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Jay Shetty PodcastJay Shetty Podcast

Ryan Holiday ON: How To AVOID BEING MISERABLE For The Rest of Your Life | Jay Shetty

If you enjoy this conversation, you'll love my talk with @garyvee 👉 Today, I sit down with Ryan Holiday to talk about living a life of discipline.

Ryan HolidayguestJay Shettyhost
May 8, 20231h 13mWatch on YouTube

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Transcript

0:00 – 4:25

Intro

Ryan Holiday 0:00 If success is this lagging indicator of commitment now, how can you be sure that you are paying your dues?

Speaker 0:07 The bestselling author and host-

Jay Shetty 0:08 The number one health and wellness podcast On Purpose with Jay Shetty. Society has gone in the direction of becoming addicted to pleasure-

Ryan Holiday 0:17 Yes

Jay Shetty 0:18 ... or pleasure-seeking. Where, from the stoic's perspective, why did we even ever go down that road? Like, why did we leave wisdom and self-control, or did we never have it at all and we've always been trying to balance it?

Ryan Holiday 0:31 I, yeah, I mean, I guess that's the big question is, like, why do we take something that we like too far?

Jay Shetty 0:37 Yeah.

Ryan Holiday 0:37 Right? So the epicureans would say, like, "Look, drinking is great, but if you have a hangover the next day, was it actually so great?" And so, you know, i- if you, if you push the or- the pleasure too far, it becomes not pleasurable. But in the moment, that feels very far away [laughs] .

Jay Shetty 0:55 [laughs]

Ryan Holiday 0:55 Right? Like, in the moment you want the thing now. Obviously sex is this thing for people. It's like, the, the thing you're attracted to in this moment, you're not thinking about the shame or the regret or the consequences or the pain or the loss or the gr- you're not thinking of all those things. You're just thinking of right now. So I think a big part of this, this is where the wisdom comes in, the ability to step back and go, "What am I gonna think about this after I get it? What am I gonna think about this later?" And realizing that your mind is very good at tricking you. Just as your mind te- often tells you, like, "Stop, you're too tired, you can't go any further," you actually have m- a lot less to, left in the tank. Your mind also tells you, "You need this thing. You won't regret it. It's ama-," you know, whatever.

Jay Shetty 1:36 Yeah.

Ryan Holiday 1:36 And it, it's, it's really good at putting those blinders on. And so part of, I think, any meditative practice, any philosophical practice, any journaling practice is, is being able to argue with yourself a little bit.

Jay Shetty 1:49 Yeah.

Ryan Holiday 1:49 To step back and have that conversation about, "Well, is what I think about this true? Is the story I'm telling myself about this true?" I think nowhere is this more important than for, like, ambitious people who have told themselves, "I will be happy when I accomplish X."

Jay Shetty 2:06 Mm.

Ryan Holiday 2:06 Right? Like, of all the things we need to be most disciplined about, ambition is one of them, 'cause it tells you this lie that, "After I become a New York Times bestseller, after I make a million dollars, after I get a gold medal, then I'll be good. My parents will be proud of me. I'll be happy. Then I can relax." And you have to have the perspective, the wisdom, to go, "Was that ever been true ever in my life before? Has that ever been true in history?"

Jay Shetty 2:31 Yeah.

Ryan Holiday 2:31 And then go, "Oh, okay, no, I can't tell myself that lie." That doesn't mean you don't work really hard to do stuff, but you're not doing it under the false pretenses that it's going to be conditional to your happiness.

Jay Shetty 2:44 Yeah. But there's a part of us that, and I, and I love what you're saying, but there's a part of us that always believes that we are the exception.

Ryan Holiday 2:49 Yes. [laughs]

Jay Shetty 2:50 That we will know how to spend money better.

Ryan Holiday 2:52 Yeah.

Jay Shetty 2:52 That we'll know how to have love in our life better. Like, we won't be the one who fumbles off the edge of a cliff. Like, we, we're smarter than all our friends even if we don't say that. We're wiser than the people who came before us. And that's, and that's ego as the enemy. But of course, like, that, that idea, I think, is what misleads us so much.

Ryan Holiday 3:11 Yes. Yeah. It's, it's like, okay, you're on the medal stand, you've just won the gold medal, and you're not feeling happy for yourself. You're thinking, "Well, I coulda done it faster." You're thinking, "Oh, I gotta do it again," right? Even in that moment you're not able to think, "I'm doing it to myself right now what I will be doing to myself in the future." And that's this sort of insidious thing. And you can understand why from an evolutionary perspective it drives the species forward. You can also see the immense personal cost that it inflicts on us, because it never allows us to be present or content or happy with what we have in that moment.

Jay Shetty 3:49 Mm.

Ryan Holiday 3:50 And so I think, again, people think discipline is the, "I always push myself to do better, do more." Discipline can also be curbing that very impulse, right? Like, um, ordinary people, when we're talking about discipline, what we're talking about is getting off your butt, working out, resisting eating candy and eating nutritious food instead. It's, you know, managing your screen time. But I think for a lot of more disciplined people or for people who have tasted the rewards of discipline, you have to learn how to be disciplined about discipline.

4:25 – 6:40

What is the real meaning of discipline in different cultures?

Jay Shetty 4:25 Yeah.

Ryan Holiday 4:25 Which is maybe the highest level of, of the whole thing.

Jay Shetty 4:30 Yeah. Yeah, exactly. Now we're, I guess now we've started talking about discipline as a tool to achieve daily or weekly, monthly, yearly tasks, but you're actually saying that we need to go back a bit. Like, how would you unpack that for how you're defining discipline there?

Ryan Holiday 4:47 Well, it's, it's like, uh, what's the number one cause of injury for athletes? It's overtraining.

Jay Shetty 4:52 Yeah.

Ryan Holiday 4:52 Right? So, like, yeah, your ordinary person, it's like you're not training enough. You're not working hard enough.

Jay Shetty 4:57 Yeah.

Ryan Holiday 4:58 But then at a n- more elite level, at a more accomplished level, actually the trouble is, hey, the, the race isn't for six weeks. Like, you, do you wanna peak now or do you wanna peak at the right moment, right?

Jay Shetty 5:10 Yeah.

Ryan Holiday 5:11 Um, or this is just a practice session. You don't have to go all out. Or, you know, it's a long season. Are you prepared for that? And so, you know, discipline has to be balanced with sustainability, with rest, relaxation, recuperation, recovery, all these other things, and that requires kind of a spiritual discipline on not just, hey, I can run an hour without getting tired, but, like, can I stop myself from doing that?

Jay Shetty 5:39 Yeah.

Ryan Holiday 5:39 That's not what I should be doing in this moment.

Jay Shetty 5:41 Yeah. And I, and what I like about that is that I feel there's different phases and stages. Like, in the first two years of my career where we would've met in New York, and we went on a walk once as well, I think, and we, we were walking around the city, and I remember talking about a few of these themes. But it was, at that time in my life, I was working probably 18-hour days.

Ryan Holiday 5:59 Sure.

Jay Shetty 5:59 Because I, I had to in order to kind of break through that first level.

Ryan Holiday 6:04 Yeah.

Jay Shetty 6:04 I was still disciplined in the sense that I would make time to eat to some degree [laughs] and, and meditate, and I would make some time to do a few things of rest, but generally I was working seven days a week, 18 hours a day. And I'm very grateful I did that. I don't look back and go, "Oh, I wasted two years." It was brilliant. But then in the last couple of years, I've taken my evenings back.

Ryan Holiday 6:22 Yeah.

Jay Shetty 6:22 And so I don't work after 6:00 PM. It's just a rule. I don't wanna work, I don't wanna be on the phone. And I was talking to a friend, and it's exactly what you said. He was saying to me, he was just like, "Well, don't you get less done?" And I was like, "No, I get more done."

Ryan Holiday 6:33 Sure.

Jay Shetty 6:33 Because I know how much I have to get done, I'm far more attentive and focused, and then I'm not working at 9:00 PM when I

6:40 – 11:05

How do you overpower your own mind and learn to argue with yourself?

Jay Shetty 6:40 can rest and recuperate, and now the next day I'm, I'm better for it. And so I, I hear that idea that that is also a discipline-

Ryan Holiday 6:48 Yes

Jay Shetty 6:48 ... although it could be seen as you being lazy in the evening.

Ryan Holiday 6:51 A- and I think it's the question of, well, is it easy for you to do that, yes or no, right?

Jay Shetty 6:54 Yeah, yeah.

Ryan Holiday 6:54 It's hard... It's actually harder for you, I imagine, to say, "I'm stopping at 6:00" -

Jay Shetty 6:59 Yeah

Ryan Holiday 6:59 ... than it is to say, "I'm gonna work all night till I fall asleep at my desk."

Jay Shetty 7:03 Yeah. [laughs]

Ryan Holiday 7:03 Right, like...

Jay Shetty 7:04 Yeah, I could do that, yeah. If my wife's not around, I could work every weekend and evening, yeah.

Ryan Holiday 7:08 And also, it's realizing that you have multiple things that you're trying to do simultaneously. So yeah, sure, working, continuing to work 18-hour days may help you continue to advance in your career. But if one of the also... the other things you're trying to work on is to stay married, or to better yet, have a happy marriage, uh, or you have children, or you have your health or whatever. Like you, you were telling me before we recorded that, like, you got in at 3:00 AM last night. Let's say you're a person who always wakes up very early. Like, I'm a person who wakes up early.

Jay Shetty 7:36 Yeah, same.

Ryan Holiday 7:37 But then I also have to understand that sleep is a discipline, and so if some changes outside my control mean that I didn't go to bed till a certain time, the fact that I wake up at 5:00, that's bad idea.

Jay Shetty 7:49 Yeah.

Ryan Holiday 7:49 And it actually requires... You wouldn't think that sleep discipline would be a thing, but in the military they talk about that, sleep discipline. You gotta get your hours because you make bad decisions-

Jay Shetty 7:58 Mm

Ryan Holiday 7:58 ... when you're not rested.

Jay Shetty 7:59 Mm.

