45: Ryan Holiday | Solving for What You Really Want from Life

Transcript for Ryan Holiday | Solving for What You Really Want from Life (Episode 45)

Ryan Holiday: [00:00:00] You will feel less pressure and less insecure if you just realize that like everybody's winging it, you know, and the people who are pretending that they're not winging it or representing it like it's all been part of a brilliant plan, are either insane or lucky or lying.

Jordan Harbinger: [00:00:19] Welcome to the show. I'm Jordan Harbinger. As always, I'm here with my producer Jason DeFillippo. On this episode we're talking with my good friend Ryan Holiday. He's been on the show before. He's a particularly impressive guy who I've known for a long time and during the time that I've known Ryan, he's authored eight books himself. A ghost wrote another six. He started a family. He worked for some well-known authors and worked directly with the CEO of American Apparel. And did I mention, he did all of this before the age of 30? This is a guy who figured out what he wanted to do and he solved for that. Today we're going to see what Ryan's process for this was actually like. Was it really as simple as figuring out what he wanted to do and then getting after it? I knew there had to be more to this story and so that's what we're going to discuss today on the Jordan Harbinger Show.

[00:01:03] We'll also get into how Ryan figured out what he wanted to do, how you can do the same. We'll be exploring some realistic alternatives to college if that's your bag and we'll discuss ways in which we can make decisions in a more strategic way when it comes to our path in life and in our career. There's a lot of wisdom in this episode. Even if you're settled where you want to be or you think you are. I hope you enjoyed this conversation as much as we did. Don't forget, we've always got worksheets. There's one for this episode as well, so you can make sure you get all the key takeaways here from Ryan Holiday, that link to that worksheet, it's in the show notes at JordanHarbinger.com/podcast. All right, here's Ryan Holiday. So when I asked my fan base, all right, I'm talking with Ryan Holiday.

[00:01:43] You've heard them in a lot of places, you've heard from him before on my shows. What is it that you haven't heard yet? Because everyone's like, “Well, I've read all the books and I have questions about some of that”, but everybody had this kind of meta questions and one that popped up over and over and over and everyone disqualified it -- I know this sounds dumb -- but they want to know, and I want to know, you knew what you wanted so early in your life and that's kind of amazing, right? How old were you when you basically said, “Screw college! I'm going to write books.”

Ryan Holiday: [00:02:14] I was like 19 or 20. I don't, but I wasn't saying, “Screw college, I'm going to write books.” I had a vague sense of where it might be leading, but really it was “Screw college. I'm going to go work for these people who are making books and know more about the industry that I want to be in than anyone at my college.” So I think I actually talked about this in my book, Ego is the Enemy. You want to make sure that you don't look at other people's stories and sort of project a clarity that was not necessarily there because it wasn't. It was not for me. I would actually say I discovered it a little bit later than some writers.

Jordan Harbinger: [00:02:57] That's a great point because I don't know if this is exactly hindsight bias, but it kind of is, right? We look at your story and go, “Man, you know,” here's what it looks like from the outside according to people who listen to the show, and I've been friends with you for awhile and I'll admit it sort of looks like this to me too. If I don't think critically about it. It looks like you went, “All right, I want to be a writer. I'm going to reach out to some other famous writers. I'm going to do some cool trickery and get in there on their radar, and then I'm going to immediately get projected 10 to 15 years ahead of where other people are in terms of connections and start writing books and then immediately knock out a couple of best-sellers…child prodigy, if you will. Right? What you're saying is, “Yeah, that's not exactly what happened. It was just kind of like I realized this college thing might be from me later or might not be from me right now. I have these other opportunities and I'm going to go down that path.” Not exactly like, “Alright, here's my path to 14 bestsellers by 29”, or whatever.

Ryan Holiday: [00:03:59] Well, I think it's two things. So one, the nature of media is to simplify, right? So like people go, “So you always knew you wanted to be a writer, right?” And then it's like, is it easier just to say yes or no? Right? It's like, no, not to give you this long, complicated answer. So that's part of it. And then also, yes, there's this survivorship bias where it's like you hear from the people who said they always wanted to be writers and then some of them turned out to be writers. You don't think about all the people who knew they wanted to be a writer in second grade and now drive a bus somewhere, right? And so I would say that for me there was this sense that I really liked reading and I really liked and admired people who were writers.

[00:04:45] And so I took a number of positive steps just in that direction, right? So it's like, let's say I wanted it to be a record producer. I didn't necessarily know that, but I got a job cleaning a recording studio and thus fell in love with the whole thing. You get yourself in the vicinity of the industry first. And so for me that way, I worked for an author named Tucker Max and then I, through him I met Robert Green who became my mentor as a writer. I met and worked with a number of other writers on top of that. So it was mostly, it was like none of my parents’ friends were writers, right? And so I didn't even really know how that worked as a job. So I just thought if I can make a living or make even a dollar being around these people, whether it's, you know, getting their coffee or you know, typing up their manuscripts for them or something, then that's a step forward and I'll be able to do something with that.

Jordan Harbinger: [00:05:42] And so you just thought any sort of table scrap that falls from Robert Green's table for example, is better than a theoretical college class where I'm maybe learning something about writing or maybe doing an essay about the Great Gatsby again, right?

Ryan Holiday: [00:05:58] Yeah. No it is. I mean it's interesting like most college professors are obligated to write books. It's like sort of part of the tenure track. I remember, because I wrote for the college newspaper, it was like I found out that one of the college professors at my college was like quoted in a Malcolm Gladwell book and I like that was like the extent of the greatness, you know what I mean? And so it was like, well, I mean I could stay here and obviously learn. These are very smart people, but like, “What if I could just send Malcolm Gladwell an email and what if I could just like meet him? Wouldn't that be really cool?” You know, this was 2005-2006, people still posted their email address on their website. There really wasn't a ton of social media like Facebook didn't wasn't even really big.

[00:06:46] It was mostly just for college students at the time. So I was just sort of taking advantage of this sort of democratize moment and going like, “I want to meet all these people whose work I really like, if it doesn't turn into a job, like who cares? Like I just got to meet this person whose book that changed my life, you know?” So you have to take that first step and then it will either turn into something, it'll turn into another step or it won't.

