The Daily Stoic - BONUS | Is Taylor Swift a Stoic?

Episode Date: October 5, 2025

In honor of Taylor Swift's new album The Life of a Showgirl, Ryan shares the surprising Stoic lessons hidden in her music and career. 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Look, ads are annoying. They are to be avoided, if at all possible. I understand as a content creator why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like The Daily Stoic going. So if you want to support a show, but not listen to ads. Well, we have partnered with Supercast to bring you a ad-free version of Daily Stoic.

We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast, completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive

bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20% off your first year. Just go to dailystoic.com slash premium to sign up right now or click the link in the show of descriptions to make those ads go away. Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of

history's greatest men and women to help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visitdailysteoic.com. So maybe you picked up on this. Maybe you didn't. There's a little behind the scenes or I guess inside baseball. But I write the Daily Stoic emails, usually a couple of them every day. I obviously take breaks.

But I usually write it whenever sort of inspiration strikes me based on what's sort of happening around me. So I listen to a lot of music and I spend a lot of time in the car with my kids, my wife. For instance, we did actually a version of this over at the Daily Dad. my kids are obsessed with Hamilton, so we've listened to Hamilton over and over and over again. And what happens is little phrases, little lines from the songs, ideas in the songs, they sort of make their way into my brain. I'll write that down. And I put that on my to-do list for the day where I send a little email to my phone. And that becomes a line that I'll build a daily stoic email around or a daily dad email around. So, you know, a little phrase here, there, a little lyric

becomes an email, a thought. Sometimes even a full article, but usually it's just enough to kind of tie to something I wanted to say about Stoic philosophy or that I needed in my life. And that's sort of how the sausage gets made. We don't run them in the order that I write them. There's a big document. It's called the unsent document. And I'm always writing the emails. And then they get taken by the editor who tweaks them and improves them. And then I do another pass when I record them here for the podcast and then they get selected for a schedule so we're not saying the same thing too many times so i might write three emails about hamilton because you know something popped into my head and then those might run in three consecutive months or two might run in one month and

then we might run another six months from now i can sometimes get that far ahead so if you're a careful listener you might have noticed over the years a number of taylor swift allusions or or ideas in the Daily Stokeyman, along with lots of other music, some of my favorite bands, while they're talking about, Allison Chains, every once on, Iron Maiden. I just wrote one from a lyric from Nathaniel Raitliff just the other day. That's just kind of how it works. And as I said, it's been a lot of time with the kids, a lot of time with my wife. So that has made me slowly and steadily, I guess, a Swifty.

You might think Taylor Swift has nothing to do with social media. But I found a way to shoehorn it in, have I not? This is actually a talk I gave at Live Nation a couple of years ago where I was talking about how we take professional obstacles and turn them into opportunities for success. When Taylor Swift's masters are sold in 2019, she's not happy about this, right? They're sold to Scooter Braun, who actually reads The Daily Stoic every day, so it's cool with me.

But she doesn't like it, right? That's what matters, is that she doesn't like it. She decides that's not something that works for her. So after she reminds herself to calm down, and then reads this tweet from Kelly Clarkson, one of the most epic tweets of all time, I think we'd have to say, she decides she's going to do precisely this, right? So she re-recorded her first five albums and has basically been putting out music almost every day since that point. Right.

So Taylor Swift was, of course, very successful, very popular, very well known before this. But it becomes this sort of springboard, the act of constantly releasing music being the cultural center of the universe now for basically three or four consecutive years. it not just transforms her and her career, but it elevates her to a level of pop stardom that I don't think anyone has ever reached before, maybe other than The Beatles. And you look at the heiress tour, the heiress tour is possible, right?

