You Aren’t Killing Time. Time Is Killing You | Ryan Holiday Answers On Ego And Mentorship

Seneca reminded himself that death is not this thing in the future, but something that is happening now. It is always happening. It is the ticking hand of the clock. It is the spring flowers. It is the fall harvest. It is the summer rains. It is the first snow of the year. This idea is a reminder that each moment is precious. It tells us to wake up and really live, not just watch time go by. To embrace the longer days and make the most of it. If that sounds like something you’re up for, why don’t you join is in what we’re calling the Daily Stoic Spring Forward Challenge? The Daily Stoic Spring Forward Challenge is set up to push you to examine those parts of your life, to examine your choices, to examine your relationships and move you closer to living your best life. Participants will receive:✓ 10 Custom Challenges Delivered Daily (Over 15,000 words of all-new original content)✓ One live Q&A session✓ Printable 10-Day Calendar With custom daily illustrations to track progress✓ Access to a Private Community Platform-On this episode of the Daily Stoic Podcast, Ryan delivered an impactful talk on "Ego is the Enemy" to a captivated audience of 600 real estate agents, aged between 30 and 60 years old, at Omni Barton Creek. This talk focuses on finding one's process and the importance of mentors. Holiday inspired the attendees to navigate their professional journeys with humility and self-awareness. The talk delved into Holiday's own experiences, emphasizing the value of continuous learning and the influence of some of his favorite books. Additionally, Holiday shared insights on overcoming challenges such as writer's block and providing practical strategies to maintain creativity and productivity.💪 Challenge yourself to spring forward to be the person you know you can be. Head over to https://dailystoic.com/spring 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.

• 0:05Ryan 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.

• 0:50Ryan Holiday?

  As winter fades and spring emerges, as we adjust our clocks for daylight savings, it's a good time to pause and reflect. Where did that time go? It seems like only yesterday that we were bundled up against the cold, watching the last leaves fall from the trees. Now the days are getting longer and the air feels warmer. We talked recently about Philip Larkin's beautiful poem about the changing of the seasons, how their circular renewal contains within them a kind of finality. The winter you just had is over forever. Those cold winter afternoons where you didn't want to go outside, where you didn't do anything, where instead you waited for the temperature to go up, a break in the snow, you weren't just killing time, that time was killing you. Seneca reminded himself that death is

• 1:33Ryan Holiday?

  not this thing in the future, but something that is happening now. It's always happening. It is the ticking hand of the clock. It is the spring flowers. It's the fall harvest. It is the summer rains. It is the first snow of the year. This idea is a reminder that each moment is precious. It tells us to wake up and really live, not just watch the time go by, to embrace the longer days and make the most of it. And if that's speaking to you, if you're feeling like that's something you want to do, well, I would love to have you join us in the Daily Stoic Spring Forward Challenge. This time of the year, we're supposed to be thinking about spring cleaning, but how many of us get our whole houses in order? Not just our physical spaces, but our minds, our routines, our assumptions. Think about how you spent the last week. How many of those

• 2:18Ryan Holiday?

  days were as efficient and productive as they could be? Where did you waste time? Where did you make things more complicated than necessary? Where have you fallen back on old habits? Where are you, like so many people, still stuck in the doldrums of winter? Well, the Daily Stoic Spring Forward Challenge, which we've been doing for many years now, is set to push you to examine those parts of your life, to examine your choices, to examine your relationships, and move you forward to living your best life to help you seize this new season that is upon us. We'd love to have you join us. It's gonna be 10 challenges, delivered every single day. It's not a long challenge, it's a short, to-the-point challenge that packs some punch. There's gonna be a Q and A session with me. It's gonna be a 10-day calendar to track your practice. It's gonna be access to a private community where you

• 3:00Ryan Holiday?

  can check in with other fellow Stoics. We should remember what Marcus really said, that, "Look, we could be good today, but instead, we choose tomorrow." So it's up to you whether you're gonna let those New Year's resolutions dissolve into missed opportunities, or whether you're gonna keep doing those things that you've always done. Or, or, you're gonna give yourself a 10-day sprint of improvement and some runway for true, sustainable change. Challenge yourself to be the person that can spring forward this year. Spring forward to be that person. And you can head over right now to dailystoic.com/spring and join us. By the way, if you're thinking about joining Daily Stoic Life, now's a really good time, because if you do that, you get this challenge and all the challenges that we do here over at Daily Stoic for free. We've got some other great ones coming up,

• 3:45Ryan Holiday?

  plus you get a bunch of other bonuses and really cool stuff. I'd love to see you. dailystoic.com/spring or dailystoiclife.com.