Jordan Harbinger: [00:07:16] Okay. I like this because there aren't a lot of people who just forged their own path. And I want to get rid of that hindsight bias and that survivorship bias, but we still want to maintain here, your path was still particularly deliberate. It wasn't just like, “Yeah, I was sending fan mail randomly to a bunch of authors and then suddenly Robert Green, this really easy to reach super famous author reached out and said, ‘Hey, why don't you work with me closely for years?’” Like that's not what happened either.

Ryan Holiday: [00:07:44] No, yeah, that's the opposite of what happened. I was working for one author, again, in Tucker Max. I was helping him with marketing for his websites and his books and he had a company that basically ran vlogs for other authors and one of those authors was Robert Green, who I was a huge fan of. I think I probably discovered through Tucker, but I was just this enormous fan of, and so through that I ended up, you know, helping Robert with his website. And then we ended up having, the three of us had lunch one day and Robert needed a research assistant and it was like, “Well, I'm a huge fan of your works. I would like to be a writer. I want to learn how to research for books can like -- what do I have to pay you to let me do that for you? -- is basically the conversation, right?

[00:08:33] Right. And then right from, you know, I think my first job for Robert was transcribing interview transcripts for a book that he was working on. So not exactly, you know, it's not like he said, “You will be my protege.” He said, “I need someone to type up these interviews so I don't have to do it.” And I said, “I'll do it.” And then it was in doing that and you know, I think I did the first one, not that great. And he gave me feedback and then the next one was better. And then I think I did better on the next one. And then he had another project that he needed help on. And so even that relationship, you know, wasn't this like foregone conclusion. It starts with, you know, a chance encounter and then it's a slow and steady proving of oneself and it's not like Robert was like, “Okay, now I'm going to reward you by letting you be a writer.”

[00:09:23] I was developed, I was writing every day on my own website and getting better. And then I would sometimes ask him for help and so it's a mix of connections. It's a mix of luck and it's a mix of being very intentional about sort of moving in a direction even if you don't know like the exact GPS coordinates of where you're going.

Jordan Harbinger: [00:09:49] Yeah, of course. And this makes a lot of sense because from the outside it's like a two-step process. Step one, figure out what you want. Step two, go out and get that. So that naturally leads to the question, step one, how do you know what you want? And step two, how do you then go and get that? And as an example, you wanted to read, you wanted to write, you wanted to create something for a living.

[00:10:08] Maybe you sort of thought so and you kind of solved for that in just like in your newest book, Conspiracy, Peter teal wanted to bring down Gawker and he kind of solved for that as well.

Ryan Holiday: [00:10:20] Yeah, no, there's a line in the book from a Greek poet who basically says like, “Life is a struggle in a dark hallway”, and it's that like, you know, like generally where you're supposed to be going, that there's this sort of light very far at the end of the tunnel, but like how far, how long it's going to take, what obstacles you're going to face in that sort of a dark journey. You don't know. And so you want to be moving forward and you're going to be taking chances and risks along the way. But the idea that it's all one evenly mapped out that it's very clear and the three, the hallway is going to be lit up and have like those lighting strips like on an airplane that show you how to get to the emergency exits.

[00:11:07] Like it's no one is going to show you that. And so in some ways, like when I hear people tell me like very certainly what they're going to do, you know, they're like, “I'm going to be a billionaire by the time I'm 36.” I'm like, “I know for a fact that you're not going to be”, like not because I don't like, because I don't think you're talented, but like you would have any chances of you being right are much, much lower than the chances of you being wrong. You know, like you're just ballparking it. Like you can't, no, at least in my opinion. And so I think people need to get comfortable sort of eyeballing it, especially when you're young because there's so much that you just don't know. Like, you don't even know what you're really good at and you don't know how you come off to other people and you don't even know like I didn't even know how the book industry works. So the idea that like at 16 I could have figured this all out. It's just like preposterous.

Jordan Harbinger: [00:12:06 ] Yeah, I think that's a good point. That again, is lost on a lot of folks who are looking back at other people's stories and trying to reverse engineer their path, but without the foresight of knowing where they're going to end up in the first place, which is impossible.

Ryan Holiday: [00:12:20] Yeah, I talk about that a little bit and you go to like, I think people get in trouble even not just looking at other people, but looking at their own successes like in the Ego is the Enemy, I tell a story of Google, like Google sees itself as this company that changed the world and so you know, they've embarked on these, they even call it like moonshots, like these sort of enormous, ground-breaking, world-changing projects. But the truth is like Google started as like a graduate thesis. Gmail was like an internal project inside Google. YouTube was founded by like some random guys to pirate, like SNL videos that Google bought, you know, like a huge percentage of Google's success was like random or something that seemed like it would be one thing and it turned into another thing. So then when they launched like Google Wave and Google, Google+ and Google Glass, they are in some ways believing their own bullshit and then surprised when it didn't work and it's like, “Oh yeah, because you were looking at like a sample size of one rather than really looking at accurately how this thing happened”, and so like the reason I tried to be really sort of humble or in some ways like dismissive of my trajectory early on, like you look at someone like Kanye West and he's like, “Oh, I'm going to be a fashion designer now.”

[00:13:45] And then it like it, you know, fails catastrophically. I think if he'd been a little bit more humble about it, he would have tried it differently and maybe gotten to where he is now with fewer sort of painful bumps along the way. And so you never want to think that you have like the Midas touch where like you think it and then it becomes true because that's not actually how it fucking happened.

Jordan Harbinger: [00:14:09] Right. That's a good point. I think it's really easy for us to look at these types of events and go through, apply bias to it and then try to recreate that path. This episode is sponsored in part by ZipRecruiter. Are you hiring? Of course you are. Posting your position to job sites or in, you know, the classifieds, to put it lightly, waiting and waiting and waiting for the right people to see it. That's a terrible idea. ZipRecruiter learns what you're looking for, identifies people with the right experience and invites them to apply for your job. In fact, 80% of employers who post a job on ZipRecruiter get a quality candidate through the site in just one day. And this sure as heck beats posting it on some other site, having a bunch of people who don't even answer their email randomly send you a resume. I don't even Jason, I think some people who apply for jobs, they don't even want jobs.

