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Love Your Work, Episode 31 – Ryan Holiday: Tame the Enemy Inside

June 23 2016 – 07:30am

RyanHoliday 2Our guest today is Ryan Holiday. Ryan is the author of a new book, Ego is the Enemy. How can your ego hold you back in your aspirations, your successes, and in your failures? Ryan covers it all in his book.

As Ryan talks about in the discussion, he sort of wrote this book for himself. Ryan had an unusual amount of success very early in life. He dropped out of college at 19 to apprentice under author Robert Greene. He worked for a Beverly Hills talent agency, advising multiplatinum musicians, and he was the head of marketing at American Apparel by the time he was about 21.

In addition to writing books, Ryan helps other authors market their books. He’s worked with authors like Tucker Max, (who we spoke with on episode 29), Tim Ferriss, and James Altucher.

In this discussion we talk about how to recognize how ego holds you back in all aspects of life and work, and what to do about it. There are lots of helpful thoughts about how to balance your passion projects with your day job, and we also talk about so-called “pageview economics,” something Ryan has a lot of insight into. If you want to know how media works, you should also read his first book, Trust me I’m Lying: Confessions of a Media Manipulator.

If you’ve been wondering: should you make your bed?, find out what a stoic like Ryan thinks.


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Show Notes


[0:00]  Save mental energy saving your word press site with easy to use DI white futures from WP engines managed word press hosting is at for up to four months free. This is love your work. On this show we introduce you to the people and give you the tools to carve out success by your own definition. I’m David Kadavy and I’m a best-selling author and entrepreneur. Every Thursday I love bringing you a new episode in which I dissect a unique path of a guest who clues up and find their calling, how do they cut out the noise to focus and where have they made compromises. Or I bring you lessons I have learned from myself. If this is your first time listening make sure to check out some of our most popular episodes: Jason Freed on episode 1 and there was scientist John [0:51] on episode 8 and Will Rhoder on episode 9. If you like what you hear please subscribe on itunes or where ever you get your podcast and writes your review. Just go to I work really hard to bring this show to you so when you subscribe and review it will help me keep doing that for you. Thanks. I guess today is Ryan Holiday. Ryan is the author of a new book: Ego is the Enemy. How can your ego hold you back from your aspirations, successes and in your failures that covers all in his book. You can buy it at As Ryan talks about in the discussion that he sort of wrote a book for himself. Ryan had an unusual amount of success very early in life. He dropped out of college at 19 [1:34-35] the author Robert Green, he worked for Beverly hills advising multi-platinum musicians and he was the head of marketing at an American apparel by the time he was about 21. In addition to writing books Ryan had some other offers to market their books. He’s worked with others like Tugger Max, who we spoke with on episode 29 and Tim Ferris and James Altarcheur. In this discussion we talk about how to recognize how ego holds us back in all aspects of life and work and what to do about it. There are a lot of helpful thoughts about how to balance your passion projects with your day job and we also talk about so called [2:14] economics something Ryan has a lot of insight into. If you want to know how media works you should check out his first book, trust me I’m lying, confessions of media manipulator you can find that at Here’s the interview:

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Kavady: I’m here with Ryan holiday author of the ego is the enemy. Ryan, what was it that compelled you to write ego is the enemy?

[3:12] Ryan: A lot of things. Really.

[3:12] Is ego is the enemy a personal story?

[3:17] Yeah. No, no. A lot of things compelled me to write the book. A big one was obviously the collapse in American apparel in 2014 in which I had spent a lot of time and energy and I believed a great deal in the company when you watch as in this firm that you watch become a billion dollar company, suddenly is not far from bankruptcy and a mentor of yours is fired by the board of directors. All of a sudden [3:49-50] it makes you wonder what happened. Is this the path that I’m on because it’ something that happened to me and the other bigger motivation because I’ve been thinking of writing this book before all that happened was just a sense of in my own view someone who has become successful relatively earlier in life. The way that success can sort of work with your mind, you tend to start to think that you are special or unique or if this is fate or if this is how it is supposed to be I found that it sort of works your perspective it sucks at your happiness and it prevents you from doing the things that you are good at so a number of factors I was really fascinated with this idea of because everyone who’s successful has to be a total asshole and totally unaware. You know I’m self-aware and maybe I wanted to prove that that’s not true.