• 3:59Ryan Holiday?

  Hey, it's Ryan. Welcome to another Thursday episode of the Daily Stoic Podcast. My dad was a real estate agent growing up. I dabbled in real estate a bit myself. One of the perks of moving to Texas, moving to Austin 10-plus years ago when I moved here was this place that I knew was growing fast. And so anyways, this is really nothing to do with today's episode, except I've had the privilege of talking to a number of real estate agents, mortgage companies, all different types of groups over the years. A couple of months back, I was at the Omni Barton Creek and talking to this group called The Agency. They're a global forum of real estate agents. And they specifically wanted to talk about ego

• 4:45Ryan Holiday?

  and how that pertains to what they do and how Stoicism could connect with what they do. As it happens, I mentioned this in the talk, which I may run at some point. But there's a great passage in one of the early Stoics, his name is Antipater. And he's talking about when you're selling a piece of real estate, what obligations do you have as far as disclosures go? If you're selling it because you hate it, it's making you miserable, there's a problem with the pipes in the bottom of the building, do you have to disclose that? Right? And there were less regulations then, less laws, you know, you didn't have to get title insurance, all these things back then. But he was talking about what are we ethically obligated to do? And so I think these are all timeless things. And yeah, maybe you think, what does Stoicism and real estate have to do with each other? Well, the point is, 2,000 years ago, the Stoics

• 5:29Ryan Holiday?

  were connecting those two things. That's not exactly what I get into in the Q and A. They asked me the questions about mentors and process, talked to me about books and writer's block, a bunch of other questions. I think you'll like this quick Q and A. Thanks to the Agency Group for having me out. And I hope you enjoy this episode.

• 6:01Ryan Holiday?

  The one I'm doing now, so I'm doing this series on the cardinal virtues, courage, discipline, justice, and wisdom. I'm in the middle of the third one, just about justice, doing the right thing, ethics, keeping your word. And so it's still, it's still an ongoing process. So that's probably the one that's taken me the longest. You get lost in them while you're doing them and then they come out and then it's all, it's all an unrecognizable blur, to be honest. Hi.

• 6:32Speaker 02

  Hi. So you talked about the process that you, you came from the corporate world and then you actually spent some time with, with somebody who coached you, your coach or your CEO.

• 6:44Ryan Holiday?

  Yeah.

• 6:45Speaker 02

  Your board is what I always call it. What was that process like to really find the person that you can connect with and understand that is somebody who's going to actually give you the hard talk when they need to give you the hard talk and the person who's going to actually push you off the ledge when they need to because you're, you know, you don't want to move forward?

• 7:03Ryan Holiday?

  I'll tell you a funny story about Robert Greene because sometimes you need to have one of those people that pushes you off the ledge when it's time and sometimes they gotta pull you back off the ledge. So I very much wanted to be a writer. So I sought out and looked who's, who's doing the kinds of books that I want to do, who's writing the kinds of things that I want to write. And Robert Greene is probably one of the greatest of all time. I call him the goat. He's just the greatest. And so I was his research assistant for many years. About halfway through my time with him, I got an offer, I got my first offer to do a book. I was maybe 23 or 24, it was way, no, 22. I was, it was much earlier than I thought it was going to be.

• 7:47Ryan Holiday?

