#169: Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More

Ryan Holiday (@RyanHoliday https://twitter.com/RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power http://www.amazon.com/exec/obidos/ASIN/0140280197/offsitoftimfe-20, and later served as the director of marketing for American Apparel. His company, Brass Check http://brasscheck.net/, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way http://www.amazon.com/exec/obidos/ASIN/1591846358/offsitoftimfe-20, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy. http://www.amazon.com/exec/obidos/ASIN/1591847818/offsitoftimfe-20 Ryan and I cover a lot in this conversation, including: Meltdowns and how Ryan handles them Workaholics Anonymous -- How it works, what worked for him, what didn't The tipping points for his last book, The Obstacle Is the Way http://www.amazon.com/exec/obidos/ASIN/1591846358/offsitoftimfe-20 External versus internal obstacles Sherman versus Grant leadership and "success" Howard Hughes versus Elon Musk Thinking of "first principles" Enjoy! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast http://www.fourhourworkweek.com/podcast. This podcast is brought to you by Wealthfront https://wealthfront.com/tim. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service led by technologists from places like Apple. It has exploded in popularity in the last two years and now has more than $2.5B under management. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it's all through smarter software instead of retail locations and bloated sales teams. Check out wealthfront.com/tim http://wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they'll show you -- for free -- exactly the portfolio they'd put you in. If you want to just take their advice and do it yourself, you can. Well worth a few minutes to explore: wealthfront.com/tim http://wealthfront.com/tim. This podcast is also brought to you by FreshBooks https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email. FreshBooks is a bookkeeping software, which is used by a ton of the start-ups I advise and many of the contractors I work with. It is the easiest way to send invoices, get paid, track your time, and track your clients. FreshBooks https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email tells you when your clients have viewed your invoices, helps you customize your invoices, track your hours, automatically organize your receipts, have late payment reminders sent automatically and much more. Right now you can get a free month of complete and unrestricted use. https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email You do not need a credit card for the trial. To claim your free month, go to FreshBooks.com/Tim https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email and enter "Tim https://www.freshbooks.com/pages/tim?ref=11864&utm_source=tim-ferriss&utm_medium=podcast&utm_campaign=2016&utm_content=email" in the "how did you hear about us section."

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 0:06Speaker 01

  Can I ask you a personal question?

• 0:08Tim Ferriss?

  Now, what is the appropriate time?

• 0:12Speaker 01

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:21Tim Ferriss?

  This episode is brought to you by Wealthfront, and this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way, set it and forget it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last two years, and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley, have millions of their own money in Wealthfront. So, the question is, why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra-wealthy, but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams, etc. And I'll come back to that in a second.

• 1:03Tim Ferriss?

  I suggest you check out wealthfront.com/tim. Take the risk assessment quiz, which only takes 2 to 5 minutes, and they'll show you for free exactly the portfolio they'd put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or, as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis, but normally aren't. Great investing is a marathon, not a sprint, and little things that you may or may not be familiar with, like automatic tax-loss harvesting, rebalancing your portfolio across more than 10 asset classes, and dividend reinvestment, add up to very large amounts of money over longer periods of time. Wealthfront, as I mentioned, since it's using software instead of retail locations, etc.,

• 1:48Tim Ferriss?

  can offer all of this at low costs that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything, they charge 0.25% per year on assets above the first $15,000, which is managed for free if you use my link, wealthfront.com/tim. That is less than $5 a month to invest a $30,000 account, for instance. Now normally, when I have a sponsor on the show, it's because I use them and recommend them. In this case, it's a little different. I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast, but because of SEC regulations, companies that invest your money are not allowed to use client testimonials. So I couldn't be a user and have them on the podcast. But I've been so impressed by

• 2:33Tim Ferriss?

  Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now, back to the recommendation. As a Tim Ferriss Show listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at wealthfront.com/tim. It's fast, it's free. There's no downside that I can think of.

• 3:02Tim Ferriss?

  This episode is brought to you by FreshBooks. FreshBooks is used by a ton of the startups that I work with or advise. Many of the fastest growing. It is used by almost all of the contractors that I work with. It is the easiest way online to send invoices, get paid, track your time for invoicing, track your clients, so they get to the point of paying you, all that stuff that you could possibly find. And right now, you can get a free month of complete unrestricted use, and you do not need a credit card for the trial. To claim your free month, just go to freshbooks.com/tim and enter "Tim" in the "How did you hear about us?" section. You can, of course, customize it to fit your brand with your own logo and color. And FreshBooks shows you whether or not, for instance, a client has looked at the invoice. They can

• 3:46Tim Ferriss?

  send late payment reminders to your clients automatically, so you do not have to think about it or chase them down. And you can track your hours. You can do all sorts of things. There are mobile applets. You take pictures of your receipts, and FreshBooks will organize them for you later. It is a great piece of software. And if you are in a small business, or maybe a fast-growing business that is feeling growing pains and you need to streamline, then this is a place to look. Because certainly, for me, this has been a headache in the past, and it doesn't have to be a headache for you. So check out freshbooks.com/tim and try it out and see what you think.

• 4:25Tim Ferriss?

  Hello, guten Tag, Gombawa, and amasakenalo for listening. I have many things to share. This is Tim Ferriss and welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers, to tease out the habits, routines, learnings, favorite books, et cetera, that you can use and test in your own life. And this episode features not an athlete, not a politician, but a strategist, a young fellow I've known for quite a long time, Ryan Holiday. And he can be found at Ryan Holiday, that is at Ryan Holiday, on Twitter's and other social. I was going to call this episode Useful Lessons from Workaholics Anonymous: Corporate Implosions and More, or, alternative title, Howard Hughes vs.

• 5:10Tim Ferriss?

  Elon Musk. But in all, it reminded me of a movie that I saw recently, featuring Sandra Bullock, called, I believe it was, Our Brand is Crisis. Ryan has survived and thrived, in some cases suffered, in more crisis management situations than just about anyone his age, I think, at least on a national stage. He is, of course, as I mentioned, a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served at, I believe, age 21 or so, as Director of Marketing for American Apparel. His current company, Brass Check, has advised clients like Google, Taser, and Complex, as well as many prominent bestselling authors.

• 5:55Tim Ferriss?

  Ryan himself has written four books, most recently, The Obstacle is the Way, and actually his brand-new book is Ego is the Enemy. But The Obstacle is the Way was translated into 17 languages and developed a cult following among NFL coaches, all sorts of world-class athletes, TV personalities, political leaders, and others around the world. He lives in a tiny ranch outside Austin, Texas, with his miniature donkeys and a whole collection of random animals, and his wife, and so on. Not saying his wife is an animal, although we're all animals, so that's okay. Ryan and I cover a lot in this conversation, including meltdowns that he has gone through. Since he last was on the podcast, how he handles them, Workaholics Anonymous,

• 6:38Tim Ferriss?

  how it works, what worked for him, what didn't, the tipping points for his last book before Ego's the Enemy, The Obstacle is the Way, why did it become such a cult classic and make its way into the Seahawks and the Patriots and everywhere else? How did that happen? We talk about it. External versus internal obstacles, Sherman versus Grant-style leadership and "success" in quotation marks, Howard Hughes versus Elon Musk, thinking and acting on first principles, and much more. So, please say hi to Ryan when you have a chance on Twitter @RyanHoliday, and I hope you enjoy this conversation as much as I did. Thanks for listening.

• 7:21Tim Ferriss?

  Ryan, good to be chatting.

• 7:23Ryan Holiday?

  Yeah, it's good to be talking.

• 7:24Tim Ferriss?

  It has been a little while since we've done this in the public forum, and I think about you every morning, and there's a very specific reason for that. I went to a hotel recently on the East Coast, and it turns out they provide quotes to people who are checking in, so they'll leave a quote on the bedside table or something like that. And the quote that was on the bedside table, I kept with me and actually taped it to my refrigerator, which is, and you may recognize this, "When jarred unavoidably by circumstance, revert at once to yourself and don't lose the rhythm more than you can help." I think I just lost the rhythm there a little bit. You'll have a better grasp of harmony if you keep going back to it. And of course, that's Marcus Aurelius.

• 8:05Ryan Holiday?

  It's one of my favorites.

• 8:07Tim Ferriss?

  It is a spectacular quote, and it makes me think of your tattoos. And I'm not sure everyone listening is familiar with your tattoos, probably not. So, as it relates to those with maxims, what do you have written on your body?

• 8:26Ryan Holiday?

  So, I just have two, and it's gonna seem somewhat self-indulgent, but I'll say the tattoos came first and the books came second, right? So, I have The Obstacle is the Way tattooed on my left forearm, which was the title of the first book that you and I did together, and that's a derivation of a Marcus Aurelius quote, this idea of "The impediment to action advances action. What stands in the way becomes the way." And then, there's the Zen saying, you know, "The obstacle is the path." And then, in late 2014, I did

• 9:01Ryan Holiday?

  I got the ego is, it just says ego is the enemy. There's no the, but ego is the enemy, which is then became the title of the book. But to me, I think in almost every situation, those two reminders either help calm you down, prevent you from doing something stupid or boneheaded, or sort of give you, I would say like some sort of dose of, the obstacles away for me gives me some sort of optimism that it doesn't really matter what's going on or how bad it is, I can get through it. And I, you know, I look at those when I wake up. I look, I love looking at them when I go swimming, when I go running.

• 9:42Ryan Holiday?

  I, you know, I see them every day and they remind me of those two really important ideas.

• 9:47Tim Ferriss?

  And I guess I haven't, I haven't developed the stomach for the ink just yet on the skin. So I'm settling for the refrigerator. But I was, I'm glad you clarified that the, that the tattoos came first and the books came second because otherwise I was thinking to myself, it'd be, it's going to be great when you have kids and start writing children's books, like with the tattoos that you'll end up on your body.

• 10:12Ryan Holiday?

  Well, it's, it's like, you know, I wrote a book on growth hacking that I'm not going to put that on, I'm not going to put that on my body.

• 10:18Tim Ferriss?

  You're not going to get a, like a tramp stamp with growth hacking on it?

• 10:21Ryan Holiday?

  Yeah, exactly, exactly.

• 10:23Tim Ferriss?

  So the, sorry guys, I've had a lot of tea today, but the, the, the very beginning of ego is the enemy opens up with you witnessing and in a way being involved with the very public implosion of American apparel, right? And then having in effect a meltdown of your own. Can you talk about that and how stoicism figured into that or didn't? Like when the rubber hit the road? I mean, I'd just love to hear you explain the circumstances for people.

