my kids and my partner says, that was an outsized reaction, you shouldn't have had it. I'm like, well, you know what? They're going to face a series of outsized reactions their whole life. They're going to face a series of people in unusual situations who act irrationally. And I think it's okay. I think that they learn certain skills that occasionally they learn, well, sometimes people have outsized reactions and maybe they even learn, well, it's not about me that I can survive someone having an outsized reaction to something.

30:56At the same time, I think, well, maybe I'm just rationalizing what is irrational behavior on my part. But, you know, Jonathan Haidt, my colleague at NYU, talks about the coddling of the American mind, that we spend so much time trying to create this utopia for our kids. We use so many sanitary wipes on their lives that they don't develop their own immunities. Is there something valuable to occasionally having an emotional reaction around your kids and teaching them that, yeah, occasionally people get angry for the wrong reasons and you need to figure out how to deal with it because it's going to happen a lot?

31:26Yeah. I mean, look, especially when they're younger, sometimes that's the only way to convey something serious. And one of the distinctions I make both as a boss and as a parent, I learned from professional basketball, which is sometimes the coach gets a technical on purpose. right? There's a difference between the coach who doesn't have command of themselves and just goes around giving the other team points. That's not a good coach. But sometimes the coach can sense that the team's a little listless or it can sense that the ref isn't taking them seriously. And, you know, a well-deliberate orchestrated technical foul can be exactly what a team or an organization needs.

32:05I watched Greg Popovich once get thrown out of a game so an assistant coach would take over, and I watched the team rally in response, right? This is what a seasoned pro knows how to do. So I think there's a difference between losing your shit and making your children think you're losing your shit. You know, there's a difference. But I would also say that sometimes we do lose our temper. Sometimes we mess up. Sometimes the heat of the moment gets the best of us. But how quick are you when you do that, when you go, that was an outsized reaction? How quick are you to talk about that with your kids?

32:41right to go hey dad was stressed because he was worried about missing our flight or dad was stressed because i'm worried about you and you're the most important thing in the world to me and i felt like i needed you to get this because i don't want anything to happen to you but i should do better my son the other day my youngest was sort of freaking out in the car and my oldest goes, I think he's just overstimulated, right? And I liked that so much because what he realized from our language with him was that there's a difference between just having a bad reaction and understanding why what's going on around you, what's happening in the world that's contributing to that reaction and having that awareness, that's what allows you to stop, you know, a downward spiral before it gets too serious.

33:36So next sort of lesson from one of the great Stoics, lessons on how to cultivate a peaceful home for our kids from Marcus Aurelius. Yeah. You know, I think about like when I talk about the airports a lot, right? Like when I think about the germs that my body is covered in when I get off of a flight, right? Like the first thing I do now when I get home, I've been traveling as I throw all my clothes right in the laundry, right? And I jump in the shower and I change because who knows what I tracked in. And if you ever think about like what you're tracking in on the bottom of your shoes when you walk into your house, it's disgusting, right?

34:11And I think about, Stoics talk about the dust of earthly life. And I think about how much detritus and dirt and disgustingness we track into our homes figuratively, not literally, right? Like you had a shitty day, everything went sideways, everyone was annoying, there was unnecessary traffic, and then you were on Twitter and you got trolled and blah, blah, blah, blah, blah. And then you just bring that into your house and you sit it down at the dinner table. And so I think the Stoics talk about how do you get that sort of reset? How do you wipe the slate clean? How do you take that minute between the transitions?

34:53How do you get faster at making transitions? I think this is something we kind of take for granted as people. We think we're good at multitasking. We think we're good at transitions, but we're not. And your kids, they pick up on it. Even if you don't mention it, they can sense the energy in their house. And I remember what it was like sometimes for my dad to come home. Like I heard, I heard a good thing when you heard the garage door opening as a kid, right? You're inside your house and you hear the rumbling of the garage door going up. What was the feeling that you had, right? Was the feeling, yes, or was the feeling of panic or scramble, or I need to go do X, Y, or Z because I don't want to get dumped on.

35:43And, you know, that's something we really have to work on as as as parents. Yeah, it's interesting. It's a mix. I don't know what it was like. It was a mix of all that for me. My dad was a huge presence and he came in and it was like, OK, the sheriff's here. Right. And I was happy to see him, but it was like, OK, you know, it's like there was a different standard of behavior. And it just cracks me up because I'm not allowed anywhere near our TV. And when I was growing up, our TV was there for our father. and occasionally if he wasn't around, I was allowed to access it. But it was just such a different dynamic.