Ryan Holiday 8:00 And other people bear the consequences of those decisions. And so deciding, hey, I'm going to skip this thing that feels comfortable to me to do, that feels natural for me to do, that I feel like I'm letting some part of myself down by not doing, I actually have to be the bigger, more self-controlled person and say, "In this moment, I'm not going to do that," right? And, and I think at the end of the day, self-discipline is the ability to have an emotion, an instinct, a feeling to do a thing, and then to catch yourself and go, "Is that actually the right thing to do? Yes or no?" And sometimes it is. Sometimes it's, "Hey, it's cold outside and it's 5:00 AM and it's still dark, and I don't wanna get up, but I have to get up because I've made these commitments. I'm behind," blah, blah, blah. Then other times it is to stay in bed, right? Just like, you know, sometimes, uh, you feel that surge of temper coming on and you have to go, "No, that's not a good..." Like, it's always the ability to step back, put the emotion, the instinct, the opinion to the test. And I think you learn this in meditation. I think you learn this for Stoicism in the journaling of going like, "Here's the thing, and I can choose it or not. I can choose to identify it or not. It is not me." Uh, the Stoics have this word assent, right? Not like ascent up a mountain, but A-S-S-E-N-T. Do you assent to the feeling or not? Do you agree to it, rubber stamp it, approve it, go along with it or not?

Jay Shetty 9:29 Do you subscribe? Yeah.

Ryan Holiday 9:30 Yeah. That's what discipline is, is about. What do you assent to and what do you not assent to?

Jay Shetty 9:35 Yeah. I, I wonder, I wanna go to a tangent. I wanna come back to that 'cause I actually really like that point, but a few words ago, there was something that you sparked for me. Sometimes I feel like with work it's doable. Sometimes with even our partner or with friends it's possible to say no, to be disciplined. I find like, and I wanna ask you this from your perspective, what about a sense of dad guilt? Like, we talk a lot about mom guilt and, you know, if, if we're speaking to mom I'd ask about mom guilt in this scenario. But from a dad guilt point of view, like you're a dad. I, I, you know, and I, I see you wanting to be a good dad and, and you're very involved with your kids. But at the same time you're a writer and you own a bookstore and you're doing activist work. Like, there's so many things that you do. Do you ever feel like that's like the hardest place where discipline... Because it's like even if a dad comes home at 3:00 AM-

Ryan Holiday 10:21 Yeah

Jay Shetty 10:21 ... and the kid wants him at 4:00 AM, like does the dad stay up? Like, what does the dad do? How does it work?

Ryan Holiday 10:26 Well, it's so insidious. What we do is we go like, "I'm doing this for my family"

Jay Shetty 10:31 Mm.

Ryan Holiday 10:31 Right? And it's like, are you? Or are you doing it for you? Are you doing it for the money? How can you be doing it for your family if you don't see those people as a result of what you're doing? Someone told me, uh, many years ago, they said, "Love is spelled T-I-M-E," and I think about that all the time. I mean, obviously I always have things that take me away more than I would like them to be. And I suppose I could do nothing, but that would also leave me unfulfilled. That would not be me setting the example I want to set for my kids. But at the end of the day, realizing that everything I say yes to also means

11:05 – 16:22

Discipline has to be balanced with sustainability, rest, and so much more.

Ryan Holiday 11:05 saying no to someone or something else. And in some ways I try to use that dad guilt a little constructively. I try to go, "Okay, this person's asking me to do this thing, or this person's offering me money to do this thing, or this is some cool opportunity. They want me to go heli-skiing in British Columbia or something." And I go, I'm, "I don't want to say no to this cool opportunity. I don't want to miss this memory. I don't want to hurt this person's feelings." Then I go, "But I am hurting a person's feelings. I am saying no to a memory. Like, I am taking something away from someone, and that person is a five-year-old, and they're gonna feel it far more deeply. Someone else will take my spot on that plane to British Columbia. No one will spend that time with my kids." And so I try to use that guilt constructively-

Jay Shetty 11:54 Mm

Ryan Holiday 11:54 ... in the sense that I'm, I'm reminding myself always that saying yes to one thing means saying no to something else, and that conversely saying no means saying yes, right?

Jay Shetty 12:06 Mm.

Ryan Holiday 12:06 And that I always, as much as I can, I want to be saying yes to the things that actually matter to me, and I want to be putting my money where my mouth is. It's like if, if someone looked at your calendar, you say you, you put your family first, you say family's important, blah, blah, blah, but then if I looked at your calendar, what would it show, right? If there was a custody hearing or, you know, if you were being investigated, if you were being audited, what would the receipts show? Do you actually value them? Do you put them first? And like It should be pretty, pretty obvious whether that's true or not.

Jay Shetty 12:42 Yeah, no, I, I have a exercise in Think Like a Monk where I ask people to do their time audit for the week, and it's literally that where it's like... And, and it's against your values because someone's values may be different, but the idea that your bank statement and your schedule show your values more than what you say.

Ryan Holiday 13:00 Yes.

Jay Shetty 13:00 Right? The words that come out of our mouth are not actually our values. They're our aspirations.

Ryan Holiday 13:05 Yeah.

Jay Shetty 13:05 Those are the values you wish you had, but the values that actually go, what do you spend your money on and what do you spend your time on, like, that's far more what your real values are.

Ryan Holiday 13:14 Yeah, I think about that. I, I saw this interview with Jimmy Carter many years ago, and he, he has this sort of crisis of faith and he goes like, "If I was put on trial for being a Christian, would I be convicted?"

Jay Shetty 13:26 Mm.

Ryan Holiday 13:26 Right? So it's not what you say, not what you think, not what you wish, but, like, what do the actions show? And I think about that with Marcus Aurelius, who I write a lot about, the, the stoic emperor. Like, he never identifies explicitly as a stoic, and one of his translators says, you know, he never even says the word Stoicism, like, in his writings.

Jay Shetty 13:48 Mm.

Ryan Holiday 13:48 But he's considered this philosopher emperor, and he probably still would've been even if his writings had never survived because the deeds are there. There's a Latin expression, acta non verba, like deeds not words. And so you have to always think not what do I write about, what do I think about, what do I wanna be true, but what do the actions show? And, um, no one is perfect.

Jay Shetty 14:09 Of course.

Ryan Holiday 14:09 And I think anyone auditing themselves, uh, is gonna be, there's gonna be some disappointments. But you want, like, the big statements of priority to be there. And to go back to the idea of guilt, when you're looking at it, you shouldn't, like, whip yourself and feel... But you should be like, "Okay, this is not the painting the picture that I want to paint," and that you're lucky enough in that moment to catch it now, not when you're 80, you know, not on your deathbed. You're, you're, you've caught it now, and so what changes are you going to make-

Jay Shetty 14:40 Yeah

Ryan Holiday 14:40 ... to, to get closer between the ideal and the reality?

Jay Shetty 14:45 Yeah. Yeah, absolutely. And, and something that, that's interesting that's coming out for me here is that pretty much everything we do every day can be defined by thinking, feeling, and doing. But I think we're living at a time where we're stuck in the feeling generation, so we do things because we wanna feel a certain way, but then when we feel things, we don't know what to do with it. So I'll give an example of what I mean by that. If you, if we feel guilt, most of us don't know how to shift from that feeling into thinking and doing something different in order to not feel that guilt again.

Ryan Holiday 15:18 Yes.

Jay Shetty 15:18 And if we wanna feel happy, we just try and feel happy, not realizing that you have to change your thoughts and what you do in order to feel happiness or whatever it may be. What I'm trying to get at there is, like, that to me sounds like a discipline too, like, but we've gone so into feeling because I think for so long thinking and doing were the only things talked about, and we didn't feel enough.

Ryan Holiday 15:40 I think realizing that almost all the things you want in life are accidental byproducts of habits, processes, systems, routines, right? So Viktor Frankl famously said that happiness can't be pursued, it must ensue. It's the result of getting those big things right, and then you just feel this kind of feeling of happiness as a byproduct. You don't, as you said, you don't go, "Today I must feel happy," right? You, it's, it's the result of having meaning and purpose and, and taking the right actions. And so people sometimes look at the books that I've written and they, like, what, like, how did you publish so many books? And it, it's like publishing is not what I think about. I think about writing.

Jay Shetty 16:20 Mm.

Ryan Holiday 16:20 I wake up every day and write,

16:22 – 22:05

If you look at your life calendar, whom are you spending most of your time with?

Ryan Holiday 16:22 and the accidental byproduct of that is the publishing, right? And so good habits, good routines, like, if you want a happier home life, it's like are you spending more time there? Are you... You know, how are you setting up systems or processes that the result is that outcome, right? You control what you put in. The, the outcome happens or it doesn't happen. And I think so often we, we just, you're right, we just want the feeling and so we try to cheat it or steal it, or we feel guilty that we don't have it, when really you could start small right now and, and just get yourself closer to it.

Jay Shetty 16:58 Mm. What, what do you think is the best discipline you've built, like, over time? Like, is it writing? Obviously that would be the obvious one, but is there another one that you think underpins that success? Like, is there a discipline you've worked on the longest?

Ryan Holiday 17:10 Well, I think writing is such a sedentary sort of, uh, intellectual, cerebral thing that I try to balance it out with, like, a physical practice. So I try to do something hard every single day. Running, swimming, biking. I do a walk once a day. Like, I do something hard every day, and part of what that is is transferable back to the practice, right? 'Cause again, it comes down to the you don't wanna do it, it's hard, it's not going the way you want it, but you've cultivated the muscle of being able to push through that. Like, there's lots of claims about the health benefits of cold plunges.

Jay Shetty 17:46 Mm-hmm.

Ryan Holiday 17:46 And they may or may not exist. That's not why I do it, right?

Jay Shetty 17:49 Yeah.

Ryan Holiday 17:49 The muscle for me is, is the cranking of the knob, of the looking at the cold plunge at my house and going, it is gonna be unpleasant to get in there.

Jay Shetty 17:57 Mm.

Ryan Holiday 17:58 But I, I have the ability to force myself to do that. That's the muscle that you wanna cultivate.

Jay Shetty 18:04 Yeah.

Ryan Holiday 18:05 Um, and I, I think, you know, people wanna be the person on the other side of that, but they don't realize that the way you do it is by just starting it. Just starting it.