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Jordan Harbinger: [00:15:35] Learn more at varidesk.com/forbes, that's V A R I D E S K.com/forbes. What does a way a listener of the Jordan Harbinger Show can -- I always feel weird saying that because it's like my name in the third person, I'm speaking of Ego is the Enemy. I got to work around that some more. How can someone come to find out what exactly he or she wants because it people look at you and go, “Look, he just, he put his finger on it”, and now you're telling us, okay, actually I deliberately stumbled through it, but it wasn't just like shooting around in the dark and there was sort of deferring hypotheses on this or I wouldn't even say hypotheses.

[00:17:36] There's different paths to this that everybody who tried to guess how someone gets anywhere, they always get this wrong. And in fact, when I ask people for their guesses to how you'd gotten to where you are, and these are people that read your work and know your story, they guessed everything from -- Did he sit down one day he's meditating? Did it take three years of journaling? I know he journals a lot. Did he do some Iowasca and then he saw the answer or did he just talk to a lot of older people who had a similar path that he wanted to go down? And so it sounds like, let's say that it wasn't Iowasca meditation or journaling necessarily, but you did gain clarity through doing the work itself.

Ryan Holiday: [00:18:13] Yeah. Well look, I'm not a great person to ask this question to if only because by finding it somewhat early, I had like less trial and error, right? Like if Robert Green for instance, like didn't become a writer until he was 40 so he has like probably a little more experience, let's say like figuring out like going down blind alleys. Like I didn't, I was fortunate in that like I sort of did nail it relatively early, not as early as people might think, but a couple of tests that I think about are, you know, like what is the thing that you just can't stop doing that you are really into? And so for me that was reading, you know, like what's the thing that you, if you're on like a long car ride and you're just like staring out the window, like what are you thinking about?

[00:19:00] What do you find yourself thinking about over and over again? You know, what's the thing you would do for free if you didn't have to worry about money, right? You know, these are good tests. That isn't to say like for instance, like let's say you're like, all I love doing, I love playing video games. Then you're not like, “Oh, then you should become a professional video game player”, right? It's not that simple. Like you might love football, but if you weigh 112 pounds, like you're not going to be a good football player. So it's, “Oh, this is the general area that I'm obsessed with that I'm sort of deeply interested in.” Now let's lay out like what are the jobs or professions or callings that are related to that thing. So like for me, I was really into writing, but writing is a thing that takes a long time to develop.

[00:19:55] So I started on the marketing side of things and the research side of things, working for other authors. So I was again, I was in that arena. I wasn't on the field per se. Like I wasn't, you know, doing it professionally. But I was involved tangentially. And then because of that, I was able to learn a lot. I was able to build up a base of skills and build up a network, build up confidence. And then so when I decided to, you know, try my hand at actually doing it, I was able to.

Jordan Harbinger: [00:20:28] That's a great point. That's a great tip. Get in the arena. I think a lot of people don't really plan for this because it seems like second place or third place, right? They go, “All right, I want to be a radio talk show host.” Cool. You don't go to a Sirius XM satellite radio and go, “Look, I'm really good at this. You should give me my own show.” It doesn't really work that way. You start off with some sort of producer intern who doesn't get paid. If you're lucky, you get a job making poverty wage in Manhattan or wherever the studio is and you get to plan out shows and book things and make sure that food has, or the refrigerator has Monster energy drink and hidden stuff like that. And then after a set of years that show that you're working on and the shows you're working on have you on for two minutes a week because they ask for your opinion, you become part of the storyline and then as you come into your own, if you're working on your own stuff, then maybe they give you a shot at the mic.

[00:21:26] I remember looking at this and thinking one day they hired a bunch of their own production staff to do shows and they got rid of a bunch of shows that were actually quite good. And I remember thinking, this is such a huge mistake. And sure enough, the network did suffer a little bit as a result of those decisions. But I now understand why they did it because people didn't go to work. They're thinking I want to be a producer Lackey for some other show they went there going, “I'm eventually going to end up on the mic.” And they had to eventually give these people their reward. So they ended up offering all these production people, microphone time to do their shows. But this is them getting in the arena. And this is accepted practice in showbiz, radio, theater, things like that. But for some reason when it comes to a lot of other industries writing, especially anything online, there's a real temptation to just go, “Well, I'm going to start from what looks like the bottom, which is I'm going to become an influencer by making YouTube videos or I'm going to start a podcast and become a thought leader.”

[00:22:24] And it's like, “Well, wait a minute. The bottom is somewhere else, but it's getting you in the arena in the right way instead of just you being woefully unprepared by trying your hand at a craft that you're not necessarily ready for.”

Ryan Holiday: [00:22:37] No, I think that's totally right. Or people think, “Oh, I need to go get an advanced degree in this topic which is true for some fields.” Like if you want to be an astrophysicist or a knee surgeon, yes, you have to get a number of qualifications. But I think it's better for most of these other professions. You want to work yourself into a position so when somebody gets sick or when a door opens, you can be the one that they call. And that that's what I tried to do. I mean look in my thing, what I did was I learned how books work from like soup to nuts first, right? Like first I learned how marketing a book works and I learned how building an online platform works. That's what I saw sort of working for Tucker and then working for Robert Green.

[00:23:26] I saw like how you go from an idea all the way to a published book. Like I remember Robert showed me like how they make the index of a book like at the back. So I learned all of these things. So then when I had my first idea for a book, I was less in the dark than most first time authos. And I think ideally that's what you want. Like the last thing, like if you were to start a podcast tomorrow, the last thing you would want to be learning is like how the entire industry of, you know, sort of the spoken word works from the ground up, you know, let alone how online marketing works and online monetization. Like it's hard enough just to make an entertaining show. So ideally you should be doing it from a sort of core competency of knowing like the business and the fundamentals of the medium first rather than trying to do like just to get thrown completely in the deep end.

Jordan Harbinger: [00:24:27] It sounds like this is one of the paths in life where it's actually better for you to start lower than you think you should in a lot of cases because you actually have an advantage going through all of the steps. And I put all of the steps in air quotes because we don't really know what all of the steps are. But when people try to jump in, like you just said, right into the, “Alright, I'm going to be in the limelight and just do this.” There's something to be said for starting and not being afraid and all that stuff. I get that, but it certainly would have been better for me personally if I went, “All right, I'm going to start the show, but I realize I have to learn how to market it and I have to learn how to actively build these skills and I have to learn online product delivery instead of just, I'm going to talk into a microphone and see what happens”, which is what I did for probably the first six or seven years of doing my other show and I developed skills because you can't not whenever you stick with something for that long, but speaking of Robert Green, the time that I turned the corner was on the seven year anniversary of my old show.

