Ryan Holiday (@ryanholiday) is the bestselling author of Trust Me, I’m Lying; The Obstacle Is the Way; Ego Is the Enemy; Conspiracy, and other books about marketing, culture, and the human condition. His latest offering is Stillness Is the Key.

What We Discuss with Ryan Holiday:

  • How successful people learn to process feedback — and consider its source in order to improve and move forward.
  • Why self-awareness is the secret weapon of some of the highest-performing people you’ll meet.
  • What can keep us striving and moving upward in a world where it’s way too easy to compare ourselves to one another and beat ourselves up in the process.
  • How Ryan found the purpose and motivation to write eight books and ghost write another six by the time he was 30.
  • The eerie, intuitive, borderline magical superpowers of Mr. Rogers, Cesar Millan, and the two daycare miracle workers who can put 15 toddlers down for a nap (including Ryan’s son) simultaneously every day.
  • And much more…

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Stillness Is the Key by Ryan HolidayIf you’ve listened to this show for more than a minute, you’ve certainly heard of today’s guest, author Ryan Holiday. Not only has he been a guest on the show before, but he’s been referenced by multiple guests, and he was even mentored by the one and only Robert Greene. He wrote eight books and ghost wrote another six by the time he was 30, and shows no signs of slowing down. He’s been cranking out bestsellers for years like a machine, with titles like Trust Me, I’m Lying, The Obstacle Is the Way, Ego Is the Enemy, and Conspiracy.

On this episode, Ryan returns to the show to touch upon his latest book, Stillness Is the Key, but we tried to have a conversation that was a little more free-form and casual than he usually gets to have when he’s making the podcast rounds on a book tour at the behest of his publishers. Listen, learn, and enjoy!

Please Scroll down for Video, Featured Resources, and Transcript!

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Transcript for Ryan Holiday | Stillness Is the Key (Episode 271)

Jordan Harbinger: [00:00:03] Welcome to the show. I’m Jordan Harbinger. As always, I’m here with producer Jason DeFillippo. On The Jordan Harbinger Show, we decode the stories, secrets, and skills of the world’s most brilliant and interesting people and turn their wisdom into practical advice that you can use to impact your own life and those around you.

[00:00:20] We will help you see the Matrix when it comes to how these amazing people think and behave because I want you to become a better thinker. Today, Ryan Holiday, he and I have been friends for years. And if you listen to a lot of different podcasts, he’s certainly made the rounds recently. I wanted to have a different sort of conversation with him instead of the same stoicism that everyone else has been drilling into lately — not that there’s anything wrong with that; I just think there’s more room for some other topics here and if you agree, then listen on. It’s just what we did today on the show.

[00:00:46] Today, you’ll hear us discuss how successful people learn to process feedback, who and what to listen to in order to improve and move forward. We will also uncover why self-awareness is a secret weapon of some of the highest performing people you’ll meet and what can keep us striving and moving upward in a world where it’s way too easy to compare ourselves to one another and beat ourselves up in the process. Again, this is a much more free form and offbeat conversation with Ryan, and I think that’s refreshing these days, especially since he’s been hammering away on his book tour. He’s a really smart guy. I’m so grateful we got this amount of time with him here in the studio, and I’m looking forward to hearing what you all think of this one.

[00:01:23] If you want to know how I managed to get all of these great folks in my circle, well, I use systems and tiny habits and I do it very consistently and it’s just a few minutes a day. I’m teaching you how to do that for free. Check out Six-Minute Networking. That’s over at jordanharbinger.com/course. And by the way, most of the guests on the show, they subscribe to the course and the newsletter, so come join us and you’ll be in great company. All right, here’s Ryan Holiday.

[00:01:49] I do this to myself all the freaking time. I don’t compare myself to somebody who started when I do. I compare myself either to somebody who started 20 years before me or I compare myself to somebody who started a year ago but has somehow managed to get the spotlight for two seconds and I go, “Oh, my god, my life is over! This person got featured on something and now what? Why even try?”

Ryan Holiday: [00:02:10] Or you go like, “Oh, man, this person is getting this thing,” and you’re like, “But I’ve also gotten that thing. Why can’t they also get it?” Do you know what I mean? You not only want things that you don’t have or you’re jealous of, but you’re also just territorial about it, and it’s not like a zero-sum game. I have to think about this with authors all the time. Like so-and-so’s book blowing up and selling millions of copies, and not only doesn’t hurt me, but a bunch of those people probably weren’t readers before and now maybe they are readers and now —

Jordan Harbinger: [00:02:43] “Wow, I bought this book and it was great. Other people who have also bought that recommend this Ryan Holiday book. Maybe I should get that.” Nobody’s like, “I already have a book, so I don’t need anymore.”

Ryan Holiday: [00:02:55] If they do, they’re probably not — you’re right, they’re not our great customers.

Jordan Harbinger: [00:02:59] Yeah, the person who listens or only watches one YouTube video a month, probably not exactly.

Ryan Holiday: [00:03:04] “I’ve listened to a podcast.” That’s not who you’re after.

Jordan Harbinger: [00:03:07] No. As long as they only listen to mine, fine! That’s the thing I’ll go like, “Oh, what other shows do you listen to?” And if they have 10, I’m like, “Screw this person. You’re not a real fan. You’re spreading your time out among other people who also create good work! How dare you?” It makes no sense. It’s a very illogical, Internet-based —

Ryan Holiday: [00:03:25] Yeah, right. It’s like, look, if you’re Coke and they’re Pepsi, that makes sense. Although even those, they’re totally interchangeable and nobody cares. You forget that actually you’re really in a race against people not listening to podcasts at all or not buying books at all. It’s not like, “Oh, they buy James Clear’s books, so they’re not going to buy mine.” That’s not what’s happening at all.

Jordan Harbinger: [00:03:47] They’re going to buy all of them and then they’re not going to read any of them, and you’re still going to get a royalty! What’s that stat, that like 83 plus percent of books that get purchased don’t get read or something like that? Or it’s a huge majority.

Ryan Holiday: [00:03:58] Well, sometimes people go like, “It must be so weird being famous,” and it’s like, okay, there’s famous and then there’s being an author. Even if you sold lots of books, people don’t know what your name is. Even if you sold lots of books, how people bother to read them? How many people have looked at the name on the cover? How many people flipped all the way to the back and looked at the photo? It’s like five percent. It is not a problem.

Jordan Harbinger: [00:04:22] At your level it’s got to be name recognition, right? Where people go, “Ryan Holiday! Oh, I think I’ve read one of your books.” That must happen at some point.

Ryan Holiday: [00:04:28] It does. Yeah, every once in a while. I mean, certainly when you start, the worst part is they go, like, “Oh, what do you do?” And you go like, “I’m an author.” And then they go, “Would I have read any of your books?” And I say, “No.”

Jordan Harbinger: [00:04:39] “No, you wouldn’t have, unless you have good taste.”

Ryan Holiday: [00:04:41] Now you’re humiliated, because the joke is like, “Oh, tell me one thing you’ve done in your life that I’ve heard of.” Like, “Have I heard of any of the insurance policies that you’ve sold?” The answer is no. But if you have a public-facing field —

Jordan Harbinger: [00:04:55] That’s true. People think if you’re in any sort of public-facing field, you’re automatically measured by your notoriety.

Ryan Holiday: [00:05:02] Yes, by your name recognition amongst total strangers. Not by how successful are you in your niche.

Jordan Harbinger: [00:05:10] Yeah. Good point. I didn’t think about that because, of course, would you have read any of the books? I don’t know. Do you read books that are for smart people? It’s not my fault if you don’t; I’m not less because you haven’t seen my book.

Ryan Holiday: [00:05:21] I mean, the other day someone recommended this book to me and I never heard of it and I pulled it up on Amazon. It had 16,000 reviews. That’s like 10 million copies. I’d never even heard of this person. It’s not that he’s not successful. It’s that I’m not clued in. So, yeah, you end up using these metrics that maybe would make sense when there used to be 10 people making a living writing books, but it’s like, that’s not how it is anymore.

Jordan Harbinger: [00:05:50] It’s like TV. Everyone watched Larry King and people wrote, “Oh, during Larry King Live, this news event happened.” Now, no one’s like, “During the time that Ryan Holiday and Jordan Harbinger did a Facebook Live, this thing happened.” No one would realistically ever care about that. You’ve done a lot of things that a lot of people are maybe envious of, or jealous of, or want to do, or say they want to do but never actually wanted to do. One of which is figure out maybe what you wanted to do for a living early.

Ryan Holiday: [00:06:17] I guess, yeah. That is an interesting thing to go to the point about comparing yourself against other people. People are like, “I’m 28. I want to be an author,” or, like, “My book came out; it didn’t do well.” When I was 28, I had nine years of experience. You have to compare yourself against people who are in your peer group and your age bracket for the amount of years you’ve been doing it or reps you have, because that’s the only measurement that really counts. The fact that I figured out that I kind of wanted to be a writer and then I started researching for a writer before I turned 20-ish, it wasn’t like a little advantage. It was an exponentially large advantage, and every year those returns are compounding. It’s like you start saving for retirement early until you get to that magical point where the graph starts to go like that. It is important but it’s not the age that you started at that’s important. It’s the time that’s elapsed since that point. It has no magical part that I was 20 when I started. It’s the eight years or now, it’s 12 years, that’s the point. You start when you’re 30, you’ll just hit that inflection point in your 40s.

Jordan Harbinger: [00:07:28] Yeah. That’s true. I started I wasn’t really thinking about radio or interviewing or anything and then I started the show when I was 26. But then I didn’t really think, “I’m interviewing people”; I was screwing around and then I interviewed Robert Greene seven years in and he’s like, “Hey, you’re really good at interviewing.” And I was like, “Well if he thinks I’m good at it then maybe I should take it more seriously.” Then I started to do that and it still took me four years after that to be like, “Oh, this is how professionals prepare for an interview. They actually read the book.”

Ryan Holiday: [00:07:56] I think there is a moment where — let’s say the 10,000-hour theory — I know there’s like —

Jordan Harbinger: [00:08:01] Back and forth.

Ryan Holiday: [00:08:02] Back and forth. But the general idea that it takes a lot of hours to become really good at something, I think that’s pretty indisputable. For me, I put up my first blog the day I graduated from high school, so let’s say it’s 2005. Let’s say I really didn’t get super serious about it until 2006. And then my first book deal happened. I started writing my first book in 2011. That’s six-ish years.

Jordan Harbinger: [00:08:26] Which is actually a really long time when you’re in your 20s.

Ryan Holiday: [00:08:29] Oh, yeah. Of course.

Jordan Harbinger: [00:08:30] Now I’m in my late 30s. So, I’m like, “Oh, I’ve known Jen, wow, I’ve known her for seven years. That’s a pretty long time.” But when you’re in your 20s, you haven’t even been a functional adult for more than five or six years.