Jay Shetty 18:15 Yeah. It's so true. I, I, I can relate to so much of that in my own life and when, when you're saying that, it's... I feel like today most of what I do, I'd say I spend a lot, I'd say I spend, like, 75% of my life outside of my comfort zone.

Ryan Holiday 18:29 Yeah.

Jay Shetty 18:29 I am constantly doing things that demand more from me than I believe I'm skilled and able to accomplish.

Ryan Holiday 18:36 Sure. Yeah, yeah.

Jay Shetty 18:36 And in a healthy way, in a, in a good sense, because I feel challenged, and I feel that challenge forces me to grow my skills, which then meet a new challenge, and then that keeps growing. But then I find myself in my personal life often resorting to comfort. Uh, because I need to kind of cushion the [laughs] amount of like-

Ryan Holiday 18:53 Sure, sure, sure

Jay Shetty 18:54 ... pressure and stress. And so it's like this ba- for me, I'm at that, that place in my life where I'm like, "Okay, I'm pushing so much. I need my personal life to be super, like, you know, cushioned to some degree."

Ryan Holiday 19:03 It, it is interesting, right? We will take... Uh, and Seneca points this out in one of his letters. Like, we'll push ourselves, we'll take risks, uh, to, to succeed financially, to succeed in business, to succeed in our careers, to buttress our reputations. But then we don't wanna do it in the other places where most of us would admit it actually matters, right?

Jay Shetty 19:26 Mm.

Ryan Holiday 19:26 My favorite passage is in Meditations. Marcus Aurelius is like, "A better wrestler, but not a better forgiver of faults-

Jay Shetty 19:32 Right, right, right

Ryan Holiday 19:33 ... a better friend in tight places." He, he's pointing out how we'll go like, "Yeah, I'm trying to..." Like, you'll talk to someone that had this well laid out plan for how they're trying to increase their back squat or their mile time, or how they're trying to, to... They've g- they've, they've got these aggressive goals for their stock price or, or, you know, how many copies they wanna sell of this thing, or w- they have... We have really clear financial and professional goals, and then in our personal life we just wing it.

Jay Shetty 20:02 Yeah, yeah.

Ryan Holiday 20:02 And I'm not saying that you-

Jay Shetty 20:03 I didn't... Yeah, I didn't mean that, but I know what you mean. Yeah.

Ryan Holiday 20:05 Yeah, yeah.

Jay Shetty 20:05 I love that point.

Ryan Holiday 20:06 A- and I think the point is, like, you have to be challenging yourself in your personal life, also getting vulnerable. You know, getting outside your comfort zone, having the conversations that y- like, I think it's because our professional stuff is so much more quantifiable.

Jay Shetty 20:21 Mm.

Ryan Holiday 20:22 And then there's other people are looking at it, whereas the other stuff is private.

Jay Shetty 20:26 Mm-hmm.

Ryan Holiday 20:26 And so we, we just, we hold ourselves to different standards.

Jay Shetty 20:29 Yeah.

Ryan Holiday 20:29 And you think about what that costs us in terms of a place you get to in your marriage in 10 years that, had you thought more consciously about or put one tenth of the focus on-

Jay Shetty 20:41 Yeah

Ryan Holiday 20:41 ... maybe you could have got there in one year and then had nine years of enjoying it.

Jay Shetty 20:46 Yeah. No, that I fully agree with, and I, maybe I didn't clarify. When I said comfort, I mean more, well, apart from, like, my sleep sk- I have so many routines that are already set up that I try and make my personal life more comfortable bec- as in my individual life of my own self-care, because I find I'm pushing myself in so many areas. But I love where you took it to, because I think that's the k- critical one, right? It's like, what you're kind of leaning towards is most people will become people they don't want to be in order to achieve something, and that external pursuit often does that. By the end of building a billion-dollar company or whatever it may be, you end up going, "Well, I don't even like the person I am anymore," or, "I've lost the person who I thought I was." Whereas the pursuit of doing it inwardly with your family, with your friendships, the, the openness that's required, chances are you'll become the person you wanna be. Like, chances are you'll become someone that you're proud of being, and I, I think that's such... I wanna dive into that. That is such a powerful way of looking at it, and you're saying it's because it's the quantifiability, which, which I think there's truth in. I also think it's the, uh, it's harder.

Ryan Holiday 21:57 Sure.

Jay Shetty 21:57 It's, it's harder-

Ryan Holiday 21:57 Way harder

Jay Shetty 21:58 ... because, like you're saying, there's no external reward. There's no number that proves you did it, and it's fluctuating

22:05 – 23:38

All the things we want in life are accidental byproducts of getting big things right.

Jay Shetty 22:05 way more. Because people's emotions, like anyone in your family and friends, you can't control it. You could... You can control or master an algorithm or the stock market to some degree, but with a person, you can't do any of that because you can't set something up and then be like, "You're [laughs] gonna stay this way."

Ryan Holiday 22:23 Well, it's like you get so used to the control and the power-

Jay Shetty 22:26 Yeah

Ryan Holiday 22:26 ... that you have from the mastery of your professional domain, right? Like, when I sit down to write, I'm in control. I'm comfortable. This is a place that I have carved out for myself. When I am arguing with my wife or I am dealing with a three-year-old who's having a meltdown, I'm not in control.

Jay Shetty 22:48 Mm.

Ryan Holiday 22:48 And I'm humbled by it, and I'm struggling with it, and I don't feel like I've got it. 'Cause I have so much less... I've literally never done that before.

Jay Shetty 22:58 Yeah, yeah.

Ryan Holiday 22:58 And I'll, and I'll have such a short window where I'll ever have to do it, right? It's not, it's not like, oh, I've been in this place in a book 12 times.

Jay Shetty 23:06 Yeah.

Ryan Holiday 23:07 Right? Like, I've only had one five-year-old.

Jay Shetty 23:09 Yeah.

Ryan Holiday 23:10 And so, you know, it's just so much more challenging. It's just a much more multidimensional, you know, N of 1, like, difficult s- thing, and so it, it's gonna demand more of you. And I think, I think it's like, look, optimizing your professional life or maximizing your professional life, very unlikely to improve your personal life.

Jay Shetty 23:34 Mm-hmm.

Ryan Holiday 23:35 But if you have optimized and maximized and improved

23:38 – 29:21

What is the hardest discipline you’ve ever practiced?

Ryan Holiday 23:38 your personal life, gotten your house in order, you're gonna be better at what you do.

Jay Shetty 23:42 Mm.

Ryan Holiday 23:42 Or you're gonna care less [laughs] in some degrees about things that used to bother you so much. And so which one are you gonna focus on, right?

Jay Shetty 23:50 Yeah.

Ryan Holiday 23:50 'Cause you can get... You can be a titan in your industry and then be a total amateur at home, right? And I think, I'm gonna go where it's easy.

Jay Shetty 23:59 Mm-hmm, mm-hmm. And that's, and that's the thing. I think discipline often gets applied to the titan in the industry, not the amateur at home.

Ryan Holiday 24:07 Yeah.

Jay Shetty 24:07 And that's how we think about discipline. We think about discipline as, what can I achieve through this?

Ryan Holiday 24:12 Yeah.

Jay Shetty 24:13 Uh, in, in an external sense.

Ryan Holiday 24:15 Yeah, and you-

Jay Shetty 24:15 At least today, that's the language

Ryan Holiday 24:17 And you can get away with so much more. If you're really talented, you know, you can be a jerk, right? You can demand a lot of pe- 'cause you're paying these people, right? Like, I'm not saying you should. I'm just saying that there's accommodations that are made for you and, and sort of insidiously, the more successful you are, the more needed you are, the more accommodations you are. But there's none of that in the other area, and so you have to... There's some humility required, right? You, you're meeting equals on an equal playing field, and the discipline to say like, "Yeah, I'm, I'm gonna wrestle with that. I'm gonna try to get better. I'm, I'm not gonna allow myself to, to- ... do these following bad habits. That, that takes a, a certain amount of self-control and focus and, and discipline.

Jay Shetty 25:02 Yeah, I gue- I guess one of the biggest challenges with discipline is that we're trying to destroy a habit that we hate. Like, there's this idea that it just has to break and go, right? If you have a habit that you don't like-

Ryan Holiday 25:15 Yeah, yeah

Jay Shetty 25:15 ... about yourself, whatever that may be, it's like you're just... Well, or at least I've found when I'm coaching clients or working with people, is that they have this, like, bitter feeling towards this thing that they have.

Ryan Holiday 25:27 Yeah.

Jay Shetty 25:27 And they want it to go at all costs, but that almost makes you hold onto it harder. Like, that makes you grip onto it-

Ryan Holiday 25:33 Sure

Jay Shetty 25:34 ... and wrestle with it more. And I remember when, when we're, when I lived in India, a lot of the time the analogy that was given or the, the metaphor that was given to, to meditate on, because we'd see all the time, was, like, snake skin. And the idea was that when snakes shed their skin, they just slither out. They don't... It doesn't, like, they don't one day just go, pff. I mean, they don't even have-

Ryan Holiday 25:52 It's not like the Hulk. [laughs]

Jay Shetty 25:53 Yeah, they, yeah, they're not like the Hulk where it's like, pff.

Ryan Holiday 25:55 Yeah.

Jay Shetty 25:56 Like, snakes just slither out, and then their skin gets left behind, and then it, you know, they'll grow more. And so the idea that it's, it's such a natural, organic process of if you just slither, if you just move forward, you naturally shed. Um, yeah, I wonder your thoughts on that.

Ryan Holiday 26:10 That, that's the beauty of process, right? You don't sit down and go, "I have to do this right now. What do I have to do today?"

Jay Shetty 26:15 Yeah.

