Ryan Holiday's Expert Method On How To Build Long-Term Success & Overcome Obstacles

Ryan Holiday 0:00 What is the things that light you up? Success should facilitate you being able to do as much of those things as you wanna do. If you don't have time to do the thing that only you can do, what kind of life is that?

Jay Shetty 0:10 He's the host of The Daily Stoic. His books have sold more than 10 million copies.

Speaker 0:13 Ryan Holiday, ladies and gentlemen.

Ryan Holiday 0:15 Just piling accomplishments on top of accomplishments is not the way one finds meaning in their life or their existence. There has to be some point where you go, "This stops with me."

Jay Shetty 0:25 [upbeat music] We're thrilled to announce that we've reached three million subscribers. We're incredibly grateful for each and every one of you. If you enjoy this episode, don't forget to hit that subscribe button so you never miss out on any of our new releases. We're dedicated to bringing you the content you love. Our team carefully analyzes what resonates most with you to bring on board the best experts and storytellers to help you improve your life. Some of your favorite topics are sleep science, weight loss, physical fitness, navigating breakups, habit building, and understanding toxic relationships. Upcoming episodes include one of the biggest names in health and science, world-renowned relationship therapist, and your favorite manifestation expert is back to drop new findings. Hit subscribe to not miss any of these episodes. If you think of someone who would love this episode, send it to them to make their day.

Ryan Holiday 1:23 The number one health and wellness podcast.

Speaker 1:26 Jay Shetty.

Speaker 1:27 Jay Shetty.

Jay Shetty 1:28 The one, the only Jay Shetty. You asked me

Jay Shetty 1:33 if I'm thinking about being a parent.

Ryan Holiday 1:35 Yeah.

Jay Shetty 1:35 And I was saying that me and my wife have always wanted to have kids, but it's really interesting because we'd set up a life that we thought we were gonna have. We bought a house right next to her parents, near all our friends in London. It was small but wonderful, and we were surrounded by the community we thought we had, and then my career took off in a very unexpected way-

Ryan Holiday 1:57 Yeah

Jay Shetty 1:57 ... which brought me to New York and now to LA. And it's really interesting that as things started to change in what we expected of life, our expectations of ourselves changed, and that hasn't changed the desire to have kids, but what did change was, you know, my wife got so immersed in discovering her passion, something that she never even thought-

Ryan Holiday 2:15 Yeah

Jay Shetty 2:15 ... she'd think about. And having discovered that, we started to have really... We've always had really healthy, open conversations around not when to have kids, because I think to me that isn't necessarily the right conversation. To me, the healthiest conversation with my wife has been, do we know how it's gonna change our life-

Ryan Holiday 2:35 Sure

Jay Shetty 2:35 ... to whatever degree you can know, and are we ready for that change right now? And that's kind of the structure that we've at least placed for our conversations to have a healthy understanding for each other.

Ryan Holiday 2:47 I think what you said at the beginning, though, is interesting because, uh, so a lot of people talk about having kids, but you said, "Are we going to be parents?" And I think that's an interesting distinction that we don't talk about enough, right? Like, having kids is biological or it's legal, right? You adopt or you get a bonus kid from, from a marriage. Like, there, there is having kids, like people who live in your house, and then there is the decision to be a parent. And unfortunately, there are a lot more people who have kids than there are people who are parents, people who decide to make this a central part of what they do, right? Having kids is doing the legal bare minimum, what you have to do to keep child protective services away from your house, and then there is the decision to say, "I'm gonna change my life around this thing. This is gonna be the main, the main or one of the main things that I do, and I'm gonna try to be really good at it," right? Like, most people spend a lot of time trying to get great at their careers. They wanna make more money. They wanna accomplish all these things, and then parenting is kind of this thing that we, we just hope that we get right. We just wing it, right? And that's a tragic, skewed sense of priorities, I think.

Jay Shetty 3:56 That's a brilliant distinction. I'm so glad you raised that. You reminded me of there's this Vedic verse that says, "One should not take on the responsibility of being a parent unless they're ready to enlighten their child."

Ryan Holiday 4:09 Yeah.

Jay Shetty 4:09 Like, there's that, that kind of, the idea of what you just said of flipping the script of like, "When should we have kids? Do I wanna have kids?" to "Do I know what it means to be a parent?" And that's hard sometimes. Like, it's a challenge because I think all of us look at ourselves and we go, "We're flawed, normal individuals with trauma, with challenges," and we're like, "Well, maybe I don't deserve to have kids."

Ryan Holiday 4:32 Sure.

Jay Shetty 4:32 You can go the other way or-

Ryan Holiday 4:34 Sure

Jay Shetty 4:34 ... "I'll never be qualified to have kids."

Ryan Holiday 4:36 Yeah, the comedian Tom Segura has this bit where he goes, you know, "People say that, uh, having kids changes you." And he goes, "That's not quite right. It's that having kids should change you."

Jay Shetty 4:47 [laughs]

Ryan Holiday 4:47 Right? So, like, if you're not ready to be changed, that's one of the things when people ask me, they go, "I'm thinking about having kids. What, what should I do?" And I go, "You have to be ready for it to change you." Like, not only can you not live and organize your life the same way, but you're gonna be opened, uh, emotionally, physically, spiritually, in all of these ways that if you're resistant to because you liked the way things were before-

Jay Shetty 5:10 Mm

Ryan Holiday 5:10 ... you're not only doing your kids a disservice, but I think you're doing yourself a disservice, 'cause this is, this is a profound, you know, sort of shift on a human level. And if you're not ready to be changed by it, you're probably not ready to do it.

Jay Shetty 5:23 Were you this conscious about being a parent before you were a parent, or is it something that came from the process?

