We’re all familiar with the stereotyping of Millennials. Like my own once-denigrated Generation X, “these kids today” are lazy and entitled, right?
From my experience with the young people I know and work with, I’m not buying it. And even if there’s some truth to the generalization, a guy like Ryan Holiday blows that perception right out of the water.
This college dropout has accomplished more before the age of 30 than most people accomplish in their entire lives. Ryan is the author of four books, runs his own PR agency, is Editor-at-Large of the New York Observer’s technology and business section, was a marketing executive at American Apparel, and continues to advise bestselling authors including Tucker Max, Robert Greene, Tim Ferriss, and Tony Robbins.
I don’t know about you, but I may need a nap just from typing all that.
Today’s conversation focuses on the subject matter of Holiday’s last two books, The Obstacle is the Way and Ego is the Enemy. Although not your typical business books, the timeless lessons these two volumes contain are some of the most valuable any unemployable type must learn.
Listen to 7-Figure Small with Brian Clark below ...
The Show Notes
The Stoic Entrepreneur with Ryan Holiday
Ryan Holiday: I’m Ryan Holiday. I am an author, and I have a creative agency called Brass Check. I am unemployable because I don’t think anyone else would pay me to sit around and read books all day.
Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one, and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advise and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course, or choose to sign up for the newsletter only, at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level.
Brian Clark: Hey there, and welcome to the show. I’m your host Brian Clark, founder and CEO of Rainmaker Digital and fiercely unemployable just like you. Today’s episode is brought to you by our own Rainmaker Platform.
If you’re looking to build you own digital marketing and sales platform, you’ll want to start your free, no-risk 14-day trial today to fully experience Rainmaker, the next-generation online marketing and sales solution that merges a powerful website, a sophisticated email service, and crucial marketing automation in one secure and maintenance-free package. Start your free trial today at RainmakerPlatform.com.
Now, we’re all familiar with the stereotyping of Millennials. Like my own once denigrated Generation X, these kids today are just lazy and entitled, right? From my experience with the 20-somethings that I know and work with, I’m not buying it. Even if there’s some truth to the generalization, a guy like Ryan Holiday blows that perception right out of the water.
This college dropout has accomplished more before the age of 30 than most people accomplish in their entire lives. Ryan is the author of four books. He runs his own PR agency. He’s Editor-at-Large at the New York Observer’s Technology and Business section. He was a marketing executive at American Apparel and continues to advise best-selling authors, including Tucker Max, Robert Greene, Tim Ferriss, and Tony Robbins. I don’t know about you, but I may need a nap just from saying all that.
Today’s conversation focuses on the subject matter of Holiday’s last two books, The Obstacle Is the Way and Ego Is the Enemy. Although these are not your typical business books, the timeless lessons these two volumes contain are some of the most valuable that any unemployable type absolutely must learn.
Ryan, my man, thank you so much for being on the show.
Ryan Holiday: Thanks for having me. I feel like we’ve known each other forever.
Brian Clark: We have. I did get to see you when you were in Boulder just a few days ago. That was awesome. Apparently, it did not convince you to move from Austin to Colorado, but that’s okay. We’ll keep working on it.
Ryan Holiday: I had a good time, but I love Texas.
Brian Clark: How long have we known each other? I know you used to write for Copyblogger, and then you became the author sensation that you are today. Take us back, actually.
You’ve accomplished more by the age of 30 than most people have done their entire lives, and I am in awe of that. As someone who didn’t really get rolling until I was 30, I’m always kind of jealous of younger people who just start kicking ass right out of the gate. So take us back.
How the Convergence of Two Paths Led to Ryan’s Success
Ryan Holiday: Well, that’s very kind. I think we must have met in maybe 2006. I was right out of college. I had just dropped out of college to be the research assistant to Robert Greene, who’s the author of The 48 Laws of Power. I had a job at a talent agency in Hollywood called The Collective, which worked with mostly mainstream actors and musicians. I ran a new media division which was, at the time, just getting going.
I was one of the first people to see that, “Hey, this new media thing, there are clients there. We could sign them, and they could make us lots of money.” I remember you and I talked, there was a young actress who was on a Disney series. We talked about making a website for her and building a whole thing.
Brian Clark: Oh my, I totally forgot about that. Are we allowed to say?
Ryan Holiday: I don’t know. I was just not going to.
Brian Clark: Yeah, let’s not.
