You Should Be In The Thick of It | How Oprah Discovered Stoicism

How are you making your impact felt? How are you bringing your beliefs—and virtues—into the world? 👉 Watch Ryan's episode with Oprah here: https://www.youtube.com/watch?v=Fiua-LIB7MY 📚 Books: Build the Life You Want by Arthur Brooks and Oprah Winfrey https://www.thepaintedporch.com/products/build-the-life-you-want?_pos=3&_sid=5d2d14f7e&_ss=r | https://www.thepaintedporch.com/products/build-the-life-you-want?_pos=3&_sid=5d2d14f7e&_ss=r https://www.thepaintedporch.com/products/build-the-life-you-want?_pos=3&_sid=5d2d14f7e&_ss=r Go Gentle by Maria Semple https://www.thepaintedporch.com/products/go-gentle?_pos=1&_sid=c8df441a0&_ss=r | https://www.thepaintedporch.com/products/go-gentle?_pos=1&_sid=c8df441a0&_ss=r https://www.thepaintedporch.com/products/go-gentle?_pos=1&_sid=c8df441a0&_ss=r The Obstacle is The Way 10th Anniversary Edition by Ryan Holiday https://store.dailystoic.com/collections/signed-books/products/the-obstacle-is-the-way-expanded-10th-anniversary-edition| https://store.dailystoic.com/collections/signed-books/products/the-obstacle-is-the-way-expanded-10th-anniversary-edition 🎙️ Listen to the full episode with Maria Semple onApple Podcasts https://podcasts.apple.com/us/podcast/the-5-step-stoic-routine-for-clear-thinking-maria-semple/id1430315931?i=1000761761546,Spotify https://open.spotify.com/episode/2IZH3QT6jXDP17nvSp4B2i, or watch it onYouTube https://www.youtube.com/watch?v=c3Sa0BpdHf8 🎟️https://www.dailystoiclive.com/DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. -- Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoic This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  You should be in the thick of it. It was the center of the world. Rome was the caput mundi, the head of the world. And the Forum was the center of Rome. It is there, in the Forum, that you found the Stoics. Cato was there giving speeches. So was Cicero. Helvidius challenged Vespasian to his face there. More than two centuries later, Marcus Aurelius stood on the rasta and delivered a funeral oration for Antoninus Pius there. The Stoics were not at home with their books. In the early days, they had been in Athens, when Athens was the center of the world, but they came to Rome from there,

• 0:57Ryan Holiday?

  literally in a famous diplomatic mission led by Diogenes. Tell the story and lives of the Stoics. Marcus Aurelius, it was said, refused to allow Risticus and Arian to remain as pen and ink philosophers. Got them to participate. He wanted them involved in things. It's a shame today that philosophers are so removed from society. You might see them on a university campus, but probably not on Capitol Hill. What issues of our time are they speaking to? What relevance does their work have? Are they starting businesses or leading social movements? Why not? More to the point, what are you? A philosophically inclined person? Or you wouldn't be listening to this. What are you doing?

• 1:42Ryan Holiday?

  How are you getting involved? How are you making your impact felt? How are you bringing your beliefs and your virtues into the world?

• 1:59Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So back in January, feels like an eternity ago, I got this Instagram message. And then I think a thing came into the bookstore, customer service or whatever. And honestly, I thought it was phishing. There's this kind of scam going around these days. There's actually just an article I was reading about it, where people impersonate a famous person and then they invite you on a podcast or to like a FaceTime or whatever. And then they're like, oh, it's not working. And then they send you a link and you click that link. And that's where they get you, right? They get you, like you're almost on, you're almost connected with them.

• 2:42Ryan Holiday?