Ryan Holiday 5:31 No, it definitely came from the process. Like, you, you think, you think you know and you have ideas, but it's not until this thing happens to you that you go,

Ryan Holiday 5:43 "Oh, all these other things aren't as important to me anymore," right? I think, I, I, I do wish... Sometimes I think about wishing that I'd done it earlier. There's this thing that happens when you achieve what you set out to achieve, right? Which is that you realize it doesn't mean that much, right? You, you write a bestselling book. You sell a screenplay. You know, you have some number in your mind, and then maybe it's winning a gold medal. You, you do something, and then you get it, and you go, "Oh." This is like nothing, right? This is, this didn't change what I thought it would change. It didn't transform me in the way that I thought it'd transform me. I feel lucky that I'd done a bunch of those things before I had kids because then I'd already... I was already wrestling with the, not the emptiness, but I was wrestling with th- the, the inescapable conclusion that just piling accomplishments on top of accomplishments is not the way that one finds meaning in their life or their existence.

Jay Shetty 6:43 What do you think it does do then? Like, what does it do in any goal, and of course, some goals, uh, have a different scale to others, but the idea of becoming a best-selling author or someone who's listening saying, "I want to launch a big podcast," or someone saying, "I want..." The way I look at it is, and I remember going on a really long walk with you once, like, through New York-

Ryan Holiday 7:05 Yeah

Jay Shetty 7:05 ... before I'd ever written a book or anything, and it was around the time when I first interviewed you. If someone honestly asked me when I was doing this type of work offline, I actually, A, never believed it would be big-

Ryan Holiday 7:19 Yeah

Jay Shetty 7:19 ... and B, was not trying to make it big. So if someone would have asked me when I was, whether I was 18 or whether I was 25 and said to me, "Jay, like, what's your goal here?" My honest answer would have been, "I'm just trying to make ancient wisdom relevant-

Ryan Holiday 7:33 Sure

Jay Shetty 7:33 ... because I get joy out of that act in and of itself." Like, the act of studying, researching, and simplifying brings me joy.

Ryan Holiday 7:41 Sure.

Jay Shetty 7:42 And I love teaching and sharing and sharing those ideas with people and hearing what they have to say about it, and so I was doing that for five to 10 people-

Ryan Holiday 7:49 Yeah

Jay Shetty 7:49 ... every week for hours every day.

Ryan Holiday 7:51 Right.

Jay Shetty 7:52 I was already happy. Now, my life changed when scale became possible, when a video by mistake went viral. Like, it wasn't that I thought it would go viral or whatever, and then life has changed, but so partly my answer to that question or my reflection to the question I'm asking you is, I don't think you should ever start something wanting it to be big in the first place. But what does a, what does having a goal achieve, and what type of goals should we set?

Ryan Holiday 8:19 Well, the stoics talk about attaching your goals only to things that are in your control. So if your ambition is to be accepted by a certain group, to move a certain number of units, to make a certain amount of money, to be invited to a certain club, you know, if things line up, great, but there's also a very significant chance that they won't line up, and so the idea is that you tie your ambition, your intention, your, your motivation to the parts of it that are up to you. I really like doing it. I get better. Like, one of the reasons I wrote The Daily Stoic and The Daily Dad is that I have become better as a person for the pr- the meditative practice of having to produce this thing on a daily basis. So if it also then goes on to be successful, then I get this sort of d- this bonus success of the rewards or the royalties or whatever. Um, so it's, I think you want to root what you're trying to do as much as possible in what is up to you. The stoics go, "If you only enter competitions where winning is up to you, you will always be a winner," right? And so if your, if your goal is to beat this other person, right, to be more than this other person, this other type of person... I, I remember I talked to this author once, and, and he was working on this book and, and he said, uh, I said, "What's your goal?" And he said, "Oh, I want to sell, like, two million copies." And I said, "Well, where'd that number came from?" And he's like, "Well, I heard somebody had sold a million copies, and I doubled it." And so the arbitrariness of just wanting to one-up some other person, it's not only sort of empty and trivial, but, like, it's not really rooted in anything that's up to you, right? And I think the best way to think about it is, is this thing up to me or not? And, and what I have found is that, uh, when you accomplish those things, it's great, but it doesn't fix whatever you thought it was trying to fix. It doesn't fill whatever you thought it was trying to fill. I wish I could give to everyone that understanding as early as possible. I do think it's probably something you have to experience at some level on your own. But ideally, you experience it not on your fifth Super Bowl ring, and you go, "Oh, it's never..." You know, ideally, that, that comes as early as possible-

Jay Shetty 10:36 Mm-hmm

Ryan Holiday 10:36 ... uh, in the process. That doesn't mean that once you figure it out, you stop doing it. You do stop... You, you, you can keep doing it, but you've just, you've broken the connection between, uh, like, your sense of self-

Jay Shetty 10:49 Yeah

Ryan Holiday 10:49 ... and these external things that are not up to you.

Jay Shetty 10:52 Yeah, yeah. That resonates. I, I

Jay Shetty 10:54 feel like to- for me, growing and learning are just such integral components of being alive-

Ryan Holiday 11:01 Yeah

Jay Shetty 11:02 ... and feeling like there's progress and there's momentum, that I try and pick goals that I'm challenged by the growth I'll have to make. I set goals based on the growth I want, not based on the goal.

Ryan Holiday 11:18 Sure.

Jay Shetty 11:18 So for example, I just finished a nearly 40-city world tour. It wasn't that I wanted to go on a world tour to go on a world tour. It was like I wanted the feeling of, can I... have I built up my health and resilience?

Ryan Holiday 11:34 Yeah.