[00:25:28] I interviewed Robert Green and he had said, “What took you so long? You know, we've been talking for years. How come this took so long?” And I said, “Oh, I didn't think it was going to be good because I'm new at this.” And he goes, “How long you've been doing this?” I said, “Six or seven years. This will be the seven year anniversary.” And he goes, “Man, you know, I've done a lot of interviews. You're actually pretty good at this.” And that lit me up so much that I thought, “Oh my gosh, if Robert Green thinks that I'm good at this, maybe I should take it more seriously.” So I bought all new equipment. I started to work on my skills as an interviewer and prepare more. And really his words were like, it almost gave me permission and encouragement at the same time to become a professional instead of just a hobbyist that was overly ambitious or overly tenacious, you know, seven years of a hobby.

Ryan Holiday: [00:26:13] He's amazing. And I've had many, many of those conversations with him. I think one of the things that's really dangerous is like we see, you know, like a Mark Zuckerberg or Evan Spiegel is a founder of Snapchat where like their first company is the first company they've ever even worked at. And we think that's the norm. And just to give you a sense of how nodded as the norm. I was just reading like a study, like the average age of a successful Silicon Valley startup founder is like late forties, early fifties. So it's actually their third or fourth go around. They might've had a number of other successful companies where they were the CFO or the CMO or they were a program or an engineer or they work their way up where they were an investor in a bunch of companies. And then it's like after they've sort of accumulated this mastery of all aspects of it, that they have a brilliant idea that they're able to successfully execute on.

[00:27:11] And so in some ways, I think I just started the process. I did started early, but I feel like I'm hitting my stride sort of right, right now as a writer and as a speaker because I've now been writing published books and giving paid talks for about six or seven years. And it was only actually on the book tour for Conspiracy, which came out like two and a half months ago. That and I'd never done that many talks so close together on the same topic that like I stopped even needing to prepare. Like it was like the first time where I was like, “Oh, I really have this.” Like I wasn't nervous. I had it nailed down. I knew what all my beats were. I knew what it was important and it came very naturally to me and it was like, “Oh, I've been working really hard for like six years.

[00:28:00] And that's why this is just paying off. And they've also done studies on this. I read a fascinating book. It's about the class of players who went directly from high school into the NBA. It's a really good book. But he was saying the advantage that these high school players had is that, let's say it takes three or four years in the NBA to just like figure out how professional basketball at that level works. And so if you start those three or four years when you're 18 then you hit your stride at 22 when your body is in like peak condition versus a college graduate who enters the league at 20 or 21 and then doesn't hit their stride until they're 24 or 25 and their body is already starting to peak and go the other direction. And so one benefit to figuring this stuff out early is that you can start the process earlier and hit your stride at a better place in your life. But none of that changes the fact, in my opinion. And I think the evidence supports it that you have to put in a lot of time, way more time than you want to put in to get there.

Jordan Harbinger: [00:29:18 ] That's really good to hear because I think a lot of folks are never sure if they're doing the right thing. And we always feel like whatever path we're on, maybe there's another faster, better path that we should be on. It's kind of just pure FOMO about the journey itself, which I think causes a lot of people problems because if that FOMO gets strong enough, we can actually abandon the path that we're on and try to go to the grass is always greener pathway. Either lose a ton of time or just simply never get where we want to go.

Ryan Holiday: [00:29:50] Well, I mean, so in my case, which then you said, you know that people thought that I knew this early and I started early in that head start. So I started really searching for Robert in 2006 and my first book did not come out until the summer of 2012 so it basically took me six plus years, a minimum of five years, but probably closer to six years to go from, you know, aspiring writer to like paid published author. So I mean that's a long time and that was like a crash course where like I was doing a lot, like I compressed that period into a shorter than typical period.

[00:30:35] I think in some ways. Like I did have advantages and so that should give people an idea that like, “Dude, this is just not going to come as quickly or as easily as you think.” Like I hear people are like, “Oh I'm going to you know, start doing stand up.” You know, and it's like it is going to, “Okay, start”, and then like start talking about it in like five years. Because that's how long it's going to take you to get good at it.

Jordan Harbinger: [00:30:57] Yeah. That's interesting. Why is stand up the skill du jour, have you noticed that? Feel like it's really popular right now.

Ryan Holiday: [00:31:04] Well, I mean I think comedians are truth tellers and that's very sort of scarce these days and it's very admirable. But I would say a huge part of it is that people think it's going to be easy. Like they're like, “Oh they just get up there and talk. I could do that.” So I think they, I think people think it's going to be easy. And James Altucher has been doing, I think now for like a year or two years. Like all he talks about is just like how hard it is, how slowly he's getting better. And he's someone who had a world-class writing background in a world-class sort of speaking backgrounds. So if anyone would have skills that would be easily transferable, it'd be him and it's still hard for him. And he has a lifetime of just experience being a human in the world. What makes you think at like 22 you're going to pick it up in March and then be like pro by August?

Jordan Harbinger: [00:31:55] Yeah, I think because I don't want to wait. I want to be good now because that's where the rewards are, right?

Ryan Holiday: [00:32:01] Right. Well, and Ira Glass has talked about this. He talks about the really hard part is that when you start out, you have good taste or you wouldn't be interested in it, right? Like if you're thinking about comedy, you know who all the best comics are right now. And you know what's funny? The problem is you're not actually good enough to do that. So it's very discouraging. So a lot of people start and maybe they're good the first couple of times and then you sort of enter this valley where you're just not nearly as good as the people you admire, or the things that you like and that just like kicks your ass up and down. Like with writing, I read, you know, hundreds of books by the time I started my first book, I've worked on really great books. I was intimately familiar with, like truly great writing. I mean that didn't make producing even semi-intelligible writing myself any easier, you know, it was still extraordinarily difficult. And that book took me a really long time and I think I only got it part way where it should be. I mean, I had to redo it twice post publication. So then there's things I still to this day regret that are in it. So it's hard. And if you think it's going to be easy, you are, you're not only sorely mistaken. That attitude is going to prevent you most likely from doing what you're trying to do.