• 10:53Ryan Holiday?

  Yeah, yeah, and it's a somewhat tough situation because, as you know, anytime there's millions of dollars involved, there's certain confidentiality agreements and things like that. And I mean, so, I mean, the short of it is, in 2014, Doug Charney, who was my mentor, he was a close friend of mine, was fired by the board of directors at American Apparel. And he did not take that news well, as I imagine most people would not. And it turned into a hostile takeover. It was a very contentious time. And I'd been called in as a consultant to help with the turnaround of the company. And I-- by the board, by

• 11:38Ryan Holiday?

  the board. So, you know, immediately, that put me at odds with someone who I'd been close to for a very long time and looked up to and admired. But at the same time, I was able to see the situation a bit more objectively than he was. So, you know, I didn't view it as a betrayal. I sort of viewed it as a commitment to the company to which I had worked for a very long time and done a lot of work that I was proud of and had a lot of friends and colleagues. And there was great people there. And so, you know, I just finished The Obstacle is the Way had just come out. I was at the end of-- you

• 12:21Ryan Holiday?

  know how it is, after you put out a book, you go on book tour and you're just looking forward to the day where that all ends. Two days after it ended is when I got the call. And so, and so, no. And so, you know, I immediately found myself back living in Los Angeles while my future wife was in Austin. You know, I'm living in an Airbnb. I'm working constantly. I've got another book that I have to-- I basically completely overcommitted myself to what became a total chaotic nightmare of conflict and intrigue and backstabbing and, you know, all the stuff that one would imagine would be going on in a hostile takeover

• 13:06Ryan Holiday?

  of a company where the founder had been unceremoniously ejected. And--

• 13:14Ryan Holiday?

  I don't want to say I had a nervous breakdown, but I very clearly realized my soon enough, I realized that I'd I've always in my life been able to take on more and more stuff. Like every time an opportunity comes up, I've been able to jump on it. And I I'd never felt like, okay, that's overreaching, right? This is when I finally hit that wall and my relationship hit that wall, my sort of personal happiness hit that wall. You know, I was as tense as a human being could possibly be. I wasn't sleeping. You know, the threats are being thrown. So it was just it was just one of the worst periods of my life. And, you know, it forced not only was I dealing with, you know, watching someone

• 13:56Ryan Holiday?

  I'd I'd looked up to behave in these ways that I didn't agree with and and looking at the consequences of some of his behavior and being forced to say, you know, is that is that what I want to be like? Is this the right thing to do? And then also having to look at, you know, this idea of like, why do I keep, you know, unthinkingly plunging myself into situations because I can't say no to money? I can't say no to, you know, the thrill of a of a chaotic situation. You know, I I can't say, hey, that's that's a great opportunity, but it's not for me. And so it just, you know, I hit this complete

• 14:36Ryan Holiday?

  wall. And I eventually ended up, you know, walk walking away, you know, amicably from the board when they decided to go in a different direction before ultimately going back in the other direction. And

• 14:51Tim Ferriss?

  What were the directions that they were thinking about going in?

• 14:54Ryan Holiday?

  So so they, you know, they reconsidered bringing him back on and then they decided against it. And then then ultimately, the company was was forced to declare bankruptcy and is now privately held. And, you know, this was it was a it was a the company was in very dire straits. And the the conflict was ultimately, I don't want to say fatal, but it but it Put it on life support from which it's not clear that it will recover. And I mean, I hope it does, but Dove walked away with nothing. Employees like myself, who had had stock options and had bought shares in the company. We lost everything.

• 15:39Ryan Holiday?

  The board lost their shares. So it was the definition of what became a lose-lose situation, which I talk a little bit about in the book. This idea of when bad stuff happens, ego is what makes us make it worse because we can't step away. Ironically, Dove has now started his own company. And it's interesting to think how different things would have been if he'd done that in 2014. But it was, what I took away from it ultimately, when I finally got back to my actual life, it was like, I carved out a career for myself, which was as a writer, which very few people can do, which I'd always wanted to do, which is what makes me happy.

• 16:22Ryan Holiday?

  And then someone dangled something shiny over here and I jumped into it unthinkingly and in a very real way, risked all of it because I wasn't able to really decide what was important to me and what mattered. And I think a lot of people find themselves in situations like that, where you wake up one day and you're like, what am I doing here?

• 16:49Tim Ferriss?

  I think probably everyone listening has found themselves in that situation multiple times. But I want to go back to you walking away from the board and I guess issuing that resignation or however it came down to it. But that day, there were all these cumulative stresses and we've known each other quite a while. I mean, we both like to kind of step up to bat and take on a lot when we're in these various projects, where we get a very cool opportunity dangled in front of us, or something we think is cool at the time. And was there a, the question I have is, was there a defining moment or conversation or incident, realization, whatever it might have been?

• 17:32Tim Ferriss?

  What was the moment of the day in which the straw was added that broke the camel's back? Where you decided like enough is enough. Okay, I'm going to walk.

• 17:42Ryan Holiday?

  Yeah, so, so, and I'm not sure what I can say. I'll say this. One thing that I, I'm glad I did, and I think I probably learned this from, from, from you and some of the stuff you're talking about. When you negotiate a contract, you want to think about these things in advance, right? You want to know, like, you want to have a ripcord in a contract. Yeah. That says like, hey, if this happens, we're walking away. And you, but you have to be prepared to, to do that. And so I was in a position where, um, you know, when, when we started to have some philosophical disagreements about how things should go, um, I wasn't able to say, hey, I disagree. Um, you know, I was able to say, look, we've, we've already

• 18:22Ryan Holiday?

  addressed this contingency, you know, it's, it's time for my buyout to come into effect, right? Um, so, so I, I, I'm glad I did that. I think, uh, there was a couple moments. Um, you know, it, this I, uh, I believe my computer had been hacked at one point. I was very nervous about that. Um, you know, I, uh, I won't say, it was just, uh, my, my, I was, I'd, I was starting to worry about my own personal security and safety. And it's like, there's nothing in, there's nothing in business that is ever worth that, right? And then there, there was an, it, but if I'm being perfectly honest, it was less about

• 19:04Ryan Holiday?

  the situation and more about who I become when I get drawn into situations like that. Like, I remember one day, I came, I, I, I got to travel back and forth, um, commute back and forth from my home on, on occasion. So I, I was, I was back in Austin and I'd come home and, and I'd, I'd written all these emails on the plane and I was waiting to get to my house so they would all send when I got wifi. And, um, I got home and the internet was down, like Time Warner, which is horrible, wasn't working. And, um, uh, and it wasn't working and I, and I, I was freaking out. Like, I, I had a legitimate panic attack that I couldn't send these totally meaningless emails at like 11:00 PM on a Friday, right?

• 19:47Ryan Holiday?

  And, and, you know, my, like, this is deadly serious to me and my wife is looking at me like I'm an insane person and I, I'm acting like an insane person and I'm, I'm not, I'm taking it out on myself and on her and, and on, you know, The person in front of us when we're driving to go to Starbucks to get internet, you know, like I'm just, I'm behaving like a, an obscene, you know, uh, monster, basically. And, and, you know, after I calmed down, it's like, none of this matters. Like, what am I doing? And so it's like, the situation was chaotic and stressful and I'm, I'm glad that I'm not in it. But it was, what I've learned about myself most of all is, um, I, you know, it's like, look,

• 20:31Ryan Holiday?

  some people can, can drink an unlimited amount and not become an alcoholic. And other people, um, you know, they have one drink and they become somebody totally different. And I'm, I'm that way with stress and chaos. And so I realized in retrospect, like, I'm heading down a very bad road. If I choose stress and chaos over the things that I've worked really hard to achieve in life and that I, I claim to be important to me, you know, like, um, I think, I think a lot of people face that sort of fork in the road. It's like, you know, are you going to choose a life or are you going to choose some career or financial or, you know, sort of, um, you know, accomplishment? And sometimes it works out and sometimes it doesn't.

• 21:16Ryan Holiday?

  And, and I think the wake up call for me was, this is, this is just not the person that I want to be.

• 21:22Tim Ferriss?

  Well, I, I mean, not to, not to throw a really hackneyed cliche out there, but I mean, the, the fork in the road that is, am I, am I working in order to live or am I living in order to work? Right? And how, what does the hierarchy of priorities look like? And for, in your personal journey, I'd like to dig into one, which is the decision not to live in places that you're very familiar with, like LA, you know, very well, San Francisco, New York City. Uh, where do you live at the moment? And what's the story with the two miniature donkeys?

• 21:56Ryan Holiday?

  So I, yeah, I mean, I've lived in, I've lived in New York, I've lived in, in, in Los Angeles for a long time. Now I live right outside Austin. My wife and I, we have a small ranch. I mean, we, we have goats, we have miniature donkeys, we have longhorn cattle, and then like geese and chickens and a dog and stuff like that. And I think what, actually what helped make, to go back to your other question, what helped make this clear is it's like, you know, here I am, living in somebody else's apartment in Los Angeles, and I'm flying home, I, I still lived in the city then, but I'm flying home to Austin. And it's like, this is my life. These are where my books are. This, like, I picked to live in Austin because I loved Austin. And here, this, you know, this job, which is not even my full-time

• 22:38Ryan Holiday?

  job, is just a, you know, this thing is pulling me away from that. And I think that tells me something, you know, right there. But, you know, I remember I would, I would come home, I was looking at my goats one day, they were in the front yard, and they were just sort of standing there.

• 22:53Tim Ferriss?

  I feel like goats do that a lot.

• 22:55Ryan Holiday?

  Yeah, they do. Like, they weren't, they weren't eating, they weren't, you know, headbutting each other, they weren't jumping on stuff, they were just standing there. And I remember thinking like, they're just being goats. Like, they don't have a job. Like, there's nothing that they're supposed to be doing. Like, they're alive, and I take care of them, they have nothing, you know, they're just being alive. And, and that reminded me of something that I'd, I'd read when, you know, in this, all this chaos, I'd actually started attending Workaholics Anonymous meetings when I was in, in Los Angeles. And, you know, they say this thing in the meetings, it's like, that it's human being, not human doing. And it's like, yeah, the goat is just supposed to be alive. And here, I've told myself that

• 23:38Ryan Holiday?

  my job is to, you know, manage this crisis that I didn't create, that it's impossible for me to actually solve, to make other people lots of money. You know, like, is this what I was put on this earth to do, to be a bundle of stress and, and angry, you know, nerves? Like, of, of course not.