Jay Shetty 11:34 Can I go on stage every night and deliver? What does it feel like to pour love into the people who support my work? I've been doing this for seven years online, yet I've pretty much never met more than 1% of my audience, if that. What does it feel like to build community again for people? And that's the stuff that gets you through it when it's tough-

Ryan Holiday 11:54 Yeah

Jay Shetty 11:54 ... because the title or the whatever the external reward would be doesn't motivate you. When I fell sick in one city and I had to cancel a show that night, and the next day I had to wake up, get on a flight, and do two shows back to back that day, and the only thing that gets you through is- I want to do this for my community. This means something to me. Like, there's this amazing thing that I always think about because it blows my mind. When Kobe Bryant passed away, his wife, Vanessa, was giving a speech, and she said that he was always playing through injuries, and everyone knew that, but no one really knew the reason. And she asked him in a private conversation, I believe, one night, like, "Why do you do it?" And he said, "It's because someone has saved up to watch me play."

Ryan Holiday 12:41 Yeah.

Jay Shetty 12:41 "And they might only ever be able to afford one time to watch me play."

Ryan Holiday 12:45 Sure.

Jay Shetty 12:46 "And I don't want to let them down."

Ryan Holiday 12:48 Yeah.

Jay Shetty 12:48 And that's how he played through injury. It wasn't that he wanted the championship more or that he wanted the, the ring more. It was that, "I want to be there for my fans who are showing up for me."

Ryan Holiday 13:00 Interesting.

Jay Shetty 13:01 I want to hear your thoughts on it. Yeah.

Ryan Holiday 13:02 I mean, you have, you have my book Conspiracy right there-

Jay Shetty 13:04 Yeah, yeah

Ryan Holiday 13:04 ... which I saw when I came in.

Jay Shetty 13:06 Yeah.

Ryan Holiday 13:06 And that's my worst-selling book.

Jay Shetty 13:07 [laughs]

Ryan Holiday 13:07 Uh, it, it is not that it hasn't sold well-

Jay Shetty 13:10 That it's not that it's bad. [laughs]

Ryan Holiday 13:11 Yeah, it's just-

Jay Shetty 13:11 Your worst seller, it's-

Ryan Holiday 13:12 Of all my books, it's, it's, it's not sold well. But it's w- it's the one that without question if people ask me what book I'm most proud of, it's that one.

Jay Shetty 13:19 Mm.

Ryan Holiday 13:20 And, and that's because I grew the most writing it. It was the most outside my wheelhouse. It was the most challenging. It was the one I had the most doubts as to whether I could pull off, and it's the one that's sort of most authentically interesting to me while I was doing it. I... You love all the projects that you do, but that one was just different. You know, it was, it was just different in so many ways. If you can find a way, when the, when the Stoics are saying if you only enter things where winning is up to you, you always win, what they're saying is that if, if it's intrinsically interesting and compelling and challenging to you, you're doing it because you like the puzzle of it, then you've already won, and then everything else is extra.

Jay Shetty 14:03 Mm.

Ryan Holiday 14:03 And, you know, for basketball, if, if you like playing basketball, and there's a reason it's called playing, right? If you like the thing, then, then all the other stuff is extra. But if for you winning is what gets you up out of bed, well, then what happens if you're drafted by a team that's not any good? Or what if you are crippled with injuries or, you know, any number of things, right? Winning is not up to you. Enjoying the, the day-to-dayness of it, the lacing up of the sneakers, the squeaking of the shoes on the floor, the bouncing of the ball, like, the warm-ups, you know, the cra- If, if you love all of that, then everything else is extra. And you got, you gotta figure out how to love, like, the, the purity of the thing itself and find something in it that is fulfilling and wonderful just to you before it's ever out. That's the purest place. And I, and I've had to do work on that. I, I've said this before, but, like, probably with my first book, I was probably, like, 90% interested in how it did and 10%, like, proud of what I'd done, and I'd like to think I've gotten that flipped. I mean, if you don't care about it at all, like, you're not gonna keep doing them, and you have partners and, you know, you have employees. You have all these things that are dependent on it doing well. But ideally, most of the success is off the table just from having done it.

Jay Shetty 15:20 Yeah.

Ryan Holiday 15:20 Because what if it comes out on the day of a terrorist attack or a natural disaster or a printer shortage? Like, there's so many things that could happen that could get between you and the thing that you wanted, but if you enjoyed doing it, then, then you've, you've picked all the fruit that's up to you to pick.

Jay Shetty 15:39 Yeah, absolutely. You reminded me of a statement by George Bernard Shaw where he said, "We don't stop playing because we get old. We get old because we stop playing."

Ryan Holiday 15:48 Yeah.

Jay Shetty 15:49 And, and it's that idea of just... You're so right. Like, I feel out of touch with myself when I'm not reading and learning and reflecting.

Ryan Holiday 16:00 Yeah.

Jay Shetty 16:01 Like, that's when I feel misaligned. If my life gets too far away from finding new ideas, experimenting with them, discovering them, trying to understand them and wrap my head around them, if I'm not filling my brain up with not just ideas theoretically but even physically trying something new, experimenting with something I've never done before, I find that's when I'm misaligned with who I am.

Ryan Holiday 16:27 Well, yeah. Look, success in your chosen field cannot be not having time to do what you like to do in said-

Jay Shetty 16:36 Yeah

Ryan Holiday 16:36 ... field, right? Like, if I don't have time to read, if I don't have time to write, if I'm not on my routine, on my schedule, what kind of success is that? I've mortgaged myself for a bunch of things that I don't want to do. You know, those things might be lucrative. Those things might be fun. Those things might be rewarding in their own ways, but the main thing, like, what got you into this, right? And if you don't have the time to do that, what h- what kind of success is that, right? It can be very easy to just say yes to all the things that are coming in, and then you wake up and you go, "It has been weeks since I did X, Y, or Z," like the things that light me up. Like, what is the things that light you up? And success should facilitate you being able to do as much of those things as you want to do. Are there always gonna be administrative things and obligations and busine- Of course, but if you don't have time to do the thing that only you can do, like, what k- what kind of life is that?