Ryan Holiday: She’s gone on to do literally hundreds of millions of views on YouTube. She’s had multiple hits. She became the thing that you and I thought she could become, although, of course, the agency was not able to get on board and capitalize on it.
Brian Clark: How did we not get in on that deal?
Ryan Holiday: I know. It was interesting. I was such a huge fan of your work. The idea that you could just own your own website, publish your stuff on it, and that would be a business, I was just in awe of that. That’s what I always wanted to do.
Brian Clark: Yeah, absolutely. You had some pretty high-powered, executive-level experience as well. This is a brand that’s had its troubles. I’d like to hear your thoughts on that, but talk a little bit about that.
Ryan Holiday: About a year after you and I had met over that stuff, I joined American Apparel. I didn’t have a position or anything. Robert happened to be on the board of directors. They needed some strategic advice on this new media stuff, and I came in, took about a year and a half, and then I became the director of marketing for American Apparel, which was, at the time, one of the fastest growing fashion brands in the world. They still do a half a billion dollars a year in sales, but the brand has taken a hit due to a lot of the controversies and some of the problems in its management.
I was doing these two things simultaneously. I wanted to be a writer. I was working for writers. Understanding how new media worked in this future of marketing, I worked my way up that chain, and I was pursuing these two paths simultaneously. Then they converged in 2011 when I wrote my first book.
The Deliberate Actions That Helped Make Ryan’s First Book a Success
Brian Clark: Yeah, let’s talk about that first book. It was certainly not a shy and retiring sort of affair, now was it?
Ryan Holiday: No.
Brian Clark: Here’s the weird thing about being in our industry. I’m friends with Peter Shankman. I’m friends with you. I don’t think you dislike Peter Shankman, but I always got to talk Shankman down because he’s still upset.
Ryan Holiday: That’s funny.
Brian Clark: No, I’m serious. I’m just like, “Come on, man. Come on. Come on.”
Ryan Holiday: For people who don’t know, the book was sort of an exposé of the media system and how the sausage gets made. One of the stunts that I did for the book was I used a service called Help a Reporter Out, where I pretended to be an expert.
I was quoted in basically every major media outlet that you could think of, including The New York Times. Then I revealed this and showed how it works, that the experts that you read in your New York Times Sunday trend pieces are not always what they seem. The guests that you see on the TODAY Show or 20/20 are not necessarily the experts or the qualified representatives that they may look.
Peter, as the founder of Help a Reporter Out, was naturally quite upset by it. I’m not going to pretend that the controversy was not exactly what I intended. I did not do this stunt and then it miraculously came out at the same time my book came out — although they were related, and they were deliberate. You don’t write a book about media manipulation and then not show how the media can be manipulated.
I think it’s interesting that Peter was so upset by it. It was almost like a he doth protest too much. When you make a service that’s tagline is, “There’s no such thing as free publicity. There is with HARO,” you know what you’re doing. I don’t think he’s personally responsible for a media environment in which the paper of record in the United States will troll for sources, but I think it does say something about how the media works — and I revealed that. He and I got into it a little bit. I’m sad to hear he’s still upset by it. To me, it’s just funny.
Brian Clark: I’m working on him.
Ryan Holiday: All right, good. Well, tell him I said hello. I’m sure he’ll like that.
Brian Clark: Okay. I’ll send him this episode. He’ll love it. You started with Trust Me, I’m Lying, and then you went and had success with a book about growth hacking. It seemed like your path was going in a certain direction, and then you went in a different direction.
To me, the last two books, The Obstacle Is the Way and Ego Is the Enemy, are who I think of Ryan Holiday is — we touched a little bit when you were in Boulder — that this is the work it seems you were born for. Does it feel that way?
The Work Ryan Was Born to Do
Ryan Holiday: Well, thank you. I do. It’s what I love doing. It’s where I feel most fulfilled. It’s funny, though, the sense of what a path that someone is on, it’s so hard to tell from the outside. The reality is, I wrote Trust Me, I’m Lying, and I was very concerned about being a marketing person. I wrote that book so I wouldn’t have to talk about marketing ever again. When I wrote this book, giving all the stuff away and when I did that stunt and some of the others, I thought, “That’s the end of it for me in this industry.”