Ryan Holiday: [00:08:39] Well, kids do that to you, too, because my son is now three and so now I think about what my other son will be like in three years. Just the idea that I can think in a three-year chunk was not a chunk of time I could comprehend before. I did those six years; I didn’t really know I was doing six years. In retrospect, it’s obvious I was paying six years of dues, but I also just thought I was writing. I was having some success, not success. I was seeing the audience tick up every day. Let’s say there’s those six years, then the book came out, and you start getting sort of rewards and recognition. I don’t know the exact conversation I had with someone but at some point, I decided I was consciously going to be putting in those hours. I’m really, in the way a comedian thinks about getting stage time. That’s less clear for other professions, but there was at some point where I was just like, “I’m going to get really good at this.” It’s really from 2012 to 2019, those seven years I probably — let’s say it was another six years — I think I got double or triple the amount of time and the amount of ROI from the time because I was really consciously deciding to get better. In not only writing my own books, but also ghostwriting. I was ghostwriting because, one, it would give me some financial freedom to write my own things but also, I just wanted to get really good at the craft. Now there’s really nothing you could put in front of me that I would — I mean, there are things that would be hard and challenging, but there’s nothing I think you could put in front of me writing-wise that I’d be like, “I’m not sure I could do that.” There are things that I wouldn’t want to do or I wouldn’t do, but I think I could write just about anything.

Jordan Harbinger: That’s a big statement. That would be like me saying, “I could interview anyone!” I’m like, wow, I don’t know.

Ryan Holiday: [00:10:29] But I bet you could.

Jordan Harbinger: [00:10:310] Probably — I would have, yeah, it’s sort of terrifying to think about doing that, but yeah, I could.

Ryan Holiday: [00:10:35] I bet when you first started, if I was was like, “Okay, you can introduce the president.” You’d probably be like, “I could do that.” And of course, you would do it.

Jordan Harbinger: [00:10:42] I would figure it out, yeah.

Ryan Holiday: [00:10:43] But you would be bad at it. You would listen to the tape and go like, “I can’t believe I blew this opportunity.” Then there’s probably a period where you would have maybe thought you weren’t ready for it. Now you would do it and you would be successful at it, is sort of what I mean.

Jordan Harbinger: [00:10:55] It’s funny to look at my — do you ever look at old work that you’ve done and go, “Oh, man, what the hell?”

Ryan Holiday: [00:11:02] Yeah, of course. I’ve had the weird privilege — I wrote my first book in 2011 on my own. I didn’t sell it. I just wrote it, and then I sold it. And then so I worked with an editor to reshape it. It came out in 2012. Then in 2013, I did an updated, revised, paperback edition, in which I changed some stuff. Then in 2016 after the collapse of Gawker and after the Trump election, I did a third edition of the book. So I’ve had this weird, unique experience of basically rewriting that book four times. And each time is a horrendous experience because it’s mortifyingly embarrassing. I published this!

Jordan Harbinger: [00:11:43] I worry about that.

Ryan Holiday: [00:11:45] And what I learned from the experience is: It’s not that it’s bad, because it’s not. And it’s not that I’m wrong, because I’m usually not. There are definitely errors in it, but what is the most off-putting and I find the least excusable is the certainty with which I was saying whatever I was saying. So it was like I might have been right, but I had not done the work to be right.

Jordan Harbinger: [00:12:09] I have no basis for this other than confidence.

Ryan Holiday: [00:12:12] Yes! Or ego, really. Or I was right, but my logic was shoddy or the example I was using was a weak one. It’s good, but most of all I’m missing a lot of nuance and empathy and even-handedness. And so that’s one of the things I try to work on now is I just try to be way less certain of everything.

Jordan Harbinger: [00:12:38] That makes sense. That’s great. In the interview, I’ve gotten more compassionate, whereas before I’d be like, “I’ve got to be challenging, because I’ve got to show — I’ve got to demonstrate authority. Now I don’t have to do that because I’ve realized it’s my show. I kind of already have some authority.

Ryan Holiday: [00:12:55] You’re like, “Why would I do gotchas? Why do I need to push back?” I think, to me, and I talk about this a little bit the new book, I feel like what that is, is that’s what confidence actually looks like. The insecurity is the need to overreach — to overstate — to assert yourself. And the confidence is like, people who will get it will get it. There’s an element of trying too hard that you don’t need to do once you’re confident.

Jordan Harbinger: [00:13:23] Yeah, that’s true. That’s true. And it’s a non-neediness that actually works really well, but I think it’s really hard to fake.

Ryan Holiday: [00:13:29] I think readers, listeners, viewers, or whatever, they can taste it.

Jordan Harbinger: [00:13:32] Yeah. I think so too. I get a lot of email from older listeners that are like, “Hey, you went too hard on this person,” or, “You need to do more about that.” And they’re usually right. And the reason they’re right is because they’re parents and they have kids that are my age or slightly younger and they’re like, “I recognize this. This is me 30 years ago,” or, “This is my kid who’s 17; you’re better than that,” you know, “Stop doing that.”

Ryan Holiday: [00:13:54] I’ll get emails and the person will just be totally wrong about something. They’ll be like, “Why’d you say this? You should have said this,” and I’m feeling I’m more confident when I can just not respond. “Cool.” It’s okay, but there’s the younger part of me that has to make sure to let this person know that they’re wrong. I think the less you have of that, the better decisions you make and the less trouble you get yourself into.

Jordan Harbinger: [00:14:22] Yeah. I mean, how do we get there, though? That’s the question. Because for me it’s just been getting older and getting tired of doing that, I think. Playing it out in my head and going, “So I got that person, then they came back and they were mad, and then I was like, ‘Oh you’re just mad because I’m right and you know it,'” and then they now hate me, so I got nothing from that interaction — you have to do that over and over.

Ryan Holiday: [00:14:42] Right, you send the email and then they’re never like, “Yes, sir.”

Jordan Harbinger: [00:14:45] “You’re right. You’re right. I’m wrong. You’re right. I like you more now —”

Ryan Holiday: [00:14:49] I don’t need to get into this giant tar pit.

Jordan Harbinger: [00:15:53] The reason I brought this up, I was looking at some of my old prep. You’ve been on the show, I don’t know, five or six times in the past 10 years. And I was like, “Oh, I’ll see if there’s anything that I didn’t ask last time that we just didn’t have time for that is still interesting.” And I was just like, “Who made this? They’re fired, whoever made this —”

Ryan Holiday: [00:15:09] Of your notes?

Jordan Harbinger: [00:15:10] My notes. I was like, “These are terrible. What was I thinking? They’re organized so poorly.” My questions that I wrote underneath the phrases from the book are just dumb. They’re not good.

Ryan Holiday: [00:15:21] Interesting.

Jordan Harbinger: [00:15:22] And I look at people who release best of shows. You ever see a podcast and it’s like, replay/best of?

Ryan Holiday: [00:15:27] Yeah.

Jordan Harbinger: [00:15:28] I don’t have that best of, that’s not — old stuff? That stuff is not good, in my opinion. It’s not as good. It’s certainly not best of.

Ryan Holiday: [00:15:36] So you’re that hard on yourself? You can’t — you couldn’t see a best of?

Jordan Harbinger: [00:15:41] I can and I’m looking — here’s what’s funny. On Saturday, I have a four-hour session planned where I’m going to re-listen to a bunch of old episodes. Some of them might get re-aired, things I did with Shaquille O’Neal and things like that. And what I’m worried about is going. “Oh man, none of these are good enough.” But I have to be kind of careful because I’ll say that about something I did a month ago, just because I’m hard on myself.

Ryan Holiday: [00:16:06] I’ve had to do that with my talks. For the first four or five years that I gave talks, I didn’t want them filmed. And if they were filmed, I would never look at them. Probably because I saw one and it was really bad, and so I told myself, “If I just pretend that it doesn’t exist, I’ll be better.” Now, I’m actually much more okay with it. I almost want it to be filmed. I’m comfortable seeing myself on camera and I want to actively think about how I can get better at it. Whereas before I wasn’t getting better because I refused to think about that I was not good. I saw this interesting — Pete Carroll, the coach of the Seahawks, who’s talking about coaches love to break down film of players and he’s like, “Do coaches ever watch film of themselves?” And so he did that one year. He did a clip of each of the coaches throughout the year and he was like, “It totally changed how they coach. It’s like I’m screaming at this person. I’m not being who I want to be or what I thought I was being in that moment,” but it’s always easier to stick your head in the sand about it.

Jordan Harbinger: [00:17:13] Yeah, that’s true. There’s a lot of that.

Ryan Holiday: [00:17:15] I guess part of it comes from a good place. Do you really want to be a person who wants to listen to hours and hours of yourself talk? It’d be weird if you’re really into it.

Jordan Harbinger: [00:17:24] That’s true.

Ryan Holiday: [00:17:25] But you have to be able to do it because you want to get better.

Jordan Harbinger: [00:17:28] That’s true. I hear about guys like Dave Letterman. Something about him going home every night watching tape of the show, shredding himself, beating yourself up, being absolutely horrible to himself. And wasn’t that show on five nights a week?

Ryan Holiday: [00:17:43] Yeah.

Jordan Harbinger: [00:17:45] I mean doing that to yourself —

Ryan Holiday: [00:17:46] It can’t be healthy.

Jordan Harbinger: [00:17:47] It can’t be healthy.

Ryan Holiday: [00:17:49] So it’s both. I think it’s a balance. You can’t just assume that you’re just constantly spitting fire, but you also can’t be treating yourself like a piece of shit.

Jordan Harbinger: [00:18:01] It’s tough because you see successful people treating themselves really poorly all the time and it’s easy to go, “That’s obviously why they’re so good at what they do.”

Ryan Holiday: [00:18:09] Yeah. I mean I talk about this a little bit in the book. You look at someone like Michael Jordan. He was clearly a collector of slights and grudges and resentment and totally manufactured feuds as a way to fuel himself. We kind of know where that comes from. There’s this moment when he says he was cut from his high school basketball team, but really he just didn’t make the varsity basketball team as a freshman or sophomore, which is not supposed to happen. It’s like, “I didn’t get kicked out of Harvard. I didn’t get accepted to Harvard.” That’s not how it works. You can’t just make that up, but he comes back the next year and he makes the team and obviously, he leaves this guy in the dust, but it’s like he tells himself it’s because he stewed on it and he shoved it in the coach’s — he also grew seven inches in the off-season! That’s a sample size of one, and he used it to direct the whole course of his life. It might have nothing to do with it — we can take these singular interactions. It’s like somebody cheats on you and you’re like, “Women lie.” That woman lied —

Jordan Harbinger: [00:19:21] — to you about something, not lied about everything the whole time.

Ryan Holiday: [00:19:25] Meanwhile, you were also lying. Also, she actually tried to tell you the truth and you refused to hear her. Anyways, we take these singular things and then we extrapolate out these like —

Jordan Harbinger: [00:19:35] Massive stories.

Ryan Holiday: [00:19:36] Yeah. And so, I think causation and correlation are definitely not the same thing. The fact that there are great people who break themselves down on film and are horrible — Jimi Hendrix was also a drug addict, and so was Kurt Cobain. Was that healthy or deeply unhealthy?

Jordan Harbinger: [00:19:53] Good point. Yeah. I think it is hard to separate high performers from some of their negative habits. That sounds really obvious because we have, I’m sure, mutual friends where we go, “Wow, he would be so much better if he didn’t shit talk everyone or drink too much.” But people from an external perspective who don’t know them that well might be like, “Oh, you know why Jordan is so good at what he does is because he blows his rails of cocaine every night. So of course he reads 17 books a week! He has all this time. He doesn’t sleep!”

