Box of Crayons Blog


Ryan Holiday Takes on Ego

ryanholidayRyan Holiday is a media strategist and prominent writer on strategy and business. His best-known book is The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph, and he has a new book out titled Ego Is the Enemy.

He’s led an extraordinary life. Ryan dropped out of college at age nineteen to apprentice under Robert Greene, author of The 48 Laws of Power. He went on to advise many bestselling authors and multiplatinum musicians. Ryan’s campaigns, created while he was director of marketing at American Apparel, were written about in Fast Company, Ad Age and the New York Times.

Ryan’s ability to put higher goals above any need for recognition has served him well throughout his career. In this interview, we discuss:

  • The difference between confidence and ego.
  • Canvas strategy — what it is, and how it can help you.
  • How to set boundaries.
  • The art of figuring out what matters.

Follow Ryan on Twitter @RyanHoliday


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Full Transcript

Michael:     Alright, Ryan, I’ve blown the trumpets, I’ve played the drums, I’ve issued you onto stage in a kind of non-ego-led sort of way, but let’s kick us off. You know, as I ask all my guests, what are you taking a stand against? What are you no longer tolerating? What’s pushed you to talk about and write about ego is the enemy?

Ryan:         I wanted to take a stand—I mean, obviously against ego, not confidence. I think the two are commonly confused. I’m taking a stand against the sort of artifice that we have built up as a culture. Obviously there’s plenty of haters and critics out there, but I also feel like—and my brethren in the sort of authors’ space are guilt of this, of sort of an endless amount of encouragement, telling people that they’re amazing all the time, that all they need to do is dare greatly or have some profound vision and that sort of success will naturally ensue. I wanted to sort of take a stand against that and, in contrast, hold up the quieter virtues of humility and self-awareness and hard work and passing on credit. You know, the sort of things that I think are ultimately not only what society needs but what truly gets stuff done behind the scenes. So I wanted to take a stand against this world where everyone needs to have a personal brand that’s as big and as brash and as popular as humanly possible, and instead maybe focus on something a little bit different and more meaningful.

Michael:     Nice. So let’s dive into that, because you started off already kind of distinguishing that we’re not talking about lack of confidence necessarily, but talking about something else. So when you say ego, because it’s a word that many people use but it has a sort of slippery or variable definition.

Ryan:         Right.

Michael:     What do you mean by ego?

Ryan:         Well, I’m not referring to the ego, which is obviously a psychological term. I’m not referring to egotism or, you know, which can be in some cases a psychological diagnosis as well. I’m referring to sort of the colloquial idea of ego. As Bill Walsh, he says, “It’s when confidence becomes arrogance, when assertiveness becomes obstinacy.” You know, I’m talking about when we cease to live in reality and we live in a world of our own illusions and self-importance.

Michael:     Nice. Well, here’s what I get told often enough.

Ryan:         Okay.

Michael:     Which is you teach what you most need to learn.

Ryan:         Sure.

Michael:     And that’s a humbling, ego-deflating approach already, but I’m curious to know what was it about your life and what’s going on for you that made you go, “If this is the thing I need to learn, let me write something about it. Let me try and teach about it.”

Ryan:         Yeah, I definitely wasn’t coming to this as—and in fact, if I was, I think it would be pretty egotistical. I wasn’t coming to this book from a place of, “Oh, I’ve achieved egolessness, and let me guide you on some spiritual journey.” What I was talking about or what I’m trying to talk about is the way in which ego holds us back and the problems that it causes that I’ve seen not only in my own life and in my research, which you know I try to ground my books in sort of historical, deep historical research, but also, you know, I was a Director of Marketing in American Apparel, which was at one point a very high-flying company and was publicly-traded and is now recently emerged from bankruptcy court. So it’s how do some of the traits that help us achieve success also serve to undermine and jeopardize that very success? You know, these are things that I experienced firsthand and did everything I could to try to prevent, but I wasn’t successful, and I think I picked up my fair share of bad habits along the way being surrounded by that environment.

Michael:      Let’s talk about that because, you know, it’s that annoying thing, which is this stuff you can understand in theory but it becomes much harder in practice because our lives are messy, complex, and you know, we’re vulnerable, flawed human beings.

Ryan:         Yeah. Right.