  And then they, oh, here's this troubleshooting thing. And then boom, that's where they get you. So just FYI, if you see or hear anyone talking about this, like if you suddenly get an Instagram DM from Joe Rogan or somebody, that's probably what it is. Actually, I got one from Aaron Andrews and we almost fell for it. So I got this message from someone who claimed to work for Oprah. You know, Oprah's production company is Harpo, Oprah backwards. And they asked if I could connect with them. They're like, I know it's a weekend, but can you connect with us? I sent them a message. They got right back to me. Well, it turns out it was real. And they asked if I wanted to do Oprah's podcast. They said, there's only one downside. You're going to have to come out to Maui to do it.

• 3:27Ryan Holiday?

  I said, oh no, would I really have to go to Hawaii in the middle of the winter? But we did. I flew out to Hawaii. My grandparents used to live in Maui, so I have a lot of memories there. So I ended up taking my kids. We stayed right down the street from where my, like one building over from where my grandparents lived. It was this wonderful nostalgic, beautiful thing. Got some long runs in. I was just then starting to train for the ultra marathon I was going to do. And I took my in-laws with us too. It was just like a lovely, lovely family trip, family time together. And I'm going to cherish that forever. But the cherry on top of it was at the end, I got to sit down and talk with Oprah.

• 4:10Ryan Holiday?

  Now, you might be asking, why did Oprah have you on? And how did she hear about Stoicism? Well, if you've read Maria Semple's new book, Go Gentle, it's this novel inspired by Stoicism. That's the answer. Maria Semple wrote this amazing novel about where the main character is a Stoic philosopher. And that made its way to Oprah. I'm stepping on this story. I asked Maria about it because I had her on the podcast. We had an amazing conversation. Let me, let me set the table with Maria. And by the way, you should absolutely read Go Gentle. Before we get into some of the Stoic practices, because I do think it's practical, I want to, I want to talk about how you are part of a Stoicism origin story for Oprah Winfrey.

• 4:56Ryan Holiday?

  How does this, how does this like? Because it's this, it's a crazy chain. Like I think about, okay, like somebody hands Mark Schrelius meditations, right? Somebody hands Admiral Stockdale Epictetus. Somebody hands, like it is this unbroken chain of thousands of years of people going, hey, like this worked for me. I think you could try. And you are the person who gave Stoicism to Oprah. How does this happen?

• 5:23Speaker 01

  It's so amazing, right? It's so crazy. So I was, I'd written Go Gentle, you know? And when, when you write a novel-

• 5:31Ryan Holiday?

  That's your Stoicism inspired novel.

• 5:32Speaker 01

  Exactly, exactly. And so, so I wrote Go Gentle, sold it. It takes a year and a half for it to come out. And during that year and a half, your publisher desperately wants it to be an Oprah pick.

• 5:43Ryan Holiday?

  Yeah.

• 5:43Speaker 01

  And that's like kind of the thing that everyone wants. And authors obviously want that, even though you don't even dream of it, because it doesn't happen to you. It happens to other people, you know? And so, so they, my publisher sent it to the Oprah Book Club team. And they all loved it and gave a copy to Oprah, apparently. And, and she read it and loved it, from what I understand. And then I get this phone call out of the blue. And the first thing she says is, you know, I picked your book and I'm, you know, and I'm in that moment acting extremely un-Stoic, just screaming and going, my life has changed. And this is the biggest thing that's ever happened to me, which is like literally undoing every single

• 6:28Speaker 01

  like thing that I should have learned my life about Stoicism. But so, so after I freaked out, she said, she said, I knew I was going to pick this book in that first scene when Adora is teaching Stoicism to the boys, to the, you know, because, because my character Adora has-

• 6:46Ryan Holiday?

  They wanted a pair of expensive shoes or something, right?

• 6:48Speaker 01

  Exactly. And then, and then she's trying to explain about externals.

• 6:52Ryan Holiday?

  Yes.