The next book I sold was The Obstacle Is the Way. It was supposed to come out first. I ended up writing an article about growth hacking, which was just something I was interested in, and I was fascinated by the way that a lot of these Silicon Valley startups had become huge multi-billion dollar companies without doing your ‘traditional’ marketing. That article got optioned into an ebook, and the ebook came out before Obstacle. It looked like I was going one direction, and then I made this radical turn. In reality, it was just a slight deviation from the path that I was on, which was towards The Obstacle Is the Way.
Those books just took a long time. The Obstacle Is the Way took a little over two years to come out. Ego Is the Enemy took two years to come out. For the outside reader, it seems like it’s this slow curve. To me, The Obstacle Is the Way was not this thing that was coming out in 2014. I was working on it every day in 2012, so I’m thinking about it on a constant basis. Maybe it’s that thing where you might not have seen someone for a few months and they say, “Oh, you look so different,” but you don’t notice because you look at yourself in the mirror every day. For me, it was much more gradual than abrupt.
Brian Clark: Got it. Okay, I want to talk about … I know Ego Is the Enemy is the current book. That’s what’s we’re supposed to talk about, and we will. But to me, the two books are required companion reading. Let’s talk a little bit about Obstacle. It’s about Stoicism, which seems to be making a remarkable comeback among many people. I think Obstacle nailed it.
The Timelessness of Stoicism
Ryan Holiday: Thank you. One of the nice parts about writing a book about something that’s 2,000 years old and writing a book that is not of the moment is that I don’t care which book is out right now or which one is newer. They’re both designed to hopefully outlast me and to sell as long as humanly possible and to do so without marketing. That’s the idea.
What’s so nice about Stoicism is that it’s this philosophy that has been battle-tested since the ancient Greeks. It’s this robust way of looking and thinking about the world that has gotten people through wars, the Black Death, the Bubonic Plague, the US Civil War and slavery, and all of these horrible things. It’s a philosophy that has clearly stood the test of time, so rooting the book in that was obviously a deliberate thing.
I would much rather write a book about something that can last than say, “Here’s some cutting-edge psychological research. Check it out.” You don’t know whether that research is going to be corrected or overwritten at some time in the future.
Brian Clark: Absolutely. I think this book and its companion, like I said, they weren’t aimed at independent business people or entrepreneurs, necessarily. They’re essentially life strategies. The biggest traction that you got with the earlier book, outside of the general readership of people who know Ryan Holiday … by the way, I’ll link it up, but he’s got a great monthly book club that you have to subscribe to. The Seattle Seahawks and many other NFL or other general sporting organizations just took to this book, and it was a phenomenon within the sporting world. Talk about that a little bit.
How (and Why) the Sports World Embraced Ryan’s Books
Ryan Holiday: It was a total surprise. Obviously, I didn’t sit down to write this book about ancient philosophy thinking, “NFL coaches, that’s who this is for,” but I think in a weird way, the life of an entrepreneur, the life of a writer, the life of a coach is the same. We’re waking up in an imperfect world and trying to make whatever we’re doing work. We’re looking for a mental edge. We’re already good at what we do. We have talents. We’ve practiced our whole life for this moment. What we’re looking for is a mental edge in the moment.
The Seattle Seahawks have read the book. The New England Patriots read the book on their way to the Super Bowl in 2014. A lot of actors and celebrities have read it — and NBA teams, the Texas Rangers in major league baseball. It’s been this surprising thing, but if you look at the Stoics, the Stoics, instead of using football as a metaphor, they used wrestling, or they used boxing, or they used fencing. We have a history of relying on sports as a metaphor or a microcosm of life, and I think the Stoics saw that, too.
Nick Saban, who’s the coach at the University of Alabama, he talks about the process. That’s what he teaches his players. Like, “Don’t think about the future. Think about this down, which is going to last for seven seconds. If you can string three or four of them together, you can go on a scoring drive.” Well, Marcus Aurelius says, “Assemble your life action by action.” He says the exact same thing.
Two thousand years ago you have the emperor of Rome talking about the process in slightly different words than the greatest college football coach of all time. There’s this weird continuity between great men and women and philosophy, this timeless wisdom. A lot of these things are clichés because they’re true, and the book just happened to tap into that.
Brian Clark: Absolutely. A good third of the book is about how we define our own world, how we perceive is reality. You have a chapter called ‘Recognize Your Power,’ the story of Rubin (Hurricane) Carter, the boxer who was wrongly imprisoned. Talk about that lesson a little bit and how entrepreneurs can understand. It’s the cult of the hustle, and yet do we know what that really means when it gets bad? How do you get by that?
