Ryan Holiday ON: The Importance of Being Disciplined With Our Ambition & How to Get Comfortable with Change

26:46So I'll give an example of what I mean by that. 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. And if we want to 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. But we've gone so into feeling because I think for so long thinking and doing what the only thing is talked about and we didn't feel enough.

27:20I 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? Right. It's the result of having meaning and purpose and taking the right actions. And so people sometimes look at the books that I've written and they're like, what, like, how did you publish so many books?

27:56And it's like publishing is not what I think about. I think about writing. I wake up every day and write. 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? You know, how are you setting up systems or processes that the result is that outcome, right? You control what you put in, the outcome happens or it doesn't happen. And I think so often we just, you're right, we just want the feeling. 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 just get yourself closer to it.

28:38What do you think is the best discipline you've built over time? Like, is it writing? Obviously, that would be the obvious one. But is there another one that you think underpins that success? Is there a discipline you've worked on the longest? Well, I think writing is such a sedentary sort of 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? Because again, it comes down to the you don't want to do it.

29:16It'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 and they may or may not exist. That's not why I do it, right? The muscle for me is the cranking of the knob of the looking at the cold punch at my house and going, it is going to be unpleasant to get in there. But I have the ability to force myself to do that. That's the muscle that you want to cultivate. And I think, you know, people want to 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.

29:55Yeah, it's so true. I can relate to so much of that in my own life. And when you're saying that, I feel like today, most of what I do, i'd say i spend a lot i'd say i spend like 75 percent of my life outside of my comfort zone i am constantly doing things that demand more from me than i believe i'm skilled and able to accomplish yeah yeah and in a healthy way 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 amount of like pressure and stress.

30:34And so it's like this balance. For me, I'm at 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. It is interesting, right? We will take, and Seneca points this out in one of his letters, we'll push ourselves, we'll take risks to succeed financially, to succeed in business, to succeed in our careers, to buttress our reputations. but then we don't want to do it in the other places where most of us would admit it actually matters, right? My favorite passages in meditations, Marcus Rios is like a better wrestler, but not a better forgiver of faults, a better friend in tight places.

31:14He's pointing out how we'll go like, yeah, I'm trying to like, you'll talk to someone that have 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, they've got these aggressive goals for their stock price or, you know, how many copies they want to sell of this thing. Or they have, we have really clear financial and professional goals. And then in our personal life, we just wing it. And I'm not saying - Yeah, I didn't mean that, but I know what you mean. Yeah, I love that point. And I think the point is like, you have to be challenging yourself in your personal life also getting vulnerable, getting outside your comfort zone, having the conversations.

31:57I think it's because our professional stuff is so much more quantifiable. And then there's other people are looking at it, whereas the other stuff is private. And so we hold ourselves to different standards. 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, maybe you could have got there in one year and then had nine years of enjoying it. Yeah. No, that I fully agree with. And maybe I didn't clarify. When I said comfort, I mean more, apart from like my sleep schedule, I have so many routines that are already set up that I try and make my personal life more comfortable as in my individual life of my own self-care because I find I'm pushing myself in so many areas.

32:45But I love where you took it to because I think that's the 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 openness that's required, chances are you'll become the person you want to be.

33:20Like chances are you'll become someone that you're proud of being. And I think that's such, I want to dive into that. That is such a powerful way of looking at it. And you're saying it's because of the quantifiability, which I think there's truth in. I also think it's harder. It's harder because like you're saying, there's no external reward. There's no number that proves you did it. and it's fluctuating 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 gonna stay this way well it's like you get so used to the control and the power 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.

34:14This 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 and I'm humbled by it and I'm struggling with it. And I don't feel like I've got it because I have so much less. I've literally never done that before. And I'll have such a short window where I'll ever have to do it, right? It's not like, oh, I've been in this place on a book 12 times, right? Like I've only had one five-year-old. And so, you know, it's just so much more challenging. It's just a much more multi-dimensional, you know, N of one, like difficult thing.

35:01And so it's going to demand more of you. And I think it's like, look, optimizing your professional life or maximizing your professional life. Very unlikely to improve your personal life. But if you have optimized and maximized and improved your personal life, gotten your house in order, you're going to be better at what you do. Or you're going to care less in some degrees about things that used to bother you so much. And so which one are you going to focus on? Because you can be a titan in your industry and then be a total amateur at home. And I think go where it's easy. And that's the thing. I think discipline often gets applied to the titan in the industry, not the amateur at home.

35:47Yeah. And that's how we think about discipline. We think about discipline is what can I achieve through this? Yeah. In an external sense. At least today, that's the language. 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 people because 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 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.