[4:50] So it sounds in a way like that you wrote the book for yourself or on yourself.

[4:56] Definitely I think every writer is writing for themselves as it meets the major part of the audience. I tried write about the younger version of myself and then where I think I’m going to be in the near future. Right? So I’m writing for myself so now when I’m writing what I wish I knew a year or 5 years ago. So when I use the word you in the book the word you in the book is referring to something that I’ve personally done. I’m not saying that you suck I’m saying that you suck [5:28-30]. It’s like you are writing [5:33-34] it’s about meditation where he’s writing you and he’s writing to himself. Look I wouldn’t want to compare myself with one of the most intelligent philosophers that ever went but you know he was only writing for himself in a purity that I think is so special and when you write a book which is never intended for publication. Honestly it’s a little bit different than someone who’s really trying to publish my work I have to think about you know I’m honestly [6:06-07] by the audience to a certain degree but I have internalized that style and [6:14] author. If the author isn’t talking to themselves, if the authors don’t consider themselves as a part of the audience [6:22-23] and that’s not particularly pleasurable to read.

[6:26] Right. So what were some of the things that you learned about ego in your lifetime in this process building up this book?

[6:38] Why I think that sometimes there’s a certain amount of survivorship bias inherited or understanding [6:47-48] you watch really successful people with huge egos because we don’t hear about all the people whose egos destroy them [6:56-7:00] so they, that’s a big part of it. And then the other part of it is like someone who has a lot to talk about them because George Marshall is sort of  a hero but [07:08-14] staff during the second world war just to the great humble man. You know after world war 2 he passed on a million dollar offer to write his memoirs so the way we hear about General McArthur or you know other generals the more than marshalls is not because one is more accomplished than the other it’s that in some ways the humility of one makes them less prominent than the other so you really have to dig [7:49] and when you really dig [7:52] the history has followed these fascinating accomplished you know brilliant individuals who just didn’t create the spotlight and just didn’t obsess about their own fantasy the way that the people we do hear about [8:08-11] someone like George marshall ultimately probably accomplished more as a statesman and as a general than anyother person of his generation and I think he was able to do that precisely because he was so selfless and he didn’t create enemies the way a patent might have or a [8:33] might have.

[8:36] And so what are the different ways that ego holds a person back.

[8:43] I think I would say that it holds one back in every single way.

[8:47] Let’s define ego too because I think that there are different understandings of ego.

[8:53] Yeah I mean we start with a certain [8:56] in definition which I don’t think is much super helpful to people. I mean the psychiatric definition is sort of unhealthy obsession with yourself. I use ego more in a colloquial sense so it’s arrogance, superiority and self-obsession and selfishness and delusions of grandeur. So I think that it’s sort of like that definition of pornography, you don’t really know when you see it. Ego is when someone’s being an asshole basically right? That’s what I’m referring. I’m not saying, I think of it as an umbrella to address a lot of destructive traits that are common in the created profession, in politics, in business and stuff. Ego is when confidence turns to arrogance essentially.

[9:56] Alright. And in the book it talks about how ego holds you back in aspirations and in success and there is no other known and in failure as well. So can we go quickly through those?

