Pod Insights The Daily Stoic Premium (🔓) Can You Pull Off This Move? | How Can You Maintain Justice Without Self-Sacrificing? About this episode A lot has happened in the 10 years since The Obstacle Is the Way came out. Ryan is a different person, a different writer, than he was back in 2014 and he was so excited to get a chance to improve and update this book accordingly. There were mistakes to fix, criticism to address (some not so fun), and new ideas to incorporate.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacleAsk DS: Does Ryan have a meditation practice that helps him achieve stillness? How do you measure if you’re happy with effort over the outcome? How do you maintain the virtue of justice without over giving or self-sacrificing? 🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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. 📢 Share | ⚙️ Manage Subscription
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:02 Ryan Holiday? Welcome to the Daily Stoic Podcast where each day we read a passage of ancient wisdom designed to help you in your everyday life. Well, on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics who are trying to apply this philosophy just as you are. Some of these come from my talks, some of these come from Zoom sessions that we do with Daily Stoic Life members, or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. Thank you for listening, and we hope this is of use to you.
0:43 Ryan Holiday? Can you pull off this move? 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
1:23 Ryan Holiday? fans who loved those songs. Instead, in a career-defining moment, she calmed down, followed 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 I've not seen since The Beatles. Her era's tour grossed more than $1 billion. 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.
2:10 Ryan Holiday? But it's not simply that she became bigger and more popular as a result, or that she seized 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, Marcus Realist
2:54 Ryan Holiday? 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 those stories I wanted to add to the 10th anniversary edition of The Obstacle is 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 Obstacle is the Way, I wasn't sure why I would do it.
3:36 Ryan Holiday? But then I kind of actually liked the idea of doing 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. It's, first one was Ryan's version, of course, but this one is the parenthetical Ryan's version. And I think it's better and I'm prouder of it, and I hope you get excited about it. You can grab a signed numbered first edition here. It comes out on October 1st, but the only place you can get these signed numbered first editions, and there's a short run, you got to remember, we sold out of the Daily Dad signed and numbered first editions, and we sold out of the Right Thing Right Now signed
4:21 Ryan Holiday? first edition. So if you want a bunch of awesome stuff, check that out at dailystoic.com/obstacle, and I'll link to that in today's show notes. And I also want to say thank you to everyone who supported the book in these last 10 years. I don't think anyone would have predicted, least of all me. That the obstacle is the way we'd go on to sell millions of copies, it'd be translated into 40 languages, that I would be here 10 years later with this new version and your support means the world to me. And I wanted to make this new version better and inform some of the things that I've heard from all of you over the years, too. Notes I got, criticism I got, all of it contributed to making the book better. You can check that out at dailystoic.com/Obstacle.
5:14 Ryan Holiday? Hey, it's Ryan. Welcome to another Q and A episode of the Daily Stoic Podcast. I was just talking to my wife yesterday and we've been going all these swimming holes in Texas. I was telling you about that. And I was like, why did we start doing this? We hadn't done it in a while. She's like, I think it was Australia. Australia kind of just, it snuck up on us that our kids were getting older, that they were more game for doing stuff. Kind of just gotten this habit. We took all these day trips while we were there. And now we've been doing a lot of those day trips here in Texas and trying to get into all these different cool swimming holes and campsites before, you know, they close for the season, which for some reason they do in Texas. And anyways, it's made us really excited about getting out to Europe this fall. In November, I'm going to be in London,
5:55 Ryan Holiday? Dublin, and Rotterdam with the family. I'm doing Vancouver and Toronto by myself. I'm going to be doing talks. You can come see me. And actually, today's episode is drawing from that Q and A. So if you want to ask me some questions in Rotterdam, London, Dublin, Vancouver, or Toronto, you just have to go to ryanholiday.net to grab those tour dates. I will see you there in November. But without further ado, I'll just dig into it. It was awesome to talk to these folks in Sydney. And I'm actually doing more Q and A in the other dates. If you buy the VIP tickets, I think we do a private Q and A beforehand, and then I do the larger audience Q and A at the end. So if you want to come see me, I'll see you there. And in the meantime, here's some thoughts from me at Sydney in
6:38 Ryan Holiday? Town Hall. I already miss it. If you were there, thanks for coming, and I hope you enjoy this little recap.
6:47 Speaker 01 I would love to get your thoughts on meditation. Not the book, obviously, because, yeah, you've done a pretty good job of explaining the book tonight, but the actual practice of meditation, do you do it? What type do you do if you do do it? And what have you found from it? Because I find it's quite, very much linked with stoicism and everything you've been talking about tonight.
7:11 Speaker 02 Yeah, I'm all right with that. My sort of favorite way to try, I tend to find either walking or running or swimming to be very meditative experiences or states for me. I find the sitting part very hard, which is maybe a sign I should do it more. But I like to kind of give it something else when I'm emptying the mind and trying to get to that place of stillness or peace. So I guess maybe I have a little more expansive definition of it. To me, the reason Marcus would come is meditation, he's called meditation. It is an act for him, a deliberative, meditative process where he is talking to himself.
