Ryan Holiday on Discipline Is Destiny

Ryan Holiday: Yeah. I guess this would have been October 2019, right? A couple things have happened between then and now.

Ryan Holiday: Well, I’m doing a series now on the Cardinal Virtues, the–I guess, it’s not even a coincidence–but one of the quirks of history is that Stoicism and Christianity have the same cardinal virtues: Courage, Self-discipline or temperance, Justice, and Wisdom.

And so, I am in the midst of a four-book series. I did Courage first. This is the book on Self-discipline. And, now I am knee-deep on the book about Justice. And then Wisdom: I’m intimidated enough about that I have not yet begun to think about, but that looms there in the future.

Ryan Holiday: You know, there was actually sort of a debate both on Discipline and on Justice about whether the disciplined thing was to push forward or to pull back. On Discipline, there was sort of a dark night-of-the soul moment where I thought I wasn’t going to be able to do it and I was going to push it. And, then as I was starting Justice, I was like, you know what, I’m definitely going to do it. But, both times, I ended up having a breakthrough and then getting really excited about it and liking it.

But, I think when I was younger, the idea of deliberately waiting on something was inconceivable to me. And, I do think I’ve gotten at least to the place where I could entertain the idea.

Ryan Holiday: Yeah. And for people who don’t know: the sweet fruit is patience. Or patience, they say, is bitter, but the fruit is sweet. Patience is hard, but what you get on the other side of patience is wonderful.

And, I think that’s probably generally true for the concept of restraint, as well, which is: it feels hard as you’re resisting doing something or holding back from doing something. But, usually, what comes on the other side of that waiting or dialing in the exact right opportunity–usually, the rewards for that are worth it. It’s just hard. It’s hard in the moment when you are forgoing something.

Ryan Holiday: I turned 35 this year.

Ryan Holiday: That’s a good question. I would say that of the cardinal virtues, discipline is the one that I feel most comfortable talking about as opposed to feeling like it’s the–when you’re writing about courage, obviously, it’s a sensitive topic because the courage of the sort of greats of history is so profound–transcendent in some cases–that it feels almost insulting to even talk about it as if you could instruct. So, this is the book that I felt most comfortable writing because I feel like I am a disciplined person. I feel like discipline is a strength of mine.

But, I definitely feel like I grew from the book, even just what we’re talking about–the idea that discipline isn’t always doing. Sometimes discipline is not doing.

I think the journey that I’ve tried to be on, and I feel like I’ve gotten better with each project–this one being a big step in that direction–is: How do you do something at a high level, be disciplined about it without it coming at the expense of discipline in other areas of your life or even just your ability to be present and show up for other elements of your life?

I think, it’s much simpler to say, ‘Hey, I’m going to dedicate myself fully to this thing and be very disciplined about it, but my family would suffer, or my health would suffer, or my reading would. So, I feel like trying to integrate as being on this track of doing books very consistently, year in and year out, I’ve had the excuse of, ‘Sorry, I can’t,’ or, ‘Hey, I apologize for my lack of temper,’ or, ‘Sorry, my lack of patience,’ or my temper, or whatever. It becomes harder to justify when you’re always doing the thing.

You don’t get the excuse of, ‘Hey, I’m on a book deadline,’ or ‘I’m in the middle of writing a book,’ when you’re always doing that thing. It’s like, if you’re an actor and you’re like, ‘Sorry, I’m grouchy, I’m on this crazy diet for this role that I’m doing.’ You can use that excuse occasionally. But, if you are always doing that, people go, ‘Look, you got to figure out how to integrate this into your life.’

Ryan Holiday: I would say much better.

Actually, as I was finishing up Discipline, my oldest was sitting at the kitchen table and he was doing some art project or something and I was sitting on the couch. I guess he would have expected me not to be sitting on the couch, but to be at the office. And, he said, ‘Dad, I’m sorry you’ve lost your job writing books.’ And, I was like, ‘Wait, what are you talking about?’ And, I realized, like, in his mind, things were normal enough that something had obviously changed at work.

