It’s Ok To Break | Ask DS

When Marcus Aurelius heard that his beloved teacher Fronto had lost a grandchild, he sent him a letter. Perhaps, if you believe in the stereotype of the unfeeling Stoic, you might expect that this letter was intended to buck his friend up, or attempted to remind the grieving Fronto that loss was a part of life and something we had to be prepared for. In our recent interview with Professor Martha Nussbaum on the Daily Stoic podcast, we talked about this exchange.---And in today's Ask Daily Stoic, Ryan answers questions from a conference of tech and e-commerce entrepreneurs after a talk he gave in downtown Austin. The topics that he covers include how Ryan manages his time between writing books and creating content, why he searches for wisdom from a wide variety of sources, and how we can balance our decisions with the context that we are making them in.📕 You can learn more about the tragedy and triumphs of Marcus Aurelius’ life as well as those of Cicero’s in Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, 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

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

• 0:02Ryan 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. While 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.

• 0:45Ryan Holiday?

  It's okay to break. When Marcus Aurelius heard that his beloved teacher, Fronto, had lost a grandchild, he sent him a letter. Perhaps if you believe in the stereotype of the unfeeling Stoic, you might expect that this letter was intended to buck his friend up or attempted to remind the grieving Fronto that loss was a part of life and something we had to be prepared for. In our recent Daily Stoic Podcast interview with Professor Martha Nussbaum on the Daily Stoic Podcast, we talked about actually this exact exchange. She actually said that she believed that the death of a child was so common at that time to Roman parents that the Stoics especially had learned from painful experience to practice a certain kind of detachment, that they didn't feel these losses as deeply as we might think.

• 1:30Ryan Holiday?

  But in fact, Marcus's letter explained that he felt his friends' suffering anguish deeply in his own bones. This was a kind of pain that Marcus knew well himself and would come to know well more in the future, having buried far too many of his own children. And so the two friends went back and forth talking about grief and loss. Fronto, who had always challenged Marcus when it came to philosophy, replied that if the immortality of the soul were ever so established, it would be the theme for the disputations of philosophers. He said that philosophy could never assage the learning of a parent. Fronto was haunted by the sweet face of his darling grandson, hearing everywhere the echo of his voice.

• 2:14Ryan Holiday?

  Well, Meditations shows several moments where Marcus is haunted the same way, and that he was not implacable under the cruel blows of fate. Professor Nussbaum herself has written a beautiful new book called Justice for Animals, which was inspired by her grief for her daughter, an animal rights activist. She spoke movingly on the podcast about Cicero, who also lost his daughter, and made no attempt to be the perfect Stoic about it. "Life is very hard, and it will subject us to pains and yearnings that no amount of philosophy can take away. But that's okay. It's okay to break under pressure and pain, even the best of us do. So as long as we figure out what Cicero, and Marcus, and Professor Nussbaum,

• 2:56Ryan Holiday?

  and Fronto eventually did, as long as we figure out how to carry on, how to carry the memory of those we loved forward, how to keep going." And you can learn more about Marcus and Fronto, actually, in Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius, my biography of the Stoics, Cicero's biography and the story of his daughter is in there also. And be sure to listen to our wonderful interview with Professor Nussbaum, and I'll link to that in today's show notes.

• 3:31Ryan Holiday?

  Hey, it's Ryan. Welcome to another Thursday episode of the podcast. I guess this would have been in June of this year. I gave a talk downtown in Austin to a big conference of e-commerce entrepreneurs. And we talked Stoicism, we talked some of the ideas in Perennial Seller, basically like sort of how you make stuff that lasts, and some of the lessons I've taken from the Stoics that have helped me do that, fittingly enough, with my work about the Stoics. And then I took some questions after, which I'm going to leave with you now. Here's my Q and A with some folks here in Austin. It's always a joy to not have to travel to give a talk, and I always love answering your questions.

• 4:14Ryan Holiday?

  And then I love getting to share those questions with all of you here on the podcast as well.

• 4:20Speaker 01

  So we've got some time.

• 4:23Ryan Holiday?

  Yeah.

• 4:23Speaker 01

  The audience is very gracious to allow us to do some questions. So if you've got a question, raise your hand. We've got writer, writer, raise your hand, I'm running over to you. I have a question myself.

• 4:35Ryan Holiday?

  All right, hit me.

• 4:36Speaker 01

  So it seems your most important thing is to write.

• 4:41Ryan Holiday?

  Yes.

• 4:41Speaker 01

  And you want to maintain an empty schedule. Would you realize putting out all this content is super helpful? How do you maintain an empty calendar while putting out all that content?

• 4:49Ryan Holiday?

  Yes. So I think a couple of things. I love writing. That's what gets me excited. That's my creative medium. But I also understand that that's not the medium that most people consume most of their content in. So stepping back, what's actually important to me is the ideas that I am writing about. So I'm willing to open the schedule up to communicate in every platform that people would consume the ideas in. So it's actually been creatively challenging and fulfilling to go, how do I take something that I spent two years writing about and turn it into a 60-second video? Or an Instagram carousel? Or a 50-minute YouTube video, right? I've actually gotten excited about doing that.