36:16I'm older than you. And I imagine, you know, it started to change. But the pivot, the focus of the household has moved from dad being the focus of all the energy and goodwill. You know, we were all sort of in service of dad to now it's all about the kids, or that's at least how I perceive it. Talk about lessons on how not to spoil are kids from Seneca. Yeah. It is funny, you know, when you read these philosophical tracks, and, you know, they're always talking about these big things. And then there's a great passage where Seneca's talking about making sure they work for it. He's talking about making sure that you don't reward them when they try to get things by yelling or screaming.

37:03And you go, oh man, 2 ,000 years ago, this philosopher was dealing with a tyrannical six-year-old, just like I'm dealing with a tyrannical six-year-old. Or they were dealing with a moody teenager, just like I'm dealing with a moody teenager. And it is, I think, important and humbling to remember that people have been doing this and struggling with this for a very long time. One of the things I talk about in the intro of the book that I think about all the time is they discovered these footprints in White Sands National Park. And it's the footprints of a parent and a child. And the footprints are side by side.

37:43And then the kids' footprints go away for a couple hundred yards. And then they happen again and they go away and they happen again. And it makes me think of the walk that I took with my kid this morning. He was good walking and then he would go, I'm tired of walking and I'd have to pick him up. Then he'd be like, wait, no, I want to walk again. And just realizing that this has been the journey for a really long time. And this tension between, you know, giving our kids what they need, giving our kids what makes them happy, you know, and the tension between making them self-reliant and also spoiling them, that this has always kind of been an attention, particularly the more well-off one is, right?

38:25When I was a kid, there was a bunch of things that I couldn't have because my parents couldn't afford them, right? That it wasn't in the budget. Most of those things are things that I don't have to worry about today. And so the question is, you know, when my kid asks for them, when he asked for a new mod on Minecraft, the fact that it costs$5, you know, it means nothing to me. But then there's this debate about, do you just give them everything they want whenever they want it? What does that mean, right? And I think the tension between can and should is the struggle of sort of parenting in times of abundance.

39:07And then the last one here, lessons on how to support our kids from Queen Elizabeth. Yes. It would have been really hard to have your mom be the Queen of England, right? And there's a great story early on. She meets, I think, every Thursday with the Prime Minister. So she has a standing meeting with Winston Churchill. The meeting, historically, for her father, is always at like 6.30 p.m. And I love the story of Queen Elizabeth having to decide to push the meeting with Winston Churchill because she wanted to be there for bedtime with her kids every night. The idea that matters of state and the state of your family being in tension with each other, I thought was so fascinating as I tell that story in the book.

39:53But, you know, she struggles, I think, and her children are an example of a struggle when one has a calling and a profession and a strong sense of duty, and then the conflicting responsibility and duties that we have to our children. There's another story where she had been gone. She'd taken like a six-month tour abroad. And she gets home. She meets her kids on the royal yacht. They're about the age of my kids. They run towards her, mommy, mommy, mommy. And she stops them. And she goes, no, no, no, not you, dear. I have to follow protocol. And it's actually in, I think, Prince Charles's first memoir.

40:36The title of one of the chapters is Not You, Dear. And his struggle with, you know, what it means to have a parent who puts basically everything before their children. We'll be right back.

40:52Support for the show is brought to you by CVS Caremark. On this show, we talk a lot about money. We talk about money on a large economic scale, but we also talk about the cold, hard cash, the dollars, and cents at the center of just about everything. And that's the sort of money talk that's on most people's minds. How are they going to access and pay for the things they need? Like prescription drugs, CVS Caremark plays a vital role in the healthcare ecosystem by helping to ensure coverage of medications to their clients' plan members at an affordable price. interested in more affordable care for your members go to cmk.co slash stories to learn how they can help you provide the affordability support and access your members need

41:49Plus 15 minutes. Plus, you'll get America's best network. No. See? No. Maybe I should switch to T-Mobile right now. This holiday, switch to T-Mobile in just 15 minutes from your phone. Check out in 15 minutes or less per line, T-Mobile is the best mobile network in the U.S. based on analysis by Google Speedtest Intelligence Data 1H 2025. So I want to ask you about your approach to some issues around parenting and if and how stoicism has influenced your approach. And I want to let you off the hook a little bit here. And that is my general observation after having read a few parenting books is nobody has any fucking idea.