Jordan Harbinger: [00:33:25] Yeah, that's interesting. Why do you think it'll prevent us from doing what we're trying to do? Because it's going to be so much harder than we think we'll give up.

Ryan Holiday: [00:33:32] Yeah. You're doing it because you think it's easy. You know what I mean? You're not doing it because you have so much respect for it because it's your call, you know you're doing it because if you're trying to be a professional boxer because you'd think there's a lot of money in it, you know, that's not going to reassure you and you're getting punched in the head. So I think you've got to have really good motivations and thinking that something will be fun or easy or like the road to riches is usually not a particularly like robust motivation.

Jordan Harbinger: [00:34:08] That definitely makes sense. I think a lot of people run into that. I got a message on LinkedIn from a guy said, “Hey, I live in your area. I would love to intern for you.” And I said, “Okay, what do you want to do?” And he said, “Well that's largely up to you,” which was, as you know, it was a mistake because I don't want to manage and figure out what someone's supposed to do. I want them to tell me what value they can add. And so instead of just blowing them off, because I always feel bad about that, because we've all been young and asked for opportunities, I said, “Why do you want to intern for me? You're in Silicon Valley. There's a lot of other things going on that are probably more interesting that standing next to me in my baby room, which has studio gear in it instead of a baby.”

[00:34:45] And he goes, “Well I really want to get into podcasting and vlogging because it sounds really great.” And the more I questioned him on this, I said, “All right, well, why does it sound great? What do you think is involved with this?” And my rule for podcasters is if you think that you would do the show, if you know that you would do the show, even if no one listened, then go ahead and do the show. But if you're secretly harboring any sort of desire for people to listen to the work that you create and have that be even a large number of people or even a medium number of people, let's say more than a few hundred then don't go into podcasting because everyone sort of goes, “Well yeah, but I think if I work hard enough, I'm going to have like a million listeners and it's, ‘Hey, there's a good chance more than a 99% chance, statistically speaking, I think like a 99.8% chance that you will never actually get more than I think what Jason, what's the figure like 109 downloads or something?”

Jason DeFillippo: [00:35:44] Yeah. If you have less than maybe about 200 downloads, that puts you in the bottom 50th percentile. So anything over 200 downloads is kind of like you've made it in the realm of all of the stats of podcasting, which is insane.

Ryan Holiday: [00:35:59] I got an email, I was just going through this because I was looking for a research assistant and I found an email chain from three months ago where someone was like, “Hey, I saw that you were a research assistant, probably for a writer, I really want to be a writer. I love researching, blah, blah, blah, you know, could I be your research assistant, or are there any other authors you could recommend me to who might be needing one?” And so, I like you, I always try to reply. So I said, “Oh, what do you like to research?” And so as I was going back through this chain, I was like, “Oh, this, I'm going to hit this guy back up.” And then I noticed that he just never replied.

[00:36:39] So he sent the email saying he wanted to be a research assistant to me. And then when he got, you know, a response from an author that just required him to explain a little bit about what he actually like researching, you know, he couldn't do it. And so what I tend to find, and I see this with people who want to write books a lot, and it's probably true with podcasts, if people don't want to make or write books, they want to have books. People don't want to be research assistants. They want to have been a research assistant on, you know, some hypothetical journey they've projected out that they're going on. And so yeah, it's like I was already researching the stuff that I was finding in Robert Green's books and reading the source material and in and finding out how he did this before I even met him. And so when he asked me if I wanted to be as research assistant, it was like, “Of course, I would do it for free. I would do it for no one. I can prove that to you.” And that's very different than people who are like, “Oh, I see what you have. Give me some of that.”

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[00:40:05] You're an author with all these books under your belt, the things that you've written for other people. A lot of things have hit the list and so that's what they want and I'm not trying to put those people down because I totally get it. I want to be a bestselling author too. I just really don't know if I want to write a book. And you and I have talked about this at length and I think you were actually quite surprised when I said, “I'm just not going to do this because it's pretty damn tempting to write a book especially when there's a check in front of you.” But I think a lot of these younger guys and gals, they don't have a realistic expectation of what to expect. And that's not entirely their fault. It's called being young and everyone's been afflicted by that at one point or another. What about people who are looking at dropping out of college? This is also very sort of de rigueur and I really, I'm a little nervous about it because I see these videos with these online marketer guys and they're filming themselves in some hallway somewhere. And the guy's like, “Should I stay in college? My parents want me to stay in college”, and then said influencers, like, “No, college is a waste of time. You've got to go and do this and you got to hustle and you got to do that. And you got to the other thing.” And I'm thinking, I don't really know if that's the decision tree. You dropped out of college, is there a mental checklist that you went through before you did that? I mean, I assume you didn't go, “You know what, I'm sitting here in this calculus class, screw this, I'm out. I'll figure it out.” You had a decision tree that was part of your deliberate process of getting what you wanted and getting to where you want it to be.

Ryan Holiday: [00:41:32] Well, I noticed the people that are most flippant about dropping out of college either never went to college or went to a really good college -- and graduated. You know, so as someone who did drop out who that decision was quite agonizing for I try to be not so certain about giving other people advice about whether they should or shouldn't do it. Because I get emailed about like all the time. To me, I guess, I don't like how college has evolved. I don't like that it costs so much damn money and that people are putting themselves into a massive amounts of debt before they've even done anything or even know with certainty like why they're going to college. I think that's very alarming, that being said, if you're already in college and you're thinking about dropping out, my question is always like, first off, are you failing out of college?

[00:42:25] Because if you're failing out of college, that's not the same as dropping out and you absolutely need to figure out why you're failing and prove that you can fix it. Prove it to yourself before you drop out. Because why do you think that the real world is easier than college? Right? It's easier to be a failure. It's actually easier to be a failure in the real world than it is to be in college. So you should be alarmed that you're not getting good grades, right? And then two, what I always say is, “Why are you dropping out of college? Like specifically, why do you need to leave college? Like what are you doing? Like do you drop out on Friday? What are you doing on Monday? If it's I'm reporting for work here or I'm, you know, starting this two-year long, you know, trip through a Nepal or it's, I've got a book deal or something like that, then I think it does make sense.”