• 23:59Tim Ferriss?

  Workaholics Anonymous is not something I have any real familiarity with. And what else helped you from that experience? Or did you take away, or that you remember?

• 24:10Ryan Holiday?

  Yeah, I mean, I took away, I took away a lot. It, this idea that your life can become unmanageable because you, you can't prioritize properly and that, and that you can't, you can't take care of yourself and that you can, I mean, we don't associate, you know, sort of stress and heart attacks and, and all these, you know, and we don't associate those things with work because, you know, work is considered a good thing and we don't see that it can become essentially a drug for people. It, it can become a thing that, like, if you think about it this way, like, let's say, like, you're having a terrible day, you know, all these things are going wrong.

• 24:55Ryan Holiday?

  You know what always goes right? Like, you sitting down at your computer, like, sending emails or, like, reading about, like, work is, if you're good at what you do, work is the most predictable, safe, manageable thing in your life because, like, you control it and a lot more than you control other people or the weather, all these things, right? So, I think for me, I was, I was sort of using it as this, it, I could just plug into it in the way that somebody else might be able to turn on the television and tune out. I could just plug into it. And so, that, it was this sort of an awareness of that. And then, you know, I, I had this awakening, you know, tied to the book, this idea that, like, hey, I'm not building this, like, monument for all time.

• 25:40Ryan Holiday?

  I'm not, like, the world is not revolving around this, you know, ridiculous project that I'm, you know, working on and, and that I don't, I'm the one that's making this feel urgent and essential and more important than anything else. I, I've brought that to the situation. And so, I think that was a big thing I took. The other thing I took is, and I don't think people realize this because they hear workaholism, but they don't realize that it's really the activity that's the addiction. So, there's lots of people who don't work a lot, or maybe they are financially secure so they don't, but you can be an activity addict too. And I certainly picked that up from my family.

• 26:19Ryan Holiday?

  You know, my parents are always doing things like they live in Hawaii, but they're always doing things. And I, I think I internalized that as a young kid. It's like, uh, I can't relax, like I can't stop. And, um, I just, I just realized that that it was that impulse that had gotten me into this situation that I then couldn't figure out how to get out of. And the, the only way to get out of it was to walk away.

• 26:45Tim Ferriss?

  So you walk away. Now, do you still go to work hall ex nonos meetings? And if not, why?

• 26:52Ryan Holiday?

  I found it very hard to relate to a lot of the people in the thing, mostly being young.

• 26:57Tim Ferriss?

  Meaning, meaning you were young, you were younger than they, most of the attendees.

• 27:01Ryan Holiday?

  Yeah, yeah, there, there, I mean, I was 27 at the time. There's not a lot of 27 year olds in work hall ex nonos. There's calls that you can do. Um, I, I, I go to a therapist who sort of specializes in this stuff. And it's also hard, you know, like, I know I just sort of told this harrowing story, but the consequences for me were like very low for all this, right? Like, I didn't destroy my relationship. I didn't, uh, you know, bet all my money on some, you know, ridiculous venture. You know, I, you know, I, I was, I was actually, I was in a great spot. I just committed to too much. So the, it wasn't like I was looking at the wreckage of my life. I was, I was peering over the precipice of what could be the wreckage of my life. So, um, I, I, obviously I read everything I could on the topic.

• 27:46Ryan Holiday?

  And then I tend to, um, I, I go to a therapist now who sort of specializes in this stuff and, and, um, is sort of very familiar with, um, the teachings of that community. So I, I feel like I sort of do it that way. But, you know, to go to your question about, uh, the, the, the decision to move it, to live in Austin, to live outside the city, to run my business and my life a certain way, are in, in a huge part, just eliminating a lot of the temptations and influence that would come from, you know, having an apartment in downtown Manhattan and a bustling marketing firm that is constantly creating fires that I have to put out.

• 28:29Tim Ferriss?

  Yeah, I think that the, the wear of happiness is really under examined. And the tendency for type A personalities, I think I'm guilty of this or have been, and maybe you have at some point, is that. I should be where the maximum number of opportunities are, often very ill-defined or poorly-defined, this like broad opportunity bucket. And then I should have the self-control to stave off all of these impulses with these various temptations, whether it's booze, late nights out, people who end up in New York and have never done cocaine and then end up doing cocaine socially because they work in an investment bank and A, B, C, D, and E happens.

• 29:11Tim Ferriss?

  And I feel like the, you should, that is wasteful in some respects, meaning that if you're smart, you should be able to create opportunities as opposed to being 100% reactive, although there's, maybe that's easier after a certain age. And secondly, that, so you don't suffer from like decision fatigue constantly and then make really bad big decisions, to choose a location where you don't have to constantly protect yourself from impulses to reach out and respond to some shiny distracting object or person or substance.

• 29:54Tim Ferriss?

  And, you know, for me, San Francisco is the right fit. And for you, it sounds like Austin was the right fit. But let's, let's look at, rewind the clocks a little bit and talk about the obstacles of the way. So the obstacles of the way comes out and a few things happen, I mean, many things happen that I think are very interesting. One of them is how quickly it was picked up, or widely, I should say, it was, it was picked up in this, in the professional sports world. And the, there's a big piece in Sports Illustrated about this, but can you talk about the, sort of the, let's, let's start with the Patriots and then maybe you can just give a couple

• 30:36Tim Ferriss?

  of anecdotes about how it spread and then why you think it spread?

• 30:42Ryan Holiday?

  Yeah, it's interesting. You know, The Obstacles of the Way came out almost exactly two years ago, so we would have been recording this a little bit before that. The book came out and it was very much because of the audiobook. The audiobook, I guess people in sports love audiobooks because they travel a lot and their readers are always looking for an edge. But because of, I know it was your podcast and it was also Shane Parrish, who runs Farnham Street. He'd written something about the book. The book got very little media attention, but because of outlets like those two, a couple different people in the sports world picked it up. And one of them was Michael Lombardi, who's a special assistant for the New England Patriots,

• 31:26Ryan Holiday?

  who's formerly the general manager of the Cleveland Browns. And he read the book and he just started giving it to other people. He emailed me a couple of months later, but unbeknownst to me, he'd just given it to other people. And he and I had started talking. I sent him some more books. And then the Patriots ended up, and I'm not taking credit for this in any way, but the Patriots won the Super Bowl that year. And it was just this sort of, it was so amazing for me to be watching the Super Bowl and knowing that some of the people involved in that had read my book. But other than that, it was a total secret, like no one had talked about it, anything.

• 32:05Ryan Holiday?

  And then the following offseason, Mike saw John Snyder, who's the general manager of the Seahawks, who the Patriots had beaten at a tryout, and he recommended the book to him. And so then the Seahawks read it and it went through that organization. And so now, all of a sudden, my book has been read by both teams who were in the previous year's Super Bowl. And from there, it just sort of caught on, not publicly, but by word of mouth. I heard from other players in the NFL, like Garrett Gilkey, who plays for the Bucks. And then it started making its way through baseball, then college sports and basketball,

• 32:47Ryan Holiday?

  Shaka Smart, who became the coach of UT, George Ravling, who was a Hall of Fame coach. He coached at USC. He actually owns Martin Luther King's "I Have a Dream" speech. And now he's the director of basketball for Nike.

• 33:01Tim Ferriss?

  That's got to be a tough one to enforce.

• 33:04Ryan Holiday?

  Yeah.

• 33:05Tim Ferriss?

  Like, do you actually chase people down or are you using the "I have a dream" to like, inspire their students?

• 33:10Ryan Holiday?

  No, no, no, no. Like, he owns, so he, he was a bodyguard for Martin Luther King on the day he gave the "I have a dream" speech on the steps of the Lincoln.

• 33:19Tim Ferriss?

  Oh.

• 33:20Ryan Holiday?

  And when he left, George, there's an amazing article about this, George just asked him if he could have the speech that, um.

• 33:28Tim Ferriss?

  Oh, he owns the original?

• 33:30Ryan Holiday?

  He owns the, the actual day of.

• 33:33Tim Ferriss?

  Oh, wow.

• 33:34Ryan Holiday?

  It's, it's one of the most like, sort of amazing historical, you know, bits of circumstance ever. Um, it's so, and, and he has it in his, in his, I mean, I don't know where he has it, but he has it. Um, and it's so, I mean.

• 33:49Tim Ferriss?

  In his silverware drawer?

• 33:51Ryan Holiday?

  Yeah, right. I, I assume it's, it's framed in under, you know, 10 feet of glass, like the US Constitution. But, um, so it had just made its way through this, through sports, and I started, uh, Arnold, uh, who I know you've had on the podcast, he read it, uh, probably, um, because of your connections with, with people in, in that world.

• 34:09Tim Ferriss?

  That's Mr. Schwarzenegger, if people are wondering which Arnold.

• 34:11Ryan Holiday?

  Mm-hmm. Sorry, not, hey, Arnold. Um, uh, but yeah, so, so it just started making its way through this world, and I started hearing from people, and, and I think, you know, people go out and they try to chase so much media attention, and it's, if something amazing is happening, eventually the media will find out about it, and, and that's what happened. A reporter at Sports Illustrated heard that the Seahawks were reading it, and then we became friends, and then, um, we, we started talking, and eventually he wrote a piece about it, and now it's been used by all sorts of other athletes. And, you know, when I, obviously, you know, when I sat down to write a book about Stoicism, and then when you published my audiobook on Stoicism, I don't think either of us were thinking the target market for this is, is NFL coaches and professional athletes. But in retrospect,

• 34:56Ryan Holiday?

  it makes sort of perfect sense, because the idea of, of having to manage your emotions, to think rationally and clearly, and to make the best of any given situation, and sort of never give up hope, is kind of the definition of Stoicism and the definition of what professional athletics are really about at the highest level.

• 35:15Tim Ferriss?

  Yeah, no, I agree. And I'll give you another story that you have not heard, which is, I was recording a podcast recently, um.

• 35:24Tim Ferriss?

  For the Tim Ferriss Show and the the guest was Chris Sommer, S O M M E R, former national team coach, men's gymnastics. And I asked him about books that he had read recently or was reading that he would recommend. And he had no idea that I knew you. And he started talking about the obstacles of the way. So that's another another feather in the in the cap.

• 35:50Ryan Holiday?