Ryan Holiday: [00:20:26] Right, right. In medicine, there’s this idea of comorbidity. Like depression and addiction, they don’t really cause each other, but they are comorbid — they come along with each other, just like obesity and depression. There are all these things that are comorbid traits. And so I think drive or ambition or talent is often comorbid with a lot of negative things. For instance, the desire to always focus on the next thing — that’s something I have. I got the sales numbers this morning for the new book, but I’m not like, “This is wonderful, let’s have a nice dinner.” I’m not only not reflecting on it, I’m actually busy negotiating the next one. So in some respects, it’s obviously served me very well. That’s why I’m always stacking projects. I know I have a lot of dead time. But that also prevents me from enjoying the thing. And so, for champions — I’m not calling myself one — in sports, it’s that desire to never be happy with what you did even if you broke a world record or won the Super Bowl. Obviously, you can see why that makes them a champion, but it also means that they never feel like a champion.

Jordan Harbinger: [00:21:36] Yeah. I find this, too. Again, we’re far from Kobe Bryant. I don’t have any rings to show for this. Yeah, we got named Best of  2018 by Apple and people were sending me messages and I remember being like, “I wish all these texts would stop breaking my focus because I’m working on something,” and friends of mine were like, “You must feel great,” and I actually felt worse by them saying that because I was like, “Well, I don’t really.” I mean yes, it’s good, but I don’t feel good and it also makes me question where am I going to be in 30 or 40 years. Am I ever going to sit down and enjoy the fact that I’ve achieved stuff, or is it just going to constantly be this way? It’s a little scary actually.

Ryan Holiday: [00:22:13] Yeah, I know. It is scary. It’s certainly a first world problem, but people just don’t really talk about how to cope with that or deal with it. I think one of the downsides of not talking about it is not only do we not solve that problem, but people become convinced. You go, “Oh, the problem wasn’t that I can’t enjoy being named the best. It’s that I was not the most downloaded.” You go like, “I’ll feel better if I get that.” Or you go, “Oh, this Super Bowl is nice but I really want to be in the club of people who have won back-to-back Super Bowls.” Or like Kevin Durant, he won all these rings with The Warriors, but he’s like, “Now I’ve got to win one for myself.” You know what it’s going to feel like when he gets it, if he does? It’s going to feel exactly the same, and he’s going to feel not good — because that’s the curse of being great. I guess what I’m talking about in the book, and what I’m working on myself — and maybe it’s not possible, but I think that it is — is like, can you get to a place where you do really great work and you perform at an elite level, but you do it from a good place? In Buddhism, they say craving is the opposite of stillness. Anything that’s coming from craving is bad. It is not that sex is bad, it’s that the craving is bad — the need.

[00:23:34] The Stoics talk about this, too. They say a wise man can use many things, but he needs none of them. It’s the place of need that’s the delusion, because you’re saying, “If I get this — if this, then that. Can I write a great book and can I continue to write great books, and can I have a career where I perform at an elite level, where I’m doing it not to prove anyone wrong, not because I’ll be happy if I get it, not because I want to have this amount of money, or I need this amount of Instagram followers? Can I just actually be in it and do it and come from there, not from that darker place?

Jordan Harbinger: [00:24:21] How do you make that shift? It’s not like I don’t know that if this happens — I’m saying if this, then that, “Hey, look if I get a hundred thousand more listeners over the course of the year, it’s going to be great. Our revenue’s going to grow like this.” I’m doing if this, then that, but I’ve already played this game before. I’ve been doing this for 13 years. Every year it’s a different goal, and every year I feel the same way. I’m happy looking back, but I’m not satisfied, ever. Is there a way where you then go, “You know what? This is unhealthy?” Clearly banging my head against the wall, the craving is still there, that part still unhealthy. Or is this just another if this, then that? “Well, if I can get this craving to stop, then I’ll be healthy and I’ll be able to enjoy myself.” That’s the exact same thing. Yes, Inception.

Ryan Holiday: [00:25:08] I was talking to Pete Holmes about this. He was talking about how he and his wife sometimes fantasize, like, “What if we could have a farm?” And I was like, “I have a farm. It’s not that great!”

Jordan Harbinger: [00:25:14] It sounds awesome! Do you have a lake or a pond?

Ryan Holiday: [00:26:16] Yeah, it’s great, but it’s not like we’ve got it. I thought it was going to be my dream house, and then the next thing I’m like, “Well, I don’t really like the floors, and I really dislike how it’s laid out.” You’re always going to do that. He was like, “What we’ve slowly realized is this is the farm — where we currently live. That’s whatever the fantasy is.” And that’s actually a mantra I have and I try to say to myself all the time, “This is enough,” or “This is it.” There’s not some other thing. There’s just this. I think presence is kind of the antidote to what we’re talking about, because when you’re thinking like, “Oh, I just need to get a hundred thousand listeners, or if I can just get the revenues up to the seven figures,” for me, I tend to think I have this sort of insecurity. So it’s like contracts, like, “If I could just get this locked up, then I can count on that,” or, “If I can just have this amount of passive income from this, then I won’t feel like I have any financial needs,” and it’s like, that’s not how that works. But just going, “This is it. This is enough.” That’s a kind of a mantra I try to repeat to myself. And the reason I think it works is that doing a great interview with Malcolm Gladwell or trying to write a book or trying to give a talk in front of this audience is hard enough. How arrogant is it to think you can do that while also using five percent or 10 percent or 50 percent of your mind over here to think about how you’re going to get more subscribers?

Jordan Harbinger: [00:26:39] Yeah. It’s a waste.

Ryan Holiday: [00:26:40] Well, it’s not just a waste. It’s just like you’re cheating the performance.

Jordan Harbinger: [00:26:44] Yeah, that’s true.

Ryan Holiday: [00:26:45] You’re not giving a hundred percent to the thing. In a way, because we all do it, it makes what we manage to accomplish more impressive. But how do you manage to hit all these home runs while also fantasizing about the next three years of your career, right? What could you hit — two more home runs with the cumulative amount of mental energy that you wasted thinking of far ahead?

Jason DeFillippo: [00:27:10] You’re listening to The Jordan Harbinger show with our guest, Ryan Holiday. We’ll be right back.

Jordan Harbinger: [00:27:17] This episode is sponsored in part by HostGator.

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Jordan Harbinger: [00:28:32] This episode is also sponsored by Mint Mobile. If you’re still using one of the big wireless providers in 2019. Have you asked yourself what you’re paying for it between expensive retail stores, inflated prices, and hidden fees? Actually, Jason, this is funny. I was talking with Scott Adams today and he has this interesting term that you will love — confusopoly.

Jason DeFillippo: [00:28:51] Nice.

Jordan Harbinger: [00:28:53] I don’t even think he made it up. Basically, mobile phone companies are the poster child for this term. It’s pretty self-explanatory. They make it so damn confusing that you don’t actually know what you’re getting for your money. So, it becomes impossible to compare. It’s like when you log into your cable provider, it’s like you get these channels but not these channels but then sometimes you’ll get this but this is a bonus, but then you get this but only the online version, and it’s like, “What?” But then you can’t log in on your iPad. You can only do it on your phone. It’s just weird. So, it’s a confusopoly. Mint Mobile is like, “Nah, we’re done with that.” They provide the same premium network coverage that you’re used to but at a fraction of the cost, because everything is done online, you know kind of like every freaking other thing in the world these days. They save on retail locations. There’s no overhead for that stuff. They pass the savings onto you as the customer and they make it easy to cut your wireless bill down to just 15 bucks a month. I know what you’re thinking. There’s probably no good data or nothing like that. Not every plan is unlimited nationwide talk and text and you don’t have to pay for unlimited data, you’ll never use you can use 3/8/12 gigs of 4G LTE data. That’s the fast stuff by the way. So, use your own phone with any Mint Mobile plan. You’re just buying a SIM card and the service here. Keep your number, keep your contacts, ditch your old wireless bill and start saving with Mint Mobile. Jason.

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[00:30:26] Thanks for listening and supporting the show and to learn more and get links to all the great discounts you just heard from our amazing sponsors, visit jordanharbinger.com/deals. Don’t forget we have a worksheet for today’s episode so you can make sure you solidify your understanding of the key takeaways from Ryan Holiday. That link is in the show notes at jordanharbinger.com/podcast. If you’d like some tips on how to subscribe to the show just go to jordanharbinger.com/subscribe. Subscribing to the show is absolutely free. It just means that you get all of the latest episodes downloaded automatically to your podcast player, so you don’t miss a single thing. And now back to our show with Ryan Holiday.

Jordan Harbinger: [00:31:04] That distracted feeling is so toxic whenever it happens, if, when it happens during an interview, or whether I’m being interviewed or talking to somebody else like you, I almost taste motor oil when I’m like, oh, God —

Ryan Holiday: [00:31:14] Really?

Jordan Harbinger: [00:31:15] Yeah, it’s not literally, but I just feel the pull, the pull is a great word because I’m over here and I have to beat that worry out. It’s like getting an email from your lawyer right before you have to give a talk and you’re just like, “Crap!”

Ryan Holiday: [00:31:27] “I shouldn’t have checked this.”

Jordan Harbinger: [00:31:28] “I shouldn’t have checked this.”

Ryan Holiday: [00:31:28] Yeah, and we do that mentally. My thing is I don’t check my phone in the morning. I don’t use it as an alarm clock. I don’t sleep in the room, and I try not to check my phone when I’m at home, it’s like a minimum of an hour. Sometimes I’m on the road; I’ve got to know if they change the call time. I don’t check my phone in the morning. I had to use my phone as an alarm clock because I’m staying in a hotel room. Tip: First thing you should do when you get into a hotel room? Unplug the alarm clock. You have no idea what horrible time some idiot set it to.

Jordan Harbinger: [00:31:59] Four o’clock in the morning.

Ryan Holiday: [00:32:01] I’ve had things where it’s like I had four hours of sleep and I could get four hours of sleep and it was actually all ruined because the person before me set the alarm clock. But the point is, I had to use my phone as the alarm clock. So I went to go turn it off, and I saw a bunch of texts from my agent about the sales numbers. I could tell they were good. From the glimpse, I could tell they were good. I wanted to check them. But I knew that’s not the best way to spend the morning. That would derail the morning.

Jordan Harbinger: [00:32:28] For sure.

Ryan Holiday: [00:32:30] Then I’ve got to call these people, I’ve got see what they are, I’ve got to have a conversation about it. My plan before I saw it was to wake up, go for a swim, write in my journal, and then get a little bit of writing done before I have to go do this thing. Why am I going to let good news or bad news get in the way of that? And so that email from your lawyer before you go on stage is to me a great analogy, because it’s like we could be in the right headspace, but then we let other things jump in — either external news, internal news, or whatever, but it’s just not where you should be. So I was like, “Okay. I’m not going to check this. I now am going to work to do this swim and actively not think. Every time it comes up, I’m going to push it away and I’m going to try to get back to whatever this experience would have been without a peek.” It’s like you know there’s a surprise party coming and you’re just going to try to forget that you know. It was work, but you have to be able to push those thoughts away because there are going to be other times with other, more serious things with higher stakes, that if you haven’t worked out that muscle, you’re just going to be like, “I just blew the opportunity of a lifetime because I saw a very unpleasant tweet from a total stranger because I was checking my phone when I shouldn’t be checking my phone and blah blah blah blah blah.”