And, obviously, that was very sweet, but also a retroactive indictment of how things had been in the past.

So, I think I have gotten better at it. I guess I’m trying to just normalize it. And by that, I don’t mean make my life crazy so the abnormal work that I do seems normal. But, to try to get to a place where: Hey, I show up at the office and I do a few hours of my thing; and then I’m not in this, sort of, adrenalized frenzy or sprint that can sometimes be the creative process, but it’s just a part of life. And I feel like I’ve gotten closer to that, although not perfect at it.

Ryan Holiday: Yeah, my father definitely worked very hard. My father had worked multiple jobs. He was a police detective and then he also sold real estate on the side. And, then he was an investor. My dad was always sort of doing multiple things. And so, I think the ability to manage a portfolio of activities or pursuits, I think, I learned by osmosis through my dad.

But, when I left college, I was a research assistant for Robert Greene, who, I think, is one of the great non-fiction authors of our time. And, Robert is one of those people that is very monk-like in their discipline. First off, he basically only does that. He’s just a writer, and I mean that in the complimentary sense. He is an artist who is committed to the discipline of what he does and has very strong boundaries about the work–won’t answer the phone at certain times; you can’t drop in and just say hello. He’s sort of monk-like in his commitment to these books. And, he’s one of those authors that will work several years on a single book. So, he and I are different in that sense.

But, I think that was meeting someone who–one of the most important things that can happen, I think, as you’re starting down a career path is to meet someone who is a pro at that thing. Obviously, anyone who is getting paid is a professional. But, when you meet someone who is just fully committed and ritualized and organized about what they do–they treat it like a discipline–I think that’s just a very powerful, transformative thing. Because you realize: Oh, there’s the wavelength that people who are just getting by are on. And then there’s the pursuit of mastery in that profession. And which one of those are you going to be?

Ryan Holiday: I think that’s right. Especially–it’s like, you can be a workaholic because it’s coming from a place of insecurity. You could be a workaholic because you’re running from something. You could be a workaholic because all you want is money. Right? So, I think what we’re talking about here is when you have decided that you have some sort of calling, and there’s a purpose to what you’re doing, and you don’t take it lightly.

And, maybe if you’re thinking about it in sports, there’s obviously people who are naturally talented, who like fame, who like the rush of the crowd, who are–or they’re very good and this is why they’re at an elite level. And, then there’s your Tom Bradys, who have decided that there is something beautiful or artistic about the game and they want to reach that transcendent level.

In that respect, you also need the ability to be disciplined about your discipline. Right? Like, to not take your commitment to that thing too far at the expense of everything else. But, I think it does start with some sort of idea that this is not just a job, this is a means of–well, this is a thing from which meaning can be derived and there is some sort of purpose to what you’re doing beyond the compensation or the external rewards.

Ryan Holiday: I do. And, you know, it’s actually funny: in the practice chapter, I had a whole section that was written about Tyler and this question that he asks. I ended up moving it to the wisdom book. But, he says, ‘How do you practice?’

Ryan Holiday: this actually does relate to my practice, now that I think about it.

So, he talks about, like–his question is: How do you practice your scales? Right? A musician goes through the scales: you go over and over and over again and it gets imbued into your muscle memory. And also, inspiration, connection, ideas come from this repetitive practice of the thing. Writing is unusual in that the practice–writing is strange to find one’s practice. And, I ultimately made the decision, as I was saying, to think that that question of what is your practice to me is the domain of wisdom. The actual act of doing it would be the self-discipline.