36:19And so you have to, there's some humility required, right? You're meeting equals on an equal playing field. And the discipline to say, like, yeah, I'm going to wrestle with that. I'm going to try to get better. I'm not going to allow myself to do these following bad habits. That takes a certain amount of self-control and focus and discipline. Yeah, 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 about yourself, whatever that may be, it's like you're just or at least I found when I'm coaching clients and working with people is that they have this like bitter feeling towards this thing that they have yeah and they want it to go at all costs but that almost makes you hold on to it harder like that makes you grip on to it sure and wrestle with it more and I remember when when when I lived in India a lot of the time the analogy that was given or 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 i mean they don't even have it's not like the hulk yeah yeah they're not like the hulk where it's like 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 want to That's the beauty of process, right?

37:52You don't sit down and go, I have to do this right now. What do I have to do today? What are the small steps? 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, 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. You have to rebuild it. But I think, you know, the Buddhists talk about willful will.

38:27Like 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. 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 a scent 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 fell asleep and you have to you have to adjust like you're no longer the center of the universe yeah 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 yeah absolutely i was talking to uh amar 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 amar 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 and I think we 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 yeah 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 because 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 and say, do you want to build like a million dollar company, a billion dollar?

40:40He'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? I think restraint is the hardest thing, right? Blaise Pascal in the 1500s said, all of humanity's problems stem from our inability to sit quietly in a room alone. It was hard 500 years ago. It's harder now when you have cell phone in your pocket when you could 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 maybe not to be physically still, but have the mind still while the body is in motion.

41:22This requires like so much discipline, so much self-control, so much self-awareness, right? Even to understand that it's hard for you, that it's something that you are naturally averse to or avoid is a step in that journey to getting better at it. Because 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 hopefully as you go, you get more and more comfortable. Because at the end of the day, that's the one constant in life.

42:00Wherever you go, 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 going to 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 that is that's 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 already there. But I think, is it that we don't, what is your take from studying it?

42:40Is it that we don't know the benefits enough? Is it that we don't like processes enough? Is it that we're just addicted and there isn't? Because I look at, 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 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.

43:15And there was lots of other interesting things to do, or I didn't need that kind of energy. When I came back. You're like the convict who's sober in prison. Yeah, exactly. Just because you don't have access to it. 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 me, because she's a dietitian and nutritionist.

43:44This is her job. She's laying out 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. And obviously it probably happened like halfway through, I'd say, like probably happened three years ago where I really started cutting out sugar. But it needed a coach. My wife was the coach. It needed a obedient or submissive student. I trust my wife on this area. It wasn't like, I didn't have an ego about it.

44:18She 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. We are. And we're also expecting that it just happens. That it's this like epiphany. If knowing what to do was enough, everyone would be in great shape.

44:52No one would have any of these illnesses or problems that we have. It's so much more complicated than that. And I do try to remind people that it's a journey that you're on your whole life. There's passages in meditations where Mark Torelius 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 realizing that if 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 going to get it, it's naive and it's also unfair to yourself.

45:34The 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 setting reachable goals as you go. It's stepping back and giving yourself credit and saying, look how far we've come, man. We're doing great. right it's not it's not just this sort of like in your face like how are you not there yetness 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 yeah this is kind of transformative you didn't have discipline and now you do.

46:35We should also think about it like having a discipline. It is a thing you do your whole life and realizing that that's how we should measure this program. One thing I've been reflecting on lately is how even the smallest choices can create a big impact over time. Whether it's choosing to spend a quiet night in to recharge or making a decision that brings you closer to a long-term goal. Those moments of intention really matter. And when it comes to the choices we make with our money, that same mindset applies. I've learned that saving for the things that truly matter, like your first home or a reliable car, starts with small, thoughtful decisions.

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48:37You're also guided by faculty who've lived the work themselves, scholars and practitioners with real experience. This is the kind of opportunity that reminds you it's never too late to go after what you want. If you've been waiting for the right moment, this is it. Head to waldenu.edu and take that first step. Walden University, set a course for change. Certified to operate by Chev. 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, 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.

49:26Like 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 Lyft, we know that. But I found it really interesting recently. Like I just went through a 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. And I have never, ever moved that slow in life in a good way.

50:05As in that every movement of the body or the mind had to be slow because if I moved fast, I could potentially relapse. yeah so i couldn't i can't i still can't pick anything above like 15 pounds if not allowed uh i i couldn't for that first month like walk 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 i was like wow i thought i was mindful yeah 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.