Jay Shetty 17:30 Yeah. And I know we both feel grateful and have tried our own, in some way, similar paths from moving from a corporate career to-

Ryan Holiday 17:37 Yeah

Jay Shetty 17:37 ... to doing what we love today, and we both, I know we both feel very grateful to be able to do that. But I want to go back to when you were there and, and even when I was there, I think about what really worked for me was... So I was at Accenture, for anyone who doesn't know. I was at Accenture after I left the monastery because I needed to find a way to pay the bills and just reconnect with the real world and, and figure out how I fit in again. And the corporate world was what I would have naturally done before, so it was where I ended up. And I didn't enjoy being a consultant. Like, that is not who I am in, in any way. But at that time, I didn't know what was possible, but I knew that I could demonstrate my own skills at work. So I started to plan these idea days at work because that was something that work wanted-

Ryan Holiday 18:23 Sure

Jay Shetty 18:23 ... where I would get to bring in speakers to help people be more curious and excited.

Ryan Holiday 18:27 Sure.

Jay Shetty 18:27 And I remember we had, uh, Salim Ismail, who wrote Exponential Organizations, come in one day, and my mind was blown because I was like-

Ryan Holiday 18:35 Sure

Jay Shetty 18:35 ... I'm getting to hang out with this guy, and there's another person who is a writer and a speaker. And so I was always trying to find ways at work to kind of dovetail my career to get me into the things I was interested by, and that worked for me as a way of satisfying me at work even though the actual job day to day wasn't. How were you doing that? I know you enjoyed marketing and always have and,

Jay Shetty 18:59 but what would you say to someone who's sitting here going, "Yeah, you guys are lucky. You get to do what you love every day. Obviously, you just have to get the percentages right, but I'm stuck in a job that I hate."

Ryan Holiday 19:07 Well, it's funny. We did have very similar paths. I remember... So I d- I, I don't believe in this idea that you have to, like, quit your job, blow up your life to pursue-

Jay Shetty 19:15 Same

Ryan Holiday 19:15 ... some sort of thing. I wrote three books while I was a full-time employee at, uh, a large fashion brand. And y- if you are good at what you do, you can get leverage at that company to, to pursue these other things. But I remember, uh, this would've been, like, the summer of 2014, I... So I'd written a couple books, and I, I had, I'd gone back to American Apparel where I was sort of consulting in the turnaround of the company. I was getting a, this huge consultant fee. I was making great money, and I remember I, I was running in the morning, and, uh, I got this, like, alert on my phone that I had a meeting, like had a staff meeting. And I, something hit me. It, it hit me. It was like how many people would kill to write books for a living, which is what I wanted to do more than anything, and here I am rushing to get to a staff meeting because it's paying well. Like, this, life is too short to be cutting short the things that you wanna do to help you be- be better at what you do, you know, to go to some meeting. And so at some point you make the transition. But for me, the, the idea was as long as my sort of corporate work was supporting and facilitating me doing the, the other stuff, it was great, and then as soon as they were fighting for the same resources, I, I made that, I made that shift. But I, I think some people think that it's, it's about this sort of bold burn the boats behind you thing, and it can be. I mean, at some point you do have to do that. But I talk to people and they're like they're quitting their job to write a book, but they haven't published a single thing online. They haven't uploaded a single video, you know? And just start. Just start. You can start way smaller than you think, and the first thing that you put out there in the world should not be a screenplay or a book or whatever. Like, you, you need, you need so much interaction with the audience to find out what they like, what you like, what resonates, what... You know, I, I, I wrote online every day for something like six years before I got paid a single dollar. I started my first website in the summer of 2005, and my first book came out in the f- summer of 2012. You know, I didn't hit the New York Times bestseller list for another-

Jay Shetty 21:25 [laughs]

Ryan Holiday 21:25 ... five years after that. It takes a long time. There's a, there's a great law. It's called Hofstadter's Law, and it says that it always takes longer than you expect even when you take this law into account.

Jay Shetty 21:37 [laughs]

Ryan Holiday 21:37 Right? Like, it's o- it's gonna take way longer than you thought. And so if you quit in this sort of dramatic gesture, you know, y- you're not, you're not gonna have the runway to pull it off, right? You need, like, a lot of runway, a lot of time. And so, uh, that, that was certainly my path is it-

Jay Shetty 21:53 Yeah

Ryan Holiday 21:53 ... it took a lot longer than I thought.

Jay Shetty 21:56 Yeah. I'm, I'm glad, I'm glad you raised that, and I love that tracking back of your journey just now, and that law is awesome because it's, it's so true when it comes to anything in life.

Jay Shetty 22:06 And for me, I, I always say that to people because obviously I've been creating online work for seven years now, and that feels like a very short period of time for most people.

Ryan Holiday 22:16 Yeah.

Jay Shetty 22:16 But I'm like, no, well, for 10 years before these seven years, I did this multiple times a week offline to groups of five to 10 people for three hours four times a week, three times a week, spending time with people, coaching, mentoring, working for no money, for no followers-

Ryan Holiday 22:35 Yeah

Jay Shetty 22:35 ... for no fame, no, no success, and then on top of that did seven years of public speaking training before that which my parents forced me to go to after the event [laughs] that I told you about-

Ryan Holiday 22:44 Yeah

Jay Shetty 22:44 ... in the beginning from age 11 to age 18. So my public speaking communication journey started at 11. I'm 35 today. That's 24 years of-

Ryan Holiday 22:54 Yeah

Jay Shetty 22:54 ... repetition.