So, it’s hard to, I think, sometimes distinguish between where one virtue begins and the other ends. For me, the building block of what I do, and I think the form of practice, is I read and then I break down the books that I’ve read onto note cards. I use physical four by six note cards. So, that–

Ryan Holiday: Yeah. So, like, these–this section here, these are books that I’ve read who I have not gone through and done the note cards on. So, I’m a little behind in my practice. But, to me, like, I know that I am getting better at what I’m doing: I’m practicing the discipline when I am actively reading and going through the note cards.

So, like, right now, I’m in the middle of writing this book. So, that is doing the act, but the building blocks of that–like, a stack of note cards is a lagging indicator as to whether I have been doing the practice.

And, if I get too caught up with speaking or podcasts or writing, six months from now I’ll see the consequences of not having done the active practice.

The other part for me that’s been–it wasn’t intentional, but it’s been very, very helpful, is I started this daily email in 2016 called The Daily Stoic, where I send out one email about Stoic Philosophy every day.

And so, I don’t do that every day in the sense that I wake up and write today’s email because that wouldn’t–part of discipline is about setting up systems that allow you to effectively do what you do. If I had to wake up every day and do it in real-time, that would be, I think, immensely inefficient.

But, I have to produce enough raw material on a regular basis to fill this daily email. So, having this thing that I have to ship every single day keeps me in shape in the way that I think is similar to the function of practice.

Ryan Holiday: Well, thank you–

Ryan Holiday: Yeah, I’m very curious.

Ryan Holiday: He’s a master.

Ryan Holiday: Yeah. I mean–that is, the question is, like: how can one get better at a craft like writing?

Obviously, as you said, you can do what you do over and over and over again and it becomes more intuitive and natural and hopefully, effortless. And, I do think–like, if you look at The Obstacle Is the Way, which is in a similar format to Discipline Is Destiny, as is Ego Is the Enemy, Stillness Is the Key, and Courage Is Calling. So that’s like five books in this style. Is the fifth one better than the first one? I would say, absolutely. I would say that the practice does get better the more you do it.

But, how does one get better overall at writing? How would one even judge if one’s getting overall better at writing? I feel like I have a practice where I do this where–so, one, I don’t do it as much anymore. But, for many years I also ghost-wrote projects. I would take on projects for other writers. And, I felt like–obviously, in Discipline Is Destiny, I talk about: what’s the main thing? You need to be committed to the main thing.

I justified these projects in two ways. One, they were economically rewarding, and so that gave me more creative freedom and security to pursue my own projects. But, two, I felt like they were giving me reps or stage time, but practicing differently.

One of the interesting lines in Meditations, Marcus Aurelius talks about using the reins of his horse with his non-dominant hand. He says, ‘You get better from the practice of doing it differently.’ And so, I would argue that part of the reason that book one through book five, there is an evolution there, it’s not just that I did that same thing five times, but I also was working on extracurricular activities that made me a better writer.

And, so I think there was that. And, then I feel like I’ve–and I’m not trying to just explain away your criticism–but I did this book Conspiracy, which I think was very different compared to my other books.

Ryan Holiday: Well, thank you.

Ryan Holiday: And, I was actually just talking to my agent this morning, and he was basically, like, ‘The publisher will fall over themselves to purchase another book in the vein of the books that you just did.’ And, my thinking was, I’m not sure I want to do that. I was thinking about what haven’t I done and might I try to do something very different to get better at the thing.

So, I’d like to think I am challenging myself in the way that you’re talking about. But, I would say that it’s hard because when you’re really good at something, it’s easy to just continue doing that thing and you get less–

Ryan Holiday: No, no. I totally take the point. And, I think about that. It’s like the reward for getting good at something should not be the closing of other avenues. And, have you had David Epstein on, his book Range?

Ryan Holiday: Yeah. I think–

Ryan Holiday: Totally a great book. And, I think specialization makes sense. Right? The most basic law of economics is the law of comparative advantage. But, I think range is also important; and it’s, I think, fulfilling, too. Let’s say, you specialize and specialize, but that specialization is leading to a kind of premature burnout, then the specialization is actually the enemy of mastery in that sense.

