This Matters Way More Than The Details | Ask DS

There can be so much about the study of this philosophy that can be overwhelming that’s intimidating. When did Stoicism start? Where did it begin? What the hell is a Stoa Poikile?? Put aside that it focuses on some of the most pressing and complicated topics in the world–good, evil, our mortality–philosophy is also filled with paradoxes and counterintuitive arguments. More pressing and practical for many of us, philosophy is filled with unpronounceable names and big words, often from languages we don’t speak. Stoicism 101 is a 14 day guided journey through the best of Stoicism. What is Stoicism? Who were the Stoics? Why have some of history’s greatest leaders practiced Stoicism in their daily lives? How can I consistently apply Stoicism to my life? If you’re thinking any of those things, you’ve come to the right place. We set up Stoicism 101: Ancient Philosophy For Your Actual Life to give you the absolute best of Stoicism in 14 days, with Ryan Holiday as your personal teacher—all for just $25. Registration is only open until TUESDAY, NOVEMBER 7TH, so we hope you’ll take a moment and sign up now.✉️ 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.

• 0:03Ryan 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. We're 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. But thank you for listening, and we hope this is of use to you.

• 0:45Speaker 01

  In the unbearable lightness of being Teresa, as the Prague Spring happens and the Soviets begin a military occupation, takes the time to rescue a crow that was hurt on the side of the road. Yet, when dissidents come and ask Thomas, her husband, to sign a political petition, he refuses, which prompts a rather interesting sentence in the book. "It is much more important to dig a half-buried crow out of the ground than to send petitions to a president." A lot of people would reflexively disagree with that. Certainly, the actions of most people do. Even though there is the saying that all politics are local, we tend to think big picture before we think little picture.

• 1:29Speaker 01

  Seneca was the same way. Look at how he expressed his priorities in the essay "On Leisure." "The duty of a man is to be useful to his fellow men, if possible, to be useful to many of them; failing this, to be useful to a few; failing this, to be useful to his neighbors; and failing them, to be useful to himself. For when he helps others, he advances the general interests of mankind." It's ironic. Seneca's impact on trying to help as many of his fellow men as possible was what drove him into politics and eventually to Nero's Court, where he probably hurt more than he helped. It was only after that failure that he retreated back to his writing and to small-town life. But what if he'd switched that order?

• 2:13Speaker 01

  What if he'd focused on the suffering crow instead of petitioning the emperor? Might the world have been a better place? These are unanswerable questions, but they raise a provocative point that goes to the core of Stoic thought. We should get our own house in order first before we try to tackle other people's problems. We should deal with what's in front of us, with how we can help those in our neighborhood and our town before we try to change the world. Because if tragedy ever befalls your family, cancer, unemployment, a debilitating accident, an untimely death, the world will not be there to take your kids to school so that you can make the doctor's appointment. The world is not who will leave casseroles on your doorstep or start a GoFundMe page.

• 2:56Speaker 01

  It will be your neighbors, your town, and you should do the same. Doing those small things won't change the whole world, but they will change somebody's world, and that is what matters. Please check out the Daily Stoic store where we sell products that we ourselves use that are designed to take these Stoic lessons to the next level. Just go to dailystoic.com/store.

• 3:35Ryan Holiday?

  Hey, it's Ryan. Welcome to another Thursday episode of the Daily Stoic Podcast. I did a lot of virtual talks during the pandemic and, you know, companies were facing obstacles, difficulties, et cetera. And now it's cool, starting to go see some of those same groups in person again and sort of reflect on, well, how did they respond to that adversity? What did become possible based on what they were going through? And one of those groups I gave a talk to, Mutual of Omaha, I think I did two virtual talks in 22, 21, 22. And then I went out and saw them when they were doing, they were doing an event here in Austin, a video that'll come out later. But I was talking to a bunch of financial advisors that had questions about applying

• 4:19Ryan Holiday?

  Stoic philosophy to what they do, both personally and professionally. And I'm excited to share some of those questions with you now. Youtube is a great one, I think it's worth pointing out also all this information. The skill of being able to separate good information from bad information, truth from bullshit. You know, like you can learn all sorts of stuff on Youtube. You can also get sucked down some pretty insane rabbit holes. I think we've met some people who have done that. And so these are like the people who can figure out how to get the good parts of the inventions or the technologies or the changes and not be corrupted by or distracted by the bad parts is, you know, I think a very underrated skill.