42:22I mean, you can read a book that says from a very thoughtful person on how the key to creativity is to give them absolutely no boundaries and let them pretty much do whatever they want from a very young age to another thoughtful book saying that the key to secure children is that they have boundaries so they feel more secure and loved. It feels like every bestseller, the first thing it does is contradict the parenting book of the year before that. We talked a little bit about can versus should. How do you instill a sense of grit or even basics like connect money with effort or effort with good outcomes?

43:00Once you're above a certain income level, you do grow up in a household of abundance or super abundance as it relates to the kid. A kid doesn't want a Range Rover. They want, as you said, more skins or a new weapon on Fortnite, which most people can afford. Have you thought about how you're going to try and instill that sense of grit? Yeah, one of the lines I take from Seneca in the book is that your kid's life should be good, but not easy, right? The idea that from struggle, we become what we're capable of becoming. So for some kids, that struggle is going to be quite basic, right? Struggle to eat, struggle to get to school, struggle to stay warm in the winter.

43:40gratefully, those are problems that we don't have at my house. But how do I make sure that their life isn't one filled of repose and ease? And one of the ways we do that is by challenging ourselves. We go for this hard walk every morning. We try to climb trees and play sports. And I try to push them in ways that gets them out of that comfort zone, that challenges them. There's a story about Theodore Roosevelt. He would take his kids on these walks every morning, and whenever he saw an obstacle, that's what he would go towards. So they'd have to climb over these rocks or walk through this freezing cold creek.

44:22I think thinking about ways that we challenge our kids is how we make them resilient. What is actually important, I don't think it's abstaining from all luxuries or nice things. I think it's making sure that on a regular basis, we are forced out of our comfort zone and forced to learn and adapt and figure things out. Talk to me a little bit about punishment. Yeah. The best line I heard that I think about is that punishment should make them better. So my son does Brazilian jujitsu and another kid slapped a kid yesterday in practice and the coach made him do wall sits, right? He had to sit until basically his legs hurt against the wall.

45:10And I think about that as being a punishment. Instead of kicking the kid out of class for doing something he wasn't supposed to do, he had to go do a thing that made him physically stronger. If we can think about punishments less as getting a pound of flesh and more about teaching them something or making them get better at something, we're probably closer to the path that we want to be on, which again, to go to your point about contradictions, that's not to say that I've never taken away the iPad because someone was doing something they weren't supposed to be doing. And I make no pretensions about being perfect at any of these things or about being totally consistent about these things.

45:53I think you're right. The idea that there is a consistent, clear, coherent parenting strategy is probably to miss the point. I would argue that this book is riddled with contradictions because life is riddled with contradictions and paradoxes. And the whole point is to find what you're supposed to do in this specific situation, which is sometimes the opposite of what you did or needed to do in a very similar situation just a few weeks ago. And your book offers 366 lessons. What do you hope people take away? What is the sensation? When I write books, I was saying, I want someone to walk away with a certain emotion or a certain sensation.

46:38What do you want parents to walk away from after reading this book? The idea to me in the page-a-day format is that it's about the process even more than the content that's in the pages. So the idea of, I have this book, I crack it open in the morning, it gives me something to think about. Maybe I agree with today's lesson. Maybe I disagree with today's lesson. Maybe that lesson is easy for me, or maybe it's totally outside the box for me. But the idea is how are we invested in always learning and growing as parents and understanding that we're going to be different people because, and you're in the book because you and I had a great conversation about this.

47:21We're going to have totally different kids five or six years from now. We're in this constant process of losing the child that we have now because they are becoming a different person. And hopefully we are becoming different people as time passes as well. So last question, you've been generous with your time. Love, establishing a more intimate connection with your partner or your kids. What can we glean from the Stoics about what every book on happiness tells you that the the key, the whole shooting match is the number of people who love you and let you love them. How has this informed your ability to establish deep and meaningful relationships with people?