[10:12] Yeah, I mean the idea is that you are any one of us who’s at either one of those phases at some point in their lives right? At any point in their lives so aspiring to do something where you are dealing with success the one way or the other or you are going through some sort of difficulty or diversity or any one of those junctures ego I see as an unhealthy ingredient to add into the equation in a destructive way. So when you are just starting out in your life trying to you know you are trying to become a writer or you are trying to become a musician or you are trying to start a company ego is a toxic variable that disconnects you from the reality of what you are trying to do and makes it impossible for you to receive feedback that alienates you from other people, that distracts you from the work that you have to do and success is when you can place it. It creates enemies, like litereal enemies for you like competitors, it makes you deluded or makes you paranoid. It makes you micro manage and does all the sort of the things that make maintain [11:22] success more difficult and then when you have experienced difficulty or failure the problem is that ego is the voice that says hey they are screwing you over, it just isn’t you fault.

[11:33] It’s somebody else’s.

[11:35] Or it says it’s totally your fault because you are a loser and you should never would have been successful in the first place or some imposter sending on. Ego is preventing you from turning this negative experience into constructive and positive way. And so the idea is just that whatever you happen do be doing you are not going to detect much from [11:58-12:00].

[12:01] Right and I think about as far as aspirations go there’s this idea of entrepreneurship I feel like there are certain people inspired of success and it becomes a part of their identities, this aspiration and in some ways that holds them back from actually moving forward and trying things and {12:29] themselves.

[12:30] Or they say okay I want to be an entrepreneur or I want to be Elon Musk let’s say and instead of holding on the work that Elon Musk does they say how can I pretend that I’m Elon Musk and so they act like that person, they act as if they have already achieved the thing that they want to achieve so there’s posturing what you call them entrepreneurs. They are acting like, they are posers really right? They are acting like they have done these things. They are reverse engineering what they think the correct pose or approach is instead of saying hey what the work that I need to be doing is? What are the relationships that I need to be doing. What weaknesses do I have like you know the person I inspire to be like you know that solve themselves etc etc.

[13:23] And you know as a put on that I’m a recovering entrepreneur myself but you know the one thing I realized today was you know it’s almost like if somebody picks up a basketball and then they’re like hey look I’m going to play like Michael Jordan now. I think entrepreneurship has a skill set that are these skills that are required to be successful at it but it has something about it which is hard to see that. maybe it’s because people don’t watch it step by step on television or something like that and that makes this nice cozy blanket that you can sit inside that you have inside identity that you have this entrepreneur and you can inspire to be like Steve Jobs or Elon Musk or someone like that witout realizing that how much work actually goes into it.

[14:22] Yeah and it’s probably a little like the iceberg theory. Let’s assume that the top 10% were more involved with the things that are under the surface and you are seeing and you and I saw Steve Jobs with his 8 packs within [14:40] when he was our age you know we did not see Steve Jobs and he was starting his company. You know we didn’t even see Steve Jobs when he was at his worst when he was fired from apple like deservingly so because he was being an asshole. We see what he is able to get away with as the CEO of the world’s most valuable company.

[15:06] It all started in 1976 and you know how long it has been for like really hit their stride like 2006th, 30 years later. Totally and you have not worked relationship the meetings he set through the and the things that he.. he didn’t show up and park in a handicap spot first day you know that’s now how it works. Now that you should have what I think you, here’s what I think people miss [15:32-33] as successful people and they confuse correlation [15:34-36] right? They think that their ego is somehow what has allowed them to be successful instead of the fact that hey, Steve Jobs is so supremely talented and so [15:50] called a handful of technological shifts in the American culture and he was able to get away with being a colossal asshole in doing these things right? And people tolerated it but even as they tolerated they shook their hands as it was necessary and they don’t need to be doing this. Why are you screaming at people you know it’s only making it harder for you. Then we see that with Kanye west, knaye west you must need to be you know insane to be a great rapper and it’s like no how much better would knaye west be  if he didn’t spend his time you know acting like a hero.