Jordan Harbinger: [00:33:50] I see that and you’re right. I think a lot of people who I find are overcome with anxiety, not everyone of course, but a lot of these people, they have too much input and they just can’t deal with it all, and they need to not be on their phone or they need to not be checking it because everything causes a fight-or-flight reaction in their life.

Ryan Holiday: [00:34:08] Look. The news, for instance, is not — there’s no money in making you feel like everything’s okay in the world.

Jordan Harbinger: [00:34:14] Yeah, that’s a good point.

Ryan Holiday: [00:34:15] I think people just consume way too much news about everything like financial news, political news, celebrity gossip — why are you consuming this information?

Jordan Harbinger: [00:34:25] Got to be up to date!

Ryan Holiday: [00:34:26] Right. It’s like, what?

Jordan Harbinger: [00:34:28] For what purpose? So that you can impress people at a cocktail party that you’re not invited to?

Ryan Holiday: [00:34:32] Exactly, exactly, and no one ever goes. “Wow, Jordan, you’re so up to date.”

Jordan Harbinger: [00:34:35] No, no.

Ryan Holiday: [00:34:36] You don’t feel like you get there, either and you don’t do anything with this information, and most of the time, consuming the information actually makes you deeply unhappy or distracted. People think, “I follow the news to be informed,” and it’s like, meanwhile how many books could you have read about history or the human experience or wisdom or spirituality or whatever that would have actually made you informed in some sort of lasting way? It’s just you talk to these people you’re like, “Okay, so, you know about the ins and outs of this investigation. But you actually have no idea how our system of government works and you tell yourself you’re informed, but you’re not informed, you just know some trivia,” and then meanwhile, there’s this other person who hasn’t turned on the news for 10 years and they could tell you exactly how this event is going to go, because they know how history works.

Jordan Harbinger: [00:35:25] I assumed maybe you’re referring to this impeachment investigation that’s going on. Somebody asked me —

Ryan Holiday: [00:35:29] That goes with any investigation, but yeah.

Jordan Harbinger: [00:35:31] Somebody asked me the other day, “Oh, yeah, so things are heating up or whatever,” and I was like, “Yeah, I don’t really know,” and they’re like, “Oh, you’re not following this?” And I said — I was so proud of myself for saying this; I’ve never uttered this — I said, “I’m going to wait for five years and then there’ll be a book about it. I’ll just read that.” Because there will be and I’ll get a very well-rounded, complete 360 of the whole thing, and then I’ll know it. I don’t need to know it now.

Ryan Holiday: [00:35:54] Well, think of the expression that you just said, “I’m not following it.” Why do we need to follow it? It should go where it ends. And look, there are things where people are like, “I’m watching the debate because I need to decide who I’m going to vote for.”  Okay, so you have said that consuming this information is going to have an impact on a decision you are going to make. But most of the people who watch the debates know who they’re going to vote for and they’re just watching —

Jordan Harbinger: [00:36:22] A performance.

Ryan Holiday: [00:36:23] Crappy sports. They’re watching the worst sport ever: moderated debates.

Jordan Harbinger: [00:36:30] Yeah. It’s moderated by Anderson Cooper. I want Anderson Cooper to moderate no sports. It’s a really good point. It’s just a really boring, slow-paced game of nothing.

Ryan Holiday: [00:36:42] Think about it this way. Debates used to be: This is the debate, and different cable stations are all recording it at the same time. So it was an event being covered on television. Now it is an event being put on by television. CNN is inventing this debate. This debate was not going to happen without CNN. It’s not the Lincoln-Douglas debates, where a bunch of people were watching these two figures in Illinois debate each other. It’s like, this is manufactured. This is a press conference, which is done exclusively for the purpose of getting media attention.

Jordan Harbinger: [00:37:17] Yeah, that’s a good point. I didn’t even think about that. You’re right, it’s not necessarily a government function.

Ryan Holiday: [00:37:21] This is an MSNBC or CNN or Fox News going, “Man, we can get millions of people to tune into an event that we don’t have to pay anyone to appear on.”

Jordan Harbinger: [00:37:32] Right, yeah, good point. There are no salaries for the athletes or anything. The advertisers involved are still going to pay a huge Super Bowl level premium probably, if they even have that.

Ryan Holiday: [00:37:41] Yeah, totally.

Jordan Harbinger: [00:37:42] You figured out what you want to do really early in life. You kind of mentioned that you’d thought about being a writer at age 19. A lot of people will write in and go, “How do I know what I want to do?” And I’m like, “Oh crap, I’m the last person to ask. I’m still figuring out; I’m 39 years old.”

Ryan Holiday: [00:37:57] I feel like it’s — how did you find the person that you’re going to marry? It’s like, “I don’t know. It just happened.” I fell into it, and then I didn’t say no to the experience, so I don’t have a great answer — although I think Robert Greene’s book Mastery is probably the book I recommended most to people. One of the things he talks about is he’s like, you’ve got to think back to your childhood, to that thing before money and pressure and what your teacher said before any of that like, what were you sort of purely attracted to that got you going? What was that thing? I kind of think, what would you do for free? What do you stare out of car windows and think about? I’m not saying that tells you the job, but it should give you a sense of the ballpark of where this career thing is. “I read lots of books. I really admire writers.” Okay, probably something in publishing. And then it’s like, where do your skills overlap with this? You’re obsessed with baseball. You could be a GM, you could work in the marketing department, you could be a professional baseball player, you could be an agent, you could be the guy that takes care of the field. There’s a lot of different things, but your subconscious told you that baseball was it. You know what I mean?

Jordan Harbinger: [00:39:17] Yeah, that’s a good point. Looking back at my own childhood, I tried to build an FM transmitter when I was nine because I wanted to talk on the radio. And it turns out it’s illegal to attach a huge antenna to those things! Pesky FCC licenses. But you know, I forgot about that for 20 years or something, not quite 20 years but yeah, close to it.

Ryan Holiday: [00:39:40] I think the other thing is people go like, “I love videogames. I should be a professional video game player.” Don’t just think of the most glamorous thing. “I love podcasts. I should have my own podcast.” It’s like, where does that overlap with your skill set and your background and what does the market need? I don’t think I was like, “I want to be a writer.” I started: “I love books. I love reading. I want to be around authors.” And my first entry point into that was marketing for authors, particularly Internet marketing and online search social media stuff with which, at the time, was a very uncompetitive space and a very poorly understood space. It was only in working with these people and meeting them and really figuring out how the process worked that I was like, “Oh, I think I could actually do this.” Maybe you go around basketball players and you’re like, “Wow, these are just totally different human specimens than me.” I didn’t have that feeling being around Robert Greene or the other authors that I worked for. I just got this sense that they had dedicated themselves to a different part of the craft and maybe I could do that.

Jordan Harbinger: [00:40:46] Yeah, you could have easily been an editor at a publisher reading other people’s work and crossing things out grammatically, which is what I kind of imagine they do.

Ryan Holiday: [00:40:55] Yeah, it’s mostly in Microsoft Word. Not a lot of crossing out, a lot of those comment bubbles.

Jordan Harbinger: [00:41:02] Oh, jeez. Yeah, maybe it doesn’t sound as fun at that point. But it is.

Ryan Holiday: [00:41:07] It’s like when in the studio, you’re like, “I love music. I love recording.” Go get a job sweeping the floors in a studio! Because I was thinking about this with sports, because my books have become popular in sports. I’ve met all these people who served as team psychologists or mental skill coaches for the teams. And I’m like, “I really wish I knew this was a job, maybe that’s actually what I would have been really good at.” Writing is clearly what it is for me, but it was like, if you told me that 19 that there was a guy who worked for the Sacramento Kings who just helped them be better thinking about basketball. I’d be like, “How do I go to school for that?” I didn’t know that was a thing. But if my parents had helped me get a job as a ball boy, I would have needed to take a step towards the industry, and then I would have found out that that profession existed.

Jordan Harbinger: [00:41:55] I feel like you are in school for that. You’re going to write all these and then someone’s going to be like, “Hey, come give a talk.” You’ll be like, “How about I give a talk —

Ryan Holiday: [00:42:01] “All the time.”

Jordan Harbinger: [00:42:03] — every week!”

Ryan Holiday: [00:42:04] You know Dan Coyle? he wrote —

Jordan Harbinger: [00:42:06] The Talent Code.

Ryan Holiday: [00:42:07] And Talent Is Overrated, I think [Ed. Note: Geoff Colvin wrote Talent Is Overrated]. He works for the Indians now.

Jordan Harbinger: [00:42:11] Nice. Yeah, so that makes sense.

Ryan Holiday: [00:42:12] Yeah, you could do that.

Jordan Harbinger: [00:42:13] For me, that’s an alien world, the sports thing, but I get it. I would have been really well served being, like, the coffee kid at a radio station.

Ryan Holiday: [00:42:23] Well, podcasting didn’t exist at first.

Jordan Harbinger: [00:42:25] It didn’t. No.

Ryan Holiday: [00:42:26] But it was you following the space enough and messing around enough and being — and that’s why in David Epstein’s book about Range, that’s why you’ve got to have all these different interests, because they converge together around something, and oftentimes that’s where new professions are created as well.

Jordan Harbinger: [00:42:45] Exactly. Yeah, I agree with that. Whenever people ask me how to figure out what to do with their life, the answer is always, “Make a list of skills that you would like to learn. Go learn those and then figure out where you can apply them in different businesses.” It doesn’t even have to be the same thing. If you want to learn forex trading, you can go ahead and do that, but it doesn’t mean you’re going to be a forex trader. You might be at some desk working with an executive who happens to touch that business. That stuff tends to come together quite nicely. This podcast never started as me interviewing people. It was me talking about how pathetic my dating life was literally 13 years ago. And then I was like, “I’m out of content. Maybe I’ll do an interview with somebody else,” and then I was like, “That was the most fun episode I’ve ever done.” So this slow evolution is the only way to do it. I think now people look at these things that they say online or that they see online or that they read in books and they go, “Oh, well, this person kind of — this fell into their lap or fell out of the sky.” And it’s also reinforced negatively by marketers who go, “Oh, my origin story? Crap. I need to come up with a good one.” There’s this really smooth curve from me having an epiphany, and then meeting the right people, and then getting really lucky, and then here we are. And it’s like, “Whoa, none of that happened. You were in the army for 10 years. You don’t even talk about that!” Or whatever.

Ryan Holiday: [00:43:58] Yeah, and Peter Thiel talks about how we have this inclination towards competition. We go, “I don’t know what I want to do with my life. A lot of people are doing podcasts. I will do podcasts.” Because we think the fact that lots of people are doing it makes it safe. When really the real gains and the real success in life usually comes from breaking some kind of new ground. So look, I’m an author, lots of people are authors, and it’s one of the older professions, I would say. But I write a different kind of book for a different kinds of audience. When I was like, “I wanted to write a book about Stoicism,” the publisher is not like, “Oh, yes, that is a very established — ”

Jordan Harbinger: [00:44:39] “That’s a hot topic right now.” No!