• 5:32Ryan Holiday?

  And anything that gets people reading or talking about the ideas, that's meaningful to me. So first off, not being a snob about what you like, and instead thinking about what the audience likes or what the audience needs is really important. That being said, if those things are preventing me from doing the one thing I like doing, then how successful is that? So I have a huge team. And like I was saying, I decided not to spend money on Facebook ads. I wanted to hire people. And I wanted those people to help translate what I was doing into these different mediums. So, you know, I'm not editing my podcast myself. I'm making this stuff. And then my team's going, hey, I think this chapter in this book could be translated into a video in this way.

• 6:15Ryan Holiday?

  And it's about empowering people, delegating, and then collaborating to take, you know, what you love and allow it to become something that other people love. So it's really, it's about the team. And I couldn't do it without the team. And constantly realizing, hey, the team needs to be bigger if we want to do more. I'm not, as much as we're doing, I don't think we're even close to hitting the ceiling on what we could do or the reach we could have, so.

• 6:43Speaker 01

  Okay, great, thank you. All right, we go audience.

• 6:47Speaker 02

  Hello.

• 6:47Ryan Holiday?

  Hello.

• 6:48Speaker 02

  As I understand, immediate reflection on what you said, is it's the thoughts you have compiled from your reading as well as your own?

• 6:58Ryan Holiday?

  Yes.

• 6:59Speaker 02

  They are most inspirational and motivational in its own way.

• 7:02Ryan Holiday?

  Sure.

• 7:03Speaker 02

  So how are you digesting it from other sources? Do you have any influence or preference for similar thought processes outside? That's part one. The second is, having all of that compiled and successfully been putting it out across, are you already doing a plan to do any leadership, motivational, inspirational kind of channel as well? Where all that we've had so far becomes a good thing for people who are struggling or pressing above the level and those kinds of things?

• 7:34Ryan Holiday?

  Yeah, great question. So I read very widely. I talk to as many people as I can. I'm always looking for wisdom anywhere I can find it. One of Seneca's great lines, he says, "We must read like a spy in the enemy's camp," right? That we're just trying to find anything that works, anything that's good, anywhere we can find it. Then we integrate that into our own lives according to our own values, what our own experiences. So I'm reading and consuming in all different mediums very widely. And then I try to come up with what I have to say that's unique or that I think is important, either inspired by that or influenced by that. And yeah, I have Daily Stoic, but I've expanded out.

• 8:19Ryan Holiday?

  We have Daily Dad, which is a parenting version. The Daily Philosopher, which is just for philosophical advice every single day. And that's what gets me excited is like finding stuff that I didn't know about, that I thought was cool, and to bring that to other people. That's, when I say, "Am I being a good steward of Stoicism?" I'm saying, "Am I taking this stuff that I learned, that someone exposed me to, and am I paying that forward and bringing it to new people and new people to it?"

• 8:51Ryan Holiday?

  Yes.

• 8:51Speaker 03

  You, you mentioned the decisions that you make a lot of. How do, how do I determine what to say no to? And how do I determine what to say yes to, right?

• 9:03Ryan Holiday?

  Yes.

• 9:03Speaker 03

  In, in life, the things that you say no to frequently conflict with the context that makes us say maybe we need to say yes. My question is to you, how do you use context to change that no to yes? Yes to no, or to keep at yes or at no?

• 9:23Ryan Holiday?

  It's, it's interesting, right? Um, serendipity, things that I didn't think I would enjoy, things that I couldn't get out of have changed my life in so many ways, right? So I, I do try to be humble about the fact that there are things that I didn't think would work, or that I didn't think were a good use of my time, that turned out to be immensely positive. So I, I try not to be too closed minded. Uh, I do try to, you know, take risks from time to time. Uh, so, so I'm not saying you have to be a monk and you say no to literally everything in the world. But, um, you've got to know what your main thing is, right? I, I talked to the Los Angeles Rams a couple of years ago and their motto at the franchise is, the main thing is to keep the main thing, the main thing, right? What's the thing that only you can do? Talked about Blue Ocean Strategy earlier.

• 10:08Ryan Holiday?

  What is, what are the roles in life, in the organization, in the niche that you're in? What, what are the things that only you can do that you feel like you were uniquely put here to do, right? And you've got to protect that, right? So when you're like, should I say yes to this? Should I say no to this? Oh, but this pays a lot of money, but this could be cool. This is a place I've always wanted to go, right? You've got to be able to go, does it get me closer or further away from the kind of life that I want? Or the kind of work that I'm trying to do, right? So I've been offered all sorts of cool things, whether it's trips to cool places or cool career or work opportunities. But if it takes me away from, you know, one, being able to wake up and write,

• 10:50Ryan Holiday?

  but two, being able to have the freedom to take my kids to school or to jump in the pool with them in the afternoon, then that's not really success, right? What is the life that you want? And you've got to back out from there. One of the things you take from this idea of memento mori is that like, don't set your life up, agree to a bunch of things that are miserable right now, so someday in the distant future, then you can do what you want. Because you get hit by a bus between now and then. And you're going to regret the time that you didn't spend doing the things that you feel like only you can do, that you were uniquely put here to do.