Precisely because she's just reintroduced a whole generation to her music. And I think what's interesting, too, is it's not just that she becomes bigger and more popular as a result of this process and seizes control of something that she didn't have control of financially before. But the songs get better, too, right? It's this remarkable example of taking something that you never would have chosen

that you thought was profoundly unfair or screwed up, right, the worst part of the music business. And it becomes this cataple, right? And 1989 is the most streamed album of all time. She's Times person of the year now, right? what we do after the thing has happened to us is what matters, right? And it's not that everything is this, right, that everything becomes the catapult that advances our career to stratospheric levels, right? That's not always how it works, right? Life is much more brutal and

frustrating and unfair than that. But we always have the opportunity to decide the end of that story, what it's going to mean to us, how we integrate it into our lives, who we become So it struck me as I was driving my kids to school this morning, listening to the new Taylor Swift album, which came out at midnight, The Life of a Showgirl. I thought, I wonder how many Taylor Swift emails have we actually done. Sometimes it'll be very clear that I'm talking about a Taylor Swift lyric. Sometimes I'll just have used it in the title, and it's just like a little inside joke that only I know about. But I wondered how many times I'd actually done this. And so I had Claire,

our producer, throw that compilation together in honor of the new album, which I thought was pretty good. I tend to find, and I think this is a quality of her music that you've got to listen to songs like many, many times, which is how I listen to music. I tend to find songs that strike me in the moment and then I listen to them on repeat until it kind of fades into the background and then I can write. So I'm only maybe one and a half listens through the hour. album. But I wanted to throw together this compilation in honor of that. And I hope that you enjoy it. If you don't, got a little stoic idea for you, just skip this one. You don't have to get upset. You don't have to send a nasty email about it or a nasty comment. You can just

not listen. And the people who do like Taylor Swift, which is apparently most people, they can enjoy. So, enjoy. Could you survive this? His father died when he was about three years old. He was raised by a single mother with an enormous fortune, and then at an alarmingly young age he caught the eye of the Emperor of Rome, a brilliant but twisted man in decline. He was groomed for absolute power, forced to come and live in Hadrian's palace,

a place lived with spies and sycophants and capricious violence. At 18, he was made a junior, magistrate in charge of Rome's financial affairs. Up and up he went the curses onorum, the ladder of offices, until he put on the purple at age 39, becoming in an instant the most powerful man in the world. When we judge the rule of Marcus Aurelius, how often do we adjust for what an absolutely deranged childhood he endured? I want to snarl and show you how disturbed this has made me, Taylor Swift sings. You wouldn't last, an hour in the asylum where they raised me. In fact, for the most powerful person in the world,

for someone who has been performing in public since she was 11, she's, Taylor Swift is pretty well adjusted. And the same goes for Marcus Aurelius. How did he not turn out to be a Nero or a Tiberius? It's almost unbelievable. The answer, of course, is Stoicism. Stoicism made the difference. The philosophy he got from his teachers, that copy of Epictetus loaned to him by Rousticus, the moral compass that is the four virtues, the spiritual practice of which meditations is a byproduct, seems to have saved him. It centered him. It guided him. But do you think it would have done the same for you? How long do you think you would have lasted in the asylum where they raised him? The real reason Marcus Aurelius wasn't corrupted by power why he wasn't made insane

by his surroundings is because he worked hard at it, incredibly hard at it. He strove actively daily, to not be Caesarified, to not be stained by that purple cloak that fortune put on his shoulders. It doesn't just happen. It doesn't matter how good you are. To survive success and fame and power to be virtuous in such a situation one must make it the work of their life. The business failure, the blown meeting, the marriage that fell apart, these things didn't go the way you wanted and it's frustrating and it's painful. It's hard to see anything good about it. Surely, that's how Taylor Swift felt when she discovered that her masters had been sold to a hedge fund in 2019 and she lost control over how her music was distributed and marketed. There were many ways that Taylor could have responded to this. She could have raised millions of dollars to buy them for herself. She could have hired a lawyer to fight her battle. She could have let her frustration sour her on her old music and stopped playing it at concerts, alienating fans who loved those songs.

Instead, in a career-defining moment, she calmed down to follow her own advice, and she decided to re-record her albums, redistributing them herself and republishing them to fans as Taylor's version. Of course, Taylor Swift was successful and popular before this. But because she's basically been releasing music nonstop for the last half decade, she became the center of culture, catapulting herself to a level of pop star of not seen since the Beatles. Her era's tour grossed more than a billion dollars.