• 6:52Speaker 01

  And that it, and what, what, you know, and she's obviously taught them. So it's basically, she's the private moral ethical tutor to a rich family and their two little, like rich kids. And the family has said, like, try to like teach, like drill some character into these kids. And so she has her after school every day. She meets them and then she uses the examples of Stoicism and philosophy. And so they want expensive sneakers and they don't get expensive sneakers. And then, or one of them got the expensive sneakers and the other one ruined the, the expensive sneakers because he didn't get them. So she's saying like, okay, what's an external? And there's like things that you, that you want that you don't have. And she's like, okay, close enough. They're 11, so let's just give it them. And so what she's saying is she's saying,

• 7:37Speaker 01

  the thing about externals is even if you get them, they make you miserable, right? That this is like the thing that she's choosing, is that once you get them, then you're in a state of fear of losing them, you know? And then you get like deranged and anxious about like, how am I going to keep it? And so she's giving this lesson to these little boys. And so anyway, Oprah loved that.

• 7:59Ryan Holiday?

  What did she say to you about Stoicism? Do you remember?

• 8:01Speaker 01

  Well, so, yeah, okay. So, so, so what happened is so she then said, she said, I knew that I would pick this book as soon as I saw that scene with the little boys. And she said, I'd never known about Stoicism. I didn't know what it was. And I, and I read your book and I got so into it that I started reading the Stoics. And, and I'm really, really into it. And I can't wait to talk to you about it and talk, you know, tell the world about it, basically. And so that was just, I couldn't believe it on all these different levels, like even just that, that I thought, wait, Oprah Winfrey now knows about Stoicism because of my novel. It's so wild. And then, and then you can explain your origin story with your Oprah origin story.

• 8:43Ryan Holiday?

  Well, then I, yeah, I got it. I got an email from her producer asking me to come out to Maui to do an interview because she had read my books after she had read your books.

• 8:52Speaker 01

  Yeah.

• 8:53Ryan Holiday?

  And I do think there is something kind of beautiful about that chain. Like somebody, somebody told me about the Stoics.

• 8:58Speaker 01

  Yes.

• 8:59Ryan Holiday?

  And you can't, you can't pay them back.

• 9:01Speaker 01

  Right.

• 9:01Ryan Holiday?

  But you can pay it forward. And you think about, yeah, why does, you know, 2,000 years ago, there's this philosophy teacher teaching this kid who's, he knows he's going to be, not kid, he's in his early twenties, but this kid is being groomed for power. And he goes, hey, I think you need to read the works of this slave.

• 9:20Speaker 01

  Yes, yes.

• 9:21Ryan Holiday?

  First off, he reads it, right? How many book recommendations do you get? And you go, eh, I'm not interested.

• 9:25Speaker 01

  Right, right.

• 9:25Ryan Holiday?

  But he reads it and then it changes the course of his life.

• 9:28Speaker 01

  Yes.

• 9:29Ryan Holiday?

  And, yeah, and history. And how many people since found Epictetus or Mark Schrelius and said, hey, I think this might work for you? And that that's kind of this, this journey that we're all on. It's not, it's not quite evangelism because you're not actually obligated to do it. But it is, Stoicism is this thing that you just didn't know existed. And when you do hear about it, you're like, this is exactly what I was looking for.

• 9:52Speaker 01

  Exactly. And then you get excited. And if you're an enthusiast like I am and like you are, you can't wait to like talk to people about it. And you're not trying to- You know, lay on any religion, but it's just, it like really has helped me. It is, it has saved me in so many ways. And, and I'm just a life of meditation, therapy, all California stuff, you know, that I did. I've tried everything and I really feel like this is, has, has come close to saving me.

• 10:19Ryan Holiday?

  And it's funny, like, you know, it, for you, it came through a novel. I remember my book, The Obstacle is the Way, made its way through professional sports and somehow Pete Carroll, who's the coach of the Seahawks, reads it. And he's reading this thing and then he calls his, the team psychologist into his office and he's like, Michael, do you, do you know about this thing called Stoicism? And he was like, yeah, we all studied it in school. And he's like, but I didn't. He's like, I was a football player, you know? And, and, and like, so it's like, some people know about it.