Ryan Holiday 26:15 "What are the small steps?" And, and you get great by minor improvements compounded on top of each other day in and day out, showing up day in and day out. And that's the same, uh, hey, we were fighting like crazy six months ago, and now things are awesome. Why is that? They made a change, and you made a change, and you made a response and a change in response to their change, and it compounded, and now you're here. That work can fall away at any moment, and you have to rebuild it. But I think, you know, the Buddhists talk about willful will. Like, almost the more intentional you are about it... That's the irony, too, is we're talking about how, you know, being intentional in your professional life often pays off. Being intentional, having clear expectations, wants, desires in your personal life is harder because it depends on other people, uh, people who are not like you, people who did not sign up for that. And I think one of the things you learn having kids and then also being married is that, like, ascent in that same sense of, like, acquiescing to things, adjusting to things. Like, I'm a routine person. Kids don't care about your routine. They fall asleep when they [laughs] fell asleep.

Jay Shetty 27:26 Yeah, yeah.

Ryan Holiday 27:27 And you have to, you have to adjust. Like, you're no longer the center of the universe.

Jay Shetty 27:32 Yeah.

Ryan Holiday 27:33 And that is such an important thing that you have to figure out and adjust and accommodate towards. You're the master of the universe here, but that you leave that behind when you walk through the front door.

Jay Shetty 27:43 Yeah, absolutely. I, I was talking to, uh, Ammar from Yes Theory. I don't know if you know the guys at Yes Theory. Yeah, they're awesome, and we've had them on the show before. But I was talking to Ammar the other day, and they just released their, um, project, Iceman, I think, their documentary, first time, like, their feature documentary. But he was talking about this, and he was saying that when they built Yes Theory, the goal was like, how can we say yes to things we would usually say no to, right? Like, that was the obvious point. And now he's learned that it's equally important to say no. But the part that really hit me when he was explaining it, I think we'd, we both vibed with the idea. He was saying that, and it's something you said earlier. He said, "I have to start saying yes to the things I find hardest." And so he was saying that today, no matter how many marathons he's done, no matter how many crazy expeditions they've gone on, no matter how many countries they survive with no money, he said the hardest thing for him to do is sit with his thoughts for 15 minutes.

Ryan Holiday 28:38 Yeah.

Jay Shetty 28:38 Like, he was like, "That's the hardest thing." He goes, "I don't look forward to doing that." He said, "If someone told me to train for something," he goes, "I look forward to that. But if someone told me to sit down with my thoughts for 15 minutes," he goes, "I don't look forward to it, so that's what I'm doing." And he was saying that's why he's trying to build that, and he was like, that's his new definition of seeking discomfort, because he said when people come up to him and say, "Do you want to build, like, a, a million-dollar company, a billion-dollar whatever," he's like, "I can get excited about that," but he goes, "I don't get excited about it." Is that a good sense of people finding what discipline is for them, or how do you see that?

Ryan Holiday 29:08 I mean, I think restraint is the hardest thing, right? Uh, Blaise Pascal in the 1500s said, uh, "All of humanity's problems stem from our inability to sit quietly in a room alone."

29:21 – 36:25

Optimizing your personal life will make other things much easier to manage.

Ryan Holiday 29:21 It was hard 500 years ago. It's harder now when you have a cell phone in your pocket, when you can get on a flight and travel anywhere you want in the world, and there's unlimited distractions, opportunities, things to get excited about. Like, it's hard to hold the mind still, to be physically still or, or maybe not to be physically still but have the mind still while the body is in motion. This requires, like, so much discipline, so much, uh, self-control, so much self-awareness, right? Even to s- to, to understand that it's hard for you, that it's something that you, uh, are naturally averse to or avoid, is a step in that journey to getting better at it. 'Cause a lot of people are just doing, doing, doing, and they're not even aware they're running away from something. They're not even aware that it makes them uncomfortable to be still. So I think we have to understand it's this journey, and that hopefully as you go, you get more and more comfortable with that. 'Cause at the end of the day, that's the, that's the one constant in life. Wherever you go, there you are, there you are, as the expression goes. Like, you're there, and if you can't get comfortable with that, can't get in touch with that, you can't see what's there, then you're gonna wake up one day and realize, "I did all of this stuff to get away from something that's been inside me the whole time," and that's very, very sad.

Jay Shetty 30:42 That is. That's, uh, yeah, that's... Well, that's the, that's the inconvenient truth of it, right? Like, that's the hard part, that you chased pleasure for so long that you completely missed what was in, what was already there. But- I, I think, is it that we don't... W- what is your take from studying it? Like, is it that we don't know the benefits enough? Is it that we don't like processes enough? It is, is it that we're just addicted and there isn't a... Because I look at j- And, and I do think looking at very daily habit changes is the easiest way to build the muscle to go, "I can do this." So I always give the example of when I met my wife, I was addicted to sugar. Like, I, I genuinely was, and I didn't even know it. I had a Sprite and a chocolate bar every day without thinking about it. It's how I got through college. It was life. When I was a monk, I didn't have either of those things, but that was more of a suppression, and there was lots of other interesting things to do, or I didn't need that kind of energy. When I came back, I-

Ryan Holiday 31:41 You're like the convict who's sober in prison-

Jay Shetty 31:43 Yeah, exa-

Ryan Holiday 31:43 ... just 'cause you don't have access to it. Yeah, yeah.

Jay Shetty 31:44 Exactly. I didn't have access to it, and I didn't... I definitely built a discipline where I didn't feel like I needed it. But then when I came back to the real world, all I wanted was chocolate and sugar. And so when I met my wife, it's like, you know, we've been married for six years now, together for 10, and she like, at first, she would just educate me, and like she would just tell... 'Cause she's a dietician and nutritionist. This is her job. She's laying out all the, all the dangers of sugar. Then she's, like, taking it out of the, like, home. Like, it's not around anymore. It's not accessible. And then almost like it's taken six years, and I would say now I'm at a place where the habit has really transformed. That's like a six-year journey.

Ryan Holiday 32:19 Yeah, yeah.

Jay Shetty 32:20 And obviously it probably happened like halfway through, I'd say. Like, probably it happened three years ago, where I really started cutting out sugar. But it needed a coach. My wife was the coach. It needed a, uh, obedient or submissive student. I, I trust my wife on this area. It wasn't like I wa- I didn't have an ego about it. She knows more than me about the body. And then on top of that, it needed a focus in the sense that in my health, we kind of did it one at a time without even trying, whereas, like we took our sugar first, we started working out next. Like, she was, she kind of did that even unconsciously. It just took so much, and I go... And I know obviously with the Stoics, we talk about mentoring and coaching, and there's always this cross-learning. But I feel like now we're all trying to do it on our own.

Ryan Holiday 33:03 We are, and we're also expecting that it just happens-

Jay Shetty 33:06 Yeah

Ryan Holiday 33:06 ... that it's this, like, epiphany mo- If knowing what to do was enough, everyone would be in great shape. No one would have any of these illnesses or problems that we have. It's so much more complicated than that, and I th- I, I do try to remind people that it's a, it's a journey that you're on your whole life. There's passages in Meditations where Marcus Aurelius is going, "You're an old man, and you're still losing your temper. You're still worried about what other people think." He's like, "You're still afraid of death, and it's almost here." And, and realizing that if s- the wisest people in the world struggled their whole life with this thing, the idea that you, who were lucky enough to hear about it in your 20s or 30s or 40s, that you're just gonna get it, it's n- naive, and it's also unfair to yourself. The question is, are you getting better at it as you go, right? Seneca says, "How do I know I'm making progress?" And my philosophy says, "I've begun to become a better friend to myself." So discipline is not just squeezing blood from the stone. It's not just whipping yourself. It's hiring a coach. It's, uh, you know, setting reachable goals as you go. It's, it's stepping back and giving yourself credit and saying, "Look how far we've come, man. Like, we're doing great," right? It, it's not, it's not just this sort of like in-your-face, like, how are you not there yet-ness.

Jay Shetty 34:35 Yeah.

Ryan Holiday 34:35 Right? It's, it's a journey, and you're not supposed to really ever get there, that... It's like the horizon. It's always a little bit further away. And so, you know, I think when we hear discipline, I think we think of, like, the marine drill sergeant.

Jay Shetty 34:50 Yeah.

Ryan Holiday 34:50 This is kind of transformative. You didn't have discipline, and now you do. We should also think about it the, like, having a discipline. It is a thing you do your whole life, and realizing that that's how we should measure this progress.

Jay Shetty 35:05 I think, though, that that's what we're banging our head against, is that the mind has been so far removed from the idea that things take time-

Ryan Holiday 35:16 Yeah

Jay Shetty 35:16 ... that patience is required, that one step at a time. Like, we hear those things all the time, but there's literally nothing we do in our lives that requires us to move one step at a time anymore. Like, it just doesn't work. And we know these examples, like whether you're ordering food to your house or whether you're getting this delivered or whether you jump into an Uber or a Lyft. We know that. But I found it really interesting recently, like I just went through, uh, double hernia surgery, and it's not life-threatening, and it's meant to be routine, but it's far worse than the doctors make it out to be, and the journey back to feeling like I can operate normally, it's been two months now, and I'd say I'm 75% there. I would say that the first four weeks were like learning how to walk again.

Ryan Holiday 36:01 Yeah.

Jay Shetty 36:01 And I have never ever moved that slow in life, in a good way, as in that every movement of the body or the mind had to be slow.

Ryan Holiday 36:13 Yeah.

Jay Shetty 36:13 Because if I moved fast, I could potentially relapse.

Ryan Holiday 36:16 Yeah.

Jay Shetty 36:16 So I couldn't, I can't, I still can't pick anything above, like, uh, 15 pounds. I'm not allowed. Uh, I, I couldn't for that first month, like walk

36:25 – 40:22

It’s never too easy to sit down with your thoughts but you can learn to get comfortable with it.

Jay Shetty 36:25 for the first week, and then I had to shimmy for the rest of it, and I had to like... When I sat down on a chair, I had to be so mindful. And I was like, "Wow, I thought I was mindful."

Ryan Holiday 36:33 Yeah.

Jay Shetty 36:33 And having this surgery has made me the most mindful person ever. I've, I've never eaten that slow because the digestion was harder, and there was pain in this area, and so it was the first time in a long time I felt that present, and I consider myself to be a present person.