Ryan Holiday: [00:44:41] If they had, that might have been better for me in the short term, but much worse for me in the long term. The key is: where do these diverse interests overlap and add up to something that doesn’t exist? People go, “I’m smart and I like arguing; I should be a lawyer.” That’s the worst move —

Jordan Harbinger: [00:44:59] That’s a hot topic, because that’s what everyone will tell you, and these are people who are not lawyers — they don’t even know any lawyers. That’s how I ended up in law school! Aunts being like, “Oh, you should be a lawyer. You can get anything you want — kind of job you want — with a law degree, and clearly you like to argue or be right, so you should do this.” I think it was Tucker Max wrote this whole post, where he’s like, “This is why all of these things are wrong.” I end up sharing it a lot when people go, “Should I go to law school?” I’m like, “You should read this,” because the answer is probably not [the same as] when your mom says go to law school based on all the stuff I’ve seen on NCIS Miami or whatever, or Law and Order. These are not good representatives of what you’re going to be doing on a daily basis.

Ryan Holiday: [00:45:42] Yeah, of course.

Jordan Harbinger: [00:45:430] It’s not going to be like JAG, where you’re flying in a jet and armed and chasing people down in Manhattan. You’re going to be in a cubicle a lot of the time if you’re lucky. You might not even have your own cubicle. It’s true though, right?

Ryan Holiday: [00:45:57] Sorry for triggering you.

Jordan Harbinger: [00:45:58] Yeah. I know, I just went off on a tangent there. It’s true, though. I think a lot of people come up with an idea of what something must be like in their head and it’s so unrealistic. We just assume that that’s at least representative, a little bit, of reality and it’s not even close a lot of the time.

Ryan Holiday: [00:46:12] Well, one of the things I talk about in the book is “Are you actually taking time to stop and think about these things?” People are like, “I’m going to be a lawyer,” and it’s like, “How long have you thought about this?” You’re saying, “I want to be a lawyer” from the fact that your mom said you were good at arguing and then this guy down the hall from you is also applying to law school.

Jordan Harbinger: [00:46:33] That’s pretty much it.

Ryan Holiday: [00:46:34] Epictetus from the Stoics, he said you’ve got to take these impressions or these inclinations and you’ve got to stop and put them to the test. Or the other way is stop, get out your glasses, put them on, and look at it. You know what I mean? Don’t just look at the vague shapes and go, “I think I know what this is.” Really stop and think about it. Not take the evening, but think about it for a couple months. Do you know any lawyers? Or do you know people that have done this? What would happen if you actually were successful in this thing? I talk about this with people who are like, “I want to do X,” I go like, “But what do you want your life to look like?” I have sort of realized I really didn’t like having a job where people could tell me what to do. So it’s like, oh, so if I become more successful — when I was a director of marketing at American Apparel — okay, so, what do you do next? I’m probably not going to become the CEO of this company because it’s run the way that it’s run. Maybe I’ll go get a job; I’ll make a lateral move or a slightly higher move. I’ll get the same position at a bigger, better company. And then it was like, “Wait, I’ll actually be less happy, because as chaotic as this company is, it feels less like a job than a normal place. Success would be me actually moving further away from what I want my life to be. But when someone says, “Hey, I’ll pay you $100,000 a year to do something that’s the opposite of how you want your life to be,” all you’re thinking about is $100,000. You’re not thinking, “Well, how much of that $100,000 am I going to have to spend to not feel like I hate my life?”

Jordan Harbinger: [00:48:18] Right, all of it, more than all of it.

Ryan Holiday: [00:48:21] Or it’s like, “Hey, I know you really love where you live. I know you have your kids in great schools and you have this great routine, blah blah blah blah blah, but I’ll pay you 20 percent more than you’re currently making and now you have to live in Buffalo, New York.” Not to hate on Buffalo, New York.

Jordan Harbinger: [00:48:38] But you’ve got to take your kids out of school, you’ve got to move your family.

Ryan Holiday: [00:48:42] Yeah, you have to do all this stuff, and your quality of life will be lower. And what are you doing with said money?

Jordan Harbinger: [00:48:48] Retiring early maybe, buying another vacation so that your family doesn’t hate living.

Ryan Holiday: [00:48:52] In Buffalo or whatever. So I think saying no to money is extraordinarily difficult, and I have a lot of trouble doing it, and I don’t do it enough. I had this experience where I got called back into American Apparel as a consultant, and I turned around and sort of detangled myself from it, and I got free. I remember this is when we bought our farm, I was there, and I spent all morning writing, and I got this unsolicited email from a very big tech company. They were like, “Hey, we need a CMO consultant to come in for four months.” It was going to pay a lot of money. There were some stock options attached to it, it would be a cool challenge. And I remember I took the call, and I negotiated some of the deal, and then I was like, “Wait, I have to move to New York, and I’m going to have to show up at a job every day, and I just worked really hard not to have a job. Why would I say yes to this?”

Jordan Harbinger: [00:49:44] Because money.

Ryan Holiday: [00:49:45] Yeah, because money. I mean, I wrote a piece about it for The Times, but I got a pretty decent offer to be a pretty high-ranking figure in the Trump administration for one of the cabinets.

Jordan Harbinger: [00:49:56] You did?

Ryan Holiday: [00:49:57] Yeah. This is like in 2016.

Jordan Harbinger: [00:49:58] That is ironic!

Ryan Holiday: [00:49:59] Yeah. It was very strange. I’m not sure it would have come all the way to pass, because I don’t think I had been vetted yet. And I think they would have realized where I stood. But the point was, I remember asking, “Do I have to live in DC?” He’s like, “Yes,” and I was like, “What do you get paid?” And he was like, “Not that much.” I was like, “And what about all the other things that I have, like books and my investments?” He said, “All these have to go into a blind trust; you can’t touch them,” and it was like, boom, boom, boom, and then he was like, “So are you interested?” and I was like, “Yes.” Because it was, in every way, the opposite of what I wanted, but it’s really hard to say no to things, and we don’t take the time to think about them. So thankfully I took the time to think about it, and when I laid it all out and I talked it — like, this is why I think being in a relationship is so important. If I was single, I probably would have jumped off that cliff. You’re not able to think long-term enough.

Jordan Harbinger: [00:50:52] Sam was probably like, “I don’t want to move to DC. They have winter there.” End of story.

Ryan Holiday: [00:50:57] She was more like, “You know this contradicts all the things that you like, right?” “Yeah, but –!

Jordan Harbinger: [00:51:03] “But how cool would it be? Secret service will drive us around!”

Ryan Holiday: [00:51:05] “But you don’t understand; it’s also a huge pay cut. Also, I’m ideologically opposed to everything they stand for.”

Jordan Harbinger: [00:51:11] “I can’t do any business or anything. I can’t work on any other projects like the ones I love.”

Ryan Holiday: [00:51:15] But it’s like people are, “What are you doing next? What about this? What about?” It’s really hard to be like, “This is my thing. This is what I’m doing. And to have the patience and the discipline to go to actually weigh the opportunities or the options against whatever that rubric is, and people just don’t do that. That’s why they plunge ahead into stuff that makes them miserable or ruins everything they have.

Jordan Harbinger: [00:51:38] It’s true, and the most important time to make those decisions is usually when you feel like you don’t have time to make those decisions. So when I was a lawyer, we had this economic downturn of 2008 and everyone went, “Oh my God, we have to find new jobs.” Even I did that, I even interviewed at some other places, and then I was like, “Wait, wait, I’m working so hard to get another job that I don’t even want.” But all my colleagues were like, “Dude, you’re not going to have a paycheck pretty soon. You have law school loans. You’ve got to repay that. What are you going to do? You’re just going to end up —” [I was] like, “Literally anything else? I would do anything else. Maybe I should go to the police academy,” and they’re like, “You’re crazy.” They all scrambled and found new jobs. And now, of course, they’re like, “Ugh, man, this life sucks.”

Ryan Holiday: [00:52:16] Right. They doubled down.

Jordan Harbinger: [00:52:18] They doubled down.

Ryan Holiday: [00:52:18] And so this idea of like, “Look, I’m going to really stop and think about this,” it’s not just about making you more conservative. It’s not like you only say no to things. It also helps you plunge ahead on things that other people are afraid of. When I dropped out of college, I was terrified of it. There’s that “Hell yes; Hell no?” All the big moves in my life have failed that test. And I was really scared about it, and so I ended up deciding to do it and I remember I went and I was like, “I’m ready to drop out.” They’re like, “That’s not how this works. It’s much more gradual than that. Just take a semester off.” Anyways, because I’d done that, because I had some experience taking a leap like that, when I decided I was going to walk away from a very good, lucrative corporate track to be a writer, I was able to go like, “Oh, I can always just go back.” That was interesting. I thought I was dropping out of college and they’re like, “You can always come back.” And I remember someone told me they’re like, “When I was in college, I got sick and I missed a year of college,” and he’s like, “Do you know how many people have ever asked, ‘What happened?'”

Jordan Harbinger: [00:53:21] Yeah! Zero!

Ryan Holiday: [00:53:22] Yeah. They’re like, “Why did you go to college this year and then graduate five years later?” It’s literally never come up. He’s like, “I don’t even think about it.”

Jordan Harbinger: [00:53:29] “Yeah, I had mono.” “Oh, okay. Next!”

Ryan Holiday: [00:53:32] And so when you look at these things, we’re super intimidated by them — because they seem scary because they’re unknown. You’re suddenly “I’m going to live under a bridge somewhere. I could get murdered.” Actually, this changes nothing. It’s not scary at all once you break it down. At the core of Stoicism and in the story I tell in the book the beginning of Mr. Rogers, which you’re almost going to have to start watching.

Jordan Harbinger: [00:53:55] Oh, I watched that documentary two days ago. Such a coincidence.

Ryan Holiday: [00:53:58] So you started watching the show and now you have a kid, but the beginning of the show, it’s a flashing yellow light, which is like, “Slow down, look carefully,” and we have to be able to do that always and particularly when stuff is coming a mile a minute. Just because someone sent a tweet to you doesn’t mean you have to respond with the first thing that comes into your head. Just ignore it.

Jordan Harbinger: [00:54:20] Yeah, probably shouldn’t do it at all.

Ryan Holiday: [00:54:21] Or you could wait 24 hours. This stuff feels like it’s real time, but 20 years ago, they would have written it to you in a letter, you know.

Jason DeFillippo: [00:54:31] You’re listening to The Jordan Harbinger Show with our guest, Ryan Holiday. We’ll be right back after this.

Jordan Harbinger: [00:54:37] This episode is sponsored in part by Xero. We’ve been using Xero. It’s a cloud accounting software. We’ve been using it forever. In fact, when it first came out, we thought wow, this is the iPhone of accounting software. It’s that disruptive. It’s fast. It’s intuitive. It’s super easy to use even for people that don’t want to do any sort of software accounting stuff at all. Xero makes this so painless and a lot of our entrepreneur friends use it. It’s great for business that’s online. It’s great for business that’s not online but has any sort of digital component at all, which assume is every single business ever. You can give access to an unlimited amount of users. So, you’re not swapping logins with people that work for or with you and they can have limited access to what’s in there. You can also pay by month. So, there’s no contract. So, if you’re just not sure about it or you’re wondering if you’re going to need something bigger smaller not use it at all. No problem there. They’re from New Zealand. So, they’re good people. That’s what that means. I’m pretty sure that goes without saying. 24/7 support, so you can mess up anything at any time, and they will set you straight before your boss finds out what you did or what you did to yourself. You can also view things from the iPhone or Android app, and this helps when you need to check your dashboard in an Uber on the way to the airport. So, try Xero risk-free at xero.com/jordan. That’s Xero with an X, X-E-R-O xero.com/jordan for a free month. You can thank me later.