48:02It's really a shame that the stereotype of the Stoic is the unfeeling, emotionless, you know, robot, the beast of burden, simply enduring the misery of a dark, terrible world. because in practice, I don't think there was anything further from the truth. There's a passage in the opening of meditations. Marcus Aurelius is thanking all the people who have influence in his life. For paragraphs, he thanks his stepfather, Antoninus, who clearly shapes him into the man he is. He thanks his mother. He thanks his stepbrother. He thanks all these people, but he thanks Sextus, the philosopher, for this really key lesson that I think about all the time because it so goes against the type of what we think a stoic is.

48:50He says, from sexist the philosopher, I learned to be free of passion, but full of love. So he's saying free of envy and anger and jealousy and ambition and, you know, all the passions that we call them, those sort of swirling, negative, toxic, competitive, you know, zero-sum emotions, if you will. And what he feels instead is a compassion, a love, an affinity for, an acceptance of, a gratitude for all people and all things. And I think that's the attitude that I try to have. I'm not perfect in it, but that's what we try to have. And from Marcus's example, this idea of starting with gratitude, I have this journal.

49:44And every morning, I try to write something that I'm grateful for. But the exercise, the thing I try to write, I never try to go, I'm grateful for my kids. I'm grateful for my health. I try to think of something frustrating or annoying or something that went wrong or something that at first glance I didn't like. And I try to will myself to be grateful and feel love for that thing. So it's not just this magical state you arrive at. I think it's something you work at. But I think the idea for the Stoics is to be free of the negative emotions and to replace those emotions with a kind of unconditional and all-consuming love for everyone and everything.

50:26Ryan Holiday has written 12 books in 10 years, including his latest, The Daily Dad, 366 meditations on parenting, love, and raising great kids. Ryan also writes two daily emails and hosts the daily podcast. His books, The Obstacle is the Way, Ego is the Enemy, The Daily Stoic, and the number one New York Times bestseller, Stillness is the Key, have sold more than 5 million copies in the U.S. He joins us from his home just outside of Austin, Texas. Ryan, I'm just so impressed with you and what you've accomplished. And I think you're bringing wonderful things to the world. And I wish you success, not just because I'm fond of you, but I think what you have to say is really important.

51:09Well, thank you very much. I'm a huge fan as well.

51:22Algebra of happiness. It's not about you. I have noticed lately, I'm being more of an asshole than I usually am. I'm being shorter with people. I'm being harder on the people I work with, the people in my life. And the first step to fixing that is recognizing it's happening. And I've done that. And the next step is trying, well, what's going on with me? Why am I depressed or angry? And I haven't figured that one out yet. But the thing that strikes me is that when you're young and people get upset or criticize your work or whatever it might be, you take it so seriously and it's so rattling. And then what you realize as you get older is that people's behavior towards you is not only a function of you, but it's mostly a function of them.

52:14What do I mean by that? It's mostly a function of what's going on in their life. whether they had lunch, whether they're stressed out. It's not a reflection on you. Some of it is, but it's mostly about what's going on with that person at that time. So when someone is not as kind, when someone is rude, when someone says something that upsets you, keep in mind that, yeah, maybe some of it is about you. Maybe your work wasn't very good. Maybe they genuinely don't like you or what you said offended them. But keep in mind, a lot of times, a lot of times, it's about them. And take it with a grain of salt.

52:51And you don't have to respond to everything. You don't have to be upset. It's not always about you and your performance. It's about something that's going on with them. And so break it down, be thoughtful about it, appreciate it, register it, ask yourself, what was the veracity of this statement? Can I learn from it? And then quite frankly, move on. Move on and forgive yourself and recognize, recognize in most situations, it's not about you. This episode was produced by Caroline Shagrin. Jennifer Sanchez is our associate producer, and Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from the Vox Media Podcast Network.

53:34We will catch you on Saturday for No Mercy, No Malice, as read by George Hahn, and on Monday with our weekly markets show. Support for this show comes from Nordstrom. Oh, what fun. Holiday invites are arriving, and Nordstrom has your party fits covered. You'll find head-to-toe looks for every occasion, including styles under$100. Dresses, sets, heels, and accessories from Bardot, Princess Polly, Dolce Vita, Naked Wardrobe, Coach, and more. Free styling help, free shipping, and quick order pickup make it easy. In stores or online, it's time to go shopping at Nordstrom. What do walking 10 ,000 steps every day, eating five servings of fruits and veggies, and getting eight hours of sleep have in common?

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