[16:32] Right and actually it’s sort of like the success makes it easier to have this extra ego and yeah and then it holds you back and then subsequently in success. I think that’s one of the things that we miss with ego. This person is successful compared to me therefore their ego must not be a problem. What we don’t say because you know you are not in the [17:03] in Kanye west’s negotiating [17:05-09] with the number of successful people I’ve worked with. You know seeing how they want to accomplish certain things but they are often made impediment or achieving that thing. Right? They are the reason you know it’s not, they are the reason that they don’t have the success that they want. Their ego’s what’s preventing them from achieving their own relative goals and I think that’s true for all of us and it’s not that anyone’s without ego. Where ever there is ego there are unnecessary problems and unnecessary difficulties and struggling.

[17:57] As a one time offer, this is something I think about in lying you know the idea of a [17:57-59] in music or something like that but he has a great hit up front and then ego probably in the fight of success feels one into thinking that they can go ahead and repeat that. now in [18:15] now look I saw this my last book was much more successful than I had anticipated it would be but I was very fortunate that I sold this book before that book came out so in some ways you know I don’t have a lot of money on the table, if I waited I wold have sold it for more money but on the high side I only noticed. I was so busy working on this book that I didn’t notice that I had to sit there and go oh this is so amazing you know I’m so special I can’t believe I’m selling it. So that was part of it and you know you experience that sort of [18:56-57] in two words. One: you can be so convinced that you know your first album was amazing that’s because you are amazing and everything you do is amazing and then what you make doesn’t hold up or conversely you make something successful and then you are so intimidated by your own success that it is so egoistically absorbed in a negative way like you are I can never do this ever again and it was luck and bla bla bla. While you should be zero [19:28-29] made why was it so successful? Well because I worked really hard because I poured a lot of creative energy into this project. I put in the time and the relationships, I put them at work and circumstances are lined in such a way that all that was able to [19:49] so luck, essentially. That is the attitude that you want to take from a successful project that ego makes difficult you know with two different you know opposite interpretations none of which is helpful.

[20:03] Yeah this is something I think about a lot as I’m trying to figure out how to write the second book and I have to work back and realize that the first or some blog post got very popular I got a book deal. You have seen [20:17-19] working on now and you know now that I’ve gone public and rift on and showing it to agents and stuff like that really humbled it. This is really some lukewarm reception and so I’m having the like regroup or how to capture that interest with too much fire and I’m glad that I did before you know I could have decided it to be published idea that was resonating with people or something like that.

[20:49] sure I mean the same thing happened to me with this book. The first proposal was rejected, the second proposal was rejected, the third proposal was kind of rejected and then the grudgingly accepted. And then the book itself became radically more different than either of us had anticipated and so you have to have that flexibility to be able to adjust like I mean if you were convinced that the proposal that you made was pure greatness or if I was convinced that what I had made was misunderstood and these idiots didn’t realize what you know they didn’t realize who they are dealing with I would have forced something that ultimately I would have been wrong about right? Like I would have there’s a quote from [21:39-40] one cannot learn that knowledge they already think they know. One can’t get feedback on something they profoundly believe is perfect or one cannot learn if they believe that they are better than everyone else so I think that’s the top situation that we put ourselves with [22:01] created profession that is so dependent on a fluid connection to a feedback and reaction.

[22:12] yeah there’s how ego affects a person in failure or adversity. How do you view that? Is it a bunch of people or idiots that don’t get what you are saying or feedback that you can use?

[22:27] right so we often fail and then we blame other people. Now we don’t think that we have failed now we think that they failed to us so that we can gobble down on whatever we did you know in the first place so that’s how you are so levelling up your failure.

[22:41] it’s another nice comfortable warm blanket that we can wrap ourselves in.

[22:45] sure yeah look at the reason ego exists is comfort really like it’s certainly not adaptive so what if therefore is to put at arm’s length the feelings we would rather not have to feel.

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[24:07] I want to go through some of the ways that you personally have fought ego or counter… You mention in American apparel and I remember hearing in your Tim Faris podcast something kind of like anti-materialism stoic thoughts. I thought that was really interesting because you know if you are materialistic and I think you might have mentioned this in your book that if you’re materialistic it can put you in financial positions where okay now financially I have to do things that are not close to my core in  order to sustain this thing.