Jordan Harbinger: [00:56:04] This episode is also sponsored by Eight Sleep. Man, I got to tell you, Jason, this Eight Sleep that you and I have been harping on about is even better when you’ve got a baby, but I got to tell you you’ve been sleeping like a rock. I’ve been sleeping like a rock, but since it does cooling and heating. Jen will preheat the side of the bed and will give Jayden a bath and then I can still cool down my side because it’s 8,000 freaking degrees in the house. No matter what and I’m always warm now. I don’t know what’s going on there, but it’s great because we basically have the heated bed. She’s comfortable, the baby is comfortable, I’m comfortable, and I’ll tell you, man, my sleep scores are through the roof. What’s your experience so far? I know last time we talked you love this.

Jason DeFillippo: [00:56:43] Oh, yeah, man. I’ve got it set for the dogs on one side, me on the other and now I’ve been tweaking my settings. So, now, it warms up in the morning and is blue in my sleep score because I’m nice and toasty warm right when I’m supposed to get out of bed and it’s digging me because I want to stay in bed longer because I’m comfy. What’s up with that? I lost three points today. I got a 97 I could have gotten a hundred, damn it.

Jordan Harbinger: [00:57:07] Well, you’re never an overachiever.

Jason DeFillippo: [00:57:10] That’s right.

Jordan Harbinger: [00:57:11] What you can do with this that I love is you can set the temperatures to raise and lower throughout the night automatically and it learns so it’s not just hot or cold you can say hey in the middle of the night I get cold. So, start heating up around 2:00 a.m., 3:00 a.m. and it’ll just do that automatically. And if you’re like me, you can have it cool down enough in the morning that you just want to get out of bed because you’re freaking cold. So, you could do whatever you need to do to get started in the morning. Jason, tell them where they can get a nice deal on the Eight Sleep.

Jason DeFillippo: [00:57:39] Right now, you can get S150 off your pod and free shipping when you go to EightSleep.com/jordan. That’s EightSleep.com/jordan E-I-G-H-T EightSleep.com/jordan for $150 off your pod and free shipping.

Jordan Harbinger: [00:57:55] This episode is also sponsored by me. Well, not sponsored at all actually, but I’m going to prison for my birthday in 2020, February 26, 2020, and I’m bringing a bunch of you suckers with me. Hopefully, it’s at High Desert State Prison in Susanville, California, which is near Tahoe/near Reno, and it’s a donation thing. All the proceeds are going towards an educational program for the inmates. I’m not keeping any of it. I promise you’re not even going to pay me. It’s going to go directly to the group that’s running this and the donation amount is approximately a thousand bucks. Give or take. We’re going to see no kickbacks from me, plus it goes to transportation. We’re going to have some meals, there’s going to be a photographer there. It’s just going to be a great thing for all of us. I’ve done this before not on my birthday, but I’ve gone to programs here. It’s just I know everyone says their thing is life-changing. This really was something I thought about and still think about all these months later. The price is priced to fund one inmate through the educational training program at Hustle 2.0. If you’re interested in unique experiences, and you want to come to prison with me, and I don’t know 50 hundred other people on February 26. We’re probably going to fly into Reno on February 25th. I’ll send you the deets just email me prison@jordanharbinger.com. That’s prison@jordanharbinger.com. And I will send you some more info as it becomes available. I think it’s going to be really fun. I’m really looking forward to it. We got a lot of cool people in my circle coming as well. And I really am excited to meet a bunch of you show fans as well behind bars. I think it’ll be a great time is weird. Is that might sound. So, shoot me an email prison@jordanharbinger.com if you’re interested in joining us.

[00:59:33] Thank you for listening and supporting the show. Your support of our advertisers keeps us on the air. To learn more and get links to all the great discounts you just heard so you can check out those amazing sponsors, visit jordanharbinger.com/deals. Don’t forget the worksheet for today’s episode. That link is in the show notes at jordanharbinger.com/podcast. And if you’re listening to us on the Overcast player, please click that little star next to the episode. We really appreciate it. And now for the conclusion of our episode with Ryan Holiday.

Jordan Harbinger: [01:00:03] Mr. Rogers is an interesting case study. Why did I watch that recently? Is it in the book?

Ryan Holiday: [01:00:08] It’s in the book.

Jordan Harbinger: [01:00:09] That must be why I watched it, because I don’t remember what jogged that. He’s amazing.

Ryan Holiday: [01:00:13] So I haven’t seen the documentary, because sometimes you kind of get this professional jealousy about things. So I started writing this book in 2016, 2017, before the Mr. Rogers resurgence. So the only books about him were these two obscure, self-published books by friends of his. There was not a lot of stuff out there. And so I sort of fell in love with it and I was reading all about it and then it’s like a Tom Cruise movie — or Tom Hanks movie!

Jordan Harbinger: [01:00:42] Talk about casting.

Ryan Holiday: [01:00:43] That would be good! An action film.

Jordan Harbinger: [01:00:48] This is actually the one that follows his story in that chain letter that everyone got that said he’s a Navy SEAL.

Ryan Holiday: [01:00:53] Then there’s a movie, then there’s this documentary. I was like, you know what? I want to preserve whatever the headspace I have about this thing is, but I think he’s one of the greatest people of the 20th-century.

Jordan Harbinger: [01:01:05] Definitely, agree. We don’t really have sainthood anymore. Maybe we will in a few hundred years.

Ryan Holiday: [01:01:11] But he would be a good saint. He was a minister.

Jordan Harbinger: [01:01:13] Yeah. Oh, that’s right. Yeah, that’s right. He has kids. I’m so desperate to know what he was like when he was super pissed off.

Ryan Holiday: [01:01:20] They talked about that in either the documentary or in one of the books.

Jordan Harbinger: [01:01:22] Must be in a book, because I don’t think —

Ryan Holiday: [01:01:24] He was kind of mischievous. When he would want to say something inappropriate, he would do it in one of the voices of the puppets.

Jordan Harbinger: [01:01:29] He did it in King Friday’s voice.

Ryan Holiday: [01:01:31] Yeah. I bet he was a totally normal human being. He would swim every morning. He was just like a normal guy, but just also an incredible person at the same time.

Jordan Harbinger: [01:01:41] It’s got to be so hard to just talk to kids and be measured. Not that he only talked to kids. His whole life was geared towards talking to small children. I don’t know if I could do that.

Ryan Holiday: [01:01:54] But there are these anecdotes about him just meeting people and just having whatever that sort of angel-like energy is and he could just go to the core of who they were. I actually think it’s more like he had some energy that was so special that it would work on anyone — and that it would work on kids is a sign of just how powerful it was. Does that make sense?

Jordan Harbinger: [01:02:19 Yeah, it does, basically —

Ryan Holiday: [01:02:20] Like Cesar Millan.

Jordan Harbinger: [01:02:21] Yeah, he’s like the kind of guy that birds probably land on his shoulder, and it just so happens to mesh well with children, so he decided to speak to children.

Ryan Holiday: [01:02:29] Because it’s so rare.

Jordan Harbinger: [01:02:30] He had a talk show for adults, and I’m dying to get my hands on it.

Ryan Holiday: [01:02:33] Really?

Jordan Harbinger: [01:02:34] I know I cannot find it. It’s not anywhere easily accessible. I’m sure it’s on reel-to-reel tape somewhere in the basement of CBS or whatever.

Ryan Holiday: [01:02:40] There’s this story where he gets a lifetime Emmy or something and he goes up and gives a speech and he’s like, “I have about 30 seconds to talk, but instead of talking I’m just going to look at my watch here and I’m going to give you 20 seconds to think about someone who meant something to you.” Wow! Who comes up with that? That’s incredible. But I think about this, like the energy that it takes to interact with kids or animals. Cesar Millan, obviously, is someone who’s operating on a totally different level than the rest of us, but my son goes to this daycare and these two Cuban ladies put 15 toddlers down for a nap simultaneously every day. We have trouble putting one toddler to nap. He’s running around. “I don’t want a nap. I hate naps.” We’ve got to strap him in the car and drive around. Imagine doing 15 kids — who are not your kids — simultaneously. If you want to talk about stillness, think of the energy and the calmness and the discipline that you have to have to do something like that. And I think those people have something that we should all study very seriously.

Jordan Harbinger: [01:03:57] How do you start studying the habits of people like that? What do you look for?

Ryan Holiday: [01:04:02] Well, I mean habit is a great place to start. It’s like, “Okay, what does Mr. Rogers’ day looks like?” He gets up early. He has some quiet meditative practice. He swims. He eats the same thing. Just even that he’s doing the same thing, it’s like he’s simplifying. He’s not picking up energy from, “Where do I have lunch? What time does the show start? Should I work out today? Yes or no?”

Jordan Harbinger: [01:04:27] He only has three sweaters! We’ve seen them all.

Ryan Holiday: [01:04:31] Exactly or it just even like, “Hey, this is the intro of the show.” I mean, it’s his show, he could have changed it up every time, but he’s like, “No. Routine.” You do something for once, you did it once. You do it for a week, whatever. You do it for a couple of months. it’s a routine, but you do it for 30 years, it’s like a ritual. You almost become entranced by it. I mean, I don’t think it’s a coincidence someone like that is also deeply spiritual or religious. I’m not saying you have to believe in God. I have trouble getting there myself, but just like, oh, it’s his sort of vulnerability and his almost willingness to submit to something larger than himself. That’s probably the key to a lot of that humility and that stillness. It’s got to be a part of it. It can’t be an accident.

Jordan Harbinger: [01:05:13] Yeah. I think you’re right. I found a lot of people, myself included, have trouble staying or getting ground, especially when we’re all wrapped up in our work. And one thing that’s been good for me is taking lessons in something that you’re not good at. Because there’s nothing quite like getting a voice coach or something for professional — but even outside of that, like getting a Chinese teacher. Because in the workplace, we kind of have to sell ourselves all the time. It’s hard to go, “Oh, gee, I’m just not really that good at this,” or “I’m working on this and this,” because you have to sell yourself as the best man for the job. And so getting a teacher in something that you’re not necessarily good at has actually been quite good for that. I’m not even talking about this general student of life mindset. I mean looking at the actual skill that you suck at and hiring someone to tell you how to do it right.

Ryan Holiday: [01:06:00] Well, I talk about this a lot in the book, like the power of a hobby is that embodied. Like Winston Churchill after the First World War, he’s in the worst sort of spot in his career, and his sister-in-law gives him this children’s paint set. And she goes, “My kids seem to have fun. Why don’t you try having fun?” And he falls in love with painting and he painted something like 500 paintings in his lifetime. And he’s not good. The paintings don’t belong in museums because they’re good. They belong in museums because of what the person who painted them was able to do through painting. You know what I’m saying?