Ryan Holiday 22:55 Yeah, you need a lot of reps. Well, you need way more reps than you think that you do.

Jay Shetty 22:59 Yeah.

Ryan Holiday 22:59 And the amazing thing about what social media and the internet does is that you can reach millions of people with your work. The nefarious thing about it is we hear about someone who uploads their first thing and blows up, and we think that that's how it goes, right?

Jay Shetty 23:14 Yeah.

Ryan Holiday 23:14 And it doesn't. It takes a long time. And I think what you're trying to do is build... You know what a flywheel is? Like, you're trying to, you're, you're trying to build this thing. It takes a long, a large number of slow, methodical turns before it speeds up and speeds up and speeds up, and then it starts to really spin and, and spin stuff off. It takes, like, a long, a long time.

Jay Shetty 23:36 Yeah.

Ryan Holiday 23:36 Um, you know, when The Obstacle Is the Way came out, it probably sold 3,000 copies its first week, you know? It's now sold millions of copies, but that's where it started, right? And it took a long time. And so when people look at this sort of algorithmic success where they just upload a video and it does millions and millions of views, they think that that's how it's gonna go, and really it's about sort of methodically building this audience person by person and also building your competence, like rep by rep- ... you know, moment by moment. So then when you, you suddenly do get the audience, you're actually ready for it. Like, if I had gotten the audience that I thought I wanted or deserved when I wanted it, it would've been, it would've been-

Jay Shetty 24:19 Pre-

Ryan Holiday 24:19 ... preposterous.

Jay Shetty 24:19 Yeah.

Ryan Holiday 24:20 Yeah. I, I rem- I, I was actually just thinking about this because I, I, I was just doing the marketing for Daily Dad, and, and I was in New York, and I did The Daily Show, and I did CBS Sunday Morning, and I did some- I, I did a bunch of shows. And I remember thinking back when my first book came out in 2012, they ha- the, the publicist had me put together a list of all of these outlets that I wanted to do, and I don't think we got any of them, right? It's not that they did a bad job, it's just, like, we didn't get any of the things is, I wasn't ready, and they, the m- media didn't care. And then I realized, like, on this launch, I did get those things, but it took more than 10 years longer than I thought it would take, right? And now I'm getting it. But if I had gotten them then, I wouldn't have been ready. I wouldn't have been able to actually deliver, you know, on those at bats.

Jay Shetty 25:05 Mm-hmm.

Ryan Holiday 25:05 And so you think you want it when you want it, but you don't.

Jay Shetty 25:09 Yeah. [laughs]

Ryan Holiday 25:10 You know?

Jay Shetty 25:10 Yeah, yeah.

Ryan Holiday 25:10 I th- I heard something about the early days of Google where they were like, "Eventually everyone's gonna try our product, but if they all try it now, we won't be able to deliver for them." They knew that they w- they knew it was getting better every day, so actually from a marketing and a promotions and a sort of trajectory standpoint, they wanted to, to backload it as much as possible, not frontload it, and that can be really hard. That requires so much discipline and so much patience to go, "Actually, I don't want this right now. I want it when I'm ready. I want it when I'm good enough." You think you're being screwed. You think, you know, other people are getting the shots that you deserve, but it's actually for the best-

Jay Shetty 25:50 Mm-hmm

Ryan Holiday 25:50 ... because you're getting better every single day.

Jay Shetty 25:52 Yeah.

Ryan Holiday 25:53 And so I think about that o- of course with having kids too. Like, if I'd had kids when I f- earlier, I wouldn't have been emotionally ready. You know? Like, so I- it's, it's, um, patience is, is, is all,

Ryan Holiday 26:04 what it's all about.

Jay Shetty 26:04 And that, that's the hard part about patience, right? Because I think there's those two sides of the coin where one's like, "I believe I deserve it," which we hear a lot about, and I wanna dive into that with you, and then the other side of it is the mentality of, "Well, no, I'm gonna be patient, and I'll be better when I get it."

Ryan Holiday 26:20 Yeah.

Jay Shetty 26:21 And it's almost like, how does someone reconcile those two things? Because I think everyone's told to, like, believe in themselves and, like, know your worth and-

Ryan Holiday 26:28 Yeah

Jay Shetty 26:28 ... kinda do this thing. And I'm more along the lines of you because so many things for me happened far more organically than by belief, and they happened far more by action than they did by thinking something. For me it was what you're saying. Like, when you first came on my show at HuffPost, it's like I went from having... I was live every single day with a guest for nine months-

Ryan Holiday 26:51 Yeah

Jay Shetty 26:51 ... five days a week, and then I did the Nasdaq thing where I was live when I was connected to great authors like yourself and other people that I could have on. So I, before I launched my podcast in 2019, I'd done at least, like, two years of being-

Ryan Holiday 27:05 Sure

Jay Shetty 27:06 ... live every day, and no one r- like, that show wasn't big or, or, you know... It was, it was good. It was good, definitely, but it wasn't what the podcast is today, and it was just like... But I got two years of reps of doing interviews. Uh-

Ryan Holiday 27:18 Well, yeah, but I w- I was telling you, like, the caliber of guests that you've been pulling on have been insane, right? Like, you've been getting people that don't do podcasts, right? And so I'm sure some of them you have tried to get on for a while, and you would've been very excited to get them in 2019 or 2020 or six months ago. But you're better now, right? So you thi- you think that you want it when you want it, but, uh, it's better to get it later-

Jay Shetty 27:48 Yeah

Ryan Holiday 27:48 ... 'cause you'll be better later.

Jay Shetty 27:50 Yeah.

Ryan Holiday 27:50 Right? And, and the, the, the patience and the confidence to be like, "I don't have to force it." There's that expression, like, don't run to catch trains. You know, it's like, uh, there's something in that. Like, you don't need to force it. If it, if it's not a fit, it'll come back around.