Ryan Holiday 36:49 I think that the root of it is this illusion we have that we're in control, right? That we're deciding how things go, and then we have an injury or a problem or something that disrupts it, and we are rudely but also, uh, kindly reminded how little ... control we have. I remember when I was, I, I moved across the country. I was writing my first book. The two days before I was supposed to start, I'm riding my bike, New Orleans, I get stuck in the streetcar tracks, I go over the handlebars, and I break my left elbow, and I'm left-handed. And so, like, all of the way that I was thinking about writing this book goes out the window for, like, six weeks.

Jay Shetty 37:23 Mm.

Ryan Holiday 37:24 I couldn't get, like, the adrenaline or the endorphins that I needed just to function as a person, so I had to go on these, like, long walks. So, you know, I get the news, and it's like, "Okay, I'm not gonna be able to work or think for, like, six weeks. This is a total dead loss for me." But then I started taking these walks, like hour, two-hour, three-hour walks just around, and what do you know? I start writing the book in my head on these walks.

Jay Shetty 37:48 Mm.

Ryan Holiday 37:49 If I had gotten things the way I wanted them to go, it would've been far less advantageous to me than me having to respond to the way they did end up going.

Jay Shetty 38:02 Mm. Mm.

Ryan Holiday 38:02 So at the core of Stoicism is this idea that we don't control what happens, we control how we respond to what happens. It seems like it's this curse, this human frailty or weakness that, like, we're not in control, but our superpower is our ability to respond to that, to find good in it, to be made better for it. And you, you go through this thing, and you realize, "Oh, this is an opportunity to practice all of the things that I ordinarily take for granted, I assume I have." There's this one Japanese Zen master, actually the, the Zen master from, uh, Zen in the Art of Archery, and he's at the end of his life.

Jay Shetty 38:41 I love that movie.

Ryan Holiday 38:41 He's, he's dying, and he, he, he goes to, like, urinate in the snow, and it- it's red. He's, like, bleeding. He's dying, and his students are alarmed. And he goes, "This too is practice." All of these things that we experience that we didn't want or we thought they should go a different way, they're actually the opportunity to practice the way-

Jay Shetty 38:59 Mm

Ryan Holiday 38:59 ... or the logos, as the Stoics would call it, in the way it's actually meant to do-

Jay Shetty 39:05 Mm

Ryan Holiday 39:05 ... if we choose to be present, recognize it, and take that opportunity instead of fighting it or resenting it or wishing it were otherwise.

Jay Shetty 39:15 Even, I love that point that you made, that, that even that was practice.

Ryan Holiday 39:18 Yeah.

Jay Shetty 39:18 That is beautiful. Like, that's, that's magical. Like, that idea that even in that worst scenario, at the end of all of it, it was still practice. And if we could only wrap our head around that, because I think we still think of practice and performing, practice and arrival, practice and the end. We still see it as separate, and, and there is nothing that's separate. Like, that tree outside that's huge is still growing and being nourished. It's just you don't see it anymore.

Ryan Holiday 39:46 Yeah.

Jay Shetty 39:46 And I almost, sometimes what I do with clients is I'll give everyone a seed, and I'll ask them to plant it and take care of it, and that's like an old way of just learning growth because it's so painful to be watering something every day and not seeing it grow, only to realize it is growing. Or, uh, I remember something they gave us, uh, in the monastery was, like, they gave us this rope. It was, like, this really old rope, and it was already tied, and we were asked to untie it, and it's like most of us spent the whole of the first day we got it trying to untie it and failing.

Ryan Holiday 40:18 Yeah.

Jay Shetty 40:19 Only by, like, day 21 to realize all we had

40:22 – 44:14

Are you getting better at becoming a better friend to yourself?

Jay Shetty 40:22 to do was pull it a little bit every day, and hopefully it would unravel because it was so tight. And so even if you sat there all day, you would just, you'd go mental, and you wouldn't achieve anything else.

Ryan Holiday 40:32 Right. Yeah. It's, it was the willful will, right?

Jay Shetty 40:35 Yeah.

Ryan Holiday 40:35 It's like wanting-

Jay Shetty 40:36 Yeah

Ryan Holiday 40:36 ... it a certain way, needing it a certain way, trying to force it as opposed to stepping back and letting it be what it is. It's like the way our mind works, whatever is happening now, you will look back on sometime in the future as formative to who you become, right? And yet, in this moment, all we're doing is trying to make it something other than it is, right?

Jay Shetty 40:59 Yeah.

Ryan Holiday 40:59 Like, we will look back on COVID and see the, the good in it, the lessons that came from it, the reminders it gave us, the weird experiences we had, the connections, all of that. We'll look at that. But in that moment, all we're thinking about is when this will be over, whose fault it is. You know, what it's cost us, right? Freud says i- in, in retrospect, the struggle will strike you as most beautiful. But it seem, it's such a, it's such a shame, so unnecessary to deprive yourself of understanding the beauty of it now. Certainly, perspective adds to it. It allows you to see it differently, but what if you could just not feel guilty, worried, anxious, resentful? Like, you know in the future this will be a story, [laughs] right?

Jay Shetty 41:44 Mm-hmm.

Ryan Holiday 41:44 You'll, you'll have learned. But you could give yourself the gift of at least some of that now by accepting it and just seeing it as what it is in front of you-

Jay Shetty 41:57 Yeah

Ryan Holiday 41:57 ... that it's practice.

Jay Shetty 41:58 Yeah, yeah. And the, and the challenge, I guess, is that because we've not had an experience, maybe in our early childhood or in our teens, where we saw that, where it was like we went through a difficulty, we built discipline, and we got over it, or we learned from, as you're saying. I find that a lot of people have experienced difficulty, but then they were given comfort or shelter, or the difficulty was somehow removed or left, so you never got the opportunity to build the discipline muscle if that makes sense. Like, my, my wife will often talk about, like, for her, if she went through a difficulty, like, her parents would come and save the day.

Ryan Holiday 42:33 Yeah.

Jay Shetty 42:34 Right? Someone would swoop in and solve the issue. Her sister would do her homework for her. And so as that happened more and more and more, it created this behavior of someone will save the day, that I don't need to build a discipline around this.

Ryan Holiday 42:47 Obviously, saving is coming from a good place. The other thing we do is we tell, "It's so bad that that happened to you. I'm so sorry. You're this victim," right? Like, uh, the first year of COVID they would describe for kids that this was, like, a lost year, and I just remember thinking, like, how-

Jay Shetty 43:03 That language, yeah

Ryan Holiday 43:04 ... h- patronizing but also self-fulfilling that- ... was for kids. Like, uh, when I would talk to my grandparents or old people that lived through the Depression or the Second World War, which were, by the way, a lot longer than COVID, they weren't like, "Oh, it was a lost time." It was a transformative, formative experience that in retrospect made them who they were, that maybe even if you'd asked them if they would have wanted things to be different, they would have said no. And we have the power to, to transform whatever we're going through into that thing. So yeah, by rescuing someone, you're depriving them of that thing, but also by telling them that there's no, there's nothing in this thing, that it's indisputably, inarguably bad, is to deprive them of the agency, the perspective, the gift that they have in front of them if they choose to see it that way. And we should emerge from this period, the very least, as you said, like, if you haven't been through stuff like this before, you just lived through an event of historic proportions. Like, you just lived through event that your kids and your grandchildren, future generations will marvel at, and you emerged

44:14 – 48:25

We can’t control what happens, but we can control how we respond to it.

Ryan Holiday 44:14 unscathed, maybe even improved in some ways. Like, you, you should emerge from this with a real sense of what you're capable of enduring and surviving and adjusting towards, and that should give you a lot of confidence as you wake up and you experience things that are so microscopic compared to that thing.

Jay Shetty 44:35 Yeah.

Ryan Holiday 44:35 Right? And, and you should feel armed with a certain set of weapons or tools that maybe you didn't have before.

Jay Shetty 44:43 Yeah.

Ryan Holiday 44:43 Like, you've been knocked around, and you didn't get knocked down.

Jay Shetty 44:47 Yeah.

Ryan Holiday 44:47 That's, that's powerful.

Jay Shetty 44:49 Yeah, yeah, absolutely. And, and in my own little way, it's like in, while I was going through my surgery, it was exactly that, where it's like I can either sit here and think this is the worst, because it did feel like the worst. For someone who's active, always on planes, and always traveling, always working, to, to be completely off, and it wasn't even restful because it was painful. Like, it wasn't restful time. Everyone's like, "Oh, you didn't work for a month, it must have been amazing." I was like, "Well, no, I was in pain."

Ryan Holiday 45:12 Yeah. [laughs]

Jay Shetty 45:13 But the idea that my mind at the time was like, "This is the worst, I hate this, and when's it gonna be over?" Right? Which is the same as COVID.

Ryan Holiday 45:23 Yeah.

Jay Shetty 45:23 Which is the same as anything. Like, those are the three thoughts [laughs] that go through our head pretty much, whether it's surgery, COVID, or anything else that's going on. And having to reframe those thoughts in the moment-

Ryan Holiday 45:34 Yeah

Jay Shetty 45:34 ... made it become a really beautiful process at the time, and now a sense of gratitude for it having moved on. But that's what I'm hearing from you, is like you will reflect, well, hopefully you'll reflect afterwards, but there is a bit of reconfiguration that has to happen at the time.

Ryan Holiday 45:50 Yeah, there's a story about Phil Jackson when he was the coach of the Lakers. He gets this back surgery, this super bad back surgery, and he can't stand on the sideline.

Jay Shetty 45:58 Mm.

Ryan Holiday 45:59 He has to sit in a chair, and the way they had him sit, it's like a, a row back. And so suddenly all the, the things that he's comfortable with as a coach are not possible. He's not able to pace the sidelines, get up in people's faces, intervene, direct people. He just has to sit back and he has to watch. It's like the antithesis of his coaching style. And yet, and he's a, a sort of a, a Zen Buddhist, uh, sage guy-

Jay Shetty 46:23 Yeah, yeah. Yeah, yeah

Ryan Holiday 46:23 ... he realizes that this is practice. That he, he realizes that now the team's having to come to him. Now the team's having to solve some of the problems. He's having to explore a different way of communicating. He's having to communicate verbally better than physically. It's a way to change, adjust. He's forced to do it differently, and thus learns some things he wants to continue doing differently. Now realizes he was taking for granted certain things that are actually super important, right? And so y- you can always take from this, like, it's this forced lifestyle experiment.