Why There Is No Good or Bad, Only Perception
Ryan Holiday: Sure. What the Stoics say over and over again is that there is no good or bad. There’s only perception. Marcus Aurelius says, “Our life is what our thoughts make it.” He’s not talking about the secret. What he’s saying is that, if you feel like you’ve been hurt or screwed over, or that everything is lost, in some ways that’s true, right? It becomes true. Just because you think something is great doesn’t make it great. Obviously, that is what the secret is, but what he’s saying is that often our interpretation of things make them worse than what they are.
Someone like Hurricane Carter, he goes into prison, and he basically says, “I refuse to acknowledge the existence of this prison. I might literally be in prison. And I understand that I’m not free, but in every sense that I am free, that’s where I’m going to focus my energies.”
He decides, “Okay. I’m going to be awake at night and sleep during the day because that’s a bit of freedom that I have in this prison. I’m going to use my time in the library to focus on my appeals. I’m not going to feel wronged.”
Ultimately, when he’s let out of prison, he doesn’t sue the state or the government because he feels like that would be admitting that he was wronged in some way. Instead, he becomes a better man than he was in prison by the time he leaves prison.
You could argue that Malcolm X becomes Malcolm X in prison as well. Robert Greene says, “Many a thinker was produced in prison where man has no time to do anything but think.” The reality is, of course, that plenty of people become worse in prison. They don’t become thinkers. They become the opposite of that. I was really inspired by people who’ve dealt with unimaginable adversity and seized whatever positive was within it, and they made it everything that it could be.
Brian Clark: Mindset is what you make it, and we touch on this over and over again. It’s interesting because I want to talk a little bit about negativity, which seems to be the opposite of what you just said, but they’re actually very congruent strategies when you’re thinking about, “Okay, I’m trying to accomplish this thing, and here’s how I’m going to go about it.”
Before we do that, though, you touch on iteration, which, of course, is a bedrock principle of our company and of the lean startup movement that came later. You lead with that, even the minimum viable product. Then you go into a historical analysis of why that type of thinking has always been, at least from a Stoic standpoint, the way to do it.
The Oft-Ignored Upside of Stoicism: Pragmatic Realism
Ryan Holiday: Well, it’s interesting. The Stoics get this reputation for being negative or being depressing. I find that, in reality, they’re just very realistic and pragmatic. They understand that things often go the opposite of the way that we want them to go, so they’re resilient.
Seneca talks about the art of negative visualization. Instead of thinking about how positively everything is going to go and how it’s going to go exactly to plan, he’s thinking about all the things that could go wrong. He’s embracing them. He’s learning from them. He’s preparing for them. He’s making adjustments to be able to expect or anticipate them, and that’s ultimately making him stronger.
When Marcus Aurelius is saying, “Assemble your life action by action,” it’s the same idea. He’s saying instead of having this grand explicit vision for how it should be, take it step by step. That doesn’t mean you shouldn’t have a plan.
Was it Eisenhower who said, “Plans are worthless, but planning is everything”? You want to have what you’re trying to accomplish, but you also have to understand that things change iteratively. You have to be receptive to that feedback, and you have to focus on the smallest unit of measurement as you go.
What I think is great about the lean startup model — and you see this in startups, whereas in books, you never see it. An author goes off and they spend two years writing some book that they magically hope will be successful. They haven’t done any research. They don’t know who it’s for. They just believe in it. That’s a great recipe for success when you’re right, but what happens when you’ve made some critical error?
I like to see things scale iteratively. I like to see them grow based on feedback and an interaction with the audience. I think it’s pretty cool that this goes back 2,000 years.
Brian Clark: Amen to that. Let’s touch on that negative thinking, I guess you would say, association with Stoics. It’s a dower-faced, resolute guy … usually a guy. Embracing the worst-case scenario is something that I’ve always done. That doesn’t mean have a plan B, which I think research shows actually makes you more likely to fail at plan A. It’s not the same thing. It’s what’s the worst that could happen?
Ryan Holiday: Right. It’s what’s the worst that can happen, being okay with that, and proceeding anyway, but not being caught off guard by it. Marcus Aurelius, he opens his meditations with this idea. It’s like, “Today, the people you meet are going to be jealous. They’re going to be mean. They’re going to be short-sighted. They’re going to be angry. They’re going to be surly. They’re going to be duplicitous,” and then he lists all the negative things that he’s going to see in the day.