Jay Shetty 28:05 Right.

Ryan Holiday 28:05 Right? And, and, and the idea that... I sometimes think that everything I've written so far, everything I've thought about, is actually all prologue or preparation for an idea or a, uh, an idea in a moment in time that I can't even conceive of yet. Like, uh-

Jay Shetty 28:26 Mm

Ryan Holiday 28:26 ... you know Michael Lewis, the author?

Jay Shetty 28:27 Mm. Mm. Mm. I like that.

Ryan Holiday 28:29 He, he'd probably written 15 books before The Big Short came out, right? When the markets melted down in 2008, he had written dozens of popular books about finance, about sports, about, uh, you know, tech entrepreneurs, and then that moment happened, and he was the person to write that book, which sold millions of copies, was turned into a huge movie. That was when the man and the moment met.

Jay Shetty 28:55 Yeah.

Ryan Holiday 28:55 Right? And I think Churchill said something about, like, you know, there comes this time in everyone's life where, you know, destiny taps you on the shoulder, and he says it would be a shame if you weren't ready when that happened. And so, you know, everyone thinks they're ready, and they want it now, but you actually, you don't know what the future holds. And, and so just this sense that, like, every day I get a little bit better. I work on it all the time. Uh, I'm putting in my reps. I'm following my process. I'm, you know, putting in the hours, and I have this... m- maybe this is a little delusional, but I just have this vague sense that there's a thing that I haven't even thought of yet, and that will be the best thing that I do.

Jay Shetty 29:34 Yeah.

Ryan Holiday 29:35 And that kinda keeps me going.

Jay Shetty 29:36 What a beautiful way to live. That, that's spectacular. And, and at one point I remember sitting with someone, and he wasn't trying to teach me. He wasn't a mentor. He was just... I was sitting with him at a wedding, and he was just telling stories of his life, and he'd had quite a fascinating life because of something that his dad did, and he used to just as a kid be following his, fun- to The Daily Dad, like, following his dad around.

Ryan Holiday 29:58 Yeah.

Jay Shetty 29:59 And he was taken on crazy adventures and experiences as a little kid just 'cause his dad had a crazy job.

Ryan Holiday 30:03 Sure.

Jay Shetty 30:04 I used to listen to him and be like, "Wow, like this guy just has so many stories." They're not achievements. They're not like, "I got an award-

Ryan Holiday 30:12 Sure

Jay Shetty 30:12 ... or it wasn't like, "Oh, and then I became invited."

Ryan Holiday 30:14 Yeah.

Jay Shetty 30:14 It was just he had a great set of stories he was sharing,

Jay Shetty 30:18 and I realized that, at one point, I realized that collecting experiences, collecting skills, collecting abilities, qualities was so much more of a better pursuit. And I look at that, what you just said, for me today, it's like I chose to be a monk without knowing what it was. Before that, I went to public speaking school 'cause my parents forced me to go-

Ryan Holiday 30:39 Sure

Jay Shetty 30:39 ... not knowing that... I never said, "Oh, I really want to be a public speaker-

Ryan Holiday 30:42 Yeah

Jay Shetty 30:42 ... at 11 years old." And then I went into the world of Accenture and learned about business and strategy, which was very, very useful. And like today I put all those three things together-

Ryan Holiday 30:51 Sure

Jay Shetty 30:51 ... and my career is based off all three of those experiences, but I could never have known that. And it goes back to that famous Steve Jobs statement of you can always connect the dots. You can't connect the dots moving forward. You only can looking backward.

Ryan Holiday 31:05 Yes.

Jay Shetty 31:05 And so when you're living, it's almost like collect experiences and skills and abilities and relationships. When I was interviewing you all those years ago, I would never have known that we would still be friends and-

Ryan Holiday 31:15 Sure

Jay Shetty 31:16 ... we'd connect and support each other. You've supported my books. But it's like you're just collecting that connection and relationship, if that makes sense.

Ryan Holiday 31:24 Yeah, one of my mentors, uh, the writer Robert Greene, he said-

Jay Shetty 31:26 Yeah

Ryan Holiday 31:26 ... one of the great things about being a writer is that it's all material, that everything that happens to you is material.

Jay Shetty 31:32 Mm-hmm.

Ryan Holiday 31:33 And so if you just go through your life going, "Hey, I don't know why I got dumped here. I don't know why my house flooded. I don't know why any of this stuff happened to me, but I'm gonna choose it as... I'm gonna choose to see it as something that's happening for me as an artist, a leader, a parent, a spouse, that this is teaching me something." Right? When we, when we say that the obstacle is the way, it's not that, hey, this thing happened, and now as a result, your business is 10X better off, right? Like it, it... Sometimes just shit happens. Bad shit happens, but you learned from it or it ch- it, it forced you to grow in some way. Just the sheer hanging on-ness of it made you stronger-

Jay Shetty 32:17 Yeah [laughs]

Ryan Holiday 32:17 ... and better, right? It's not, it's not that, hey, there's this magical, you know, opportunity in this, that there's this just slightly secret silver lining and then everything's awesome. No, it's, it's much deeper than that.

Jay Shetty 32:29 Yeah.

Ryan Holiday 32:29 It's, it's that the stuff that happens is shaping you and forming you and, and giving you opportunities to, you know, evolve as a human being. That's, that's what that idea is.

Jay Shetty 32:42 Yeah.

Ryan Holiday 32:42 And so, you know, there are things that I've gone through in my life that end up shaping my writing for things that I don't even know, I didn't know until I sat down that day that that would come back out, right? And so it's just this, yeah, it's this process of accumulating experiences, accumulating insights, accumulating, you know, things that you've read, and then it all funnels ultimately in, into the work.