  It's so crazy to me because you know, like you write a book and you want like you can write a book and and lots of books sell well of, you know, somewhat dubious quality, right? And so for me, like as a writer, to know that people who are way more accomplished than me, who have done things that I am aghast at and like so inspired by that it sort of passes their test is like all that like the book could sell zero copies. But if like the 10 people who have reached out to me about it in, you know, at this sort of level that they thought it was good. That's like all that matters to me.

• 36:26Tim Ferriss?

  Well, I think that it also underscores the the the observation that Eric Weinstein is a sort of mathematician and investor. He's managing partner at Thiel Capital and works directly under Peter Thiel, who is the first outside investor in Facebook billionaire several times over co-founder PayPal, etc. Also Palantir. The point being, he made the point to me once that generalized fame is overrated. In fact, it's undesirable on many, many different levels. But selective fame, if you could say pick your 3000 people to be known among, can be very, very useful. And, you know, would you rather be recognized

• 37:11Tim Ferriss?

  by the guy waving the wand and TSA as you walk through? Or would you rather be recognized by everyone in the crowd of TED but no one else? Right? And there are different objectives, not one is not necessarily better than the other. It's like if you're if you're going for the former, you'd need to think very wide and kind of cross demographic, People Magazine, television, extremely popular cable shows, etc. If you're going for the latter.

• 37:39Tim Ferriss?

  You can be very surgical and very strategic in how you set it up. And for anyone who's wondering how this applies to, say, product launches or businesses, I would encourage you to read two things. The first is 1,000 True Fans by Kevin Kelly, which is an essay online. You can read it for free. And then there is also Small Giants. I always want, I always forget if it's Small or Little Giants by Bo Burlingham, about companies that choose to be the best and as opposed to the biggest. But they, each, each of these companies is highly focused on a small demographic. And I think when you do a book launch, you can attempt to target in that way, which I think is worth the effort and planning.

• 38:21Tim Ferriss?

  And identifying maybe the 1,000 true fans or 100 true fans or 10 true fans in highly niche areas where those people are thought leaders, right? In the case of, say, NFL coaches. And then paying attention, like really watching maybe verified accounts on Twitter or whatever it might be for at mentions to see if a seed has been planted somewhere that you can help cultivate, right? In the case of the NFL, for instance. Sure. And it's like, I've noticed with the podcast, like a handful of NBA players are not, yeah, NBA players are listening to the podcast. And some of them have heard me sort of make jokes in Spanish because I used to live in Argentina.

• 39:02Tim Ferriss?

  And so like, like Ginobili from the Spurs has heard the podcast and he heard the mentíme que me gusta, which is this like lie to me because I like it kind of joke in Argentine Spanish. And you just need to be observant and follow the things. But if we're looking at observation, learning, why, why ego? I mean, yes, there are components of examining the ego in Stoicism, for instance. But why did you decide to write about ego? And I think also this, this is probably among many people listening, they will have mixed feelings about that term, right?

• 39:47Tim Ferriss?

  They will feel like it's not 100% negative, nor 100% positive. Why did you decide or how did you come to end up writing about this?

• 39:57Ryan Holiday?

  Well, sure. I mean, look, just I think a very accessible answer or way to answer that, what you were just talking about, the sort of difference between going huge or going smaller and influential and then knowing that you grow from there. I think one of those approaches is probably driven by ego and the other is driven by sort of a colder rationality and a more sort of purpose-driven approach. So, you know, it's when I hear someone's like, oh, I want to sell a million copies. You're like, why a million? And it turns out that they just pulled that number out of their ass or, you know, they heard that their friend sold 500,000 and they want to do twice as much, right? So it's very easy to be motivated by vanity or ego, but it takes discipline and purpose

• 40:41Ryan Holiday?

  to know, okay, these are the thousand true people that matter to me and that's what's important. And so, I mean, part of it just came out of my experience, you know, working with, in the marketing front and working with companies and brands, seeing how often ego makes people act in their own, against their own interests, sort of to do destructive, negative or inexplicable things. And so, you know, seeing American Apparel collapse, that sort of brought me closer to this idea, you know, seeing, you know, people I looked up to and admired, you know, ruin things that they built or ruin relationships that mattered to them. These are, these are me sort of, you know, over time, experiencing some of the difficulties of ego.

• 41:26Ryan Holiday?

  When I sat down to write the book, I guess I was thinking, okay, if, if the obstacle is the way is about external obstacles, which we all face, ego is the enemy is about what I would call our, our biggest internal obstacle, which is, you know, our ego, the, the way in which our pride and vanity and self-absorption and delusions and, you know, need for control and greed and all these other things that we know about. The way those things prevent us from accomplishing what we want to accomplish or hollowing out what we do accomplish or, you know, making a difficult period in our life even more difficult, I sort of, I'm not saying, I'm not

• 42:07Ryan Holiday?

  Talking about ego in the Freudian sense, or you know, some complicated psychological definition. Ego, we know ego when we see it. It's, you know, Bill Walsh, another great football coach. He said it's, you know, it's, it's, it's when your ego gets bigger than your ears. That's the problem when you can't hear the things around you. Cyril Connolly saying, you know, ego sucks us down like the law of gravity. I think we know how ego has ruined people around us. And we know when we've done egotistical things that have caused problems in us in our life. It's, it's that that I'm talking about, not some general notion of the ego. That's the problem, if that, if that makes sense.

• 42:49Tim Ferriss?

  So if I were trying to then just wrap my head around it, is, is ego? How much of ego, as discussed in the book, is trying to build or conform to an image that you hope others have of you? I mean, it's sort of like an image reputational driven issue.

• 43:16Ryan Holiday?

  I think, I think it's a, it's a, it's a huge part. It's, it's this idea of needing to be, needing to be what you've always wanted to be, needing to be what other people, what you want. It's, it's, it's needing to be the, the number one, the center of attention. You know, it's that, I guess it's that sort of like petulant child that, that needs to get their own way over anything else. Or, you know, it's like, I've got to get, I've got to get all the credit. I've got to get all the attention. I need people to know how smart I am. I need, I need to be in control and, and sort of seeing every, not being able to see

• 43:58Ryan Holiday?

  anything bigger than yourself is probably a decent definition of, of where ego becomes a real problem. And so that starts to distort the react. Like, here's another way to look at it. Creativity and sort of doing great things, I think we both know, requires a real.

• 44:17Ryan Holiday?

  A real connection to reality, right? Like, if you can't, there's an Epictetus quote where he says, "One cannot learn that which they think they already know." So if ego has told you, "You know everything," all of a sudden, it's impossible for you to learn. Or if you think the thing you made is the greatest thing ever done, now, all of a sudden, you're not able to sense from the audience where the improvements need to come, or what changes need to be made, or to make sort of realistic assumptions about, you know, your chances of success. These are the way I think ego becomes this kind of haze that prevents us from connecting to the reality that's so important to doing great work.

• 44:57Ryan Holiday?

  I'm not saying you can't be ambitious, or optimistic, or, you know, driven by ideals, but it also has to be rooted in reality if you hope to accomplish any of those things.

• 45:09Tim Ferriss?

  Let's talk about, because I think the ego pornography integrity, or lack thereof, they're perhaps most easily illustrated and defined with examples.

• 45:22Ryan Holiday?

  Sure.

• 45:23Tim Ferriss?

  So let's talk about one from the book, which is Sherman versus Grant. Could you give us some context and explain that story?

• 45:34Ryan Holiday?

  Sure. So one of my heroes is William Tecumseh Sherman. He was a general in the Civil War. He sort of has this reputation as being the guy who destroyed the South. In a sense, he did. He's actually probably the greatest strategic mind to ever wear a United States military uniform. I think, you know, you compare someone like Sherman to a Napoleon. Napoleon is someone who sort of always believed that he was destined for greatness, that he was the greatest thing that ever walked the earth, he was deserving of being a dictator, right? You compare that to someone like Sherman, who later in his life, after the Civil War, was famous for declining the presidency. He was like, "If nominated, I will not run. If elected, I will not serve."

• 46:17Ryan Holiday?

  So he is sort of this opposite of what we think of when it comes to the military. He was, you know, he started very, he started very young. He was sort of constantly underestimated. He was- Sent in all these backwater postings, sort of, you know, by the time the Civil War broke out, it was like his career was essentially over and he was, he was, he'd not been successful. Nobody knew who he was. And it was only in the Civil War and this sort of immense trial that, that he showed himself to be this strategic genius and he sort of earned his place at the, the top of the heap. And there's this wonderful quote from, from one of my favorite biographers. His name is B. H. Liddell Hart. I talk about him a little bit in Ego, but he's this, this brilliant writer. He's a World War I hero.

• 47:01Ryan Holiday?

  And he, he talks about, actually I have it. He says, he's sort of the difference, he's like, he's saying there's the difference between the kind of people who are, you know, utterly confident about the things they're going to achieve in life and the other people who sort of, whose image is a, is a slow accumulation based on achievement. And, and who, he says, like, the last type, their own success is a constant surprise and therefore like the fruits are more delicious. And then he says, you know, in that is poise and not pose. And so I think we tend to think ego is this like braggadocio and boldness and whatever. And we, we sort of discount the problems that that has. And what I like

• 47:46Ryan Holiday?

  about someone like Sherman is that it was, his sense of himself is growing confidence when he decides to, to do this March to the Sea, which was in many ways a counter to a lot of military theory at the time. He's abandoning his supply lines. His, he's not doing that based on ego. He's doing it based on confidence which he earned. He earned it based on his actual performance, the, the work that he put in, the knowledge that he built over time. And then the other story I tell in the book related to Sherman and Grant. So at the, at the end of the Civil War, Grant, who's also a hero of mine, Sherman and Grant are basically the two most famous men in America. They're war heroes. They've led armies of millions of men. At the end

• 48:30Ryan Holiday?

  of the war, Sherman continues to be a soldier. He serves for a few more years and then he retires, basically, in what amounts to happiness. And Grant, who did not know politics at all, in fact, was a good general because he was so bad at politics, decides to run for president. He's elected in a landslide and then serves two of probably the worst terms in US presidential history. He was surrounded by corruption because he wasn't good at sussing people out that way. Reconstruction stalls. He's just a bad president, and I say that as someone who admires him. He's a bad president. He leaves the presidency

• 49:13Ryan Holiday?

  and then he opens a financial brokerage with his son and a partner. That partner turns out to be like the Bernie Madoff of his day. And he loses all his money. He ends up having to essentially put up his war mementos to earn money to pay off the investors. And then he writes his memoirs as he's dying of cancer to leave his family something to live on. And there's this letter from Sherman to someone. Sherman is saying, Grant was this great hero, and yet he pursued these things that he had no skills in, being the

• 49:52Ryan Holiday?

  president. And then Sherman is saying, he tried to make money to impress people who would have given all the money in the world to have won one of Grant's battles. And that really hit home to me because I'd just gone through this stuff in my life. It's like, wait, he'd done this miraculous thing, but because he couldn't understand how impressive it was, and he had this endless need to impress other people, he ended up losing everything to impress people who were already impressed with him. And to me, I think that's such a great example of where ego can take us. It takes us so far past our capabilities

• 50:34Ryan Holiday?

  and our needs because it's insatiable. And Grant died a painful, sad death.