Jay Shetty 46:58 Yeah.

Ryan Holiday 46:58 Just see it as that, right? Like, COVID, the biggest forced lifestyle experiment in human history. Things that people said were impossible had to become possible. Remote work, you know, e-commerce, all these things. And then you wanna throw that away by saying, "I can't wait for things to go back to normal," right? It's like normal is what caused this, right? Normal was you before you learned the things that you learned in that intervening time. And for COVID, for, for Phil Jackson's back surgery, insert whatever disruptive event you're undergoing in your life.

Jay Shetty 47:31 Yeah.

Ryan Holiday 47:32 You don't want things to go back to how they were. You want them to go to a new place where you have the old perspective and the new perspective fused into something new. When, when Marcus Aurelius says, "The impediment to action advances action. What stands in the way becomes the way," the Zen expression is, "The obstacle is the path." Same East, West coming to the same idea. It's like this thing has opportunities inside it to make you better, should you choose to accept them.

Jay Shetty 47:56 Yeah. And, and that's what I like. It's not the simplistic idea of, and, and I'm always trying to address this, it's not the simplistic idea of look for the positive in the negative, right? Like, that's not what we're saying here. This isn't the idea of like, "Oh, there's a, a, a, a beautiful side to this." That's not the point. Let's, let's get into that a bit, because I feel like people kind of simplify and go, "Oh, no, that just, yeah, we'll just look for the silver lining," which is not what we're saying.

Ryan Holiday 48:19 Well, do you know the Stockdale Paradox?

Jay Shetty 48:21 No, tell me.

Ryan Holiday 48:21 So James Stockdale, he studies stoic philosophy, and then he's shot

48:25 – 53:52

How important is it for us to go through something difficult and grow the muscle to overcome it?

Ryan Holiday 48:25 down over Vietnam. He's, i- and he's taken prisoner. He spends seven years horribly tortured in this Vietnamese prison camp. Afterwards, he's speaking to Jim Collins, who writes, who writes Good to Great.

Jay Shetty 48:35 Yeah, Good to Great, yeah.

Ryan Holiday 48:36 And, and he formulates what becomes known as the Stockdale Pro- Paradox. Jim Collins says, "Who has the worst trouble in the prison camp?" And Stockdale says, "Oh, that's easy. The optimists." Right? The people who thought, "I'm gonna be out by Christmas. I'm gonna be out by the spring. This isn't gonna be hard." When Stockdale's parachuting into this camp, he says, "I am leaving the world of technology and entering the world of Epictetus." He says, "It's gonna be seven years at least." But he said, he said, "The first step is I had to unflinchingly accept the reality of my situation, which is that I might not get out, which is that I'm probably gonna be tortured, which is that I'm not in control, which is that there's so much unknown pain and suffering ahead. I have to accept that. This is not gonna be fun. This is not gonna be easy." He says, "But simultaneously, I said to myself, 'If I get out-" I want to have transformed this into something that, in retrospect, I would not have traded away. That's the paradox of what we're talking about. Stuff happens, life gets in the way, you lose someone, your company goes bankrupt, the market shifts, you know, a natural disaster. Your life can get flipped upside down at a moment's notice. You have to unflinchingly accept the reality of that situation, the unfairness, the unexpectedness of it, your blamelessness or your blameworthiness for it, and then simultaneously go, "Okay. I'm not saying this is wonderful, that I'm glad it happened, but I can make choices now that derive positive benefits from this, that make me better for having gone through this." And I, I was, at the beginning of the pandemic, in the middle of opening this bookstore. I'd sunk my life savings [laughs] into opening this bookstore that, by the time it was ready, it was impossible to open. It was looking like this enormous failure, mistake, you know, like albatross around my neck. And I, I wrote this note card to myself, and I have a picture of it 'cause I took ... I wrote it to myself, I was thinking about it every day, and I took the picture in front of the bookstore. Uh, and I just wrote to myself, I said, "2020 is a test. Will it make you a better person or a worse one?" Right? I have no idea whether the bookstore will work. I have no idea where things are going. I have no idea what life is going to look like. What I control inside that is, do I emerge from it a better person, right? More community-minded, a better spouse, a better thinker, a better writer, more patient, more self-aware. Those are the things I control within it. And so when we say the obstacle is the way, we're not like, "Oh, it's great this terrible thing happened to me," but you're saying, "What I took from this terrible thing," or maybe you're trying to strip the labels altogether, but you're saying, "What I took from this was positive. I made from it." That's the paradoxicalness of it.

Jay Shetty 51:27 Yeah, yeah. That's a great breakdown. I'm so glad you went into that because, yeah, I've heard the example in the same way of when there were soldiers who said, "We'll be home by Christmas."

Ryan Holiday 51:35 Yeah.

Jay Shetty 51:35 They- their hope was shattered-

Ryan Holiday 51:37 Yeah

Jay Shetty 51:37 ... because they weren't home by Christmas. And whereas the people who said, "We'll figure out a way to get home, and if we get home, we'll see our family," and that person was more likely to be able to deal with the fact that it didn't happen by this time. And I think, I think that's become our obsession with controlling time-

Ryan Holiday 51:55 Yeah

Jay Shetty 51:55 ... is partly where that comes from, where it's like, we want this done by this time.

Ryan Holiday 52:00 Yeah.

Jay Shetty 52:00 And then whether it's positive or difficult, when it doesn't happen, we're completely demoralized, right? Like, it's almost like it's all over just because it didn't have- happen by an arbitrary date.

Ryan Holiday 52:11 Well, you're setting yourself up for disappointment or frustration or resentment or despair by attaching to an outcome that's not yours. If you get lucky, sure, you'll feel wonderful, but if you work for years on a book and success or failure of it was, did it win awards? Did it sell lots of copies? Did your parents read it? You know, those are things that are not in your control. But if it was, "I understand this-

Jay Shetty 52:40 Yeah

Ryan Holiday 52:40 ... better than when I started. I am more confident than I was when I started," you know? Like, "I said something ... I, I got on the page what I thought only in my head at the beginning," right? Like, when, when, when you move the outcome or the goal to something that's up to you-

Jay Shetty 53:00 Yeah

Ryan Holiday 53:00 ... you'll always win, and I think that's what wise people do. They're ... It's not that they're not ambitious. They are ambitious, but their ambition is things that are up to them. And, and so when Marcus is saying better wrestler as opposed to better philosopher, better friend, whatever, he's shifting from, like, this external societal-driven thing to this internal thing that he controls, that he gets to judge the success or failure on. And it's not so quantifiable either. It's something deeper, more human, more connected. And so as you shift that, not only do I actually think you do better work, but you are increasing your chances of feeling good about yourself at the end of that.

Jay Shetty 53:46 Yeah. And I think the challenge, Ryan, though, is that today we want both, right? We want the, we want the feeling

53:52 – 1:00:40

Ryan explains the importance of making choices that derive positive benefits in the most difficult situations.

Jay Shetty 53:52 of, "I did something that was true to me-

Ryan Holiday 53:55 Yeah

Jay Shetty 53:55 ... and it resonated with a lot of people," or, or whatever that means, right? Like, and I feel like that's where, where everyone kind of gets stuck because it's like, you know, when, especially when people watch people do what they love and it gets received well, it's like, "Oh, well I wanna do that too." Where do you think people go wrong in that journey? Because, like, what are the mistakes we make on that path? Because I feel like that's pretty much where, where people are headed.

Ryan Holiday 54:20 Well, yeah. I mean, I think we're sometimes not honest. You're like, "I'm just, I want this album to be true to who I wanna be, my artistic expression," blah, blah, blah. That's why you made all these sort of individualistic decisions, but deep down you have this sort of secret lie, which is that you're actually judging yourself on where it lands on the Billboard charts-

Jay Shetty 54:40 Yeah

Ryan Holiday 54:40 ... right?

Jay Shetty 54:40 Yeah.

Ryan Holiday 54:41 So that's the worst of both, right? 'Cause you're not going, "Well, what do I need to do to be commercially successful?" And I'm consistently judging myself on whether it was commercially successful or not. You're, you've set yourself up for maximum disappointment. But if you can say, "Look, here, my goal is to do my absolute best. My goal here is to get to the truth of what I'm saying, to express my in- what, what's true inside here, and that's what I'm gonna focus on and I'm not gonna waste any time on these other things," I actually do think, I'm sure you've found this, is that that does make better work.

Jay Shetty 55:13 Yeah, it does.

Ryan Holiday 55:13 It makes truer work, it makes more authentic work, more relatable work. It, it actually does make a better product, but only if you are fully and honestly and deeply committed to doing it. It can't be like, "I'm making the charitable donation. I'm doing it anonymously." But I still hope everyone sees how wonderful I am.

Jay Shetty 55:34 Yeah, yeah, yeah.

Ryan Holiday 55:35 You know what I mean? It, it's, y- you can't have your cake and eat it too.

Jay Shetty 55:39 Yes, exactly. And, and I think it's, goes back to what you were saying a few moments ago, where it's like you have to accept the reality, which includes your own intention. Like, I know that I like creating things that are, are true to me, but are commercially successful. That is important to me. It's a value of mine, and I'm okay with that.

Ryan Holiday 55:55 Yeah.

Jay Shetty 55:56 Uh, because i- I don't wanna lie about those things to myself, uh, at all, because I enjoy the idea of creating thoughts and ideas that can affect lots of people. Like, that, that is something that gives me a sense of, uh, feeling that I've understood an idea and been able to communicate it well enough. I, I guess what I'm saying is that it comes back to what you were saying at the beginning, that I don't set out to write a commercially successful book or launch something commercially. Like, that isn't what I set out to do. Set out to understand, articulate, communicate with myself, and write an incredible book, and then that leads to that. But at some part of that process, you have to think about the sharing of it.

Ryan Holiday 56:37 Yeah, of course. And, and I've learned a lot from you in this regard. Like, you're not helping yourself or your ideas by rejecting what makes them accessible or shareable or turning your nose up at this tool or that tool. Like, look, like, when I want to learn about an idea, I want to read long-form books about it.