[00:43:20] But like, you know, Mark Zuckerberg was well on his way to Facebook taking off by the time he dropped out. He didn't like quit Harvard and then go, “Hah! Let's think about social networking.” And so I think it's really important that you have that viable option first. And if you can't develop it in college, I'd like to hear the reason why.

Jordan Harbinger: [00:43:45] Yeah, that's a really good set of questions. I don't think a lot of people are asking, what does your parents think when you are like, “Hey look, I'm out of college. This isn't for me.”

Ryan Holiday: [00:43:53] They did not think highly of it. We had a number of very unpleasant conversations about it that led to us, let's say, not speaking or having a good relationship for a pretty extended period of time, which was really hard. And like, I think they regret it now obviously and I think they see where they made their mistakes and I see where I, you know, sort of sprung it on them in a way that made it harder for them. So I don't think your parents not liking the idea should really in any way sway you. But what you should have is a somewhat clear path. I mean, you know, Rick Ruben started Def Jam Records in his dorm room at NYU. Why do you need to leave college to start a vlog? I don't understand. Or to be a YouTube star.

Jordan Harbinger: [00:44:46] So you didn't really overcome this, right? It just sort of time went on, your parents were still pissed and then eventually the results spoke for themselves. Is that kind of what happened? Is that kind of how this process ended up healing itself?

Ryan Holiday: [00:44:56] Well, I mean, I don't want to make it seem like they're only okay with it because, you know, it turned out okay. I think it was more like everyone else in their life was like, “What the hell are you people doing?” Like you're being insane. It's not like your kid joined like a cult or you know, chose a life of crime. He’s doing like good things. If he needs to go back to college, he'll go back to college and they sort of realized they were being completely overreacted and taken something personal that really had nothing to do with them. But you know, it took time and then worse, you know, it took time just for wounds to heal, like on both sides. So I mean it's something I think about now having a young kid, like what do I think he should do and what are my expectations and what if he radically discards those expectations. How would I react?

[00:45:52] What I sort of learned from the process is like, “Look, the job of your parents is not to make sure you are happy, but to make sure that you don't die a horrible death. That you don't end up starving under a bridge somewhere. And that's, I think, why they reacted so negatively to it.”

Jordan Harbinger: [00:46:09] Yeah. I can see that. Especially your dad was a police officer, right?

Ryan Holiday: [00:46:13] Yeah, he was. Although I found out later and somewhat hypocritically that he had also dropped out of college.

Jordan Harbinger: [00:46:19] Maybe that's where that fear stems from though. Maybe he regretted that decision.

Ryan Holiday: [00:46:23] Yeah, of course. But you know, it wasn’t he was like, “Hey look, I've been in your shoes.” He was just like, “How could you do that?” You know, let’s say they didn't handle it well in the way that lots of parents don't handle lots of things well. Whether it's someone coming out or someone marrying outside the religion or you know, whatever. Parents are people and they make mistakes like everyone else. That just hurts more when it's your parents.

Jordan Harbinger: [00:46:50] So how did you avoid the pole of that sort of societal slash parental mimetic desire? Yeah. Your parents are pressuring you and you'd already made your decision, but there had to be other people that went, “This is a huge mistake.” How were you so resolute in what you had decided to do? I don't know, you don't strike me as someone who's stubborn. You strike me as somebody who's more measured. Granted I didn't know you when you were 19 but still.

Ryan Holiday: [00:47:16] No, no, I wasn't and to me it wasn't like an interview. I think part of why I was able to do it is that I didn't actually see it as a particularly huge risk, right? I was very scared by it. Actually, that was one of the things I realized when I went to drop out, I mean I'd already made the decision, but had I been smarter, I would've talked to someone at the registrar's office first. She was like, “Oh yeah, you know, you could just take like a semester off and then re-enroll in classes or not re-enroll in classes if that's what you so choose.” She was like, “You'll probably lose your scholarship.” So there was like a real loss there. But I was like, “Oh wait, okay. So if I take this, you know, potentially life-changing set of opportunities and it works out, none of this matters. If it doesn't work out, I have to go back to college and I have to pay for it like a normal person.” That's not so bad, I could navigate that. And so that allowed me to go,

[00:48:12] in fact, in some ways that made, you know, the reaction from my parents hurt a little more, but also easier to deal with. It was like they don't get like they don't see that this isn't such a big deal. And one of my mentors, I was like, “Look, Brian, when I was in college”, he caught some rare contagious disease and he spent a year in the hospital and so it took him five years to graduate and he's like, “Do you know how many people have ever asked me about why it took me five years to graduate from college?” He was like, “Zero. It's like nobody even knows that it happened. Unless I tell them about it.” And I was like, “Oh wait, that's a really good point. If I do this and it doesn't work out for three years, you know, who cares?”

[00:48:57] And actually I read a quote a couple of years ago, I think it was the founder of Angie's List, she had gone to her father and said, “Hey, you know, I'm thinking about starting this company, you know, what do you think?” And she's like, she was saying, “You know, it might not work out and it might take, you know, two years of my life.” And he's like, “You know what the difference between like being 25 and starting over, and 27 and starting over?” And she was like, “No, what?” And he was like, “You're two years older. That's it.” You know, and so that's sort of what I realized, she's risking some time and it had a big potential payout. And so I was okay to do it.

Jordan Harbinger: [00:49:36 ] So now you live on a farm, you had your gig with American Apparel, you write all the time, you help people with their books and things like this. How do you avoid the trap of the grass is always greener. You're doing a lot of great stuff of course. But do you have to remind yourself, “This is the life I want. I want to live on this farm. I want to have my wife and son. I'm not missing out on anything”, because you have a lot of opportunity coming at you all the time or so it would seem. Do you have to constantly remind yourself to stay on track? I mean, I'm not thinking, I'm not saying, “Yeah, every day that goes by you're like, I should leave him and my son and go travel through Europe or something.” But there's always opportunity. How do you stay focused?

Ryan Holiday: [00:50:13] No, that's a good point. Because I think when you're younger you have lots of opportunities, right? But they're just opportunities. It's like I could be an opera singer or I could be a construction worker or I could live in France or I could be a ski bum. You know, there's all these things you could do, but they're all equal in the sense that like no one's asking you if you want to do them. Like there's no like path paved for you to do them. But as you get older and you accomplish things, not only are the people that sort of asking you if you want to take up certain opportunities like, “Oh, do you want to do this? Do you want to do that?” But they're attempting to pay you to do said opportunities, right? So when I'm at home, I'm not like, “Oh, I would love to leave my beautiful place and my family and go on the road for the hell of it.”