50:44And I consider myself to be a present person. 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 kindly reminded how little control we have. I remember I moved across the country. I was writing my first book. The two days before I was supposed to start 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.

51:21I couldn't get like the adrenaline or the endorphins that I needed just to function as a person. I had to go on these like long walks. So, you know, I get the news and it's like, okay, I'm not going to 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 hours, three hour walks just around. And what do you know? I start writing the book in my head on these walks. If I had gotten things the way I wanted them to go, it would have been far less advantageous to me than me having to respond to the way they did end up going.

52:00So 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 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 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 Zen master from Zen and the Art of Archery. And he's at the end of his life, he's dying and he goes to urinate in the snow and it's red.

52:44He's like bleeding. He's dying and the students are alarmed. He goes, this too is practice. All of these things that we experienced that we didn't want or we thought they should go a different way, they're actually the opportunity to practice the way or the logos, as the Stoics would call it in the way it's actually meant to do if we choose to be present recognize it and take that opportunity instead of fighting it or resenting it or wishing it were otherwise even i love that point that you made that that even that was practice yeah 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 was still practice and if we could only wrap our hand around that because i think we still think of practice and performing, practice and arrival, practice in the end.

53:31We still see it as separate. And there is nothing that separate. Like that tree outside that's huge is still growing and being nourished. It's just, you don't see it anymore. 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 I remember something they gave us 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.

54:11And it's like most of us spent the whole of the first day we got it trying to untie it and failing. Only by like day 21 to realize all we had to do is 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. Right. Yeah. It's, it was the willful will, right? It's like wanting 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.

54:51Right. And yet in this moment, all we're doing is trying to make it something other than it is, right? Like we will look back on COVID and see 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, in retrospect, the struggle will strike you as most beautiful. but it's such a shame, so unnecessary to deprive yourself of understanding the beauty of it now. Certainly perspective adds to it.

55:32It 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, right? 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, that it's practice. Yeah, yeah. 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 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.

56:22So 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. Yeah. 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. 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 that language 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.

57:18It 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 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 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 live through an event of historic proportions.

58:04Like you just live through event that your kids and your grandchildren, future generations will marvel at. And you emerged unscathed, maybe even improved in some ways. Like 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, right? And you should feel armed with a certain set of weapons or tools that maybe you didn't have before. Like you've been knocked around and you didn't get knocked down. That's powerful.

58:47Yeah, yeah, absolutely. And in my own little way, it's like 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 be completely off. And it wasn't even restful because it was painful. Like it wasn't restful time. And everyone's like, we didn't work for a month. It must've been amazing. I was like, well, no, I was in pain. But the idea that my mind at the time was like, this is the worst. I hate this. And when's it going to be over, right?

59:19Which is the same as COVID, which is the same as anything. Like those are the three thoughts 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 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. It's like, you will reflect, well, hopefully you'll reflect afterwards, but there is a bit of reconfiguration that has to happen at the time. Yeah, there's a story about Phil Jackson when he's a coach of the Lakers.

59:50He gets this back surgery, super bad back surgery, and he can't stand on the sideline. He has to sit in a chair. And the way they had him sit, it's like a row back. And so suddenly all 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 sort of a Zen Buddhist, a sage guy, he realizes that this is practice. He realizes that now the team's having to come to him. Now the team's having to solve some of the problems.

1:00:29He'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 you can always take from this, like it's this forced lifestyle experiment. 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, e-commerce, all these things.

1:01:08And then you want to throw that away by saying, I can't wait for things to go back to normal. It's like normal is what caused this. Normal was you before you learned the things that you learned in that intervening time. And for COVID, for Phil Jackson's back surgery, insert whatever disruptive event you're undergoing in your life. Yeah. 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 Mark's real says the impediment to action advances action, what stands in the way becomes the way, the Zen expression is the obstacle is the path.

1:01:45Same 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. Yeah. And that's what I like. It's not the simplistic idea of, and I'm always trying to address this, it's not the simplistic idea of look for the positive and the negative, right? Like that's not what we're saying here. This isn't the idea of like, oh, there's a beautiful side to this. That's not the point. 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.

1:02:17Well, do you know the Stockdale paradox? No, tell us. So James Stockdale, he studies stoic philosophy and then he shot down over Vietnam and he's taken prisoner. It's been seven years, horribly tortured in this Vietnamese prison camp. Afterwards, he's speaking to Jim Collins, who writes Good to Great. Yeah, Good to Great. And he formulates what becomes known as the Stockdale 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.

1:02:50When 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 going to be seven years at least. But 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 going to 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 going to be fun. This is not going to 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.