Jordan Harbinger: [01:06:36] Yeah, he was defeating Hitler and he’s like, “Here’s a crappy landscape.” Well, you also were defeating Hitler at the same time.

Ryan Holiday: [01:06:43] But it’s not like they’re related. It’s not like he’s into BDSM and it’s a secret. It’s like the process of painting —

Jordan Harbinger: [01:06:51] It’s a weird visual.

Ryan Holiday: [01:06:51] The process of painting and the relaxation that comes from it, and the joy that comes from it, and the presence that comes from it, was what allowed him to manage the terrible stress that was the insane burden that he was under.

Jordan Harbinger: [01:07:07] That’s true, I think, and also to your previous work, I think getting feedback and criticism in an area that you don’t have maybe a ton of ego attached to, it helps you go, “Oh, maybe I should consider doing that in this other area that is my whole life or that I had an importance attached to.”

Ryan Holiday: [01:07:22] Yeah, and deciding that results are not the primary motivation for doing it. I’ve run and swam for a long time now, and people are like, “Oh are you training for a marathon?” or “Why don’t you train for a marathon?” I’m not trying to get better at my hobbies. I’m am going to get better at them, but I’m not trying to win my hobbies and I don’t need any more competition in my life. The win is that I made the time for it.”

Jordan Harbinger: [01:07:50] That’s a good point. I think for me with languages, for example, it’s really clear because I can go to any bubble tea shop. There will be a seven or eight-year-old or 10-year-old whatever kid in there and they’re speaking more fluently than me. They’ve got a fourth-grade reading book and they’re reading it and I need a dictionary to read that same book, and it’s just it’s really hard to be like, “I’m the best at this.” It’s like, nope this child who can’t even tie his shoes is actually better than you at this right now.

Ryan Holiday: [01:08:16] Yeah, and how often do you get that as you become better and better at what you do?

Jordan Harbinger: [01:08:21] Yeah, it’s rare.

Ryan Holiday: [01:08:22] There’s fewer people who are like, “Jordan you’re doing a horrible job. You need to get serious about this.”

Jordan Harbinger: [01:08:29] Yeah. Yeah, it’s tough. I actually just emailed Marc Maron the other day and he replied today. He was like, “I can’t help you.” I was like, “Hey, I’ll pay you for some consulting on interviewing,” and he was like, “I can’t articulate what I’m doing. I can’t be of any help to you at all. It’s not that I don’t want to do it. I just can’t do it.”

Ryan Holiday: [01:08:46] That’s interesting. You reached out to him not as a peer?

Jordan Harbinger: [01:08:49] I was just like, “Hey, would you consider going through your prep process, your interview process? And I obviously would pay you for that,” because otherwise, he’s just like, “Everyone’s going to ask me I do this.” And I’ve done that with a few journalists and stuff and a lot of them are like, “Yeah, let’s do it. Come to New York. We’ll do it.” And Marc Maron was just like, “I can’t actually help you. I know this already.”

Ryan Holiday: [01:09:08] Oh, interesting.

Jordan Harbinger: [01:09:09] Thought that was interesting. I reach out to people like that all the time to try to get it. It is hard to find somebody who’s going to be at a higher level that’s also willing to sit down with you and help you do it.

Ryan Holiday: [01:09:17] I was thinking about this for something that we’re doing for Daily Stoic right now. My books certainly made their way through professional sports. The amount of coaches — who are best in the world at what they do — that send me emails having read the books has blown my mind. It’s not a reflection of me. It’s a reflection of them. Most people don’t read. Most people think they’re good at what they do and they’re good enough. Then there’s a certain percentage of people that read. That’s great. That’s like self-improvement. But what percentage of people are like, “I wonder if there’s anything more I can learn from this person?” Do you know what I mean? I’ve been very impressed and inspired by the culture in sports of like, “Oh, this person’s the best in the world at this thing that’s vaguely related to what I do? I’m going to see if I can learn from them.” So sports — in a way that a lot of business doesn’t — has a culture of like, “Hey, let’s bring in speakers.” I spoke to the University of Alabama three years ago. Nick Saban sat in the front row and asked the first question after the talk. I don’t think that was a reflection of how riveting my talk was. I think it was a reflection of one, he’s trying to model to his players like, the idea of being a perpetual student, and then maybe there’s a one percent chance that I’ll actually have an interesting thing to say and maybe he will learn something from the question. But the point is he’s not thinking, “I’m Nick Saban, I’m the greatest coach in the history of collegiate athletics. What could you possibly show me?” It’s the exact opposite.

Jordan Harbinger: [01:10:45] Yeah, that’s interesting. And plus, I would imagine, he found it through some other coach that maybe at some level competes with him or could have —

Ryan Holiday: [01:10:53] Yeah, maybe.

Jordan Harbinger: [01:10:54] You’ve obviously talked with a lot of NFL teams and things like that. They’re sharing it with each other. These coaches aren’t like, “Ooh, I’m not going to share this Ryan Holiday book; that’s my little secret.” It’s everywhere.

Ryan Holiday: [01:11:04] No, and that’s why I was asking about Maron, like I would think that you, given what you’ve accomplished, would be able to just say like, “Hey, Marc, do you have any advice?” Do you know what I mean? But it’s also cool that you offered to pay.

Jordan Harbinger: [01:11:17] Yeah, I always do because otherwise, the problem is a lot of people have responded, “Oh, I wouldn’t take your money. I would love to do this for you. The problem is I’m so busy for the next seven months.” I’m like, “Well, I bet you’re busy doing things that pay you,” so if I add money to the equation, maybe it speeds the timeline up six months.

Ryan Holiday: [01:11:32] That’s true.

Jordan Harbinger: [01:11:34] And also, if you pay, you get a lot more than just a two-line email of advice, generally.

Ryan Holiday: [01:11:39] No. No, that’s true. I just hired — do you know Jon Bier?

Jordan Harbinger: [01:11:42] Yeah! Oh, he mailed me about doing this.

Ryan Holiday: [01:11:44] Yeah, I work with him on a thing, and it’s like you have friends who are really great at stuff, and you’re like, “No, I want to pay you because you are the best in the world at what you do.” What is it — Jack Taylor? He has a great publicity firm. “I’m not going to ask you a favor as a friend. I want the full thing.”

Jordan Harbinger: [01:12:04] The full treatment.

Ryan Holiday: [01:12:05] Yeah, and that’s a weird thing. I think earlier in my career I would have been like, I’ve got to get a deal. Actually, expertise is expensive.

Jordan Harbinger: [01:12:13] I’m the same way. I like to pay knowing that I’m going to get the full treatment. If somebody says, “Look, I’ll do this for free because I only have 30 minutes of stuff for you,” then fine. I don’t want an eight-week training program for free because it’s going to just build resentment. If it even exists.

Ryan Holiday: [01:12:29] What I figured out with my marketing business, because so few people actually were in a position — a lot of people wanted to pay for the full treatment. A lot of people actually were not a good fit for the full treatment. So I was like, “Here’s what we’ll do. You can buy an hour of my time, and I’ll tell you everything I think you should know and everything I think you should do, and then if it does make sense for us to work together, that’ll just apply to the fee.” When we were talking about lawyers, I like the lawyer model of “This is what an hour of legal advice costs.” It doesn’t have to be the like, “Oh, let’s go through this big pitch dance and come up with this thing.” I think in a way we should be a little bit more transactional towards expertise and go like, “This is what 30 minutes of Jordan’s time costs about starting a podcast — buy it or don’t.”

Jordan Harbinger: [01:13:20] I’m happy to talk people out of doing it. That course is free! If you’re at an event where I’m giving a talk, I’ll talk you out of doing a podcast.

Ryan Holiday: [01:13:27] Please, yeah! You talked me out of it.

Jordan Harbinger: [01:13:30] Did I?

Ryan Holiday: [01:13:31] I mean, we talked about this.

Jordan Harbinger: [01:13:33] Oh, at MMT or something? Yeah, that’s what I’m referring to. I’ll go to these events and they’re like, “Talk about podcasting,” and I’m like, “Let me save all of you a lot of time. Don’t do it.”

Ryan Holiday: [01:13:42] I do the same thing. “You should not write a book.”

Jordan Harbinger: [01:13:44] We talk about this sometimes in text where I’m like, “Here’s a book. What could this possibly be about?” It should never have been written. This is one of those books where they wanted a book so that they could say, “I have a book.”

Ryan Holiday: [01:13:55] People want the results of having a book and kind of want the results of having a podcast, but they don’t actually want the thing.

Jordan Harbinger: [01:14:02] That’s true.

Ryan Holiday: [01:14:03] When I think about that, now I have a podcast that’s on my terms that I like. For Daily Stoic, I just read the email. It’s like a two-minute podcast. It not only doesn’t take my eye off the ball of what I like doing, which is writing, but it complements the writing. It’s just bringing the writing to people who don’t like to read.

Jordan Harbinger: [01:14:21] It’s a good point.

Ryan Holiday: [01:14:21] And so it’s been wonderful. And maybe there are 50 people that I want to interview at some point and maybe I’ll do that. But it’s like what I don’t want to do is be interviewing five people a week, because it’s not what gets me out of bed in the morning.

Jordan Harbinger: [01:14:38] Yeah, it will keep you up at night, though, I’ll tell you that!

Ryan Holiday: [01:14:40] That’s actually a great contrast. People, not only do they not do things that get them out of bed in the morning, but they do things that keep them up at night.

Jordan Harbinger: [01:14:48] Yeah, there’s something clever in there.

Ryan Holiday: [01:14:51] Yes. There is.

Jordan Harbinger: [01:14:52] A way of phrasing it.

Ryan Holiday: [01:14:52] Maybe that should be your book.

Jordan Harbinger: [01:14:53] There we go. Yeah. It’s kind of a long title. All right, in closing, I’m wondering what keeps you driving so hard at your goals, but I know it sounds like a stupid question. But on the one hand, there’s a lot in Stillness is The Key about how success is ephemeral, our goals are not really that meaningful, or at least not as we previously thought, then you look at your kids and you’re like, “Wow, nothing I do matters except for raising this kid.”

Ryan Holiday: [01:15:17] But then you still show up for work every day.

Jordan Harbinger: [01:15:18] Yeah, and you’re doing a crazy long book tour to try to get this thing going and get it into people’s hands. So I guess what I’m asking about is like, what daddy issues do you have that are all coalescing —

Ryan Holiday: [01:15:28] I got a lot of them. I got a lot of them. I do feel like a lot of very successful men, maybe it’s women too, I only know about the male experience what’s it’s like, “Daddy, can you please be proud of me now?”

Jordan Harbinger: [01:15:39] Yeah! Finally.

Ryan Holiday: [01:15:39] It’s not going to happen. If you have to say that, it’s not going to happen. There are people who become President, and then their parents are like, “But you weren’t as good as FDR,” or whatever. I’ve got a little bit of that. But I think there is this fear. People think, “If I’m content, if I have some idea of enough, I won’t make good work anymore.”

Jordan Harbinger: [01:16:01] Yeah. “I’ll lose my edge.” Same with humility. Ego is The Enemy had something like this, and I’m totally guilty of this. We think if we’re humble, we’re totally screwed because your edge is gone.