Jay Shetty 33:06 And what a great way to live knowing that your best work is still ahead of you.

Ryan Holiday 33:10 Yeah, I hope so.

Jay Shetty 33:10 Yeah.

Ryan Holiday 33:10 I mean, maybe not, right? Maybe not.

Jay Shetty 33:12 I believe it.

Ryan Holiday 33:13 Uh-

Jay Shetty 33:13 I believe it for you. I believe it for me. I think that's a great way to live and think.

Ryan Holiday 33:17 Yeah. I, I mean-

Jay Shetty 33:18 Your best work doesn't have to be your most successful work.

Ryan Holiday 33:20 Of course.

Jay Shetty 33:20 Yeah, that's what I mean. Yeah.

Ryan Holiday 33:21 Yeah, yeah. I, I'm just saying that's, that's how I get up every day-

Jay Shetty 33:24 Yeah

Ryan Holiday 33:24 ... is that I think, "Hey, I'm... There is this thing in the future. Maybe I won't be ready for it. Maybe I won't be around, but I, I, I like to think that it's all building towards something."

Jay Shetty 33:34 Yeah, yeah,

Jay Shetty 33:35 and I feel like when I look at, back at some sages in, you know, the Vedic tradition and even in the Hindu tradition, there were these amazing people that excavated temples, like old sites that historical things had happened at.

Ryan Holiday 33:55 Yeah.

Jay Shetty 33:56 But no one really knew about it, so no one would really visit. But today, 500 to 1,000 years later-

Ryan Holiday 34:03 Sure

Jay Shetty 34:03 ... pilgrims visit these places.

Ryan Holiday 34:05 Yeah.

Jay Shetty 34:05 And they did that believing and knowing that one day this place will be of significance, but not maybe in my lifetime.

Ryan Holiday 34:12 Yes.

Jay Shetty 34:13 And so they were able to fast-forward their service in one sense or their passion, knowing that one day this will serve others, one day this will mean something to people, even if it doesn't right now, even if it's seen as valueless right now.

Ryan Holiday 34:27 No, it's, it's kind of beautiful to go through life and go like, "Hey, somebody planted this tree.

Jay Shetty 34:31 Yeah.

Ryan Holiday 34:31 Somebody built this road. Somebody created this institution. Somebody fought for a very specific way of setting it up or thinking about it. Somebody went to prison over this," right? Somebody crossed a n- like, all of us are the, the lucky recipients of investments that people made a long time ago.

Jay Shetty 34:51 Mm-hmm.

Ryan Holiday 34:51 And there's this Christian idea, like you've been given a free gift, so you have to give freely yourself, and the idea that like, yeah, we are the... we in the present are living in a future that other people dreamed of, right? And so h- what is it that, that you are contributing to the, the next future, right? What trees are you planting? What difference are you making? What work are you creating? And again, like, yeah, you're writing this book and you hope it sells now, but maybe it sells 500 years from now. Maybe it's rediscovered then. Like the, the... We, we, we consume works of art that were totally obscure or unappreciated in their own time-

Jay Shetty 35:31 Mm-hmm

Ryan Holiday 35:31 ... that, that we came back around to.

Jay Shetty 35:33 Mm-hmm.

Ryan Holiday 35:34 And so the idea of, of owing the future something I think is a really beautiful idea. There's that, that quote like, uh, "The world is great when old men plant trees in whose shade they'll never know."

Jay Shetty 35:45 Mm-hmm.

Ryan Holiday 35:46 And what about you, right? Like what, what have you planted? What have, what are you contributing? Um, what are you giving away-

Jay Shetty 35:53 Mm-hmm

Ryan Holiday 35:53 ... is, is a, is a way to measure your own life.

Jay Shetty 35:56 Yeah,

Jay Shetty 35:57 yeah. One of the chapters that stuck out from your book that I loved, uh, is called, wait. See, I wanted to pick it up. Oh yeah, Raise a Reader.

Ryan Holiday 36:04 Yeah.

Jay Shetty 36:05 And it, and it stuck with me because I was- A kid who never liked reading until 14, and now I consider myself a-

Ryan Holiday 36:16 Sure

Jay Shetty 36:16 ... like a voracious reader. I absolut- it's my favorite way of learning, and I realized it was because school always gave us fiction books, and so we'd get storybooks, and a big one we'd get a lot of was Goosebumps.

Ryan Holiday 36:29 Yeah.

Jay Shetty 36:29 And then you'd read-

Ryan Holiday 36:30 I read those

Jay Shetty 36:30 ... Roald Dahl-

Ryan Holiday 36:30 Yeah

Jay Shetty 36:31 ... and you'd read, you know, these incredible authors, but fiction just never resonated with me, and I remember it took my dad giving me, like, a biography or an autobiography that triggered it, and I remembered my first-ever books that I got really into were, uh, David Beckham's autobiography, Dwayne The Rock Johnson when he was a wrestler's bi- uh, autobiography, and then the biography of, like, Martin Luther King and Malcolm X. And so it was really interesting to me how my parents wanted to raise a reader, but it took them a long time to understand what that meant. How are you raising readers, and what does that mean to you, and why is that important?