In some ways, he’s preparing for that, so it doesn’t catch him off guard. Then he’s also saying, “Knowing this going into it, don’t take it personally, and see what you can do about it.”
I actually find that Stoicism is practical and pragmatic, yes, but in an optimistic way. Someone said of FDR that his caution was always held in conjunction with an assumption of advance. So even when he’s being cautious, the default is always still, “We’re going to move forward. We’re just going to do it the right way.” I think that’s definitely true of the Stoics, that the Stoics are always going to be preceding — they’re just going to be doing so in an aware, intelligent manner, not a naïve or ignorant manner.
Brian Clark: Let’s talk a little bit about the new book, Ego Is the Enemy. Why was this the next project for you?
Overcoming Our Internal Obstacle: Ourselves
Ryan Holiday: Obstacle was about external obstacles, naturally. It’s about the way that things we encounter can hold us back or fuel us, so to me, Ego was about our internal obstacle. Not obstacles — our internal obstacle, ourselves, the way that we get in our own way, the way that our arrogance when we’re successful holds up back from being more successful, the way that our naïve confidence holds us back from succeeding in the first place.
I think worse, when we fail, the way that our insecurities and our fears hold us back from rebounding. To me, it’s just about this toxic force that I think is in all of us — ego. I’m not talking about the ego, not the Freudian ego, I’m talking about ego in the colloquial, the Donald Trump sense of the world.
Brian Clark: Yes, and I appreciate your letters to your father on Trump by the way, just as an aside. You’re doing the Lord’s work. I read Ego when it came out, and it was a good thing. I found myself struggling or focusing, I guess I should say, on external results more than I usually do. I’ve been a student of the topic that Ego Is the Enemy covers. I think a person like me must contain and understand my own capability to be arrogant or something of that matter. It’s a driving force in my life not to slip into it. Does that make sense?
Ryan Holiday: Totally.
Brian Clark: The first thing that you have to do is recognize that you’re capable of it.
Ryan Holiday: Yeah. What I notice talking to people about this book is how we all know that ego is a problem in other people. We all see how ego holds our competitors back, how it holds sports stars back, how it holds politicians back. But then when it comes to us, we don’t want to look at our own decisions that we’ve made out of ego or just the petty way that ego interrupts and poisons our life.
“This person wanted to meet here, but I want to meet over here — not because it’s easier for me, but because I don’t want to let them decide.” Or, “How could they treat me like this? Don’t they understand who I am?” Just the things that we cycle through, even on the course of a normal day, that no one could say are for any objective reasons or any real benefit.
It’s just emotion and ego trying to one up other people. I’m just fascinated by the incredible amount of energy we waste doing that and all the problems, fights, conflicts, and issues that are created because of it.
Brian Clark: It’s like you create drama out of nothing, which is not the point. Early in the book, and this is the story that caught me in my tracks and really helped me realize that, “Okay, Brian you’re doing it. You’re thinking of becoming something instead of just doing.” That was the story of John Boyd. I believe the name of the chapter was ‘Do or Be’?
Ryan Holiday: ‘To Do or To Be.’
Brian Clark: Exactly, and it was perfect. That was exactly what I needed to hear at that point a couple of months ago or whenever it was. Talk a little bit about John Boyd. He was Air Force, Pentagon, but an amazing man.
Why Every Choice Has a Trade-Off
Ryan Holiday: Basically, the probably greatest strategist in America since the second World War. When he worked in the Pentagon, he was a famous mentor of other young talented pilots and officers. As he would see someone have potential — and knowing the corrupting force of rank, bureaucracy, and status inside the military — he would give them this speech. It’s called the ‘To Do or To Be’ speech.
Basically, he’s saying, “Look, are you going to try really hard to get promoted and become an important person, or are you going to do important work?” because they are not the same thing, but they are very easy to confuse with each other.
John Boyd never advanced beyond the rank of colonel even though he was instrumental in our strategy in the first Gulf War. He shepherded through the F15 and the F16. His theories on maneuver warfare and dog-fighting are essential reading. The OODA loop is something that every fighter pilot has to study now. He did all this as a doer, not as a person who kissed asses and played the game. He did the work.
I think that that’s an inspiring thing for us to think about. It’s like, “Look, as a writer, do I want to chase critical opinion, do I want to win fancy awards, or do I want my books to have impact on people who are out there doing things that I admire?” That has been a choice that I’ve had to struggle with.