• 10:48Speaker 01

  Yes.

• 10:49Ryan Holiday?

  And, and it's this kind of open secret. And then there are these other people, usually people who are too busy doing things or outliving. They just didn't know that there was a philosophy that could help them with their life, because it's not what we think of philosophy as. We think of philosophy as theoretical and abstract, or, you know, that it's academic. It's not a thing that you would have a tutor come teach your kids so they'd be better human beings. But that's what they did 2,500 years ago.

• 11:14Speaker 01

  Right. And the Romans really turned it into pop psychology, you know? And that's what I love about it is it really is, and it's, you know, AA, it's CBT, it's all, it's the let them theory. I mean, I'm sorry, but I'm just like, gonna say that all of that is Stoicism, you know? And so, um, so it, it, it is psychology and that's, that's how I kind of trick people into reading it. I'm like, it's really just self-help. And they're like, oh, really? Because people love self-help. They don't want to read philosophy, but they want to read about themselves.

• 11:41Ryan Holiday?

  It was surreal to have Oprah, when we did the interview, she's like, reading, she's like, oh, and this is my favorite passage. She's reading out some thing, which is me just riffing on the Stoics. But it's just like, you know, when I sat down to write about an obscure school of ancient philosophy and my publisher was as uninterested in it as they could be.

• 12:01Speaker 01

  Wow.

• 12:01Ryan Holiday?

  Was not, this is not where I expected it to go, you know, 12 years later.

• 12:05Speaker 01

  To be in Oprah's house in Maui.

• 12:07Ryan Holiday?

  Yes.

• 12:07Speaker 01

  Having her read parts of your book back to you.

• 12:10Ryan Holiday?

  Exactly, exactly.

• 12:11Speaker 01

  So crazy, right? It's so weird. And, and I, I mean, I feel this with you. I feel it more with her, which you understand because she's whatever. But, but it's like to be sitting across from the person, you're like, wait, what? Like, and Oprah, I'm sure you felt that. You're in the middle of an answer, you were like, wait, hang on a second. Like, Oprah, it's right there. It's crazy, right?

• 12:32Ryan Holiday?

  Yeah. And that, and that this is, I mean, I guess there's probably some people who are not upset, but they're like, well, what? I'm like, I want as many people to know about this as possible. And I don't really care the entry point that you come in. Like, she has such a direct line to so many people that probably, again, would not think, oh, I want to learn about philosophy from a bunch of old dead white dudes.

• 12:52Speaker 01

  Yeah.

• 12:53Ryan Holiday?

  And what could they possibly tell me about my modern life?

• 12:56Speaker 01

  Yes.

• 12:57Ryan Holiday?

  And it's like, actually a lot. And, and so anyone that wants to be part of that thing, whether it's Oprah, or I guess talk about it on Joe Rogan, like, I'm, I'm all about it. Like, to me, I, I, no judgment. Like, if you have a platform, if you have an audience and you want to take this to them, like, how can it help? Okay, so, so Oprah loved Go Gentle and she made it her book club pick, right? And then I've noticed this about like, successful, interesting, influential people is when they're interested in something, they go down a rabbit hole. This is, this is my habit too. Like, I hear about something, I read about something in a book or whatever, and I go, I gotta know more. Now, sometimes they have an assistant to track this stuff down for them.

• 13:39Ryan Holiday?

  Brian Grazer famously had, had like a curiosity czar, like he had a full-time assistant whose job it was, was to chase this stuff down. So anyway, somehow Oprah went from Maria to my books. And I know she went to my books because as we were talking, I could see Oprah's marked up copy of The Obstacle is the Way. It was just an absolutely surreal experience. First off, that she's doing it's the new 10-year anniversary edition. Like, 10 years ago, if you told me, hey, Oprah's going to be reading, not only is this book going to come out and eventually find its audience and do well, but you're going to do a 10-year anniversary edition and then Oprah's going to read that 10-year anniversary edition? And then you're going to be talking to her about it in Hawaii? I said, dude, what are you talking about? That is deranged.