Michael:     I mean, reading in the book, you’re like, “God, I kind of knew this stuff!” And yet, I got suckered into it nonetheless. How do you think you got suckered into some of the traps that you’re seeking to lay clear and help us avoid in the book?

Ryan:         Yeah, I feel like I probably wouldn’t use the word “suckered into it” because it makes it seem like I wasn’t responsible for my own choices.

Michael:     Sure, right.

Ryan:         But I think what it is is you tend to—egotistical people, although they are incredibly self-destructive and toxic, wouldn’t be able to be successful if they weren’t also very charismatic and really good at what they do, right? A completely delusional egotist, unless they hold some absolute power like a monarchy or something, has to survive by bringing people in and making it worth their while, right? So I would imagine the people who work for Donald Trump see him profoundly differently than you and I might see him from watching him on the news.

Michael:     Right.

Ryan:         So you know, when you see people who have accomplished really great things, you’re aware of their ego but you feel like it’s a worthy trade-off, right? You feel like it’s part of their greatness and that sometimes it’s your role to help mitigate some of that ego so they can accomplish what you’re all trying to accomplish together, or whatever the situation is. And sort of with some perspective and distance, I’ve started to be able to see that, in fact, the people are successful despite their ego, and that if you’re around them for long enough, you can pick up some of the bad habits: the way they treat people, the way they act, that sort of—I would imagine Steve Jobs was not the only person with a reality distortion field at Apple. I bet he had a number of lieutenants who sort of started to develop a reality distortion field of their own.

Michael:     I’m sure that’s right. So let’s dig into some of this. I mean, you set up the book nicely. You’ve got just three broad sections, aspire, success, and failure, and each one of those sections has some specific chapters in it.

Ryan:         Mm-hm.

Michael:     And I’ve just picked a few of the tactics or the ways of framing life that kind of caught my eye, and I’m interested in the canvas strategy. This is a lovely metaphor. Can you just untangle what that is?

Ryan:         One of the things that I learned starting out, you know, I dropped out of college and I was a research assistant for a really prominent author, and what I learned very quickly is that my job was to make my boss look really good, right? And that if I could put my ego aside, like if I could say, “I don’t care about credit at all, I don’t even really care about what I’m getting paid, I just care about contributing and adding as much value as humanly possible to this process, I’m going to go much further and eventually I’m going to become indispensable to the point where I am going to get paid or I’m going to be referred to other people who are going to have to pay me.” And I think this is, my generation, the millennials, have started to push back against unpaid internships. There was a controversy a couple years ago where Sheryl Sandberg was in trouble for offering an unpaid internship. And to me, what I—I don’t see that as her being exploitative, I go, “What is an hour of Sheryl Sandberg’s time worth?” Probably priceless.

Michael:     Yeah.

Ryan:         And so, she’s offering, in exchange for not paying you $9 an hour or whatever minimum wage is, she’s offering you the chance to shadow her. That is an incredible deal. And so, I see the canvas strategy. I see when you’re just starting, you have to put aside your ego and be able to almost willingly be exploited by someone who’s more talented and more skilled than you because what you’re doing is you’re sort of embezzling an education throughout this process, right?

Michael:     Right.

Ryan:         And if you think that you already know everything there is to know and that you have an incredible amount to add and that you’re very valuable, all of a sudden you start to chafe under those conditions and you miss out on something very essential.

Michael:     I can understand that value of a degree of humility and a degree of service and a degree of how do I make the person I’m working with or in service to, you know, shine for their sake? But also because there’s some benefit to me around that.

Ryan:         Mm-hm.

Michael:     But I’m curious about when the pendulum swings not towards egotism and that kind of absorbing charisma, if you like.

Ryan:         Sure.

Michael:     But swings the other way where you somehow start losing your sense of self, you lose your boundaries, you actually kind of lose a sense of who I am and what can I do to serve this world? How do you protect against that if you come with that mindset of service and apprenticeship?