Jay Shetty 56:56 Same.

Ryan Holiday 56:56 That's the medium that I'm comfortable in. I don't think TikTok, but millions of people do think TikTok or Instagram. And to turn your nose up or close your heart off to those people because they're not like you is not just snobbish, but if you actually care about the ideas, it's selfish. And, and so I don't think they're mutually exclusive, but I also think if you're on those platforms and you're letting the algorithm decide what you do and don't do-

Jay Shetty 57:25 Correct

Ryan Holiday 57:26 ... you are sacrificing the whole reason you became a creator in the first place.

Jay Shetty 57:30 Correct. Absolutely. And I think that's the, that's the balance, right? It's like there's, there's people who just completely sell out for the algorithm, and then there's the selfish creator or the snobbish creator on the other end who thinks they're too cool.

Ryan Holiday 57:43 Yeah.

Jay Shetty 57:44 Like, it's kind of like this badge of honor where it's like, "Oh, yeah, I don't need to do that," like, "I don't care about..." And I, and I'm like, that, that defeats the whole point because I'm hoping this book was a compassionate expression of service, hopefully, and maybe it wasn't. Maybe it w- just was a selfish, arrogant move of professing your ideas, and that's, like, the best thing about it. And so you have sell-outs on one end, and you have selfish on the other end. And to me, like, service is kind of in the middle, where it's like service means I understand people's needs and interests and concerns and where they're at, but I always have to serve them what's most beneficial.

Ryan Holiday 58:16 Well, it's like you meet people where they are.

Jay Shetty 58:18 Yeah.

Ryan Holiday 58:18 And, and, like, it, there's almost a greed to it. It's like, "Well, I wrote in a book. If you want to hear it, you can buy it," right? Well, what if they're not ready for that? What if they're too busy for that? What if they already did buy it-

Jay Shetty 58:29 Yeah

Ryan Holiday 58:29 ... but they just need a reminder of it, right? And so there's different, uh, just in the way that, like, look, I also read in English. That's the only language that I speak. But I don't turn up my nose at all these different translations. I go, "Oh, yeah, there's a process. These ideas get translated into those languages, and they reach people who otherwise wouldn't have consumed it."

Jay Shetty 58:48 Yeah, yeah.

Ryan Holiday 58:48 And understanding that different people have different native languages. Some people like audiobooks. Some people like podcasts. Some people like s- uh, this social network or that social net- network. And that by thinking that, you know, one is superior to the other, in fact, you should be translating your work in all these different areas, long-form, short-form, audio, video, text, what... You should be everywhere that's, that's possible and understanding that the win is that the ideas are reaching people and helping them in their life. If some of those things translate to sales or followers, great, but, like, I, I always think about, like, again, what is success? At the end of the day, like, if your thing sold zero copies, but it changed the world, you'd be like, "That was, that, that was a win."

Jay Shetty 59:34 Totally.

Ryan Holiday 59:35 So why don't you just do the stuff that changes the world and trust, again, trust the process that you'll probably be able to make a living? [laughs]

Jay Shetty 59:44 Absolutely. Absol- And, and most things that do change the world or have an impact started non-commercially, right? Like, in that sense of especially creation or ideas, I mean, uh, maybe not businesses, but, but ideas. Like, when, when I started creating content, even the first few interviews I did with you, like, I di- I mean, that NASDAQ, that whole NAS- I never got paid for that whole series.

Ryan Holiday 1:00:02 Yeah.

Jay Shetty 1:00:02 I was interviewing authors every week because I was fascinated by the idea that I get to sit down with people that I find interesting.

Ryan Holiday 1:00:09 You're also putting in your hours.

Jay Shetty 1:00:11 Yeah.

Ryan Holiday 1:00:11 You're getting good at this thing.

Jay Shetty 1:00:12 Yes. You get... Yeah, yeah, yeah.

Ryan Holiday 1:00:13 Yeah.

Jay Shetty 1:00:13 Exactly, and you're getting good at it. You're enjoying it. You get to meet awesome people. Uh, and even, even when we did the show at HuffPost, it was like, it was, I was leading the show of what kind of show we wanted it to be. It wasn't like-

Ryan Holiday 1:00:24 Yeah

Jay Shetty 1:00:24 ... it was already set up. And so, yeah, I look back, and I think, like, all stuff that had an impact and grew was always from that deep intention, pure intention of, I wanna create something that will hopefully help people have these conversations, and that was m- what it was for me. I felt,

1:00:40 – 1:09:44

You are bound to get disappointed by attaching to an outcome that is not yours.

Jay Shetty 1:00:40 when I started creating content, there weren't, there were so many people who had deep, thoughtful conversations offline, but there was no spaces online really to have those, or there wasn't a piece of content you'd send to your friend and be like, "Did you see this?" Like, "Have we talked about this?" And I wanted to create an excuse for people to have more meaningful, thoughtful conversations based on ideas.

Ryan Holiday 1:01:00 I mean, look, I think at the end of the day, it's like you create a lot of value, and if you can capture a small percentage of it, you're good, right? Like, I think about Craigslist. Like, the vast majority of stuff on Craigslist has been free since the very beginning, and yet Craigslist still makes $1 billion a year in revenue. Like, when you create a lot of value, I create so much content, and, like, the only part that is not free are the books.

Jay Shetty 1:01:24 Yeah.

Ryan Holiday 1:01:25 Right? And the books fund that work, and then that work also funds the books. It's, you- you're creating kind of a flywheel of stuff- I was thinking about one of my books that, that hasn't sold as well as the other books.

Jay Shetty 1:01:36 Which one is it?

Ryan Holiday 1:01:37 Uh, Lives of the Stoics-

Jay Shetty 1:01:39 Oh, yeah

Ryan Holiday 1:01:39 ... is different than my other books, but I personally use, and then also-

Jay Shetty 1:01:43 [laughs]

Ryan Holiday 1:01:43 ... have reused stuff that I learned while writing that book almost every single day. So, like, the monetization, you know, to use that word, the value creation there, was a personal one. And the book has done extremely well by, like, any-

Jay Shetty 1:01:58 Yeah, yeah

Ryan Holiday 1:01:58 ... sort of standard. But, like, the primary beneficiary was me.

Jay Shetty 1:02:03 Yes.

Ryan Holiday 1:02:03 And again, if you, whatever you're doing, you can say, look, the primary beneficiary of this is me having gone through it, changing, developing, learning, and then the byproduct is that I paid my rent or that, like, you know, this happened, that then you've, you've won, and all the stuff that's out of your control is the extra.

Jay Shetty 1:02:24 Yes.

Ryan Holiday 1:02:25 That's where you wanna be.

Jay Shetty 1:02:26 Yeah, yeah. I couldn't agree more. And, and that requires just so much, I think that requires refining of the intention. It requires having a sense of belief and confidence. I think, I think for me it was the other, and, and for you, too, I, from, from your journey that we've talked about before, like, I spent 10 years doing this without any followers or without any commerciality to it anyway, because it was all offline.

Ryan Holiday 1:02:49 Yeah.

Jay Shetty 1:02:50 And it was speaking to rooms of five to 10 people, if they showed up. And so it was like, for so long I was doing it without any care of how far it went, because it was just so powerful, it was so beautiful to live in that world of, even if I had one meaningful conversation with someone after an event, that would make my day. Like, I'd talk about it for weeks.

Ryan Holiday 1:03:09 Let me ask you this, because I've been thinking about it lately.

Jay Shetty 1:03:10 Yeah.

Ryan Holiday 1:03:11 The work that you're doing now, or that I'm doing now, is the result of work you did a long time ago.

Jay Shetty 1:03:18 Yeah.

Ryan Holiday 1:03:18 It's a lagging indicator of sacrifice and commitment and study and practice from however long ago. Sometimes what keeps me up at night is I go, "But 10 years from now, 15 years from now, am I putting in the work doing the stuff now that will pay off then?" And how do you know? How do you know? If, if success is this lagging indicator, or growth is this lagging indicator of commitment now, how can you be sure that you are paying your dues?

Jay Shetty 1:03:46 Yes. I'm so glad you said that, because I literally just, I've been talking to my team about a few things that we're doing. I've literally asked us to find three new coaches. Like, I've, I've literally gone, I've always learned through one-to-one coaching or mentorship. Like, that's my favorite, apart from books, that is my favorite way of learning. Uh, and especially when it comes to self-transformation. So I love ideas through books, but when it comes to me actually changing, I'm better when I'm working with one person and getting mentorship or coaching.

Ryan Holiday 1:04:13 So you're thinking about who are, who are your teachers to get you to the next level, a level you might not even know exists yet.

Jay Shetty 1:04:19 Correct. And so I'm, I'm trying to identify those people right now. So when I was a teen, I was reading Malcolm X, Martin Luther King, Steve Jobs, right? Like, well, Steve Jobs a bit later, actually, but Martin Luther King and Malcolm X, like, that's who I was reading at 16 years old.

Ryan Holiday 1:04:31 Sure.

Jay Shetty 1:04:32 They were hugely, uh, formative in my i- ideology in so many ways. And then in my 20s, obviously, I lived with a monk, so that was hugely that. And then went to public speaking school when I was 11 years old, so that has, that has lasted far too long and needs to be refined again. Uh, and, and so yeah, I completely agree with you. I look at all the skills I have today and I go, where do they need to be refined?

Ryan Holiday 1:04:54 Yeah.

Jay Shetty 1:04:54 And then I look at, well, what are the things I'm missing out on because I'm not exposing myself? Now, I do think that, I do find having the podcast very fortunate because I do get to sit down with a lot of people that I seek mentorship from in an informal sense, and then I can be like, "Oh, well, I'm really gonna do a deep dive on that person's book," or-

Ryan Holiday 1:05:12 Yeah

Jay Shetty 1:05:12 ... like Gabor Mate was just on.

Ryan Holiday 1:05:14 Yeah.

Jay Shetty 1:05:14 He's amazing. Like, you know, and, and people have known about him for a long, long time. This was the first time I interviewed him, but I'm, like, now doing a backwards reading [laughs] of all of his books.

Ryan Holiday 1:05:22 Sure.