Ryan Holiday: Well, thanks–

Ryan Holiday: It’s weird to have to put this aside, but put aside the legitimacy or the necessity of the monarchy–right?–because it’s a separate question. She doesn’t choose whether to be born into this. She doesn’t choose whether that should be the system of government of the country she’s born into. She is born into a role. Right? She is chosen for a role; and then she chooses to fulfill that role over the next 70-odd years. And that, in and of itself, is impressive.

I opened the book, I tell the story of Lou Gehrig. You compare Lou Gehrig’s streak to Queen Elizabeth II’s streak, and they’re not even in the same ballpark. Literally or figuratively. I mean, there are no off days to that job.

One of my favorite achievements that I was reading about of hers is that she fell asleep in public or on the job one time in 70 years. And, she was in her 80s, and it was a lecture about magnets.

Even from a physical perspective, the people who have–like, her security or the people who will travel with her on one trip when she was alive–again, would remark at just the sheer physical toll of the role, which she–to talk about effortlessness–she, as a little old lady, made you think, could it possibly be hard?

And, then you go: ‘Wait, she just met 10,000 people in four hours.’ Like, that would be physically grueling. In the sun.

So, I guess what I came to think about her–and I feel like as I’ve gotten better at what I’ve done, and gotten older, my empathy/respect for professions that I maybe previously would not have had really any admiration for–clearly, there’s a lot of people throughout human history have been born into some sort of royal family. Not millions; but this is a longstanding system of governance of which those families tend to have–there’s lots of people who have had this role, and very few of them have, at the end of their life, left with any sort of admiration or respect. Just like they say, the hardest thing to do is to leave politics with clean hands.

To be a royal and to prove yourself worthy–even remotely worthy of the unearned privileges that you got at birth–is an extreme accomplishment that we should respect, even if we disagree with whether people should get those privileges.

Ryan Holiday: She’s never given on-the-record interview.

Ryan Holiday: Well, I think she embodies one of the interesting elements of discipline at the high level, which is: the rigidity actually becomes flexibility or the strength is not in the rigidity, but in the adaptability.

So, if you look at what the monarchy was in the 1950s to what it is today, it’s both totally familiar and totally unrecognizable. And, she had a motto–and it comes from some Italian novelist whose name I’m forgetting–but it was: If things are going to stay the same, things are going to have to change.

And so, she had this sense of, ‘Well, the institution, as a whole, needs to remain or should remain. My job is to protect and prolong it, but I have to be flexible and adjust because the world is always changing.’ She’s almost kind of an embodiment of the Ship of Theseus. Everything is changed, but it’s also somehow the same thing.

And, to me, there’s a lesson in that for all of us. If you want to be great at what you do–like, I am a writer, it’s a profession that has existed for thousands of years. It’s not the oldest profession, but it’s close to the oldest profession. And yet, what I do is laughably different than a writer 40 years ago or a writer 100 years ago. Just as the world that I existed in when my first book came out a little more than 10 years ago and then hopefully, if I’m still doing this decades from now, you have to have this ability to respect the discipline, but also be willing to change everything inside the discipline to be able to continue doing it.

Ryan Holiday: Yes, yes: Not a good idea, let’s not do that. And, that goes to–

Ryan Holiday: Well, she gets asked to do a lot of things. Right? And people have a million suggestions for her, and there are a million changes that people do demand of her. And, they have this motto of ‘Better not,’ which, to me, is the wonderfully polite British version of just ‘No, not going to do it, hard pass.’

And so, she has this sense of what to do and what not to do. And, that’s actually what I opened the book with. There’s a quote from Epictetus. He’s asked to describe at its core what stoicism is, what the philosophical life, what a virtuous life demands.

And, he says, ‘It’s two words: Persist and resist.’ It’s this paradox of not doing things, and also doing other things, and knowing what those are. I mean, obviously, now we’re in back into the discipline of wisdom. But, that strength to do and to not do is the paradoxical nature of discipline.