I think what you said what you went through is something we all struggle with. Some of us don’t make the right choice. Some of us chase being the important, fancy VIP, but when we actually look at the end of their life about what they’ve accomplished, what they’ve contributed, it doesn’t add up to their rank or to their place in the hierarchy. To me, that’s not who I wanted to be or what I wanted to do.
Brian Clark: It’s a recurring theme on this show that some entrepreneurs, especially of the hard-charging, world domination disruption level, they’re compensating for something. It could be your dad didn’t love you enough, or you’re short. Or you have abandonment issues, whatever. That’s a function purely of ego. You’re trying to fill a hole in your soul, and it’s never going to get filled, no matter how much you succeed. Much better to do something that matters.
Ryan Holiday: Yeah, and it’s just bad fuel. Think about the startups that are trying to be valued as unicorns — not because it helps them advance their goals, but because other startups they know were valued at unicorns. It’s always a bad motivation to try and do something because someone else you don’t know — or ironically, it’s often someone you don’t respect — has done something, that you feel like you have to accomplish it just so you’re back to even.
I think that’s bad motivation, and then, of course, to think that, “Hey, if I accomplish this or do that, finally I’ll feel good about myself.” It’s not true. You never feel that way. You’re trying to fill a hole with something that’s not going to stick. Even the worst part is that you find that, when you’re not successful … let’s say you think your success says something about you as a person.
Let’s say you’re one of the lucky people who becomes the billionaire, the unicorn, or whatever, and now you feel awesome. That’s great, but what happens when you experience a setback, there’s some negative article about you, or someone else does more than you? Now, all of a sudden, you think that says something about you as a person, and you think that it says you’re a lesser person. And that’s equally untrue. It’s just bad logic, and it causes an incredible amount of pain and waste.
Brian Clark: Yeah, that’s a hamster wheel I just never wanted to be on. It’s interesting that I always say on this show that ‘should’ is a dirty word. We’re a bootstrap company. We never took VC. We never took investment. Every time I think, “I should,” I end up becoming unhappy.
Ryan Holiday: Yep, same for me. I think also an adult understands that choices have trade-offs. John Boyd understood that being a certain way and focusing on doing the work, he was trading off getting or acquiring certain ranks. I think that’s the other thing. I see this with authors. They go, “Okay, I don’t want to chase critical acclaim. I want to chase impact and sales.” They do that and they get it, and then all they can think about is how they don’t have this other thing. If that’s what you wanted, that’s what you should have gone for. You made a choice, and choices have trade-offs. It’s only ego that thinks you can make that choice and still get both. It’s absurd.
Brian Clark: Another chapter in the book is focused on always staying a student. To a certain degree, it’s meant as a humbling mechanism in the sense that, as the older I get, the more I know I don’t know. But if you’re a young hot shot in your 20s and you think you know the ‘thing’ — whether it be growth hacking or whatever the case may be — it can be incredibly damaging.
Now, it’s also a very pragmatic thing because all we hear about is we’re all life-long learners now, and yet, you run up against people who are like, “I’ve got this,” and yet they end up losing to someone else.
The Benefit of Embracing What You Know You Don’t Know
Ryan Holiday: Look, when I look back at my own writing, the only thing that I don’t like is when I see a sense of certainty or simplicity, or simplification, that I didn’t deserve. That’s when I cringe, and I am embarrassed for myself. That’s something I try to think about now. I try to go, “Am I acting like I know it all about this topic, or am I actually being open and receptive and leaving the possibility that someone could teach me something? What gives me the right to think that I know everything about this?”
If Socrates, the wisest man who ever lived, would go around reveling in what he didn’t know — and he was considered wise precisely because, as you said, he knew what he didn’t know — who am I to think that that rule doesn’t apply to me? The less certain you are about your own intelligence, the more you’re going to learn, the more things you’re going to be open and receptive to — and by the way, the less of a d*** you’re going to be.
Brian Clark: Yeah, that helps. Ryan, thank you so much for being on the show.
Ryan Holiday: Thanks for having me. It was awesome. We’ll have to see each other in Texas.
Brian Clark: Yeah, well, not in the summertime. That’s why I left. Seriously, people, this is an easy one for me. If Amazon has that bundle deal where they say, “People buy Ego Is the Enemy and Obstacle Is the Way,” do that. The two books will get your head in the right place. It’s ancient wisdom, and it’s time-tested — and that’s really what we’re looking for here. Do that, and keep going.