• 50:43Ryan Holiday?

  At a young age, and I think you have to attribute that ego to part of that.

• 50:47Tim Ferriss?

  Well, it brings a couple of things to mind, and then I have a question for you, which relates to the question, why, right? So we have the characteristics of their respective careers. One, in I think retrospect, clearly more desirable than the other. But what made them different is the question I'm going to come back to. But I guess there are a few observations. There's one, and I might be getting this quote slightly wrong, but I've heard this said, and I'm going to paraphrase it here before, which is, "We work doing things we don't like to get money we don't need to impress people we don't like."

• 51:23Ryan Holiday?

  Yeah.

• 51:24Tim Ferriss?

  And that's kind of the first one, which I think is related to, you know, the engine that drives that disaster is ego. As discussed earlier, a component of which being caring a lot about what other people think. And then the other is actually pulled from, I just pulled up the PDF of some of my line notes, because for those people who don't have the background, I read a very early manuscript of The Ego is the Enemy and went through and really just digested every single line and highlighted things that I found particularly appealing or helpful.

• 52:08Tim Ferriss?

  And one of them was, and I'm going to probably pronounce this incorrectly, but the performance artist Marina Abramovic, I'm guessing, puts it directly,

• 52:15Ryan Holiday?

  Yeah.

• 52:16Tim Ferriss?

  "Quote, if you start believing in your greatness, it is the death of your creativity." End quote. So I think that could be a very much related piece of it.

• 52:25Ryan Holiday?

  Sure. There's a line in Billions, which Brian Koppelman, who's, I think, also on the show,

• 52:31Tim Ferriss?

  Yeah, great show.

• 52:32Ryan Holiday?

  The creator of, yeah, and it's at the end of the season, and the guy's just made this sort of disastrous bet, Axe has, and the therapist is asking him why, and he's like, "When people call you Superman long enough, you start to think that you're Superman." And I think with Grant, it is like, he had just won one of the greatest military victories in history. And this This is why ego is so toxic. He just sort of defied all of the odds. He'd remade the world, literally like changed the course of history with his sheer persistence. And, and, you know, he didn't listen to the doubters. So like, part of doing a great thing is that you are, you are, you know, putting a middle finger up to what everyone else is saying.

• 53:15Ryan Holiday?

  And that it, that works, except for when you're wrong. That's when it leads to disastrous things. So like, I'm sure people were like, you know, like Ulysses, like, don't run for president. Like, you're not good at this. Like, it's not going to end well. Or like, what do you know about Wall Street? Why are you creating a financial firm? You know, and it's that, it's when we bulldoze right over those, those really reasonable questions, because we, we can't say no to things, or we want things too badly. That's where we overreach. We believe in our own greatness, like that quote is saying. That's the death of our, of our connection to the reality, which is what made us good in the first place.

• 53:53Tim Ferriss?

  So the, I was, I was given some advice. I think it was just in the first week or two that the Four Hour Workweek hit the New York Times Bestseller list, 2007, I suppose it must have been. And I was told, you're never, just remember, you're never as good as they say you are, and you're never as bad as they say you are. And so I've, I've repeated that to myself quite a lot in good and bad times, right? And I'm just looking at this marked up PDF again, and you have Demonicus, right? You have a number of quotes, but one is, "Abhor flatterers as you would deceivers; for both if trusted injure those who trust them." And.

• 54:34Ryan Holiday?

  Totally.

• 54:35Tim Ferriss?

  Yeah, there's, there's a, there's a lot to dig into there. But let's talk about someone who is lionized by many people, and perhaps unrightly so. And I should also highlight the point that, and we'll probably get into this, that I think believing you are the greatest and drinking that Kool-Aid, believing your own hype, that doesn't preclude you necessarily from being financially successful. Because I think that many people will say, well, what about this person? What about this other person?

• 55:05Ryan Holiday?

  Sure.

• 55:05Tim Ferriss?

  Who has clearly an enormous ego. I mean, they're on television, talking about how great they are and how brilliant they are constantly. And what I've noticed at least is there is, there's a big difference between financial and career success as subjectively defined by the masses or by any of us. Somebody who has a lot of money and gets seen on TV a lot, for instance, and someone who is even remotely content or pleasant as a human being to themselves and others. And it's been my observation, at least in Silicon Valley, that the people who tend to like bang their chests the most and make the most noise are very rarely the people

• 55:49Tim Ferriss?

  who left alone for 10 minutes to sit with themselves, who are happy with what they see, or can even sit still at all. I mean, they tend to end up being pretty miserable for the most part. But getting ahead of myself, Howard Hughes.

• 56:02Ryan Holiday?

  No, no, no. Look, I think that's a great point, and that's something I've thought about a lot in the book, because people always go like, you know, what about Steve Jobs? Or what about Kanye West? And I think one of the distinctions you have to make is, just because someone is successful to you, that doesn't mean that they have accomplished what they are trying to accomplish or what's important to them. So like, you look at someone like Kanye West, clearly a musical genius, clearly one of the greatest rappers to ever live, he's made amazing work. Like, and then when, you know, his last album came out a few months ago, or I think it's sort of in this weird release thing that he's doing, but, you know, he's admitting that he's like millions of dollars in debt because like this fashion line that he keeps trying to launch like isn't working.

• 56:44Ryan Holiday?

  And I would argue that it's probably because his ego is most out of control there, whereas he put in so many hours previously on his music when he was, you know, aspiring to do this thing as a kid, that he's so talented that it's able to. To compensate for this monstrous ego, right? And so I think in some ways, it's like ego is dangerous when you're aspiring to something, no question. But it's when you're successful and you've built this thing and then you're trying to do your next thing, when you're convinced that everything you do touches to go, everything you touch turns to gold, that's where ego is the most destructive. Cause it's like you're trying to do this other thing.

• 57:28Ryan Holiday?

  You're already rich, famous, you know, talented. You've done this great work, but ego is, is there shutting that door in your face. And that's not as visible to the rest of the public in the way that it is, you know, when we see some young kid implode before they've been able to accomplish what they're trying to accomplish.

• 57:44Tim Ferriss?

  Let's, let's talk about Howard Hughes for a sec. And what is your opinion of Howard Hughes?

• 57:50Ryan Holiday?

  So I think Howard Hughes is a great example of actually what we're just talking about in the sense that, you know, most people who are egotistical, they try something and they fail, right? And then we never hear from them again, sort of they're edited out by the survivorship bias, right? Like, we don't hear from the people that tried to do something and then never made it onto our radar. Howard Hughes is a great example of someone because he had millions, ultimately billions of dollars passing his way through the, the monopoly that his father had created in the oil drilling business. He was able to repeated, repeatedly fail and waste hundreds of billions, and again, ultimately billions of dollars in his own lifetime on these ridiculous.

• 58:33Ryan Holiday?

  I think you could argue, although he was clearly a genius pilot and a, and a wonderful inventor, he was arguably one of the worst businessmen of the 20th century. I mean, he lost tens of millions of dollars in the stock market speculating on stocks. He, he owned RKO Pictures, which had like thousands of, tens of thousands of employees when he bought it and ended with like a couple hundred. He lost, you know, I think something like $20 million in terrible movies with RKO. He, the spruce goose, which he was so famous for in that movie Aviator, he built this huge plane out of, out of wood. Like, it's a, it's a interesting project, but you don't realize like, hey, that was

• 59:17Ryan Holiday?

  a, you know, a $20 million government contract for a plane that was late, that flew one time, and then he stored it in a warehouse for 40 years at a million dollars a year. Right? Like, you don't realize that Howard Hughes, he did all these, he did sort of these Elon Musk-esque projects that were inspiring and bold, and they almost never came to anything. And the only reason he was never really held accountable for any of them is the fact that Hughes Tool Company, which was what his father created, which after his father's death, Howard Hughes literally never stepped foot in ever again, was the, was the cushion from

• 59:58Ryan Holiday?

  which all these preposterously egotistical failures would land upon. And, you know, ultimately, at the end of his life, he had some mental illnesses, but they even trace most of his mental illnesses back to plane and car crashes, which he caused by being reckless, right? So I see him as this sort of cautionary figure, and Elon Musk has actually said that he sees Howard Hughes as a cautionary tale. It's someone who was so incredibly talented and had so much potential, but had very little discipline and order and, and objectivity in his life, and it ultimately ended in a very, very bad place for him.

• 1:00:40Ryan Holiday?

  And, you know, when I read a really great book on Howard Hughes called Howard Hughes: His Life in Madness, I read this right around the time, you know, the American Apparel stuff was happening, and I, it was, it was deeply even uncomfortable for me to read, seeing some of those, those similarities behind this kind of visionary genius on the one hand, but also their own worst enemy on the other, and watching those two forces battle each other.

• 1:01:05Tim Ferriss?

  So, two questions. The first is... Let's just say that you sat down with Howard Hughes. At what point would to to provide him with advice, or he actually wanted to solicit advice from you? And let's just also assume that he is open to that advice, right? So maybe he time traveled, hung out with Steve Jobs and took some LSD. And what advice would you give him? And is there any particular point in time? Or how would you try to correct course?

• 1:01:39Ryan Holiday?

  I don't want to dodge your question, but I would imagine you relate to what I'm going to say. Have you ever, because you've got your people like famous or important or wealthy people will sometimes reach out to authors and invite them to their house or even pay them for like a consulting session where you sort of, they want your advice on some project they're working on.

• 1:02:04Tim Ferriss?

  Sure.

• 1:02:05Ryan Holiday?