  And so I went to Robert, I said, Kane, you know, I got the offer. What do you think? And he was like, you gotta turn it down. And I was like, what? You know, this is what I wanted. And, and basically he was saying, look, first off, it's not a good offer. Second, he's like, I just don't think you're ready. He's like, every day you're getting Better and you I he's like, I know you think you've been at this a long time, but you're actually just getting started and in a few years you'll be much better equipped. The book will be better. And he's like, I know it doesn't seem like it, but he's like, there'll be better offers in the future too. And that was a terrifying thing to do. That was felt like it was going against every, you know, bone in my body, but he was completely right.

• 8:30Ryan Holiday?

  And he had an ability to see where I was on a path because he himself had been on that path. And I was obviously there for the first time. And so one of the reasons you have to have mentors, advisors, a board of directors, as you're saying, is for the exact reason the board of directors exists. A board of directors is supposed to be made up of a diversity of perspectives, experiences, voices, ideally older, wiser people who are not as entrenched in the day to day of what you do. So they can see threats on the horizon. They can see common mistakes. They can advise the senior leadership, you know,

• 9:10Ryan Holiday?

  how to make better, less egotistical, less emotional decisions. And, and Robert helped me do that. He helped me make the decision to not jump on that opportunity. And then a few years later, when I left my corporate job, I was the director of marketing in American Apparel, and moved across the country and had this crazy book idea that I had, and then my other subsequent books, which

• 9:35Ryan Holiday?

  to go from marketing books to books about an obscure school of ancient philosophy, that was another, you know, leap. He was, he, he helped me make those leaps also. So you, you really want to cultivate people who, who are, who are truly rooting for you and truly understand you, not just telling you what you want to hear. And I wish I had, I was like, these are the five criteria, or this is the directory where you find those people. It's tough, but, but you gotta look for them. And when you find them, you gotta hold on tight to them because it's a very, very special thing.

• 10:11Speaker 03

  I have, I have a question. What do you do if you hit writer's block? I guess I ask that because it can be applicable to life in general. There's a fine line between being humble and losing some confidence.

• 10:27Ryan Holiday?

  So what is the question about writer's block? And so here's what I do when I feel like I have writer's block. I remind myself that writer's block doesn't exist. And what I'm actually dealing with is a deficiency of preparation. And so what I do is I go do more research or more thinking and then I come back to it. Right? If, if, if my understanding is that writing is expressing the ideas and I don't have the ideas to express, that's a, instead of sitting there and hoping it magically happens, I try to go further upstream, right?

• 11:09Ryan Holiday?

  I try to go, you know, do the research that I need to, to generate the material. So I, I find that when writing is going well, it's, it's because I have a surplus. I have all these things that I want to say and all these things that I'm excited about. I need to communicate that I've gathered up and, and it takes a while to accumulate those things. So I, I try to go backwards. Now, there is that sense of imposter syndrome. Sometimes it's there. I get that. I have, I have a little note card next to my desk. It's a, it's a quote from the, the choreographer Martha Graham. She says, um, "Never be frightened of material. The material knows when you are afraid and it does not help."

• 11:52Ryan Holiday?

  And the point is like that imposter syndrome, that fear that you don't have what it takes. You're not good enough, you know, that it's too hard of a thing you signed up for. That may be true, but sitting there worried about it, letting it know that you're afraid of it is only going to make it harder. So I try to push that out and go, okay, well, what's a concrete, a constructive thing I can do here? I can go read more. I can go interview more. I can study more. I can prepare more and that, that'll put me in a position to succeed when I'm actually typing up words. Look, I think he's asking, do I have this passion for the sort of figures I'm researching

• 12:35Ryan Holiday?

  in ancient history, whether it's philosophers or military figures or whatever? Yeah, I feel like there is this enormous amount of experience and lessons and accumulated wisdom in the past. And the idea that you're just gonna bump along and try to figure things out by yourself as you go is to do it the hard way. And so I love studying biographies, life stories, memoirs, cautionary tales. I just love to read and learn about how people who are not that different from us went through things not that different than what we're going through. And then I try to, obviously, I try to incorporate that into my writing,

• 13:16Ryan Holiday?

  but I'm also incorporating it into my life. It's helping me understand crazy, scary things that are happening in the world. It's helping me understand why people do the things that they do. I want to understand what it means to be a person, why people, societies, cultures, countries, economies do the things that they do. And those answers are there if we avail ourselves of them. So yeah, it's just what I love to read. Obviously, there's all sorts of books that are great, but I have a bias for stuff that's really old. And I find that it's the most informative, it's the calmest, it's the least political and partisan, and it gives me ironically the most clarity about the present moment.