Ryan Holiday: [01:16:13] I would dispute whether the hunger is the edge. So I do have some issue that makes me not want to rest between books, like, always have one. And there’s a part of me that always wants them to be bigger. At the risk of oversharing, I’m in the middle of negotiating this deal for the next book and I saw my dad and I was like, “Dad, is this a very large number?” He was like, “Well, you shouldn’t think about it today,” or something like this, and then later he was like, “How much do you think this house cost?” He wanted to talk about anything but that thing. There’s a part of that, there’s clearly a part of that that drives me a little bit — but I don’t want to be driven by it! Okay, so maybe that’s what created nine books in seven years as opposed to four books in seven years or whatever. But the actual books themselves, that’s not an edge. That’s the opposite of an edge. The craving or the need is not making them better — if anything, it makes them worse because you’re trying to rush through them. So you really want to be coming at it from a place of “I actually really have something I want to say; I really love this,” and this goes to the Robert Greene thing. I would do this for free — even if I wasn’t getting paid, would [I] do it for free? So I do talk about how you have to have some idea of enough and success is ephemeral and no amount of external accomplishment is going to fill a hole in your soul, but I don’t think that’s the same thing as genuinely loving the process or the craft of the thing. I feel like if someone handed me a billion dollars tomorrow, all that would do would make my books better.

Jordan Harbinger: [01:17:55] You have a nicer desk.

Ryan Holiday: [01:17:56] I’d have a nicer desk, but I’d also probably even be writing from a slightly purer place. I’d still be writing. I’d be able to dictate terms slightly better. I could think longer term. So to me, that’s a sign you’re in the right thing. You know what I mean?

Jordan Harbinger: [01:18:12] If I had a billion dollars, I’d be like, “Oh, cool. I’ll just build my own studio and I’ll fly everyone in first class.” But otherwise, we’re still sitting in chairs shifting around after an hour.

Ryan Holiday: [01:18:21] Casey Neistat said that to me one time. He was like, “You don’t do the work to make money, you make money to do more work.” So there’s a version of that that’s unhealthy, like, “I’ve got more and more and more,” but there’s also, “No, this is the most satisfying thing,” and the success is about encouraging and facilitating the chase of that meaningful experience rather than the experience as a means to the end of having the stuff. I mean if you have kids or you zoom out a little bit, it does help you to go — there would have been a time where if somebody ran in the room and was like, “You’ve got to stop! Your son wants to go swimming.” I’d be like, “I have to finish this.” And now I’d go, “I don’t. There are other things that are important.” And if you told me I could trade a certain amount of books for having a really great family, I would take that trade in two seconds because it’s not the output of the books that’s important to me. It’s that I just get to keep doing it.

Jordan Harbinger: [01:19:21] I think it’s hard for people who haven’t done anything that they feel successful having done or maybe it’s actually harder when you do have success. I’m not sure now.

Ryan Holiday: [01:19:29] Yeah, a lot of this is, these weren’t things I was wrestling with when I was 20. I was wrestling with like, “How do I get my shot? And how do I not blow said shot?”

Jordan Harbinger: [01:19:37] And not be broke.

Ryan Holiday: [01:19:38] Right, but it eventually becomes an issue. And writing can be a great profession. It’s not one of those things where like, “I don’t have to work anymore.” I do have to pay bills, right? And my roof isn’t free. So if I’m going to do something, I want it to be something that I like. It’s also important that you make life decisions that don’t force career decisions.

Jordan Harbinger: [01:20:02] Oh, that’s good.

Ryan Holiday: [01:20:03] You know, people decide to live in New York City or they decide they have to have two Teslas or, you know, that they have to fly first class everywhere or whatever. And then that makes it hard for them to make a really good career.

Jordan Harbinger: [01:20:17] You’ve got the golden handcuffs. You go to the big law firm, you buy the house in Nantucket because you’re miserable in the city, and then you get a boat and you’re like, “I can’t quit. I got –”

Ryan Holiday: [01:20:25] There’s a reason that corporate firms will sometimes co-sign on mortgages for you.

Jordan Harbinger: [01:20:30] Jeez, I didn’t know that.

Ryan Holiday: [01:20:33] Yeah, because they want that —

Jordan Harbinger: [01:20:34] That’s evil, evil genius.

Ryan Holiday: [01:20:35] Sometimes, CEO’s companies will loan them money. Upton Sinclair has this thing called the dress-suit bribe, and it was always really powerful to me to think — this is obviously from the early ’90s — so you think, “Oh, I paid a quarter to have [my] shoes shined,” but how much are you paid to have to shine your shoes? You think they’re taking you out to a fancy lunch, but really they’re giving you a new baseline of what lunch is, and then this becomes this thing, then you can’t get out of it. I was very lucky on my first Stoicism book, I was paid fairly based on what people thought I could do, but I could think long term with the book, because financially I make good decisions. You know what I mean?

Jordan Harbinger: [01:21:18] Yeah, I do.

Ryan Holiday: [01:21:19] And so that’s another reason people are like, “I’m quitting my job to start a podcast.” It’s a really bad idea.

Jordan Harbinger: [01:21:25] Terrible, like one of the worst. The only thing worse than trying to make that podcast money is trying to get rich selling books.

Ryan Holiday: [01:21:32] Yes. There’s actually much better money in podcasts right now than there is —

Jordan Harbinger: [01:21:38] Which is not saying a whole lot!

Ryan Holiday: [01:21:40] Right, but it’s like, know you have your job, love your thing, build a parallel track that eventually you can jump onto. It’s like quitting your job to be a blogger. The kind of blogging you have to do to keep from starving is not conducive to the kind of reps you need to get great.

Jordan Harbinger: [01:21:59] That’s a good point. It’s about the quality of the reps and not just making sure that you’ve screwed yourself over so that you have to do it full-time, 14 hours a day blog.

Ryan Holiday: [01:22:07] Yeah, people think there’s something glamorous or you know, sincere about blowing up your life to start —

Jordan Harbinger: [01:22:13] The whole going all-in thing. Oh, that’s a whole different show. “You follow your passion! Go all in! Tell your parents to go screw themselves if they won’t let you become an entrepreneur!” All terrible advice, but probably advice for another time.

Ryan Holiday: [01:22:25] All right.

Jordan Harbinger: [01:22:26] Thank you very — oh, by the way, who chooses the form factor for these books? This is small.

Ryan Holiday: [01:22:28] What do you mean?

Jordan Harbinger: [01:22:29] Who chooses like, “Oh, I want it to be a miniature version of a book!” A snack size.

Ryan Holiday: [01:22:33] So The Obstacle Is the Way, they were like, “Hey, what about this size?” And I held it, and I liked it, and I was like, “That’s great.” And then what we realized was there’s something really powerful about a smaller book that you could read in one sitting. Suddenly you do a 30-minute show and your downloads spike and you’re like, “Oh, you know, that’s how I should do it.” And so it was just a random chance thing, but there’s a very distinct reason now that the three books are the same size, the same length, the same format.

Jordan Harbinger: [01:23:00] They’re going to look good in the box set.

Ryan Holiday: [01:23:02] The box set’s coming next year!

Jordan Harbinger: [01:23:03] I figured as much, that’s good. That’s your best of right there.

Ryan Holiday: [01:23:06] Yeah, it is.

Jordan Harbinger: [01:23:07] All right, Stillness Is the Key, almost said “the Way.”

Ryan Holiday: [01:23:10] I’ll take it.

Jordan Harbinger: [01:23:11] I’m sure that’s happened, also.

Ryan Holiday: [01:23:11] Also true.

Jordan Harbinger: [01:23:12] Stillness Is the Key. It’s easier to find if you get the title right. Much easier to find if you get the title right. Ryan, thank you very much, man!

Ryan Holiday: [01:23:18] Thanks again!

Jordan Harbinger: [01:23:21] Thanks to Ryan for coming out and spending so much time with us. The book is called Stillness Is the Key links to that will be in the show notes. There’s a video of this interview on our YouTube channel at jordanharbinger.com/youtube. And there are worksheets for every episode including this one. So, you can review what you’ve learned here today from Ryan Holiday at jordanharbinger.com in the show notes. We now also have transcripts for each episode and those can be found in the show notes as well.

[01:23:47] We’re teaching you how to connect with great people and manage relationships using systems and tiny habits over at our Six-Minute Networking course, which is free. That’s it jordanharbinger.com/course. Don’t do it later do it. Now. I know you think you’re going to just do it when you have time. You got to dig the well before you get thirsty. Once you need relationships, you’re too late. Procrastination leads to stagnation when it comes to your personal and business relationships. And you know, that’s true because it kind of rhymes. These drills are designed to take just a few minutes per day. This is the stuff. I wish I knew decades ago. It’s not fluff. It is crucial and you can find it all for free from me at jordanharbinger.com/course. By the way, most of the guests here on the show, they subscribe to the course and the newsletter. So, come join us, you’ll be in smart company. Speaking of building relationships, you can always reach out and or follow us on social. I’m at @JordanHarbinger on both Twitter and Instagram.

[01:24:37] This show is created in association with PodcastOne. This episode was produced by Jen Harbinger and Jason DeFillippo and edited by Jase Sanderson, show notes and worksheets are by Robert Fogarty, music by Evan Viola, and I’m your host Jordan Harbinger. Our advice and opinions and those of our guests are their own and yes, I’m a lawyer, but I’m not your lawyer. So do your own research before implementing anything you hear on the show and remember, we rise by lifting others. The fee for the show is that you share it with friends when you find something useful or interesting which should be in every episode. So, please share the show with those you love and even those you don’t. In the meantime, do your best to apply what you hear on the show, so you can live what you listen, and we’ll see you next time.

[01:25:18] A lot of people ask me which shows I listened to and of course Kevin Rose has been a friend of mine for a long time. He has The Kevin Rose Show. He’s been tech investor early in the game and is now thinking about more important stuff like family and psychedelics and meditation and things like that. They’re not trending for the sake of being trendy, but they’re trending because they’re important and recently. You’ve got Tim Ferriss who everyone’s heard of but hasn’t been on a lot recently. What’s he going to drop on your show, Kevin?

Kevin Rose: [01:25:42] Yeah. Well, Tim and I have been doing podcasting even before he had his show, we did a show together called The Random Show where we’d get together and have a couple of beers and just talk about life really like a little bit different than his show and that.

[01:25:55] You know, no one ever gets a chance to interview Tim and he’s such a fascinating dude and has so many odd obsessions that he doesn’t really cover because normally he’s interviewing other people for his show. When we get together, it’s more just like a couple of guys hanging out and having casual conversation about what’s going in our lives and relationships in our life, all kinds of crazy. crazy body experiments, and different hacks that we’re trying because both of us are obsessed with trying these different techniques, whether it be like the cold showers that we do or the continuous glucose monitors or some extreme fasting. So, this episode is going to be packed with all that type of information.

Jordan Harbinger: [01:26:30] You can find that at kevinrose.com. And of course, we will link to that in the show notes as well for this episode. So, you can go directly there and The Kevin Rose Show. If you’re searching in your podcast app and you’ll find them. It’s the big picture of Kevin’s face in the show art. Thanks, Kevin.

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