Jay Shetty 1:05:23 And so I love that, you know?

Ryan Holiday 1:05:24 Yeah, yeah. It's like, what rabbit holes are you falling down? What sort of new... It's like a great athlete, it's like, well, what am I adding to my game this off-season?

Jay Shetty 1:05:32 Totally.

Ryan Holiday 1:05:32 And, like, how do you not get complacent and coast? 'Cause you could be coasting for a long time-

Jay Shetty 1:05:40 Yes

Ryan Holiday 1:05:40 ... and not realize-

Jay Shetty 1:05:41 Of your lost skills, yeah

Ryan Holiday 1:05:42 ... that your skills are, your speed is slowly decreasing-

Jay Shetty 1:05:45 Diminishing

Ryan Holiday 1:05:45 ... before, and then it's, it's too late.

Jay Shetty 1:05:48 Yeah. That's such a good point. And, and I think the thing that hit me there of what you just said is just, it's also what skills do I need that I'm not trying to see the results now?

Ryan Holiday 1:05:55 Yes.

Jay Shetty 1:05:55 Like, what is something I'm happy to let kind of simmer and build and just, uh, organically grow rather than like, I'm gonna learn this skill because next week we're gonna launch this thing. Like, that's not what I'm talking about here.

Ryan Holiday 1:06:06 Well, all the things you were talking about that made you who you were, those were never means to an end, because the end was inconceivable, right?

Jay Shetty 1:06:12 Right.

Ryan Holiday 1:06:12 Like, none of, it didn't even exist.

Jay Shetty 1:06:14 Absolutely.

Ryan Holiday 1:06:14 But somehow it was the perfect, like, training montage for who you became.

Jay Shetty 1:06:19 Me too.

Ryan Holiday 1:06:19 And how do you make sure the montage is continuing as opposed to this once in a formative thing, and then, you know, every once in a while I'll do a talk and, like, it's the person before me, you're like, "Oh, you've been doing this a long time the exact same way, and you, you stopped. You stopped."

Jay Shetty 1:06:36 Yeah.

Ryan Holiday 1:06:36 And you don't-

Jay Shetty 1:06:37 Yeah

Ryan Holiday 1:06:37 ... you don't want that.

Jay Shetty 1:06:38 Yeah, exactly. And I, and I think partly that's also me allowing my- at least for me, and I'm only talking about myself, but I, I think this is helpful for people. I think you have to allow yourself to become different things, and giving yourself permission to follow that bliss, as Joseph Campbell would say, because, right, for example, when I, when I wrote Think Like a Monk, that was, uh, the kind of end and beginning of a new journey in my life. Like, I was kind of encapsulating what I've learned over the last 15 years, and then it was like, well, now I'm in a new space. Like, I'm a married man now. I'm, I'm, I'm a business person. I'm a, I'm a, I'm so many more things. And so it was almost like me saying, "Okay, well, I'm gonna put this wrapper on this right now," and now my next book's all about love. And there's loads of people going, "Jay, like, why are you writing about love? Like, why?" And I was like, "Because I'm fascinated by love." Like, and I'm okay with answering that question-

Ryan Holiday 1:07:31 Yeah

Jay Shetty 1:07:31 ... of why love. I don't want to continue to write books I mean, by the way, The Love Book is full of wisdom I learned during my time as a monk. Of course it is. But the point is that I don't wanna be defined by that, and I don't wanna limit myself to any human experience, because then I'm basically saying I have to be this, and that's what performers do.

Ryan Holiday 1:07:48 Yeah.

Jay Shetty 1:07:49 I have to play this character for the rest of my life, and then you get typecast in your own life, and you don't let yourself... And I'm like, "Maybe my next book will definitely not be about love." I know that for a fact my next book's not about love, but I'm okay with that. Like, I like the idea of I'm letting myself go in the direction of whatever I wanna become, because why, why would I limit it now?

Ryan Holiday 1:08:10 When we talked about, like, you know, cranking the shower handle, that that's a muscle, right? My first book was about marketing.

Jay Shetty 1:08:15 Yeah.

Ryan Holiday 1:08:16 I could have sold my next book about marketing, my next book about marketing. I could be still doing that. I could still be speaking about that first book. And when I went to my publisher and I was like, "You know, I wanna write about this obscure school of ancient philosophy," they were like, "What?"

Jay Shetty 1:08:27 [laughs]

Ryan Holiday 1:08:28 You know? They were like, "How's half sound?" You know, they gave me half what I got for my first book. But that's that muscle.

Jay Shetty 1:08:34 Yeah.

Ryan Holiday 1:08:34 I was like, "I don't care. This is what I wanna do."

Jay Shetty 1:08:36 Yeah.

Ryan Holiday 1:08:37 And so when you cultivate the ability to, to do that hard thing, the challenging thing, the different thing, the investing in, like, being bad at something to get good at something. You think about Tiger Woods, he's changed his swing three or four times from the ground up. That's the real muscle-

Jay Shetty 1:08:53 Mm-hmm

Ryan Holiday 1:08:53 ... that prevents you from sort of ossifying or declining. It's the ability to go like, "Just 'cause I'm here doesn't mean I'm gonna stay here. I wanna try and do something radically new or different that I, I hope will work commercially, but I know personally I will emerge bet-" Right? Like-

Jay Shetty 1:09:14 Yeah

Ryan Holiday 1:09:14 ... like let's say that the, the book doesn't work. I'm sure it will. Let's say it doesn't work.

Jay Shetty 1:09:18 Yeah.

Ryan Holiday 1:09:18 But you're like, "Hey, my, my marriage is better-

Jay Shetty 1:09:20 [laughs]

Ryan Holiday 1:09:20 ... as having done it," that's a win from top to bottom, right? And then, you know, you take that with you as you go.

Jay Shetty 1:09:27 For me writing it, I wrote a completely different book than the one I thought I was gonna write, and I wrote it three times. And the first time it was too raw and probably too, like, it was, it was probably t- too tough a read. And the second time it was too shallow. Like, it was totally, like, not

1:09:44 – 1:12:05

When you create a lot of valuable things in life, the returns may double.

Jay Shetty 1:09:44 what I would wanna do. And then the third time we got the balance right.

Ryan Holiday 1:09:46 Yeah.

Jay Shetty 1:09:46 It's funny what you said about earlier, like the discipline of trying to get out of doing things wrong, but the discipline of ambition. Once you've had one success in anything, most people grip onto it, because now you've had a taste of it.

Ryan Holiday 1:10:00 Yeah.

Jay Shetty 1:10:00 And now you're scared that if you don't be that person you will lose it. And I just wouldn't wanna live that way, because then you are just acting-

Ryan Holiday 1:10:11 Well-

Jay Shetty 1:10:11 ... and not being

Ryan Holiday 1:10:12 ... it's like, what, you think that having the success, proving yourself, should make you more courageous, less risk-averse, 'cause now you've done it, but in fact the opposite is true.

Jay Shetty 1:10:25 Yeah.

Ryan Holiday 1:10:25 Right? This is where courage and discipline are related. Uh, it, it's the opposite. Now you have something to lose. Now you don't wanna change, go in a different direction, because the expectation is set with the first one. So you imagine how scary it is. Tiger Woods, you're like, you know, the best swing in golf, and you're like, "But I think it could be better, but I'm gonna have to go have a bad swing for months to get to the other side of that." And so the ability to say, "I decide whether I'm successful or not, not the external results, and that's why I'm willing to go down this detour, try things differently, do this," that is that sort of key skill, and courage and discipline have to be related. They complement each other. And yeah, like it was comfort. My first book came out, it debuted on the bestseller list, it was controver- But if, who I would be today if I continued down that road would be a caricature of that first person, 'cause I would've been, it would've been a copy of a copy of a copy of a copy. Instead, I went towards something that was interesting to me, which opened up another thing that was interesting. And, and that, like, I wouldn't be who I am had I done the safe thing. And so all, they say all growth is a leap in the dark.

Jay Shetty 1:11:31 Mm.

Ryan Holiday 1:11:32 Right? You have to continually take that leap. And one of the things I, I hope you learn when you do that is, first off, it's not as scary as you thought, but then sometimes, like, it doesn't work, and you go, "Oh, but I feel great about it." And then it decouples external recognition from the internal process. And then you go, "Yeah, I just do what I want. I do where it takes me." And a lot of times it works out, sometimes it doesn't, but it's called being a creator for a reason. You're making something. You're

1:12:05 – 1:13:42

Why should you allow yourself to become different things?

Ryan Holiday 1:12:05 the leader. You're not a follower.

Jay Shetty 1:12:07 Well said. Ryan, this has been so much fun, uh-

Ryan Holiday 1:12:09 The best

Jay Shetty 1:12:10 ... diving in with you. We were talking for ages. I had no idea where the time went. Uh, but it's been such a joy just to always, like, just getting into it with you, and I hope that everyone who's been listening, hope you go and grab a copy of Discipline Is Destiny: The Power of Self-Control, uh, by Ryan Holiday, and of course any of the other books that we've recommended before on this show. If you love this episode, you can go back and listen to a ton of other episodes with Ryan. Uh, and again, I hope today's episode, I tried not to do, for everyone who's listening, and you know I've been trying this more recently, I tried not to do a systematic conversation of breaking down how to build discipline and which d- You know, I, I've been avoiding that kind of hack kind of conversation recently, which I think you've been really resonating with, because I think sometimes the penny that needs to drop isn't the how to, it's kind of like the, the churning of the idea in your own self of, of coming closer to what it truly means for you and making sense of it. So that's been my attempt at least, uh, and I hope that's coming through. I hope you enjoyed this. Please do give me feedback on, on Twitter or Instagram. Tag Ryan and I both with your greatest insights, the nuggets of wisdom, uh, and we'll see you on another episode of On Purpose. Thank you, everyone. If you loved this episode, you'll enjoy my interview with Dr. Daniel Amen on how to change your life by changing your brain.

Speaker 1:13:29 Everything in moderation, which is the gateway thought to hell. It's the gateway thought to cheating. As soon as you hear someone say, "Everything in moderation," they're gonna do something bad for their brain

Episode duration: 1:13:42

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