[00:51:02] But it's like, “Oh, someone is asking if you want to come to Chicago for one day for $20,000”, that is a different set of temptations. Then like, “Hey, why don't I ditch all this and become a backpacker in Europe?” Right? I'm not as good at navigating it as I'd like to be. I'd probably say yes too often, you know, knowing that I say yes too often, I try to make sure that like I bear the consequences of that less, you know, the people around me try to build routines around it. And then, yeah, I'm trying to work on sort of separating good opportunities from bad opportunities, realizing that you only have so much time on this planet and it might seem like you're selling it for a lot of money, but you know, when you're 80, would you rather have, you know that day or would you rather have $20,000, you know, that set, if you look at it a long enough timeline, the math doesn't seem quite such a no- brainer.

[00:52:03] And so that's just something that I struggle with. It's certainly the definition of a first world problem and I feel very fortunate to have it, but, I do. It's less, is the grass always greener and more like, would it be irresponsible to say no to this? That sort of thing.

Jordan Harbinger: [00:52:21] Oh, that's an interesting reframe. So instead of, is this a good opportunity? If yes, take it because you might be overloaded with those. It's more like, am I a complete dumb ass for foregoing this particular opportunity or check?

Ryan Holiday: [00:52:35] I don't necessarily know if it's a good thing. I'm saying like, because of what I bring to it, I bring a certain like sort of working class mentality to it where it's like, can I justify turning down this much money to go to Ohio? You know, like, isn't that really irresponsible, even the way? Or you know, do you want to work on this project for this like sort of known scumbag? And it's like, “but it's so worth the money”, you know, like it's hard. It's hard. It tests you. I think people who think it's easy to turn down money, have not turned down a lot of money, you know? So you try to be as objective as possible. Do I want to do this or not? But you end up sort of as an adult who is in the real world who has responsibilities and sometimes like some sort of childhood issues of how money and such. You're like, “Am I stupid but it's only one hour of work?” You know, I'm just going to sit at home instead. But you know, is the reward for success that you have to go to Chicago and you don't have a say in it. I don't know.

Jordan Harbinger: [00:53:46 ] So how do you analyze the situation, like an opportunity or a job offer and decide, “this helps me move forward” versus “this does not help me move forward” because I feel like humans aren't automatically strategic. It's a learnable skill. You certainly you're good at it but it's not as simple as going, “Well this fits my income goal this month or so”. There's something else going on here, right? Do you have a system for this or is it just kind of feeling based?

Ryan Holiday: [00:54:09] Do you have a system? Because I just don't, I desperately need one, but I don't have one.

Jordan Harbinger: [00:54:15 ] My system is workaholic can do everything and unless it's physically impossible.

Ryan Holiday: [00:54:20] Yeah, no, that's my default. And that works, until one, you either burn yourself out too. You burn your partner out, or three, you don't have a relationship with your kids or worse that I think for the worst, you know, one of the worst part is that you end up betraying the skill or mastery that you worked so hard to obtain. Like I see lots of really talented authors who don't have any time to write because they're always on the road. And so, and you know, before I sort of judge them for that and now I understand a little bit more where that poll comes from. And so it's something that I wrestle with and it's definitely something that I would not pretend to have a clear answer about or any sort of, you know, admirable discipline about.

Jordan Harbinger: [00:55:13] So how do you decide what you're going to write about then? Because Conspiracy is different than your other books. It was about something completely different, I noticed none of your books are ever about you, which I know that sounds funny, but in today's world everybody's got books that are pretty much only about themselves and yours are not really like that, at least not any more. And even when they were, they also taught other skills.

Ryan Holiday: [00:55:38] I guess that's true. I mean, part of it like, look, I think that book is like five days younger than my son. You know, like it was insane that I even tried to write that book that I squeezed it in, you know, with a five day old at home or whatever. I felt like it was this sort of once in a lifetime opportunity. I mean, I had access to Peter T., all this billionaire, I had access to Nick Dan, who is the founder of Gawker. There were these sort of too mortal enemies who just spent like 10 years and tens of millions of dollars trying to destroy each other. And they were both willing to talk to me and a publisher was willing to publish the book and I felt like I was the only person on the planet that could write it the way that I thought it should be written. I felt like it was crazy to say no. I ended up having to say no to some other things or push other things, certainly to make it happen. But I felt like it was one of those things I would definitely regret not having done.

Jordan Harbinger: [00:56:39 ] Yeah, that makes sense. So it's kind of a part of becoming a more complete writer maybe.

Ryan Holiday: [00:56:45] Yeah. No, it was, I've never written anything like this. Whatever comes out the other side, you know, whether the book sells zero copies or a million copies, it gets made into a movie, you know, wins an award, whatever. I will be a better writer for having tried and succeeded or having tried and failed. And I would like to think I'd be a better person to just for the experience. So yeah, I felt like this was a chance to level up. And you know, my wife was very supportive. My publisher and agent were both very supportive, so I rolled the dice. So the book was I think a gamble in a lot of ways. In some ways the gamble has paid off and in other ways, you know, I think it remains to be seen, but what you said is sort of exactly what I was thinking.

Jordan Harbinger: [00:57:26] On the interviewing for the book, when I was reading Conspiracy, so I was talking with this attorney and he said, first I'm going to do this, and then my second step of the strategy is going to be that, and then this event happened during this and that changed the direction. I'm impressed that he remembered that, but I'm even more impressed that you are able to do such a good interview and such good research with him, that you were able to get such a complete narrative. How do you get that complete amount of information, jog memories about things that happened months or years ago from somebody who's got other things on their plate and then turn it into – this happened, this happened, it's so amazing that these guys, like I said, even impressive that they remember what happened, let alone that you got it out of them.

Ryan Holiday: [00:58:10] Thank you. Thank you. That was like my terror writing the book that I wouldn't be able to do it or I get something like embarrassingly wrong, you know, which so far hasn't been the case. I guess it could change, but I think the first thing I did on the book, and this is kind of something I learned from Robert Creon is like you don't just like start writing and then figure it out. You figure it out first. You do all your research, you have everything outlined, you have everything done before you move forward. And so like before I really interviewed anyone, I read, you know, like 20,000 pages of legal documents. Thankfully this was like, because this was a court case, a huge percentage of this had already been documented in all these different places. And so I was able for the first time to put it on one place, I wrote a like 150 page, 55,000 word timeline of the events.