Even the movie about the tour made hundreds of millions. And this was all possible because a new generation discovered her music and wanted to be part of her team and join in her fight. But it's not simply that she became bigger and more popular as a result or that she sees control over something that was previously outside her control. It's that her songs got better, her concerts got better, she got better. And on top of all that, she made herself the underdog in the process. It's quite a move, she pulled off, a level of career and public relations jujitsu without parallel. And it's also a remarkable example of taking something you never would

have chosen, something you thought was profoundly unfair, and using it as fuel to find new potential within yourself. What we do after that thing happens to us is what matters. We get an opportunity to decide the end of each story. When jarred unavoidably by circumstances, revert at once to yourself, Mark's Reelis writes in meditations, and don't lose the rhythm more than you can help it. You'll have a better grasp of harmony if you keep going back to it. This story about Taylor Swift, how she turned the obstacle into the way, is actually one of the stories I wanted to add to the 10th anniversary edition of The Obstacle as the way. I just thought it was so fascinating the way she outsmarted and outmaneuvered the music industry, which is notorious for taking advantage of

artists. And I put that in the chapter, maybe you remember, about channeling your energy. Because she showed that we can redirect the negativity thrown at us into something positive for ourselves and others. When I got asked to do a 10th anniversary edition of The Obstacles Way, I wasn't sure why I would do it. But then I kind of actually liked the idea of doing a a Ryan's version, getting to update and change and tweak, getting to take all the things that I have learned and gone through in the intervening 10 years and use it to make the book better.

And that's what this new version of the obstacle is the way is. You're on your own, kid. There are moments when we feel more alone, of course, after the divorce, when we head off to school for the first time, when we strike out on her own, start working for ourselves. when we do something that people don't understand that engenders criticism. We realize we're on our own that we have to blow our own nose, as Epictetus said, that we'll have to be our own savior while we can't, as Mark's Surrealis wrote.

No one but us can solve our problems. No one but us can manage our emotions. We only control what we control. We can only demand the best from ourselves. But this is not new. You have always been on your own, as Taylor Swift put it, and you always will be. you can instead let these moments when we feel more alone serve as reminders that we have the tools to change that we only get to choose how we react that we evolve into whomever we want to be because what do you have

to lose you are already on your own kid and no one can take you away from you only you can do that The smallest man who ever lived. They had hoped he would grow into the job. They hoped a tutor like Seneca would teach the boy some wisdom and gravitas. Instead, Nero seemed to get worse as he grew up and gained power. He tried multiple times to kill his own mother, eventually succeeding. He banished a poet for being too talented. He forced Roman crowds to listen to him perform.

He eliminated potential successors. He exiled philosophers. Even when this all came crashing down and he was driven to suicide to escape the consequences of his mismanagement and his enemies, he had to ask a secretary, Epictetus's owner, as it happens, to do the deed for him. Nero was to paraphrase the song lyrics, the smallest man who ever lived. He might have possessed a great kingdom, but he did not command himself for his urges or his ego. He was vain and cowardly, petty and vindictive, murderous and untalented. He was rust on a sparkling empire.

The question is, as we've talked about before, is how did Seneca get so mixed up in it? What was he doing, writing speeches for this guy, advising him, supporting him when he was so obviously unsuited for power in every conceivable way? James Roms' fascinating biography dying every day, along with Emily Wilson's The Greatest Empire, offer several answers. Seneca was greedy. Seneca was hypocritical. Seneca was a martyr. He thought he was the adult in the room. whom, saving Rome from worse. Seneca was weak and then became strong when Nero finally turned on him. In truth, Seneca was a lot like us, probably. He knew what he should do, but he made excuses.

He had trouble seeing what his salary and his status depended on him not seeing. He hoped that he could do things through Nero. He told himself it was not as bad as everyone said it was, told himself he was waiting for the right moment. Well, we're in an election year here, not just in America, but across the world. Let us learn from Seneca. Let us be reminded what happens when you let a man-child run a country, when ego and incompetence run amok. Don't be this kind of friend. They've always been with us. They were there in Nero's court, telling the king what he wanted to hear. They were there in the slave quarters, too, as Epictetus would have known, notions of solidarity being tossed aside for an extra scrap of food or slightly better treatment. Seneca would have known them in his literary salons, too. It's rare to see Marcus Aurelius get as specific or as judgmental as he does in Meditations 1115,

when he talks about despicable phoniness, which he calls a knife in the back. We've all known these people. They do one thing and say another. They virtue signal, but act without virtue. They are, as Taylor Swift sings, vipers dressed. in impath's clothing. But it's important that we understand when Marcus Aurelius is saying that false friendship is the worst and that we must avoid it all costs. He's not saying that we can get through life without experiencing false friendship. That's unavoidable. What he is saying is that we make sure that we aren't false friends. Remember, we don't control what other people do, whether they lie to our faces or stab us in the back. We don't control other people's