Ryan:         Yeah, that’s a great question. I mean, one of the things, obviously I don’t see sort of humility as being the opposite of ego, I see it as sort of the mid-point between ego and self-loathing or worthlessness or any of those feelings, so I sort of see it as a middle ground rather than an opposite. And so, I think that that is important. You have to know what you’re trying to do and you have to know what you’re trying to accomplish and what’s important to you and what your—there’s a quote from Goethe where he’s saying, you know, “A true failing is to value yourself as more than what you are and to value yourself as less than your true worth.” And so, I think that’s that essential balance. It’s something I think you figure out, right? Usually you figure out by probably going too far in either of the directions and starting to feel some of the consequences of that approach, and then, you know, you touch the stove, you realize it’s hot, and you don’t touch it as much anymore.

And I think I’ll say that it’s extraordinarily difficult in that sort of service canvas strategy relationship; it is hard to ever go—like, if someone is—if you are working for someone and they’re not paying you, it’s very hard to go from that to them suddenly realizing that you’ve changed and you’re worth a certain amount. Usually, in my experience, it’s moving on from that relationship and then starting a new relationship on new terms with someone else.

Michael:     So how do you help people find that middle path? I mean, that path between ego on the one hand and, you know, self-loathing or worthlessness, as you put it, on the other. I mean, one of the metaphors you used is like reaching out, touching the hot stove, learning that it’s a hot stove, not doing that anymore. But I’m wondering if there are other strategies to help you refine that sense of worth, just like that Goethe quote is.

Ryan:         Yeah.

Michael:     That doesn’t involve you actually having a scar at the end of it. Or maybe scarring is some sort of wisdom entrance through the wound, is the only to move forward on this.

Ryan:         I mean, I actually do think that. I think that, I mean, I have a chapter in the book about these sort of moments in our life where all that artifice and hubris is knocked down by the world around us. I do tend to find that it’s very difficult for us to just go, “Hey, you know what? I’m being a little egotistical,” or, “I’ve become very egotistical and I’m going to change,” right? It tends to be some sort of painful wake up call, sadly. In addiction circles, they say there’s very few ‘two cars in the garage’ addicts, right? Where they go, “Hey, you know, this is getting bad, but I haven’t ruined anything yet and it’s time for me to fix things.” It tends to be, you know, they had to sell the house, their wife left them, and they’re living on the streets that they finally wake up to it.

So I think there’s a part of that, but look, for me, writing this book, I’m not like some guru about ego and I have this seven-point checklist for solving it. I think it’s a very personal journey and I’m just trying to more diagnosis the disease then maybe sell a specific cure.

Michael:     Right. Right, right.

Ryan:         But I think when you put yourself into the—I’ll say this. For instance, for me, a task like writing is such a humbling, complex, difficult sort of career that it inherently attacks the ego. And so, for me, as long as I keep working and I keep pushing myself to do more difficult things, I remained humbled and it suppresses the ego. So I tend to find it’s sort of not, “Hey, if you meditate in the morning, you won’t have ego anymore.” It’s more like a sort of series of life choices and priorities that help sort of keep this thing at bay.

Michael:     Yeah, I think that and, you know, not necessarily meditation, but it feels to me that that degree of willingness to reflect on yourself, reflect on the impact you’re having in the world, reflect on the feedback you get to hear about others, from others, is just part of that process.

Ryan:         Mm-hm.

Michael:     Without that kind of things pinging back to you going, “Here’s where you stand. Here’s your radar,” it’s hard to notice when you might get off-track.

Ryan:         I think so, and I think one of the things that I don’t like about a lot of books is they’re sort of designed—like, it’s this belief like, “Oh, if they tell you this thing once, then you’ll know it forever.” I tend to find that that’s not true in theory or in practice.

Michael:     Right.

Ryan:         And so, I’ve tried to—I think it’s the reading and the thinking, and the thinking about it again and again, that helps you make tiny bits of progress. So for me, writing the book was a huge sort of exploration of the idea. I don’t sit down and read my own book, obviously, but I read the stuff that went into the book and the quotes that are inside the book that, like, I say that the wisdom in the book is not from me; it’s from other people. So I think it’s exercise that one must do in terms of keeping their ego at bay. It’s not, “Hey, if someone could just tell—we all know that ego is bad, so it’s not simply an awareness that it’s bad once that will magically solve this. It’s being reminded and catching the myriad ways that ego will manifest itself in any given situation.

Michael:     Okay, Ryan, so let’s jump into some of these quick questions. The first one is this. What’s the crossroads you came to that when you took it, took one direction or the other, made all the difference for you?