[24:44]Yeah totally if you’re… I mean even with my books right like because I have a successful business, I’m able to play the long game with my books where as if I was forced to eat off the revenue for my books, I might have to compromise myself artistically or message wise to be able to sell more in a short term. But I think what happens is people get themselves in a position where they think their material possessions say something about them as a person so having a nice car is central to your identity. Having an impressive house that you know takes people’s breath away is central to your identity. Having your kids in private school is essential to your identity. Any number of these things and then it prevents you from seeing transactions or life choices in an objective way because having that money is necessary to continue this sort of illusion that you’ve created for yourself so you don’t want to walk away from your wall street job to do some other thing that might actually make you happier because you don’t know who you would be if you’re not driving a BMW or because you believe that an apartment has to be X number of square feet or larger or it has to be an X neighborhood or better. You know you are now unable to be as flexible and as fluid in your decisions in the pursuit of goals or objectives because you have to maintain a certain lifestyle or a certain identity and so it makes difficult things even more difficult.

[26:38]And you live out in the country basically outside of Austin correct?

[26:42]Yeah I live about thirty minutes outside of Austin and Austin itself, I know you spent some time there, is not the epicenter of the United States. I sort of see it as a nice mix of a big city and a small city, but because the people who I see every day are not the kind of people that I need to work particularly hard to impress because they don’t really care about what I’m doing and what’s going on. That allows me to focus on my own sort of internal score card, my own internal matrix of what I think is impressive and what I think is important. Like I live on a dirt road. If I drove a fancy car, I would not only not be impressing anyone, I would be being like quite stupid and so it just sort of takes a lot of those things off the table.

[27:33]Yeah and this reminds me of kind of, the antithesis of this being the place where you and I met was in New York.

[27:41]Yeah totally. I mean like we met at a penthouse apartment that’s probably three or four times my mortgage and it wasn’t even close to the nicest apartments that I’ve been in New York. You know what I mean? So there’s one other thing that I found in New York too was you go around, you go to parties. First off there was a constant pressure to be places right? Because there’s so much going on you felt like there’s a lot of fomo. Like if you say no to this to sit in your apartment, you feel like you’re making a poor decision whereas I sat in my living room in Austin last night, I didn’t feel like I was missing out on a party in New York City because it would be silly for me to fly there and go to it right. But I also think it’s… you know when there’s a lot of jaded materialistic people around you and they’re like what do you do for a living and you describe it and then they make you feel… you know they’re judging you. It’s like you’re on a track and a lot of people are zipping around you feel like you subconsciously have to pick up your pace even if you’re quite happy with the pace that you’re at.

[28:57]Yeah and we had a little bit of conversation about mini lives then I think spending a month or two in various places. That strikes me as very relevant to the idea of ego or recognizing one’s ego because living in a place for a period of time helps you get a better sense of who you are as a person. Is that something that you found?

[29:25]Yeah well like I was talking to someone yesterday and he was trying to sell me out going to TED and I was like I just don’t have that much interest in going but he’s like here’s why you go. It’s very expensive. But you will go there and you’re the least successful person there so it’s very humbling and he was like all the things that you’ve done you know pale in comparison to all the things that these other people have done and that sort of puts you in your place a little bit and I know that somewhat contradicts what we just talked about but I would wonder if one of the benefits of the mini life is that you go somewhere where you kind of don’t know anyone, you’re kind of starting from scratch. You’re not just walking around like you’re the king of the neighborhood, you’re walking around in a more open, receptive mindset where you’re… it’s inherently a curious, intake focused mindset rather than the way one might walk around the neighborhood in which they spent their entire lives, that they think that they own and Is a part of them.