• 4:59Speaker 02

  Yeah, and getting a couple of like good mentors that you know offer solid stuff. So I think my original entry drug into Youtube was Tim Ferriss, right? Following Tim Ferriss turned me on to you, turned me on to Jaco. I mean, I was early on Jaco, Jaco's first podcast with Tim Ferriss 200 years ago. Bought the book. I mean, so following, you know, where does Ryan show up next? Well, okay, I'm probably gonna know that that's a good person I should be listening to and trust me in terms of, because there is a lot of crap out there, right? You look at our business and the amount of garbage out there on Youtube about our business and financial independence, terrible. So you have to have the right voices, the right mentors. So, you know, get a list of the authors that you like and then go from there, because they're always on somebody else's podcast or Youtube channel.

• 5:44Speaker 02

  Yeah.

• 5:45Speaker 03

  Kirk.

• 5:46Ryan Holiday?

  Hi.

• 5:47Speaker 03

  Hello. Thank you, Ryan, for coming here. I want to point out a couple of things. Thank you, by the way, for writing Stillness is the Key.

• 5:57Ryan Holiday?

  Oh, my pleasure.

• 5:58Speaker 03

  That was a book that A.J. turned me on. A.J.'s been my mentor to getting to detach. And for several years, I get a little overly passionate about things. That's been an impactful book to me as well.

• 6:09Ryan Holiday?

  Oh, wonderful.

• 6:10Speaker 03

  So my question is more of a life question. So as leaders, we've trained ourselves, we've coached ourselves to detach emotionally and make decisions, to think more logically in work life. What are your thoughts on... When you get around your family and you have a spouse or children or family members that need that emotion.

• 6:31Ryan Holiday?

  Sure.

• 6:31Speaker 03

  We've shut it off all day long in a logical detached decisions, but then they crave that emotion from you, so you're not robotic. It's more of a life question.

• 6:41Ryan Holiday?

  Yeah, I do think it's important that we don't see the Stoics as robots or as emotionless, because they weren't. You know, they were people who had jobs, like all of us here, and they were in high stakes, high pressure situations, but they also had families, they also enjoyed going to the theater, they told jokes. There was a Stoic who died of laughter, literally, like, there's a Wikipedia page of list of unusual deaths, and he's like, the Stoic Chrysippus is at the top. He told some joke he thought was so funny. He didn't just die of a joke, he died laughing so hard at one of his own jokes, which may be a sort of a Stoic argument against emotions, maybe, I don't know. But the idea that the Stoics were unfeeling, I think, you know, when you actually look

• 7:23Ryan Holiday?

  at the lives of the Stoics, what they did, what they cared about, the decisions you made, they made, you see that they weren't these sort of detached, disconnected people. They tried to be disconnected and detached from, you know, as I said, fear or anger or frustration, especially when that made no difference to a situation. But as far as, you know, caring about other people, trying to, you know, connect with other people, I think this is, you know, this is, it's not where they're putting the Stoicism aside, but it's by getting rid of the other stuff that you actually have room for that stuff that really matters, right?

• 8:03Ryan Holiday?

  If you're spending your whole day in some state of rage or frustration or, you know, you're bouncing between these different extremes, when you come home, you're gonna be emotionally exhausted, you don't have time to understand, hey, this toddler is dealing with some stuff, and I'm gonna be, you know, a safe spot for that, and I'm gonna be able to help them through it, because I'm not, you know, I'm not at the end of my rope. So I think it's really important that we see that in the more beautiful parts of the Stoic tradition. Seneca, who goes through all sorts of adversity and difficulty in his life. He writes these three essays called Consolations. And one is to the daughter of a friend who had died, the other's to his mother when Seneca gets exiled.

• 8:47Ryan Holiday?

  And I'm forgetting who the other one is for, but he's basically coaxing someone through extreme grief and sadness. And he's saying, you know, you can't deceive it, you can't pretend that it doesn't exist, you can't just stuff it down. You're gonna have to process this, and you're gonna have to deal with it. And so I think it's important that the Stoics not only do that with themselves, but when other people are going through something, if someone else is emotional, just going, hey, you're being very emotional right now, this is not rational, you know, that's a good recipe for making them even more irrational. And having some patience and empathy and understanding, I think, is part of what we're talking about here, too. Hey, Jay Dax, what up here from Tolu?

• 9:25Speaker 04

  Hi, Ryan. Thank you. In the book, The Obstacle of the Way, you discuss living, I believe it's actually in the trusted process section, living moment to moment, day by day, paycheck to paycheck. I think a lot of people in this room might be taken back by that comment right there.

• 9:44Ryan Holiday?

  Sure.

• 9:45Speaker 04

  I was hoping you could maybe help kind of, you know, bridge those two thoughts.