  And so I found myself in situations like that. You're called to someone's mansion or their penthouse apartment. You get there and this is someone you've admired, you thought had it together, you're very, you're a fan of their work or you're envious of what they've accomplished. And you get there and they're ranting and I've seen them in these sort of manic fits. They're ranting and raving about these things. It's like, hey, they're obsessed with what some person on a tiny blog said about them or they're convinced that they have to do this thing or they, you know, they're like, I'm doing this project and I want it to be the big, you know, I want it to sell 100

• 1:02:50Ryan Holiday?

  million copies. And you're just like, with all your knowledge, you just know that that thing is impossible, right? And so often you see it's like, man, this person, this person has become so successful. You realize that to give this person the truth would be a kamikaze mission. You would like to tell them what you actually felt or thought or what they, what you thought they needed to know would. implode any chance of you working together. And so I, I see ego doing that. I think you definitely saw that with Howard Hughes. He would be this guy, he would have, he'd be waging the corporate takeover of, you know, TWA and then also writing a, dictating a thousand word memo about how employees shouldn't

• 1:03:34Ryan Holiday?

  look at him in the eye, right? Or that, you know, how no one should touch anything without putting a Kleenex between their hand and the doorknob, you know? He was this person who-

• 1:03:43Tim Ferriss?

  I don't know how you got a hold of my, my prep sheet for guests to my house, but we can talk about that later.

• 1:03:51Ryan Holiday?

  But you know, you know what I mean? You, you get called to, you, you real, it's very sad. You're like, this is, this is in some ways hopeless because like, imagine if Richard Nixon had called you and asked you for advice. You're like, uh, dude, you've really backed yourself into a corner here. Like you, you shouldn't have done any of this. This is insane. And the only, you know, they themselves, just a few years, you know, before or after would have, would, would be able to see that, but they're so caught up in the moment and they're, they, they were, you know, they were similar to how I was when I was, you know, wound way too tight and it way overcommitted. They, they're not able to step back and see what's happening with any measure of, of realism. And I think

• 1:04:35Ryan Holiday?

  that's, that's the kind of thing that happened to someone like Howard Hughes, John Delorean, who's another hero of people. It's like, he ran his own company in the ground and then he, he thought he could try to save it with a $60 million cocaine deal. It's like, this is not, this is not, uh, the rational mind thinking. This is ego in full sway, convincing you that you're untouchable, um, you know, convincing you to do bad, stupid reckless things.

• 1:05:02Tim Ferriss?

  So let's look at then maybe take a different tack. What do you see as the biggest differences between Elon Musk and Howard Hughes? Cause Elon Musk is very good at executing. Um, I've been very fortunate to, to meet him, uh, maybe two times, two or three times briefly, but it seems very highly rational.

• 1:05:25Tim Ferriss?

  And I'm gonna, I'm gonna give also a bit of a tease for one of my, one of the paragraphs that I underlined in Ego's Enemy, which is, it begins as follows, and I'm not trying to, I'm not trying to hand you this as the answer, so feel free, I want to hear other thoughts. But, "A young basketball player named Louis Alcindor Jr., who won three national championships with John Wooden at UCLA, used one word to describe the style of his famous coach: dispassionate." Okay, so, I found Elon to be very dispassionate, but in a confidence inspiring way. And he also has a meticulous, so I guess I'm kind of answering my own question a little bit,

• 1:06:06Tim Ferriss?

  but meticulous attention to detail, which I'm sure Hughes had in some respects, meticulous attention to detail in the same way that Wooden had. So Wooden, I heard a anecdote about him, which went roughly as follows. When he had new recruits to the team, he would sit them down, and he would walk them through how to unlace and lace their shoes.

• 1:06:27Ryan Holiday?

  Sure.

• 1:06:28Tim Ferriss?

  And I don't know if you've heard this story?

• 1:06:30Ryan Holiday?

  I have.

• 1:06:31Tim Ferriss?

  Okay, and the reason being, he said, "If you, if you lace your shoes improperly, you get blisters. Blisters cause shots, missed shots cause games, missed games, or lost games cause seasons," right? And he just had this meticulous attention to detail, even with the unsexy aspects. But what would you say are the biggest differences, otherwise, from, say, Hughes and Musk?

• 1:06:56Ryan Holiday?

  Sure. Well, related to that, another story that I've heard about Elon Musk, and I think it's in that big biography of him, but I read it in a Business Insider article. But it was when he was starting SpaceX, originally, they were thinking they were gonna buy these rockets and then build this sort of rocket company, right? And that's what a, sort of a dispassionate person would be like, "That's the idea, we've got the money, we're jumping into it, let's go, let's go, let's go." And that's that sort of, that manic mindset of, "I'm rich, I'm famous, I'm Elon Musk, I can do whatever I want." But that's not what Elon Musk did. They got quotes on the rockets, and they were incredibly expensive. And Elon Musk did a thinking exercise, which comes from Aristotle, called going to first

• 1:07:39Ryan Holiday?

  principles. And he sort of cautioned the team, he was like, "Look, you guys have got to..." Well, let's actually look at what building a rocket costs. So instead of saying like, hey, this is what these, you know, defense companies would charge for a rocket. What does it cost to make a rocket? And they did the math and it turned out they could make their own rockets for like 10% of the cost of what they could buy them. And so SpaceX really comes from that very simple thinking exercise. And that's obviously what John Wood- John Wooden isn't. There's a story about a football coach. I forget who it is, but you know, he calls the team in and he, it might be Lombardi and he picks up the football. He's got the team gathered and he goes, this men is a football, right?

• 1:08:24Ryan Holiday?

  He's like, these people, they've been playing it their entire lives. And he's like, this is what a football is. That's going to first principles to almost an absurd degree, right? This is how you tie your shoes. And Elon Musk is saying, hey, let's actually do the math on what this company should be and do and what, what we're going to be making and what it costs. Let's not just take other people's premises for granted and let's also not make decisions based on our presuppositions and our emotions. And so I think, you know, not knowing Elon Musk and not knowing a ton about him, I would say one of the things that he's at least done thus far, and who knows, he could blow it all up tomorrow.

• 1:09:06Ryan Holiday?

  He's, he's been very rational and he does these things step by step. And I think, you know, he didn't launch Tesla in this, he like, he even looked at someone like John Delorean and looked at the mistakes that he made and rethought it. And when he launched Tesla, he was learning from that experience rather than needing to make those costly errors himself. So I think that sort of dispassion, that objectivity, that, that willingness to go to first principles is certainly something that is, has made him incredibly successful so far.

• 1:09:42Tim Ferriss?

  And I think the, correct me if I'm wrong, but the bio that has been recommended to me a few times now, which I've not yet read, I'm embarrassed to say, is Elon Musk, Tesla, SpaceX and the Quest for a Fantastic Future by Ashley Vance.

• 1:09:57Ryan Holiday?

  Yes, that's the one I'm thinking of.

• 1:09:58Tim Ferriss?

  So there's a, there's, there are a number of points in.

• 1:10:04Tim Ferriss?

  You're writing across multiple books where you talk about the importance of not only accepting critical feedback, but soliciting critical feedback. Right? I'd like to bring up a term that I mentioned for the first time publicly a few months ago in conversation with Eric Weinstein, which was bigot ear. Right? And the, the, the basic definition of a bigot ear being someone who seeks to profit in some way from calling other people bigots, whether it be sexist, racist, fill in the blank. Right?

• 1:10:47Tim Ferriss?

  Whether that's simply getting attention for themselves, drive, driving clicks to a particular article because that's how they're compensated. Could be any number of things, material or otherwise. But the, the reason I thought having a term like that is important, bigot ear, and, and we may bounce around a little bit in this particular, as it relates to this question, but is that there are people who currently would call themselves or are called social justice warriors, where there's no real negative consequence for hurling these terms around that can cause a lot of damage. Right? And, and you've written an article separately about, I guess it was, help me out here, Fahrenheit 451. And, and it was about protecting everyone's feelings and the problem with trying to protect

• 1:11:32Tim Ferriss?

  everyone's feelings and how that can backfire. And so maybe you could start with the, the, one of the common misremembrances of Fahrenheit 451, which is who actually mandates that the books get burned? How did that start?

• 1:11:48Ryan Holiday?

  Sure. Yeah. I mean, so everyone reads Fahrenheit 451 in high school and, and they think the takeaway is like, oh, firemen are burning books because like a controlling government is asking them to do that. And when, when I read the book again about a year ago, and, and you realize that actually in the, and Captain Beatty, I think is the, is that the name? I'm forgetting, but the, the, the captain, he tells him. No, look, we do this because the public doesn't like to be offended. The public doesn't like to be upset. That's why we ban books. It's not a government mandate. It's a mandate from the people for the government to enforce getting rid of ideas that are unpleasant. And so Fahrenheit 451 takes on this new light.

• 1:12:33Ryan Holiday?

  In that sense, you're realizing that it's the desire not to offend that drives most censorship. Most censorship is not controlling. It's well-meaning. And I think it all stems from this idea that someone, my wife says this, I'll be like, "You're frustrating me." And she's like, "Someone can't frustrate you." Like, you can be frustrated, but no one has the power over you to frustrate you. That's something you have. And that's a very stoic idea. Epictetus, he says, "If someone succeeds in provoking you, the problem is you, not them." He says, "Your mind is complicit in the provocation." And I think- That's a good one. That's a good line.

• 1:13:18Ryan Holiday?

  That's what we have trouble accepting. So like, it's not the person, it's like, "Hey, that's offensive to those other people. Don't say that." It's not those people standing up and saying, "I'm offended." It's us trying to be this sort of thought police, protecting all these other people. And so I think what we've seen, at least media-wise, especially when we're in this environment that's so driven by clicks and traffic, is people see someone else do something that could be interpreted as offensive. So they interpret it as offensive and they write about it, and then they rile other people up. So like, you know, Curt Schilling is a professional baseball player, just got fired by ESPN like two days ago for posting some dumb thing on Facebook that I totally disagree with

• 1:14:02Ryan Holiday?

  and is totally offensive and closed-minded. But it's like, why- Like, he did not say it on television. He said it on his private Facebook page, which he should probably be allowed to do. And also, you know, we live in a world of ISIS and Donald Trump and all these other things. Is this really the target that you want to go after? And so I think, you know, what we're seeing, Ray Bradbury said, there's more than one way to burn a book. It's not just this overt censorship. It's this idea that we need to protect everyone's feelings, be hypersensitive all the time, be pressing the outrage button constantly.

• 1:14:43Ryan Holiday?

  It exhausts people and it makes it, I think ironically, very hard to deal with some actually alarming or offensive or dangerous ideas, you know, out there in the world or, you know, currently running for president or what have you.