[30:28]Yeah and so the various places that you’ve been for a month or two are like New York, New Orleans…

[30:35]I’ve never done like a month. So I spent a year in New York. I spent two years in New Orleans. I spent 5 years in L.A and then I travel and I spent longer periods of time you know I’ll spent two weeks in Miami or I’ll spend three weeks in Europe and on a speaking gig/writing you know etcetera or whatever so I spent a lot of time in different places but I have felt, every time I’ve gone somewhere I’ve had to kind of reinvent my life. Even moving to the city at Austin and then moving to the country, you’re forced to relate to new people and remake your routine in a way that I think is good because it breaks down some of the bad habits that you might have accumulated elsewhere.

[31:26]Right. I want to circle back to your first book because I’ve had a few conversations on my podcast about page view economics and the erosion of focus in culture and how page view economics drives that so maybe you can give us an introduction to page view economics.

[31:52]Well I think people are more familiar with it than maybe they realize. It’s like why do you think, few years ago why was every article broken up into five pages? Or into a slide show? It’s to get you to click more. Why does facebook auto play its videos whereas youtube doesn’t? it is to get you to watch more videos. In a world where the media is advertising supported versus subscriber supported and it is really easy to do design tweaks all of these products are designed to be as addictive as humanly possible. To generate as many clicks as possible and so that’s why every headline is inflammatory, every article is polarized, every image or thumbnail that you see is provocative. The idea is how can we get you to click so we can sell that click to another person in essentially a real time auction. That’s how the media works today and the result I think has been a complete collapse of any political or social or cultural order and it’s very difficult to make sense of.

[33:07]Right and I thought a great observation that you had in there was oh if you are a journalist and you invest in a company, it’s considered unethical for you to write about that company right?

[33:20]It’s a conflict of interest.

[33:21]Conflict of interest. However, a lot of these media companies or maybe all of them, even I’ve heard of friends who are journalists that what I consider to be *unclear* little publications, their performance is evaluated on the number of page views that they’re able to generate.

[33:37]Yeah so that makes, in my opinion, every article that they write a source of conflict of interest. Totally and it’s not as if they’re sell… you know when an author is selling their book on a stand they want you to buy it but that’s a financial exchange that you’re entering willfully. What’s different is, when you see a headline you think oh is that true? And then you don’t realize that the person who wrote it, who positioned it was incentivized to make you click it and there’s zero consequences for you being disappointed once you’ve clicked. You can’t un-click, you can’t unlike. There rule is to steal as much attention from you as they possibly can.

[34:31]Right. Perfect example of this. I was just listening yesterday to a Louis CK podcast interview and he just released his series *unclear* and how its turned sad, oh you know I still haven’t made my money back yet and so everybody, which is ridiculous because there’s no way he could make it back that fast. He had to take debt to make the show and of course all the journalists run with it. Louis CK is broke, Horrace and Pete was a failure etcetera, etcetera and the actual story is just done pretty well and he hasn’t made his money back yet.

[35:09]And what I think is so fascinating about it is all those people, many of them cover entertainment for a living and they know that most entertainment projects do not make money immediately and the entire concept of the entertainment business is that you lose money for the first few years and you make up the money over the long term right.

[35:37]Once it’s streaming on Netflix…

[35:39]Right a single Netflix deal will make him whole on that project from what I’ve heard about it and so you see they’re not… it’s not just that they’re sensationalizing, it’s people who know the actual truth, deliberately presenting things in a misleading or inaccurate way because that’s in their interest. So people are reading things that are genuinely presented as true but are knowingly false because that’s what suits the interest of the people writing it.

[36:12]And look at the way that ego fuels that you know these people are surrounded by the people living the same sort of lifestyle and you know maybe they live in the… go ahead and…

[36:26]Yeah, yeah no look. They’re all… oh did you see business insider got a million pages writing about Louis CK being broke. They’re all competing with each other to get more traffic than each other. It’s all how many followers do we have? How many views did this article get? It’s just competition and no one is thinking the longer game of ‘hey does anyone trust us anymore?’, do we have any actual readers who give a shit about what we’re talking about?