[00:59:06] Like that alone was just the sort of beat by beat of what happened over like 12 or 13 years of, you know, events on either side of this. That allowed me to then, you know, as I'm sitting as a, maybe you're talking about Charles Harder who is a Tools attorney and Hogan's attorney. You know, I was like, “Okay, on, you know, March 15th of 2014, you filed this briefing that said this, why did you do that? What were you thinking? You know, was it related to X, Y or Z ?” Like, I think if I tried to do the interviews first and then plug it into the timeline, I probably would have gotten a lot of inaccurate information because they would've been pulling from their memory rather than me sort of rooting it in the objective verifiable facts as I could find them.

Jordan Harbinger: [00:59:58] So how do you know when you've got enough information to create what you're going to? Obviously some of that's experience where you go, “All right, I can create a story out of this.” I would never have a clue. I always over-prepare and then just cut things out later. Is that what you do as well?

Ryan Holiday: [01:00:11] Yeah, definitely. You should definitely, like I do all my research on note cards. You definitely should have way more note cards at the end than you need. That's a good sign because it means, that was one of the things I learned from Robert. I'd like find stories for him. You know, I want a story about a black boxer or a Robert Baron or you know, somebody who did this and I'd go find stories and he’d be like, “These are OK. Or this one's good. But I didn't end up using it”, and I was like, “But you paid me to go find it. Like why wouldn't you use it?” And then that to me that was, “Oh, if you're leaving material on the cutting room floor, it means you're making strong judgments and you're having high standards.” And so if you're not leaving some of your prepared materials out, it means you're just including everything, which means you're not being very discerning in my opinion.

[01:01:06] To answer your question, you never know when you have enough or not enough. Because there's no, like, you know, you get to this point and the bell rings and then you know, but like, you know, on my first book I had no idea, on my second book I had slightly more of an idea, third book, you know, and by the eighth book, I've gone through this enough times that I've got at least a little bit of a gut feeling of like, “Okay, I think I'm getting closer, I'm two thirds of the way there or something.”

Jordan Harbinger: [01:01:35] Okay, interesting. So you do have a gut feeling for it based on experience, but killing your darlings is what they call that in show business, right? Where you create something amazing and you're like, “This is going to be great.” And then either you or the editors say, “But there's just no room for it.”

Ryan Holiday: [01:01:49] Yeah, no, that's a line from Stephen King, its -- Kill your darlings. Even if it breaks your heart. -- And so in some ways like you almost seek out the things that you think are your favorites because then the reason you're leaving them in is not because they're great, but because they're great for you and you're not the audience for your work, you know, 90% of the time.

Jordan Harbinger: [01:02:11] Ryan, is there anything else that I haven't asked you where you're like, “I want to make sure I deliver this. I want to make sure everyone knows this.”

Ryan Holiday: [01:02:18] Let's circle back to where we are. It's like you will feel less pressure and less insecure if you just realize that like everybody's winging it, you know, and the people who are who are pretending that they're not winging it are representing it like it's all been part of a brilliant plan, are either insane or lucky or lying. Be okay. Just having a vague sense that you're going in the right way, in the right direction. At least from my experience. That's been plenty.

Jordan Harbinger: [01:02:46 ] Ryan, thank you very much man. Super enlightening and lot of useful advice here for people young and old who are looking at the next step with a little bit of, probably bias based upon other people's narratives or their own expectations. Thank you. All right, Jason, what do you think? You know, he's one of those guys that if you like him, you love him, but if you don't like him, you hate him because he makes you feel bad about what you haven't accomplished in your life. Am I right?

Jason DeFillippo: [01:03:12] Yeah, pretty much. It annoys me that he's done so much before 30, right? Yes. I was introduced with him with Trust me, I'm lying. And I thought it was such an amazing book because it outlined everything that we knew in the blogging world and kind of brought it to light. He's kind of like the pen and teller of marketing, you know, he's like, “Here's the trick and I'm going to show you how we did it.” And from that point on, I've been a huge fan of his, and this book was no different at all because I listened to it in a day because I was so hooked on it, but we didn't even talk about the book that much this time. We just talked about how to get better at the stuff that you do, which I think is fantastic.

Jordan Harbinger: [01:03:50] Yeah. Yeah. I think the book is something that some people will either really love and they'll be like, “Why am I reading this?” And also there's such a great amount of knowledge that Ryan brings to the table. I just didn't really focus on only the book this time around, so we branched off and I don't regret it at all. Great. Big thank you to Ryan. The book title is Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue that'll be linked up in the show notes. If you enjoyed this one, don't forget to thank Ryan on Twitter, that of course his Twitter handle will also be in the show notes at JordanHarbinger.com/podcast. Tweet at me your number one takeaway here from Ryan. I'm @JordanHarbinger on both Twitter and Instagram, and don't forget, if you want to learn how to apply the things that Ryan discussed here today, make sure you go grab the work sheets.

[01:04:34] Those are also in the show notes at JordanHarbinger.com/podcast. We've got an Alexa Skill which gives you a daily flash briefing. Little clips from the show if you want to refresh your memory on a show you've already heard or you want to hear a little tidbit of a show that maybe you haven't caught yet, you can install the Alexa Skill on your Amazon Echo by going to JordanHarbinger.com/alexa and logging in there to Amazon. Or you can poke around on the phone app, the Alexa phone app, and you can search for my name and there it is. You'll find some show clips in the flash briefing every morning. It's kind of cool. Thanks to Doug P for setting that up for us. This episode was produced and edited by Jason DeFillippo. Show notes are by Robert Fogarty, booking back office and last minute miracles by Jen Harbinger and your host, Jordan Harbinger.

[01:05:19] Throw us an iTunes review. Those really help. There are instructions on how to do that at JordanHarbinger.com/subscribe. You're going to need a very unique nickname or it won't let you submit, but when you write something nice, we share it with the whole team. So please go ahead and do that. In addition, share the show with those you love and even those you don't. We've got a lot more like this in the pipeline and we're excited to bring it to you. 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.