• 1:14:59Tim Ferriss?

  No, I agree. And this conversation, just so people don't think we've gone off the reservation into sort of political speak, these are closely related to the individual self-regulation or conditioning using stoicism, for instance, right? I mean, it's just a macro example, but the macro is just a conglomeration of the micro, right? And one of my most popular, most retweeted liked tweets in the last two years was, if you're offended easily, you're a bad resource allocator. It's a waste of energy and attention, which is a greater sin than wasting time.

• 1:15:42Tim Ferriss?

  And so if you're trying to be a good resource allocator, right, and you recognize that your mind is complicit in the provocation if you allow yourself to get upset unnecessarily, excessively, well, two things I would say. The first is that my greatest fear, I was speaking it to a group of students at UCLA a few months ago, and they wanted to talk about artificial intelligence and the dangers and the promises of artificial intelligence, the threats of, say, whether it be ISIS or other types of... types of existential threats towards humankind, right? And my, how I would kind of rank, order them and so on, which I have no credibility for answering,

• 1:16:25Tim Ferriss?

  but I do spend a lot of time around people in Silicon Valley and technologists who do have a good read on these things. And I said, my biggest concern for the US specifically is the existential death of free speech, driven by, among other people, college students who are going on witch hunts.

• 1:16:45Ryan Holiday?

  Sure.

• 1:16:46Tim Ferriss?

  With this very Fahrenheit 451 type mentality where like anyone who, who causes discomfort, anyone who offends, anyone who, God forbid, questions the accusations of racist sexist, fill in the blank, or asks us at least how we are defining these terms should be lynched from a career standpoint, at the very least. And that, that is my biggest fear is that we're slowly going to kind of choke the life out of

• 1:17:21Tim Ferriss?

  free speech and First Amendment in the United States with this like death of paper cuts, where it's not against the law to speak your mind, but it might as well be because the, the public has become so sort of trigger shy and aversive to honest conversation that that is the knee jerk response.

• 1:17:41Ryan Holiday?

  Sure. I mean, like, I think it's like, you know, if someone told you that saying something was illegal, you'd probably still say it, just like you speed or you know, you, you do, you break other tiny laws. But it's like, if someone told you like, hey, if you talk about this subject, everyone on the internet is going to hate you and boycott your things and, and you know, get your clients to fire you and pull your advertisers away, you're like, well, I'm probably not going to say that. I think Scott Adams, he had a great thing because he's always getting in trouble. He was saying it's like.

• 1:18:11Tim Ferriss?

  The creator of Dilbert, for those people who don't recognize it.

• 1:18:15Ryan Holiday?

  He's saying that, you know, being creative is like drilling for oil. Sometimes you miss, sometimes you find it. And he's like, sometimes the, sometimes it catches on fire, you know, and, and we have to be willing for that to happen. And if we're not, if we don't understand that, hey, sometimes smart people say dumb things, you know, sometimes it's much more complicated than the two-minute soundbite, you know, 500-word blog post that you read. Sometimes, you know, people are deliberately misleading you. I remember all these people that were super mad at, you know, remember a few years ago, Cheryl Sherrod, who was, you know, an African-American woman who'd supposedly been caught saying

• 1:18:57Ryan Holiday?

  something racist, and Breitbart posted a video, and then she was fired, like personally by the president. And then it turned out that the video had been, like, you know, misleadingly edited.

• 1:19:07Tim Ferriss?

  Yeah.

• 1:19:07Ryan Holiday?

  Or Whole Foods just got in trouble last week here in Austin because someone accused them of, of, of, you know, writing a gay slur on a, on a cake for a gay wedding. And then the security footage so far has revealed that it wasn't on the cake when it left the store, and that this guy might be trying to shake them down for money. And so you don't, getting pissed off immediately before you all know all the facts is bad. Not being able to understand nuance is bad. And not being empathetic that like, hey, we all, you know, I've heard my parents say dumb things, I've heard my grandparents say anachronistic offensive things, you know, that's just, that's part of life. And if you get provoked,

• 1:19:49Ryan Holiday?

  you're not helping the situation, you're probably making it worse.

• 1:19:53Tim Ferriss?

  Yeah, and I, where I wanted this to lead was asking you, well, let me make a plea to the audience. That is, number one, have the uncomfortable conversations. If you get unfairly accused of fill-in-the-blank-ist, don't respond with, I am not fill-in-the-blank, right? Respond with, that's actually, that seems really outrageous to me. How are you defining X? Force them to define it, and you will find out very quickly, nine times out of 10, they cannot do a good job. Or they just end up making themselves look ridiculous. So don't fight someone or debate someone before you make them fight themselves and debate themselves because they'll very often just punch themselves out. So that'd be number

• 1:20:35Tim Ferriss?

  one. And number two is don't, and I was given this advice actually by, I'm not going to name names here, but a very high level kind of political advisor I was having dinner with at one point, we had some wine. I was talking about various initiatives and so on that I wanted to undertake, including supporting research related to psilocybin at Johns Hopkins and trying to change the legal status and blah, blah, blah, blah, blah. There are quite a few things. And he said, well, that's a big, long list. He said, you should assume, he said, that you have, you have one gun has six bullets. You get six bullets a year. He's like, any more than that, it's like you have to aim at the right targets. Any

• 1:21:15Tim Ferriss?

  more than that, and you make people kind of deaf, dumb and blind to your pleas and to your messages if you're constantly hitting people. And you should feel that way yourself. But like by complaining or being offended easily, number one, you're wasting your own resources and making your life worse, not better. Number two, for the real things that matter, you have, let's just say six bullets a year. So like, save the ammo for the right targets. But I'm going to get off my soapbox here. And I want to ask you, Ryan, what do you do in terms of practices, routines, to instill in yourself, these, the characteristics

• 1:21:58Tim Ferriss?

  that you would like to have as it relates to stoicism or ego? Like, would, how does someone improve themselves? In other words, but I want to hear your personal approach.

• 1:22:08Ryan Holiday?

  Yeah. I think, I think journaling is important. So every morning when I wake up, I write in a, in a muskine, I do about two pages. And I write not just what happened the last day, sort of how I feel about it, and what, what I'm working on. I feel like if you don't know what yours, like, you know, I want to be less sensitive, or I want to be More empathetic, or you know, I want to, I want to stop losing my temper. You know, you sort of write these things down. It's, it's, you're, you're having to articulate your goal. It's not just this sort of vague notion.

• 1:22:51Ryan Holiday?

  One of the other things I write, two things that are really important in my diary. So one, I write the amount of time that I spent exercising the day before, which keeps me accountable. And I find that I do a lot of sort of work on myself. I feel that flow state is very meditative. I do a little bit of meditating, but I really feel like, like I do distance running. And so I feel like my distance running is my form of meditation. But the other thing I started writing down, and this is after I read Cal Newport's book, Deep Work, I record how many hours I spent in deep work the previous day. And one of the things that helps keep me accountable with some of my, you know, my, my problems getting distracted and overwhelmed is if that's not, if that tally isn't

• 1:23:33Ryan Holiday?

  three or four hours, like I didn't spend three or four hours really working on like my actual creative important projects, then I know I overcommitted to phone calls, meetings, you know, running errands. I'm not managing my life really well. And so for being, writing these things down has helped me, keep me really accountable. The other thing is actually writing and talking about these ideas. Like ironically, you know, you write a book about Stoicism, then you write a book about ego. It's very, people are going to not be very forgiving with me if I complain about stuff or I, you know, I blame other people for my problems. Or if I, like, I even have to think as I'm marketing this book, like, you know,

• 1:24:15Ryan Holiday?

  if I say something that sounds very egotistical, like somebody's going to call me out about it on Twitter. Like, I think being somewhat public with what you care about and what you're working on is, are two other ways, I think, to, to attack some of these.

• 1:24:28Tim Ferriss?

  Well, doing anything with social accountability, right? I mean, you can have

• 1:24:32Ryan Holiday?

  Sure.

• 1:24:32Tim Ferriss?

  The, you have to have consequences, or I should say incentives, right? Like economics is the study of incentives. I mean, in its simplest form. And in that case, I mean, same, I mean, personally, I can also say like the four hour body or the four hour work week, right? I mean, blessings end a curse, but it's like, if I'm in a coffee shop on a laptop for more than like three minutes, somebody's going to walk by, take a photo of me, make a fucking four hour joke and like put it on the internet. It's like. I have to be like.

• 1:25:01Ryan Holiday?

  Yeah, or if you got in horrible shape.

• 1:25:03Tim Ferriss?

  No, it's like, I can't be fat. I cannot be fat. So that's great. I'm not allowed to be fat. It's, it's just, I would never live it down. Now, you don't need to write books to have this type of social accountability. You can create a betting pool. You can, for instance, for weight loss. So you could have four or five people put in a hundred dollars each and the person who loses the most body fat, key, not just scale. So you can use DEXA scans for this or any number of different tools, then wins the entire pool, right? And what's cool about that is you will actually work harder to not lose your hundred dollars and to beat the other people than you will to earn the 500 or 600, whatever it might be. Right? So that could be one example. Another

• 1:25:47Tim Ferriss?

  would be using a site like coach.me or stick, S T I C K K dot com. Diet Bet is another. Just gonna rattle off a few. Another would be simply making generally subconscious responses more conscious. And so for instance, I think something that is very helpful for both implementing Stoic practices in a very kind of proactive, proactive, that's a new word, proactive, operating system type sense where you, it's a, it's a system for making better decisions. And in a way to address ego in, in quite a few different manifestations

• 1:26:30Tim Ferriss?

  is to do a no complaint experiment where you have, say, and this is from Will Bauer, who's Reverend, I believe, or preacher at the very least, has a large congregation and he puts up a rubber band effectively or a bracelet on one arm and you, you're not allowed to complain for 21 days. And every time you complain, you snap it on your wrist, you put it on the other wrist and the clock starts over. 21 days without complaining. And people can search 21 day no complaint experiment in my name if you want more on that. But the, the point being, I think that it's, it's quite one thing to read about these things, which is very important. I think you need to have like the owner's manual and to deductively or inductively.

• 1:27:10Tim Ferriss?

  Whether you're going from concepts to examples or examples to concepts, ingrain this and have a firm understanding of it. But then, when the rubber hits the road, you have to actually condition yourself and practice this, just like you would go running, just like you would meditate in the morning using an app like Headspace, just like you would commit to scheduling anything else. You need to make this a practice, I think. And that's where a lot of people fail is with any type of nonfiction or how to, and I've certainly done this myself, is read the book. You're like, great, so happy I checked that off. And then you put it down, like six months later, you're like, oh, yeah, that book, wow, I haven't done anything that was in that book. So what advice would you give to people who want to make the leap

• 1:27:53Tim Ferriss?

  from the written page to real life? Any other thoughts?