[36:54]Right and you know this is media little bit abstract but on the outside of that is just the sort of existential crisis they might be having. Like oh this is important to my career or gosh I’ve got to pay my $3000 a month studio apartment rent in New York somehow and all these things that create the few of them to continue that.

[37:20]Totally. Jake Dopkin who runs Gothamnet which is one of my favorite New York sites, he’s talked about for a long time just the sheer ego and ridiculousness of the New York Times pretending that they need to do these things to compete with pager journalism when really they could sell their headquarters in Times Square for billions of dollars, move the paper to some less sexy place whether it’s New Jersey or Philadelphia or upstate New York, produce the exact same quality of work that they were famous for funded by their ability to say hey our address does not define who we are as an institution and so even in Austin which I’m sure you saw that the Austin chronicle, no the Austin statesmen is on this beautiful river front property right next to downtown which is worth probably tens of millions of dollars meanwhile the newspaper producers crap to appeal to page view hungry meters on social media, well they could move to the suburbs and avoid all of that. But you know ego is what sticks you there.

[38:34]I mean is there any way out? Seems like this has gotten so out of hand that the economic equation just feels so broken. What’s the solution?

[38:45]I mean I wish I was smart enough to come up with a solution. I don’t know what it is. I think what first has to happen is that audiences have to realize just how manipulative… the people who are doing the manipulation are not suddenly going to wake up and be like hey we’ve got to stop manipulating people. I think audiences have to be the impedance for that change. But look there’s plenty of success stories you think, I read an article recently about the wire cutter you know which is a… the wire cutter did a hundred and fifteen billion dollars in e-commerce transactions last year with like the staff of ten people because instead of supporting their site through advertising they support it through actually recommended products that people like and buy that’s through affiliate links and so there are people who are experimenting with different economic media models but sadly they’re only an exception in the rule.

[39:44]I know this is something that personally I’m starting to… okay there’s a podcast that I listen to, I try to donate to it or subscribe it on New Yorker like I try to… it’s like going to whole foods and buying some healthy food instead of some junk food.

[39:59]Not all calories are created equal and not all calories are equally ethical right and we think we’re starting to realize that about information as well.

[40:11]Yeah I feel like people are starting to wise up a bit. There’s been some backlash I think.

[40:19]Hopefully. Hopefully.

[40:22]Which actually makes me think about your love for books. When I first met you I remember you first looked at me just really sincerely and you said I love books and I can see because you have a huge wall full of books behind you. I’ve seen pictures of it before. That’s something that I’ve thought about a lot myself you know it’s like wait, when you said that I was like oh wait I think I love books too but I haven’t had really been doing something about that. But you know since then I have done more like try to buy books all the time and see it as an investment and such.

[41:00]Yeah I mean look I think books are immune in some ways to the economics that we’re just talking about because they are a transaction between consenting parties and if you read a book and the author let’s you down obviously you don’t have recourse you can’t just get a refund but you don’t buy from that author anymore. You know that guy sucks. If someone bought my book and hated it, they’re not going to be tricked into buying my other books the way that they might be with an article. Also look books are a physical product. A book is designed to stand the test of time. We still read homer, we still read Tricinities you know these are books that have lasted for thousands of years and that’s not to say that what I write is going to last for thousands of years and I don’t know that would be ridiculous to think so but trying to last more than a morning or more than a weekend on social media sharing. I’m trying to make something that lasts for a year or ten years and so I’m less incentivized to take shortcuts or to bend the truth or the facts because it doesn’t suit me.

[42:11]Eaah we are getting really close to the end of our time here so I want to get to some of the rapid fire questions.

[42:18]Let’s do it.

[42:19]What’s the biggest compromise that you had to make to get you where you are today ?

[42:23]I mean look making a book is a never ending series of compromises from the cover to the title to the content right so I feel like traditional publishing has been quite a few compromises for me but ultimately I don’t think I’m giving anything up I think it’s that compromise that’s getting me closer to what I need or want to do anyway if given my own way immediately I wouldn’t have thought of.