7:52 Speaker 02 And so I did a journaling and what I do with data scope is a version of that also. So I've got to have a grand, I have a different practice, but I'm not someone who like sits for 30 minutes a day. But I do try to actively take little chunks of time, kind of count the breath, get to nothing, get to stillness, clear the mind, and that's a big part of my practice. So, great question. Uh, something else?
8:16 Speaker 03 Hi, um, yeah, thank you, talk's been great.
8:20 Speaker 02 My pleasure.
8:20 Speaker 03 Um, you've mentioned before that when you're working on something, you try to be happy with the effort as opposed to the outcome. I guess what are some of the watermarks you look for when you are looking for? What do you have in with your effort or not?
8:35 Speaker 02 Yeah, uh, did I do the work or was I making excuses, taking shortcuts? Was there stuff that at the outset I said I was gonna do or wanted to do and then, you know, didn't end up doing? Uh, but mostly it's about like, am I giving my best? My favorite story in the, in the discipline, I think, I think it's in the discipline book, is about Kim Carter, who maybe wouldn't resonate as much with you guys not being Americans, but he, this...
9:06 Speaker 02 Young kid is being interviewed by an admiral in the Navy. And the admiral is asking him, you know, how did you stand in your class at the Naval Academy? Talking about his grades, his class rank. And then the guy asks him, "Okay, but did you always do your best?" And Jimmy Carter asks, "Stop, let's think about it." And then his instinct is to say, "Yeah, of course, obviously." But he decides to answer truthfully and says, "No, I didn't." And the admiral says, "Well, why not?" And then it gets up and leaves the room. And that question kind of hangs over Jimmy Carter for the rest of his life. Did I do my best? Did I give everything that I had in me in this project, in this office that I have, in this job that I was doing?
9:51 Speaker 02 And so that's kind of a test, like, did I actually do my best here? Did I cut short, did I make shortcuts, did I make excuses? You know, did I lose something unfinished? And so I kind of think about that, even in the course of the day. Okay, I said I was supposed to work this chapel, this section. Was I actually present for the hours that I was doing it? Or was I checking things? Was I distracted? Was I on my phone? Was I settling? Did I say, "Hey, this is good enough"? You know, I think about, did I do my best today? Because I don't even control if what comes together, if it gets published. Or did I get my bus or get cancelled or something? I don't know. But I do control if I did my job today. That's up to me, so that's how I think about it.
10:34 Speaker 04 Hi, Ryan.
10:34 Speaker 02 Hi.
10:35 Speaker 04 Thank you so much. That was incredible.
10:37 Speaker 02 Thank you, Carter.
10:39 Speaker 04 Thank you so much. "Obstacles Way" honestly changed my life and really set me up into such an incredible trajectory in my career and personal life. So just honestly, hot up, thank you for the work you did.
10:52 Speaker 02 Appreciate it.
10:53 Speaker 04 Thank you. Thank you very much. I'm somebody who's deeply oriented towards the value of justice. And I think sometimes to a detriment. I think there's, you know, I have a desire to deeply help the less fortunate, homeless. And sometimes it means that I'm self-sacrificing, over-giving, a bit of a martyr experience.
11:15 Speaker 02 Sure.
11:16 Speaker 04 I don't want to change that orientation towards justice, but I do want to, you know, sort of find my own sense of conviction that I don't have to give myself and lose myself to get to this justice.
11:30 Speaker 02 I mentioned the Aristotelian, are you very familiar with that concept? So Aristotle said that all virtues sit as a midpoint between two vices. So he said courage is actually in the middle between recklessness and cowardice. And he would say generosity is in the middle between giving everything away and being a miser, right? And so I think if we can think of these virtues as being something of a moderation, a midpoint between two vices, that could be really helpful. Now, are there some moments, some very heroic, wonderful, almost holy moments where someone
12:11 Speaker 02 gives everything in a moment of greatness or decency or justice? Yes. But day by day, we should probably be thinking about these virtues as this sort of middle ground. Because if we're giving so much of ourselves out to strangers and we don't have anything left to our family, we'll have to form an injustice also, right? Or if we are so focused on working on the immediate symptoms of a problem that we don't have the effort or the energy or the relationships or the acumen to solve the problem holistically or systematically or politically or what have you, again, there's a vice in that selflessness also.
12:53 Speaker 02 So if we can think about that as a midpoint, the person rushes headlong into battle without a plan, right, without any thought of the dangers to themselves is actually endangering other people and depriving the group of that strength. So if we can think about these virtues needing to be mitigated, and that is the virtue itself of temperance or discipline, maybe that can help us.
13:19 Speaker 04 Okay, thank you.
13:25 Ryan Holiday? Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple 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.
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