Ryan:         Yeah, that’s a tough question. I think for me it was deciding that I was going to be in charge of my own education and that there wasn’t really anything that school could teach me or that I would be magically gifted with but that I had to—if I wanted to learn about life, I had to do it on my own.

Michael:     Beautiful. Question number two here. Whose work has influenced your work? You know, be that be a writer, be a role model, be somebody else; whose work has influenced your work?

Ryan:         I don’t think that I would be a writer that I am or a writer, period, if it wasn’t for Robert Greene, who wrote The 48 Laws of Power, he wrote Mastery. He’s not only one of my favourite authors, but he happened to be a mentor of mine. He really showed me sort of the craft that is writing. And so, he’s probably been my largest creative influence.

Michael:     You know, it’s interesting to see the connections between his books, which are very historically-rooted.

Ryan:         Yeah.

Michael:     You know, he has an amazing breadth of reading and understanding and historical precedence that he draws upon, and that shows up similarly in some of your books as well.

Ryan:         Yeah, I mean, I hope that I’m paying homage in that way. He taught me how to do that. I feel silly abandoning it.

Michael:     So the third and final question. You know, at Box of Crayons, we talk about doing less good work and more great work.

Ryan:         Sure.

Michael:     Good work is your job description, if you like. Great work, the work that has more impact, the work that has more meaning. So how do you think about or frame your great work right now?

Ryan:         So for me, I have a creative agency that is, you know, financially successful. We have a lot of great work. But I always sort of remind myself when I decide what client I’m taking or what I’m thinking about working on, is like, I would rather be writing. And so, it’s helped me decide to only take on really, really great work that I’m proud of, and we sort of have that rule of thumb. We say, like, we do work that either facilitates our other creative projects or is in itself a creative project. And so, it ends up obviously costing us some money, but I think I like what you’re saying. It’s like if you say yes to everything that’s good enough or that pays well, you will find that you have precious little time to do the things that you actually like doing.

Michael:     That’s awesome. Perfect. Let’s get back to the interview. One of the early chapters in that first section around aspire is entitled “To Be or To Do?” And I’d like you to just tease apart what those choices actually mean. That’s a nice headline, but what are you talking about? And is there one of those that better serves a way of avoiding the ego or getting entangled in the ego than the other one?

Ryan:         The question “To Be or To Do?” comes from a speech from John Boyd, who’s probably one of America’s greatest military strategists, and he was saying—as young people would work for him, he would give them this speech, and to him, the distinction between being and doing is not what you would think. It’s, “Look, are you someone who has all the trappings of success? Like, you are a general or you have been promoted and you appear powerful? Or do you live that life? Like, are you doing the thing?”

So John Boyd was someone who had an immense amount of influence in politics and the development of things like the F-15 and the F-16, but he was doing it as sort of quietly behind the scenes. In fact, he never advanced beyond the rank of colonel, and I think he died, not impoverished, but you know, without much to his name.

And so, he was saying it’s like, “Look, there’s a difference between doing impressive things and being an impressive person.” And I think it’s doing the impressive things, like actually doing them, is the less egotistical thing to do. It’s easy to get credit for stuff; it’s harder to actually earn it.

Michael:     And you know, tied to that, one of your chapters is called “Talk, Talk, Talk,” but you’re not really saying “Keep Talking.” You’re actually saying …

Ryan:         No, I’m saying the opposite.

Michael:     Right, exactly.

Ryan:         Yeah. I mean, I think it’s never been easier, through social media, to have access to a platform and an audience and to feel like you’re doing work. Because, like, look, you know, I probably checked Twitter 100 times over the weekend and that felt like I was working, but really I was just, you know, gawking at things that were happening, right? And if I had taken that energy and I instead had sat down and wrote something, I think that would have been a better use of my time.

Michael:     Yeah, I get that. You know, that feels like it’s connected to the next question I want to ask you, which takes us to the section of failure, when one of the chapters you suggest here is about why it’s important to maintain your own scoreboard. So I think people will kind of intuitively get what you’re talking about, so the question I want to ask is: how do you figure out what matters in terms of what you measure? Because that’s what a scoreboard is. It’s a measurement of something.

Ryan:         Sure.

Michael:     So how do you figure out what are the things that speak to what matters and what are the things that perhaps speak to ego? For instance, you know, “I’ve got one billion Twitter followers.”