1:03:33That'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.

1:04:12I was at the beginning of the pandemic in the middle of opening this bookstore. I'd sunk my life savings 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 wrote this note card to myself and I have a picture of it because I took, I wrote it to myself. I was thinking about it every day and I took the picture in front of the bookstore. 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.

1:04:49I 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 paradoxical 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 yeah they their hope was shattered yeah because they weren't home by Christmas.

1:05:38And 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 is partly where that comes from, where it's like, we want this done by this time. 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 happen by an arbitrary date. Well, you're setting yourself up for disappointment or frustration or resentment or despair by attaching to an outcome that's not yours.

1:06:19If 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 better than when I started, I am more confident than I was when I started, you know, like I said something, I got on the page what I thought only in my head at the beginning, right? Like when you move the outcome or the goal to something that's up to you, he'll always win. And I think that's what wise people do. It's not that they're not ambitious, they are ambitious, but their ambition is things that are up to them.

1:07:09And 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. Yeah. And I think the challenge, Ryan, though, is that today we want both, right? We want the we want the feeling of i did something that was true to me yeah 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 especially when people watch people do what they love and it gets received well it's like oh well i want to 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 people are headed.

1:08:18Well, yeah. I mean, I think we're sometimes not honest with you. You're like, I'm just, I want this album to be true to who I want to 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, right? So that's the worst of both, right? Because 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've set yourself up for maximum disappointment.

1:08:51But 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 what's true inside here. And that's what I'm going to focus on. And I'm not going to waste any time on these other things. I actually do thing, I'm sure you found this, that that does make better work. It makes truer work. It makes more authentic work, more relatable work. 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.

1:09:33You know what I mean? You can't have your cake and eat it too. Yes, exactly. And I think it 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 true to me, but are commercially successful. That is important to me, is a value of mine. And I'm okay with that. Because I don't want to lie about those things to myself 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 use 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 yeah of course 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 that's the medium that I'm comfortable in.

1:10:56I 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 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, you are sacrificing the whole reason you became a creator in the first place. Correct, absolutely. And I think that's the balance, right? It's like, there's people who just completely sell out for the algorithm.

1:11:35And then there's the selfish creator or the snobbish creator on the other end who thinks they're too cool. 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 it. And I'm like, 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 just was a selfish, arrogant move of professing your ideas. And that's like the best thing about it. And so you have sellouts 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.

1:12:11But I also have to serve them what's most beneficial. Once you meet people where they are. and like 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, but they just need a reminder of it, right? And so there's different, 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 in those languages and they reach people who otherwise wouldn't have consumed it.

1:12:46and understanding that different people have different native languages. Some people like audio books, some people like podcasts, some people like this social network or that social 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, you should be everywhere 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 always think about like, again, what is success?

1:13:25At the end of the day, like if your thing sold zero copies, but it changed the world, you'd be like, that was a win. 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. Absolutely. Absolutely. 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, maybe not businesses, but ideas, like when I started creating content, even the first few interviews I did with you, like, I didn't, I mean, that NASDAQ, that whole NASDAQ, I never got paid for that whole series.

1:14:00I was interviewing authors every week because I was fascinated by the idea that I get to sit down with people that I find interesting. You're also putting in your hours. You're getting good at Yeah, exactly. And you're getting good at it. You're enjoying it. You get to meet awesome people. And even when we did the show at HuffPost, it was like, I was leading the show of what kind of show we wanted it to be. It wasn't like, 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 want to create something that will hopefully help people have these conversations.

1:14:34And that was what it was for me. I felt 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. 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.

1:15:11Craigslist still makes a billion dollars 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, right? And the books fund that work and then that work also funds the books. You're creating kind of a flywheel of stuff. I was thinking about one of my books, that hasn't sold as well as the other books. Which one is it? Lives of the Stoics is different than my other books, but I personally use and then also 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.

1:15:53And the book is done extremely well by like any sort of standard, but like the primary beneficiary was me. 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 by-product is that I paid my rent or that like, you know, this happened, then you've won and all the stuff that's out of your control is the extra. Yes. That's where you want to be. Yeah, yeah, I can 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 for you too 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 yeah and it was speaking to rooms of five to ten 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 let me ask you this i've been thinking about it lately yeah the work that you're doing now or that i'm doing now is the result of work you did a long time ago it's a lagging indicator of sacrifice and commitment and study and practice from however long ago.

1:17:23Sometimes 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 this stuff now that will pay off then? And how do you know? How do you know? 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? 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.

1:17:56Like that's my favorite apart from books. That is my favorite way of learning. 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. 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. Correct. And so 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, Malcolm X, like that's who I was reading at 16 years old.