• 14:00Speaker 04

  I was actually just gonna ask you a few of your favorite books that have profoundly affected you.

• 14:05Ryan Holiday?

  Can you give me topics? I have so many.

• 14:07Speaker 04

  I know, that's a deep, deep reservoir. I guess a few that have maybe really changed the way you see the world.

• 14:16Ryan Holiday?

  Sure. I mean, Marcus Aurelius's Meditations is an incredible book that I recommend to everyone because there's really no book like it. You have the most powerful person in the world writing, not even as I write, which is for an audience. He's writing to himself about what he's struggling with. And that makes such a...

• 14:40Ryan Holiday?

  For such a unique perspective on on light, right? And so I just love that book. I recommend it all the time. And and I think it's just great. I'd recommend Cal Newport's book, Deep Work, about sort of focus. You know, how we talked about stillness here? How do you sort of lock in to what's in front of you? How do you tune out social media? I think Deep Work's a great book. And then there's a book I try to read every day by by Tolstoy called A Calendar of Wisdom. And it's one page a day of sort of like quotes that that this great, you know, wise novelist accumulated over the course of his life. And I try to read a page of that every day.

• 15:23Ryan Holiday?

  And then one of my other favorites is is Steven Pressfield's The War of Art, which I think is important, whether you're an artist or not. But but that's a book I try to read on a regular basis as well. So those are maybe four quick ones.

• 15:39Speaker 05

  What would be the takeaways from your time at American Apparel of what not to do? Like, how did they get so big and then just fuck that up?

• 15:47Ryan Holiday?

  Yeah. A CEO should not have physical relationships with their employees. That's that's not OK. It's also illegal. And, you know, was at the at the root of so much of what ultimately went wrong there. But, look, actually, the the bigger cautionary tale of American Apparel is, I think, a very relatable one. So the idea of that company is insane in many ways, right? He's like, I'm going to manufacture clothes in America. I'm not going to use sweatshops. I'm going to pay fair wages. I'm going to not use professional models. I'm going to design my own clothes. I'm going to own my own stores. I'm going to he's going to do all this stuff that everyone said it's never going to work,

• 16:32Ryan Holiday?

  which were all the reasons that it did work, right? It worked in violation of all the conventional wisdom of fashion, retail.

• 16:41Ryan Holiday?

  The current expertise, right? Like all ideas do, pretty much everything that has ever worked, most people said that's not going to work, right? That's what being an entrepreneur is. If everyone thought it would work, they would have done it already. So as an entrepreneur, it's this very dangerous, tricky thing where you become successful by not listening to critics, feedback, doubt, warnings, et cetera. And then now you have that success. And to maintain it and to continue to be successful, you have to become a person who can collaborate, who can listen, can hear, who has to follow standard and best business practices, all of that.

• 17:25Ryan Holiday?

  So Dove does fatal flaw in a lot of ways was that the maverick who ignored all this stuff is also the maverick who's ignoring, you know, Wall Street's advice to hire a competent CFO or to, you know, not do things that are illegal. And, you know, to not over, you know, to not open 80 stores in the middle of the financial crisis. Or, you know, they're saying not to do things, not because they're haters or they're small minded, but that there are established best practices that you have to follow. And so by ignoring all of that wisdom, by thinking he was special, it was different, you know, the rules don't apply. You know, he was, he was hurtling towards a cliff, which he eventually ran right off.

• 18:09Ryan Holiday?

  And so that is, that is something that I think we all have to be worried about. You have to have that maverick streak in you. It also can't calcify into ego and entitlement and, you know, a sense that the rules don't apply to you.

• 18:41Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.