[42:51]Right and you’ve used this phrase already I promise this is actually one of my canned questions. When was the time that you left money on the table? And what did you get in return?

[43:04]A lot. I think one of the things, I’m an air bnb rental, I’ll give you this, I’m an air bnb rental and *unclear* but often times it’s an inconvenience to me so I was thinking recently like oh this person wants to pay me this and then I realize that I will then have to drive there then I don’t have access to and it’ll be hugely inconvenient and I did do this calculation which I don’t do enough which is what is an hour of your time worth? Like what is your time worth? And are you making more, in equal or more amount to that time and if you’re not then it’s not usually worth it and I have to think about it a lot you know it’s like hey it would be easier to, it’ll be cheaper if I drove my car there but if I take an uber, I can sit in the back of the car and I can work or I can do a phone call or you know stuff like that. So I try to leave money on the table when it’s… I’m not actually leaving money on the table, it just feels like I’m leaving money on the table.

[44:11]So you have to make a counter-intuitive calculation.

[44:14]Yes. Yes.

[44:15]What was the last book that you read that changed the way you saw something?

[44:19]All the time. I just read this book called Lincoln: an ethical biography, which I loved and you’re from Chicago right?

[44:28]Well I mean that’s where I spent the last eight years or so.

[44:33]Okay well Lincoln’s a fascinating character. This book was talking about how we bend over backwards to deny or pretend that Lincoln wasn’t a politician which is really counter-productive. He’s like look Lincoln was a career politician. That was his job. He just also happened to be an ethical human being who believed in what he believed in and so to me it was like oh wait politics doesn’t have to be dirty and disgusting and awful in fact pragmatism and purpose can *unclear* with each other and it’s exceptions like Lincoln that should sort of urge all of us to a higher standard.

[45:13]Do you make your bed?


[45:17]Do you not want rituals or anything?

[45:19]I’ve heard great things about making it a ritual but I usually just wake up and leave.

[45:24]You know actually I’m surprised very few of the guests are bed makers.

[45:29]It’s very easy in theory to tell people to do it and then I just never do it.

[45:36]Give a final message for our listeners who are looking to carve out success by their own definition.

[45:42]You know no I don’t have any specific advice I would say you know in my life one of the things that has helped, mentors have been very helpful to me sort of building those relationships, attaching myself to people who I wanted to be like and helping them and learning from them and then the other thing is that we sort of lionize passion in our society like you’ve got to pursue your passion and we don’t realize that often times having something that you’re pretty good at but not super passionate about that might be lucrative can help find or make those passionate projects more sustainable so I urge people not to be so close-minded about having a day job or a profession or whatever.

[46:31]Where can people find more of you?

[46:34] or @ryanholiday on twitter.

[46:38]Great. Well there is so much more I wish I could talk to you about right now like for example all those index cards and I know what those are behind you.

[46:47]Oh yeah. Yeah. I was going through my books recently yeah.

[46:51]Yeah but we are out of time and I have to thank you so much for coming on the show and Ego is the Enemy is a great book. Congratulations.

[47:00]This is amazing man. I really appreciate it. We’ll talk soon.

[47:03]Alright thanks.

[47:12]There we have it I hope you enjoyed that episode with Ryan Holiday. You can get his book Ego is the Enemy at . if you enjoyed the conversation, particularly if you enjoyed the part of the conversation about media, about page view economics, you might want to check out my conversation with Neil Real on episode 21. You can also subscribe to my book recommendations mostly the non-fiction on a variety of topics at sign up and you’ll get my first set of recommendations right away and you’ll be supporting the show if you buy any of those books through the links in the email. This has been lovely work and I’m David Kadavy. The theme music for this show is See In You performed by the Albumleaf courtesy of sub pop records. Love your work is a production of Kadavy.

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