1:18:30They were hugely formative in my ideology in so many ways. And then in my twenties, obviously I lived with the monks. So that was hugely that. And then went to public speaking school when I was 11 years old. So that has lasted far too long and needs to be refined again. 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? 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.

1:19:07And then I can be like, oh, I'm really gonna do a deep dive on that person's book or like Gabor Matei was just on. He's amazing. 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 of all of his books sure and so i love that you know 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 totally and like how do you not get complacent and coast because you could be coasting for a long time yes realize your last skills that your skills are your speed is slowly decreasing before and And then it's too late.

1:19:46Yeah, that's such a good point. And I think the thing that hit me there, what you just said is just, it's also what skills do I need that I'm not trying to see the results now? Yes. Like what is something I'm happy to let kind of simmer and build and just organically grow rather than like, I'm going to learn this skill because next week we're going to launch this thing. Like that's not what I'm talking about. 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? Like none of it didn't even exist. But somehow it was the perfect, like training montage for who you became and how do you make sure the montage is continuing as opposed to this once in a formative thing.

1:20:24And then, you know, every once in a while I'll do a talk and like the person before me, you're like, oh, you've been doing this a long time, the exact same way. And you stopped, you stopped and you don't want that. Yeah, exactly. And I think partly that's also me allowing myself, at least for me, and I'm only talking about myself, but 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 wrote Think Like a Monk, that was the kind of end and beginning of a new journey in my life.

1:21:03Like I was kind of encapsulating what I've learned of 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 a business person. I'm so many more things. And so it was almost like me saying, okay, well, I'm going to 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? And I was like, because I'm fascinated by love. And I'm okay with answering that question 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.

1:21:37Of the point is that I don't want to be defined by that. And I don't want to limit myself to any human experience because then I'm basically saying I have to be this. And that's what performers do. 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 is 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 want to become, because why, why would I limit it now?

1:22:08Well, we talked about like, you know, cranking the shower handle, but that's a muscle, right? My first book was about marketing. 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 want to write about this obscure school of ancient philosophy. They were like, what? You know, they were like, how's half sound? You know, they give me half what I got for my first book, but that's that muscle. I was like, I don't care. This is what I want to do.

1:22:34And so when you cultivate the ability 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 that prevents you from sort of ossifying or declining. It's the ability to go like, just because I'm here doesn't mean I'm going to stay here. I want to try and do something radically new or different that I hope will work commercially, but I know personally I will emerge better, right? Like, let's say that the book doesn't work.

1:23:14I'm sure it will. Let's say it doesn't work, but you're like, hey, my marriage is better 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. For me writing it, I wrote a completely different book than the one I thought I was going to write. And I wrote it three times. And the first time it was too raw and probably too, like it was probably too tough a read. And the second time it was too shallow. Like it was totally like not what I would want to do. And then the third time we got the balance right. 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.

1:23:50Once you've had one success in anything, most people grip onto it because now you've had a taste of it. And now you're scared that if you don't be that person, you will lose it. And I just wouldn't want to live that way because then you are just acting and not being. It's like what you think that having the success, proving yourself should make you more courageous, less risk averse. Because now you've done it. But in fact, the opposite is true. This is where courage and discipline are related. It's the opposite. it. Now you have something to lose. Now you don't want to change, go in a different direction because the expectation is set with the first one.

1:24:35So you imagine how scary it is, Tiger Woods. You're like, you have the best swing in golf. And you're like, but I think it could be better, but I'm going to 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 comfortable. My first book came out. It debuted on the bestseller list.

1:25:07It was controversial. But who I would be today if I continued down that road would be a caricature of that first person because I would have 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 that, like, I wouldn't be who I am had I done the safe thing. And so they say all growth is a leap in the dark, right? You have to continually take that leap. And one of the things 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.

1:25:42And 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 the leader. You're not a follower. Well said. Ryan, this has been so much fun diving in with you. We were talking for ages. I had no idea where the time went, but it's been such a joy just 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.

1:26:19The Power of Self-Control by Ryan Holiday. And of course, any of the other books that we've recommended before on the show. If you love this episode, you can go back and listen to a ton of other episodes with Ryan. 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, you know, 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 churning of the idea in your own self of coming closer to what it truly means for you and making sense of it.

1:27:06So that's been my attempt at least. And I hope that's coming through. I hope you enjoyed this. Please do give me feedback on Twitter, Instagram, tag Ryan and I both with your greatest insights, the nuggets of wisdom. 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. 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 going to do something bad for their brain.

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