Ryan:         Right. Well, I’m always surprised at how rarely people ask themselves what it is they’re trying to accomplish, like on a given project or a thing. And so, like with a book, if you’re just doing a book because other people say you should do a book, for instance, then all of a sudden when you’re trying to judge whether you did good or not, you’re forced to take up other people’s metrics.

Michael:     Right.

Ryan:         If you wrote a book because you want to get a message out or you wanted to make your dad proud or, you know, whatever your personal metric was, then it’s much easier to judge whether you’re successful or not. And so, I see so many people focusing on this sort of external scorecard like, “Hey, I was recognized,” or, “Hey, the reviews said it was good,” and we don’t really ask ourselves whether—like, why are we giving these people power to decide whether we are successful or not?”

Like, it would be bad for me to decide—like, the first week of sales for this book is done, and so I’ll know in two or three days what the sales were. But it seems silly to me and very unphilosophical to basically be sitting here and going, “I will learn on Wednesday whether a very flawed methodology for counting sales, which is The New York Times and BookScan, when they give me back a number and then I compare that number to other people whether I was successful or not.”

To me, it’s far better to say, like, “Hey, this was successful because it was the best piece of writing that I’ve done so far in my life,” or that it started this conversation that I decided I wanted people to have, or because my fans liked it. Or you know, anything that (inaudible). Or it made—my parents liked it. Or you know, whatever; whatever the (inaudible) is.

Michael:     So let me be nosy, Ryan.

Ryan:         Yeah.

Michael:     How are you measuring success? Because you’ve had external measures of success; you know, you’ve ticked various boxes before.

Ryan:         Yeah.

Michael:     And in some ways, you could say, well, that means that you don’t search that out so much. In other ways, you may go that just makes you go, “I have to …”

Ryan:         Right.

Michael:     I mean, I was talking to Neil Pasricha the other day. Neil is the author of the Awesome Life books.

Ryan:         Mm-hm, yeah.

Michael:     You know, and they sold a bazillion. I mean, like, just, you know, millions of copies, and now he’s got his new book out called The Happiness Equation. And it’s interesting just watching him, and him watching himself go, “On the one hand, I know how this external stuff can kind of warp me and pull me out. On the other hand, I’m still twitching as I look at the bestseller list and the how many reviews in Amazon list and what’s my rating on Amazon and all that sort of stuff.

Ryan:         Sure. Mm-hm. No, totally.

Michael:    So I’m curious to know: how did you frame success for yourself with Ego is the Enemy?

Ryan:         Two-fold, and I think you’re totally right, and I think about this a lot. So the two metrics for me are, one, is it the best writing that I’ve done? So I was trying to judge it based on the actual quality of the work. And did I put everything I possibly could into that? Like, that to me is a huge metric of success. And then the second one is not looking at sales and not looking at reviews, but looking at its practical utility to sort of high-performers or people whose opinions I respect. So does the book find a place with people in high-performing fields where ego is a real problem, right? So my last book was about stoicism and it ended up becoming popular in a number of different fields that I hadn’t anticipated, but to me validate the theories in the book, right?

Michael:     Right.

Ryan:         People in the military have liked it, people in professional sports, people in Hollywood; people who actually sort of face—and entrepreneurs. People who face real obstacles and have had to overcome them. They’ve said, “Hey, this book succeeds; delivers on what it claims to deliver on.” And so, to me, those are the metrics, and I know there’s this quote from Bill Walsh where he says, you know, “If you sort of take care of everything else, the score will take care of itself.”

Michael:     Right.

Ryan:         And the way I see it is if I do those things, if I deliver a book that’s the best that I’m capable of, and passes the test of pretty skeptical people who actually have to practice these things, then it will sell. It might not sell a billion copies the way that, you know, a more motivational book might, but it will sell enough to justify the effort that went into it.

Michael:     Beautiful. Ryan, I enjoyed the read. It’s short but, as you say, it’s quite dense in terms of the layering of scholarship within that. If people want to find out more about you or about the book, where do they go on the Web to kind of stumble across that?

Ryan:         Yeah, they can just go to and the book is available in bookstores everywhere.

Michael:     Ryan, it’s been a pleasure. Thanks for your time today.

Ryan:         Thanks for having me.

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