• 14:25Ryan Holiday?

  But that's exactly where it found us. And we had a lovely conversation. You can listen to the whole thing, you can watch it on YouTube. But I just, I thought I'd bring you my favorite part. So here is me and Oprah diving in to a little Stoicism.

• 14:42Speaker 02

  Now, when I read Obstacle is the Way, uh, I was struck by how simple the idea is. And yet how radical it also becomes when you actually try to live it. That the very thing, y'all, blocking your path, might actually be the path. So Marcus Aurelius, Emperor of Rome, around the year 170, wrote, "What stands in the way becomes the way."

• 15:09Ryan Holiday?

  Yeah.

• 15:09Speaker 02

  Yeah. And I had not come across that as a philosophy or the, how, how does what's standing in the way become the way, Ryan?

• 15:19Ryan Holiday?

  I think what he's specifically talking about makes it very clear. So the obstacle he's referring to, because he's writing in meditations, which is just his private thoughts.

• 15:27Speaker 02

  Yes.

• 15:27Ryan Holiday?

  So he's not saying it to us, he's saying it to himself.

• 15:30Speaker 02

  Yeah.

• 15:31Ryan Holiday?

  And he's talking about difficult and annoying people. He's saying that difficult and annoying people can get in our way, they can cause problems for us, right? Our opponents, our competitors, anyone can cause problems for us. But they can't prevent us from moving forward because they're actually presenting us a new way to move forward. Whether it's patience, whether it's forgiveness, whether it's creativity or perseverance. So for the Stoics, when they say the obstacle is the way, look, sometimes you can transform what you're dealing with into some huge opportunity to move forward in a professional capacity.

• 16:04Speaker 02

  Yeah.

• 16:04Ryan Holiday?

  But always in a personal capacity, we're being challenged and tested. We're given an opportunity to practice some kind of excellence, some, some reach for us that maybe we wouldn't have done under ordinary circumstances. But this circumstance we're in gives us the chance to do that. That's what he's, what he means.

• 16:25Speaker 02

  Well, one of the, one of the sentences, the first sentences that stood out for me is, "It doesn't matter what happens to us. It can be for the best if we use it to be better for ourselves and others."

• 16:38Ryan Holiday?

  Yeah.

• 16:38Speaker 02

  I think that's true.

• 16:39Ryan Holiday?

  Mm-hmm.

• 16:40Speaker 02

  Sounds crazy, but also really challenging to apply. And in order to make it real, you organize a book around the three principles, perception, action, and will.

• 16:50Ryan Holiday?

  Yeah.

• 16:51Speaker 02

  Okay.

• 16:51Ryan Holiday?

  That's how the Stoics try to approach every situation they're in. First, how do we think about this? What's the story I'm telling myself about it? What's my view on it? The Stoics remind themselves that, you know, it's not things that are the problem. It's our opinion about those things, right? How we, the story we tell ourselves about it, you know, this was unfair, this was cruel, I was humiliated. These are all subjective interpretations of an objective event. So first, how do, how do we see this? That's really, really essential.

• 17:20Speaker 02

  Well, that's so interesting because since reading so many of your books and other people's books about Stoicism, I now ask people, I used to say, oh, say, tell, tell me what happened. I now, I've now caught myself saying, what's the story you're telling yourself about this?

• 17:37Ryan Holiday?

  As I said, you can watch the full episode on Oprah's YouTube channel. I believe she also just did this new deal with Amazon Prime. So I think you can see it on Amazon as well. You can listen to it anywhere you get your podcasts. And go read Go Gentle. And I had Oprah sign the book that she wrote with my friend, Arthur Brooks, which is also lovely. And I will link to that in today's show notes.