• 1:27:59Ryan Holiday?

  Yeah, look, I think that's the tough part. How does knowledge become experience? There's a quote, I think I use it in the book, but it's from Plutarch. He was talking about, actually, I forget what he's talking about. But basically, he's saying, it was not so much from the words that I got the knowledge, it was from my experience of the words. I'm butchering this quote, it's horrible. But basically, he was saying, look, it wasn't the words that helped me with my experiences. It was the experiences that I brought to the words that helped me understand them in a new way. And I think, so it's got to be this mix. Like, if you're not leaving a book or something you've read,

• 1:28:40Ryan Holiday?

  if you're not leaving it with a, okay, now I'm going to do X because of this, then, you know, you're just pursuing it for its own sake. I don't want to say it's masturbation, but it's close, right? Like, you're not achieving anything. You just spent a year, a week, reading a self-improvement book. But it's like, tell me what you're going to do with this information. And so, you know, I think that's what you've constantly got to do, whatever you're reading, whatever your thinking is. Okay, I'm now going to put this thing into practice. It doesn't have to be a huge thing. It can be the smallest possible thing.

• 1:29:23Ryan Holiday?

  But if you don't leave with some sort of actionable thing, you're really just... Deluding yourself. And I think it's like, look, you can read a book about Brazilian Jiu-Jitsu. That doesn't make you, that doesn't make you any better at it. It's only if you, you know, you, you try that out on the mat. And against another human being, that's going to lead to any sort of real improvement. It's got to become, it's got to become muscle memory, especially if you intend, you know, it was Stoicism. It's if, if you're not applying these things in a small way in insignificant situations. What are the chances that you're going to be able to do it in an extremely adverse, stressful, overwhelming situation?

• 1:30:07Ryan Holiday?

  It's very, it's very slim.

• 1:30:09Tim Ferriss?

  Slim to none. Yeah. So the, the Plutarch quote, I think this is it. For it was not so much that by means of words I came to a complete understanding of things, as that from things I somehow had an experience which enabled me to follow the meaning of words. That is a tough one to remember. But to your point, then this is one of my favorite quotes. I think it's archilochus is how you would say it, but we, we do not rise to the level of our hopes. We fall to the levels of our training. And so in my experience with training, let's just use the athletic example. You have planning, right? Or programming, right? You have planning, then you have, then you have practice, and then you have reflection or review. And that review piece is very important.

• 1:30:52Tim Ferriss?

  So I want to underscore something you said about journaling. There's a, there's a, there's a book called The Five Minute Journal, which you can use. I use pretty much every morning and every evening. Two and a half minutes in the morning, two and a half minutes at night to accomplish two things. All right. To, to have clarity on this kind of prep and review portion of the day. Practice being the rest of the day in between. Also to cultivate the practice of gratitude and actually writing down three, even three things that you're grateful for each day, including one that is very small. Not anything necessarily all encompassing, like the, the health of my friends and family. Right? That's fantastic, but you can very quickly go on autopilot and just list that off every day.

• 1:31:37Tim Ferriss?

  And I've talked this, about this before in my morning routine, so I won't be labored here. But the, the point being that when I've spent time with, say, Tony Robbins, for instance, who is one of the most, I think, effective, is certainly impressive.

• 1:31:52Tim Ferriss?

  Interventionists when it comes to personal crises that I've ever seen in my life. It's really fun. It's just mind blowing what this guy can accomplish in a handful of minutes with someone he's never met before. And he, he has said before, and it really made sense when I started reflecting on this, that most of our suffering and misery comes from a focus on me. It's just a self focus. And I think that this gratitude helps to relieve that pressure and that compulsion somewhat. So that, that journaling, I think, is particularly important. Well, Brian, I know we're, we're probably coming up on time here. Is there anything that you would like to leave people with? Anything for them

• 1:32:35Tim Ferriss?

  to think about or to consider to take with them?

• 1:32:40Ryan Holiday?

  Yeah, I mean, I liked what you were just saying about Tony. I think that's really interesting. It's this idea that it's, one, it's when you make something all about you, it, you stop seeing it rationally. And I think the other thing I found that, that was helpful for me, it's this idea of like, this thing, like, however many copies my book sells, or however much money I make, or whoever I know, none of the, it's like, if you can, if you could start to realize that none of these things say anything about you as a person, right? And I think that's why we get so caught up. It's like, we're like, the kind of car I drive says something about me as a person. You know, like, the number of Twitter followers I have says something about me as a person. So then we're like,

• 1:33:24Ryan Holiday?

  so possessive and aggressive and ambitious and controlling about them, because like, we've, we've wrapped our identity up in them. When I was first writing the book, the original title is based on a, a quote from Paul Graham, where he says, keep your identity small. Because the smaller your identity, the more able you're, the more you're able to be flexible and adaptive and creative and, and, you know, see, see changes and disruption coming in the world. And so I think this idea of wrapping our identity up. In our work or, you know, in, in material things, what, what things that the Stoics would put in the category of, um, you know, what we don't control, that's where we start to

• 1:34:06Ryan Holiday?

  get in serious trouble because now, you know, something can always threaten that thing. Someone can repossess your car, you know, you're, someone can give you a negative review on your book and now all of a sudden you're reacting super negatively and emotionally and angry and, and that's when you do things that you're not proud of.

• 1:34:26Tim Ferriss?

  Here, here, right. Training yourself to value most the things that cannot be taken away.

• 1:34:31Ryan Holiday?

  Totally. And, and I think that's, that's a scary idea for people, but it's, it's ultimately very freeing, right? Because you're, you're immune to the fluctuations of events. That doesn't mean that you can't live in a nice house and, you know, you can't have fun and you can't be, you can't have things that you're trying to accomplish. But you want to, I think, cultivate that resilience that like, hey, you know, if I had to start over tomorrow, I would still be me and I would have all the skills that I bring to the table and I'd be, I'd be pretty good. That, to me, that's much better than like, you know, being Richard Nixon ranting on the White House tapes about all these people who are trying to screw him over, you know?

• 1:35:09Tim Ferriss?

  And stay out of politics would be the corollary. But yeah, unless, well, yeah, unless you're, unless you're perhaps a Sherman who in the first place doesn't want to be in politics, but would probably do the best job. Uh, the irony of the age in which we live. But, uh, Ryan, this is always a pleasure. I love being reminded always of the, the first principles in some ways of living the good life, whether that's choosing to use certain things as tools, uh, that make terrible masters, whether that's money, possessions, otherwise. Uh, and really.

• 1:35:46Tim Ferriss?

  Keeping in mind, I suppose, in many ways, just the Serenity Prayer. And the two very separate buckets of things that you can control and things you can't control, and then working methodically, dispassionately, very often, on the things that you can control. Because, I mean, these little actions cumulatively are the big actions. And I suppose, on that note, I will thank you for taking the time. I really appreciate it.

• 1:36:15Ryan Holiday?

  Thank you for having me. It's always good.

• 1:36:17Tim Ferriss?

  And for everyone who is wondering about show notes, links to everything that we have discussed, of course, ego is the enemy and many other things, different figures and so on, you can find those all in the show notes at fourhourworkweek.com/podcast. And until next time, thank you for listening.

• 1:36:40Tim Ferriss?

  Hey, guys. This is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric, as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short.

• 1:37:22Tim Ferriss?

  It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to fourhourworkweek.com. That's fourhourworkweek.com, all spelled out, and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by FreshBooks. FreshBooks is used by a ton of the startups that I work with or advise, many of the fastest growing. It is used by almost all of the contractors that I work with. It is the easiest way online to send invoices, get paid, track your time for invoicing, track your clients, so they get to the point of paying you, all that stuff that you could possibly find.

• 1:38:04Tim Ferriss?

  And right now, you can get a free month of complete unrestricted use, and you do not need a credit card for the trial. To claim your free month, just go to freshbooks.com/tim and enter "Tim" in the "How did you hear about us?" section. You can, of course, customize it to fit your brand with your own logo and color, and FreshBooks shows you whether or not, for instance, a client has looked at the invoice. They can send late payment reminders to your clients automatically, so you do not have to think about it or chase them down. And you can track your hours. You can do all sorts of things. There are mobile applets, you take pictures of your receipts, and FreshBooks will organize them for you later. It is a great piece of software, and if you are in a small business, or maybe a fast-growing business that is feeling growing pains and you need to streamline, then this is a place

• 1:38:49Tim Ferriss?

  to look. Because certainly for me, this has been a headache in the past, and it doesn't have to be a headache for you. So check out freshbooks.com/tim and try it out and see what you think. This episode is brought to you by Wealthfront, and this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way, set-it-and-forget-it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last two years, and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley, have millions of their own money in Wealthfront. So the question is, why? Why is it so popular? Why is it unique?

• 1:39:30Tim Ferriss?

  Because you can get services previously reserved for the ultra-wealthy, but only pay pennies on the dollar for them. And this is because they use smarter software instead of retail locations, bloated sales teams, etc. And I'll come back to that in a second. I suggest you check out wealthfront.com/tim, take the risk assessment quiz, which only takes two to five minutes, and They'll show you for free exactly the portfolio they'd put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or, as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis, but normally aren't. Great investing is a marathon, not a sprint, and little things that you may or may not

• 1:40:12Tim Ferriss?

  be familiar with, like automatic tax loss harvesting, rebalancing your portfolio across more than 10 asset classes, and dividend reinvestment add up to very large amounts of money over longer periods of time. Wealthfront, as I mentioned, since it's using software instead of retail locations, et cetera, can offer all of this at low costs that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything, they charge 0.25% per year on assets above the first $15,000, which is managed for free if you use my link, wealthfront.com/tim. That is less than $5 a month to invest a $30,000 account, for instance. Now, normally, when I have a sponsor on this show, it's because I use them and recommend them. In this case, it's a little different.

• 1:40:56Tim Ferriss?

  I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast, but because of SEC regulations, companies that invest your money are not allowed to use client testimonials. So I couldn't be a user and have them on the podcast. But I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now, back to the recommendation. As a Tim Ferriss Show listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at wealthfront.com/tim. It's fast, it's free. There's no downside that I can think of.