hypocrisies or their vulnerabilities. We do, however, control who we are. We control how we treat others. We control what kind of friend we are. Can you do it even when you don't want to? When the weather is nice, it's easy. When you've had plenty of sleep, it's easy. When you like the taste, it's easy. When everyone is rooting for you, it's easy. In these cases, it doesn't take much discipline, but just as courage is only courage when there's a risk when you're pushing past fear, discipline is a virtue that comes into play only when things are hard. When I was in Canada for the Daily Stoic Life Tour, I just did, I was talking about physical practices running and swimming and lifting weights and walking anything that forces you to confront and push past the resistance of not wanting to do it. I was saying that these are mental and emotional practices. But instead of quoting from a Stoics and she was in town,

I quoted a lyric from Taylor Swift, lights, camera, bitch, smile, even when you want to die. Can you hit your marks when you're tired, when you're sick, when your kids are sick? Can you do it when the weather is bad? When you think people are laughing at you? Can you do it even when it's hard, even when you don't want to, even when you think that maybe you can't?

That's what discipline is about. That's the muscle you cultivate from a physical practice. The muscle of doing the thing even when you don't want to do the thing, even when it's extra hard to do the thing, even when you think you can't do the thing. Can you do it with a broken heart? It's one thing to get up there and perform. It's one thing to show your kids a wonderful day.

It's one thing to go make the sale. It's one thing to put in a full 12-hour shift. It's another thing to do it after a wrenching custody handoff. It's another to do it as you're grieving. It's another to do it when you're filled with shame. It's another to do it when you feel terribly alone. Stoicism is not the absence of emotion. We have stories of Marcus Aurelius crying, multiple, in fact.

We have incredibly thoughtful essays from Seneca on grief and loss. My favorite translations in the painting porch, I'll link to that. The Stoics made beautiful works of art. they wrote poetry, they loved the theater. These were people that felt, no question. But they also understood that life, especially leadership, requires being able to balance these emotions with the responsibilities and duties that each of us have.

Taylor Swift sings, and I can do it with a broken heart. We can imagine Marcus Aureli is trying to hit his marks, trying to perform the public duties of the emperor, even as a plague devastated Rome, even as he grieved the loss of another one of his children, even as he was suffering from his own debilitating health issues. We have to process these emotions to be sure. We may also have to put them aside for a second

because our children are depending on us because we've got to go make our living because we made a commitment because the world is counting on us. Life doesn't care if you have a broken heart, only that we hit our marks. No one likes to be insulted. No one likes to be attacked or slandered. Feels great to be praised. We like being celebrated, renowned, and recognized. But the Stoic in us has to remember that these things are not worth very much, don't mean very much, one way, or another. Why? Because they're not in our control. When the rapper and music mogul Birdman demanded that the radio host and Daily Stoic fan Charlemagne the God puts him respect on my name, he was asking for something outside his control. however powerful he was in the business.

More important, what would it have been worth anyway? What matters is self-respect, not obligated acknowledgement. The Stoic understands that deserving a good reputation is what we strive for. Actually getting it matters so much less. It cuts the other way, too, another music reference in her song, but Daddy I love him, Taylor Swift, and no stranger to gossip and criticism sings. We should remember that no one can demean or harm us with their insinuations or expectations. No one can truly damage us with scandal or controversy.

Our name is ours. Can we disgrace ourselves, though? Absolutely. You're only harmed, Marcus Reelis wrote to himself, if your character is affected, not impugned, but affected. Meaning, only you have this power. So remember, they can praise you, they can insult you, they can raise you up or tear you down, they can spread your name far and wide. They can ignore you. They can love you or hate you, but really the only thing matters is who you are to yourself. What matters

is whether you are living up to your standards, whether you are following those virtues of courage and discipline and justice and wisdom. Are you putting respect on your name? Are you disgrace in your name? That's what counts. Not what anyone else says or says you do. Hey, it's Ryan. Thank you for listening to The Daily Stoag podcast. I just wanted to say, we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word, tell people about it, and this isn't to sell anything. I just wanted to say, thank you. I don't know. I don't know.