• 9:48Ryan Holiday?

  Yeah, I don't mean sort of literally spend all of your paychecks, but the point is, you know, sometimes we're getting so like, what am I gonna do 20 years from now? What am I gonna do 10 years from now? What about this? What about this? What about this? And so this sort of, that creates this kind of anxiety doom spiral that doesn't allow you to sort of make good decisions here in the moment. So I think it's a tension, right? The Stoics talk about sort of meditating on the things that could happen, so you're prepared for them, you're not caught by surprise, and at the same time, to not be suffering in advance because something may or may not happen down the road. So I think it's a balance, you're trying to balance that out.

• 10:33Ryan Holiday?

  But I do think generally, being present is better than, say, dwelling on the past or...

• 10:42Ryan Holiday?

  Fearing the future and just go, hey, what's going on right now? What do I need to do right now? And then as far as, I mean, I often think from a financial standpoint, you know, the more you automate things as far as like in the present, you're automating things, so it's recurring without you having to use sort of in the moment willpower, you know, that's one way to sort of counterbalance that impulse to either be too conservative or too irresponsible, right? It's like, hey, based on the math, based on the information, what should I be doing? What's the right thing? And how do I make that decision one time? And then it makes it on a recurring basis for me. I'm sure you guys talk to your clients about this all the time.

• 11:25Ryan Holiday?

  Now that I'm right here under the right conditions with the right advice, what's the decision I can make? And how do I make it once? So I'm not in the moment sort of dwelling, what am I going to do when I'm retired? When I retire every day, every moment of every day? You know, that's not a, that's not a good recipe for succeeding at work right now.

• 11:43Speaker 05

  With a journal, how much do you process?

• 11:45Ryan Holiday?

  Oh, with my journal?

• 11:46Speaker 05

  Yes.

• 11:46Ryan Holiday?

  So with my journal, I try to, I try to just have a little conversation with myself about what I'm thinking and what I'm doing. I think so often we're just sort of unconsciously going through life. You know, we're upset by this, we're worried about that, we're excited about this. And what I try to do on the pages is just create a little distance and try to spell it out. And then I go, is that actually true? Do I actually believe that? Is that who I want to be? And creating that practice allows me to, I think, be a bit more objective about myself and get a little distance from it. That, that's kind of how I think about journaling. There's a daily Stoic journal that I have that gives you like a sort of Stoic themed prompt

• 12:30Ryan Holiday?

  every day, once in the morning and once at night. So I use that. I also use a little journal that I have like a sort of a free-form journal where I just put down thoughts. And then I have another journal where I just write, it's got five lines and you keep it for five years. It's called the one-line-a-day journal. I actually have them in my bookstore, but it's one-line-a-day and you just write, I just write one thing about the day that just happened. And it gives me this really good kind of running log about where I was last year and where I was the year before and the year before. And it gives me a sense of kind of the rhythms. I go, oh, I was worried about this last year and then it got handled. Oh, I was in the middle of my book on this day 24 months ago and now it's out.

• 13:15Ryan Holiday?

  And I, in that moment, I probably, I was so afraid it wasn't gonna happen. And that's why I trust the process, right? It's because, hey, I've been, I have documentation that I've been through this before and it works out. And so just kind of having that, you know, ongoing dialogue with yourself is to me what journaling is about. It's not for publication, it's not for posterity, it's just for you to work out that stuff. And I, I really don't think there's a wrong way to do it. You can do it on your phone, do it in a document on your computer, you can do it on, you know, notepads in a hotel room. I don't, just whatever gets you doing it is, I think, the best way to do it. We've got one here.

• 13:53Speaker 05

  All right, so a lot of us are in kind of new positions, maybe on new teams or different capacities. I think it's gonna be really important for me that that we should do a routine.

• 14:04Ryan Holiday?

  Sure.

• 14:05Speaker 05

  You talked about that upfront. What's some of your advice on doing that?

• 14:09Ryan Holiday?

  Well, first off, I would just say congratulations. I think sometimes, and we work, we have this goal way off in the future and we work really hard on it and then it happens. And then we're in that position, right? And because we're now in the thick of that position, we don't really get to appreciate like how crazy we thought it would be not that long ago to ever be here. Like we, you did it, you know what I mean? So I would just congratulate yourself and soak that in for a second, because I think celebrating wins is something often we're not good enough at. But as far as a routine goes, I think one of the things I've learned, I used to have a very specific routine. This is what I did every day, how it had to be. And, you know, then I had, I had kids and now I don't have that routine anymore. Because they blow up stuff, right?

• 14:53Ryan Holiday?