Ryan Holiday: No, no. I think about that a lot. My instinct tends to be to say yes, so I have to cultivate a discipline of saying no.

But, I just got this new thing. It’s at a frame store being framed. But, I’ve fallen in love with Harry Truman, who I’m writing a lot about in the next book. And, I found this letter–I guess the Presidents just produced so much paperwork, you can buy this stuff relatively cheaply. It was like $500. But, it’s a letter–it’s a series of memos. It’s all of the memos, but it culminates in this little piece of paper, like an interoffice memo at the White House, where right after Truman has been elected, or I think reelected. Actually, no–this is right after he becomes President.

And so, his secretary is writing this interoffice memo and it says, like, ‘Should we say–is the policy that we should start saying no because the President has too many commitments?’ And, the memo makes its way to Truman’s desk and he underlines, We must start saying no because the President is too busy. He underlines it, signs it, and writes: ‘The correct policy is elucidated in this memo.’ And, I’ve got this framed and it’s going to go right next to my desk.

The point is to say yes to the things that are important–your family, the work you’re trying to do, the people you want to connect with, relationships, etc. You have to say no to most things. And, even the serendipitous, fun, crazy experiences that, like–let’s say, your decision to move across the country or to move across the globe to have this new job–that’s a big yes. But, you wouldn’t have been in a position to say that yes if you hadn’t been disciplined over the course of your career. But also, imagine if you’d taken on so many other big commitments that it was impossible for you to extricate yourself from them to be able to be in a position to be like: Yes, I want to change my life to do this big thing.

Ryan Holiday: The point was the secretary was, sort of hypothetically, ‘Should we start saying no to more things?’ And, he underlines it and is, like, ‘Yes, we must say no.’

To me, it’s this cool document that even the President of the United States is having to put in place policies to create–I don’t know, just that the President signed this thing to remind his secretary that you have to say no. It’s just so wonderful to me.

Ryan Holiday: Are you not a Truman fan?

Ryan Holiday: Interesting.

Ryan Holiday: Well, so I do have–I’m just telling–so, basically, I’m giving away the plot of the book, but I’m so excited about it, I love talking about it.

So, the–I’m splitting justice up into three domains. The first of which is personal justice–having, like a–being person of honor, having a code of ethics, being honest, being straightforward. And Truman, I find to be this fascinating figure in that basically an average person is thrust into the White House–

Ryan Holiday: And, he does a good job because he was a fundamentally decent human being. He wasn’t this brilliant visionary and classically trained–he was a self-taught Christian man of honor; and then, thrust into power, manages to do a pretty good job because he has that baseline. But, in the–

Ryan Holiday: in the second part of the book, I’m talking about how does one bring justice into the world. And, one of the chapters I was most excited to write, I talk about the proximity to power. One must have a proximity to power to bring good into the world. You can’t be this sort of theoretical outsider.

And, I tell the story of Eddie Jacobson, who Truman meets as a young man in Missouri. He probably never met a Jewish person. And, then you flash forward 50-odd years, maybe more, and Eddie Jacobson is the only person who can get a meeting with Truman. Because Truman has decided he doesn’t want to hear about Israel anymore.

And, Eddie Jacobson walks into the Oval Office; and he’s told by the secretary on the way in–to go to our point about controlling [?] access–he says, ‘Whatever you do, do not mention Israel to Truman.’ And, he says, ‘But, that’s the only reason I’m here.’ And, he starts to talk to him about it and Truman shuts him down. And, Eddie Jacobson looks at him and he says, ‘I have known you my entire life. This isn’t like you. My hero would like to meet with you to talk about Israel. I need you to do this for me as a friend.’ And, without that personal proximity to power, that lifelong relationship, Israel might not exist as a country.

Ryan Holiday: I would love that.