  And life blows up stuff. And so one of the things I've tried to get better at is having routines, plural. I have a routine that I do when I travel, when I have... In some ways, more control over what I'm doing, but also less control because I'm not at my house, not with my stuff, you know, it's a different time zone. I have, you know, sort of the routine I do when the kids wake up when they're supposed to, and I have the routine when we're scrambling last minute and they don't, you know what I mean? I have, I think about it more like, what are the important practices that I should try to do every day that ground me, that allow me to do what I do? And then what's the best order for them to go in?

• 15:34Ryan Holiday?

  But to have a little flexibility, or let's just say not rigidity, because life is unpredictable. And, you know, if you're someone who it has to be this way at this time, well, what happens when your plane is delayed, or what happens when somebody wakes up sick, or what happens when, you know, you check traffic and it's going to take you an extra hour to get there, right? And so I think the ability to have a broad sense of like, what are the best practices? How do you do them? You know, what order should they come in? But at the same time, being, being a bit flexible is maybe a better way to think about it. But, you know, when are you at your best? And build around that, right? When are you at your best? What's the most important thing for you to do?

• 16:19Ryan Holiday?

  What are the things that only you can do? And I try to build my routines or my day around that. So I'm not putting the important thing off. Like, one of my rules is do the important stuff first, or do the hard stuff first. I tackle it early. If I've accomplished that, the rest of the day is kind of extra. But if I get tied up in a lot of trivial, you know, inconsequential stuff early, and then something intervenes in the afternoon, well, now all I have to show for that day is like this paperwork that I did.

• 16:49Speaker 02

  So do you have a list of books that are, I mean, I know you have a monthly, like a reading list, so if you, if you haven't signed up for his newsletter, he, he processes so many books, it's, it's, you probably should do that, so, you know, a little promotion there for you. But do you have, if someone said, hey, what's the top three books, top five books that have impacted me the most in my life? What would you tell them, or could you boil that down?

• 17:13Ryan Holiday?

  I don't know if I could boil it down to that. I mean, one of the reasons I opened my own bookstore and one of the perks of opening my own bookstore is that I only carry books that I like. I don't carry what's new, I don't care what's popular, it's only books that I like, which maybe isn't the best business decision, but it allows me to go like, "Just come," and I promise you, one of these books will be good, or all of them will be good, because I've personally read them. But as far as like a couple favorites, just off the top of my head, I would think Marx Realist's Meditations, one of the most incredible books on leadership I've ever read. I very much was influenced by and continue to recommend Robert Greene's works, so The Forty Laws of Power, The Laws of Human Nature. Sometimes people go, "Oh, isn't that book sort of evil?"

• 17:56Ryan Holiday?

  Or, "I'm not interested in power." I usually go, "That's exactly who should read this book, because you're wanting to be the world, you're wanting the world to be different than it is, and there might be a little bit of naivete or wishful thinking there." It doesn't, it's not saying you have to be very Machiavellian, it's saying that you have to understand the Machiavellian tendencies of human beings and organizations, you have to understand how these things work. And then another book that I really like is Doris Kearns Goodwin, the biographer, she has a book called Leadership in Turbulent Times. And it's sort of a, she's obviously been a master biographer for, you know, many, many

• 18:38Ryan Holiday?

  decades, but this is sort of a greatest hits album of the people she wrote about, which is Theodore Roosevelt, Lincoln, Franklin Delano Roosevelt, and Lyndon Johnson, but it's the moments of turmoil and crisis and difficulty of their life and their story. And so it's, I think, you know, leadership, when things are going great, is easy. You want to, you want to study what the leaders did in moments of crisis and difficulty, because that's most likely where you're going to need to lean on them, so that's a book I'd also recommend.

• 19:07Speaker 02

  So you own a bookstore.

• 19:08Ryan Holiday?

  Yeah.

• 19:08Speaker 02

  Do you also have a library in your house?

• 19:10Ryan Holiday?

  Uh, well, one of the trades I made with my wife was that I would move all the books out of our house into, uh, into the office so it wouldn't look like we were hoarders. Um, but, uh, yes, of course, I have, I have many, many, many, many books and I, I only try to read the physical ones and I try to keep them and I'm trying to create a library in the sense of I want to go back and reread those books and I want to see what struck me in the past, but I also want to have them as a resource. Hey, didn't so-and-so talk about this in one of those, I want to go back to it and I want to find it and I want to have my sort of notes or my thoughts there. Um, so yeah, I'm always sort of not just reading, but accumulating and sorting and

• 19:53Ryan Holiday?

  organizing that information in ways that it's accessible and usable.