Ryan Holiday 37:11 It is strange. I think one of the things that gets in the way of people falling in love with books is that there's kind of a snootiness in it. There's this sense that there's literature, and then there's all these other books. It's weird that we tell high schoolers that they should read these, like, sort of artistic novels and that this is what literature is, and then they go, "Well, I didn't like The Great Gatsby," which is an incredible book, or, "I didn't like Grapes of Wrath, so I'm not a reader." Meanwhile, there's all these books about what it's like to be a teenager. There's books, there's memoirs from athletes that they... There's all these awesome things that they would actually, that would actually reach them and speak to them that could sort of inculcate that, that identity of being a reader. And so, like, with, with my, with my oldest son, who's six, like, we don't read the books that I like, that I think he would be into. We read books about Minecraft 'cause he's obsessed with video games. And, like, to me, this is, like, barely a book, but-

Jay Shetty 38:08 [laughs]

Ryan Holiday 38:08 You know, but to him, it- it's, it's a way to learn more about this thing that he's interested in, which is what reading is. And they, they've, they've done this interesting study of, of kids reading. Like, um, if you remember as a kid, you know, you'd have to read some, like, essay or short story or whatever, and this is how they would test your reading comprehension. Well, they found that if they gave kids, say, a paragraph about baseball, they would read it much better than if they gave them some weird story about, like, some girl with a cookie or something, right? And what they were finding is that when the kids knew what they were reading about or interested in it, they would- it would resonate with them more. I just don't like the idea that we exclude people from this amazing, wonderful thing that is reading. And you see this even in publishing where, like, physical books are considered higher than audiobooks and e-books. And I personally don't read audiobooks, and I don't like reading e-books. I'm a physical book person.

Jay Shetty 39:06 Same.

Ryan Holiday 39:07 But all I want is for people to read, right? Like, I want them to consume it in whatever medium they want to consume things in.

Jay Shetty 39:15 Yes.

Ryan Holiday 39:16 And so just meeting people where they are, to me, is the main way that you raise readers, and it's, it's, uh, we just get in our own way on these things. Like, I've read so many books even, uh, since I, since I've gotten older, like, about where I grew up, and I'm like, "Why didn't anyone tell me that, like, like Joan Didion is from the, the same town that I grew up in?" And nobody told me that, right? I had to read these other novels that w- that didn't resonate with me, but if I-

Jay Shetty 39:44 [laughs]

Ryan Holiday 39:44 ... this lady was from where I'm from, that would have resonated with me at such a deeper level, right?

Jay Shetty 39:48 Yeah, yeah.

Ryan Holiday 39:49 And I try to think about, what does a person want to learn? What do they have a problem with? How do, how do we find a book that solves that problem? 'Cause that's when the light bulb flips, when a book solves a problem for you or there's an ROI to it, right? That's what lights you up. And then maybe you'll go read something that's purely artistic, that doesn't have any of that, but you really gotta find where the book does something for someone.

Jay Shetty 40:13 I'm so glad you

Jay Shetty 40:14 brought that up because I think a lot of people ask me, like, "Jay, what should I read?" Like, and, and my number one question to them is, "What are you struggling with?"

Ryan Holiday 40:21 Yeah.

Jay Shetty 40:21 Like, that's the question-

Ryan Holiday 40:21 Yeah

Jay Shetty 40:21 ... I like to ask back, and I say, "I, I could recommend a lot of books, but what are you struggling with?" And I find that that's often where someone gets stumped, where that's not necessarily how they've been trained to look-

Ryan Holiday 40:31 Yeah

Jay Shetty 40:31 ... for reading. We've been trained to look for in terms of entertainment, which is great-

Ryan Holiday 40:34 Sure

Jay Shetty 40:34 ... and I have nothing against that. Or we've been trained to be like, "Oh, it's the smart thing to do" or like-

Ryan Holiday 40:40 Yeah, yeah

Jay Shetty 40:40 ... that's what, what... Like you're saying, this elitist mindset of if you're reading, then you're thoughtful, which I don't subscribe to at all.

Ryan Holiday 40:46 Yeah.

Jay Shetty 40:47 And so then you actually lose it. Like, for me, we were growing as a team. My company was growing over the last couple of years, so literally all I've read is hiring books, culture books, leadership books. That's all I've been reading-

Ryan Holiday 40:59 Yeah

Jay Shetty 40:59 ... and it has been the best investment, and it has solved so many problems, and it has solved so many challenges or mindsets I didn't have. And I think that's such... I'm s- I just want to highlight that point because I feel the same way, that if you're struggling to know what to read, look at what your challenge is, look at what your struggle is, look at what problem you're trying to solve, and you'll naturally be more inclined and immersed.

Ryan Holiday 41:22 It's important to realize that pretty much anything you're going through, someone has gone through before and written a book about.

Jay Shetty 41:29 Mm.

Ryan Holiday 41:29 Maybe they, they succeeded, and they wrote a book about their successes, or they failed, and they wrote a book about their failures, right? There are almost no new human problems. People have been doing whatever it is that we're doing for thousands of years, and to not avail yourself of that knowledge is insane.

Jay Shetty 41:49 Yeah.

Ryan Holiday 41:49 Uh, General Mattis, uh, was a four-star general in the Marines, he was Secretary of Defense, sort of this... He's, he's known as this kind of warrior monk 'cause he's not just this war fighter, but he's also this deeply thoughtful sort of student of his craft. And he, he pointed out, he points this out to, like, young soldiers. He says, like, "Hey, people have been fighting on battlefields for-" As long as humans have existed, and the earliest literature is about this, right? You know, whether we're talking about Homer or Gilgamesh. You know, the idea that you would not avail yourself of the lessons they've learned, he's like, "Is insane." You know? He's like, "The mistakes you're making cost people things, and so to make a mistake by trial and error that someone else has already gone through is reckless and irresponsible." And he, and he has this great quote I think about all the time. He says, he says, "I- if you haven't read hundreds of books about, like, what it is that you do," he said, "you're functionally illiterate." Right? Illiterate not in the sense that you can't read, but illiterate in the sense that you haven't read.

Jay Shetty 42:55 Mm.

Ryan Holiday 42:55 And it's the same thing, right? If you haven't read it, you don't know about it.

Jay Shetty 43:00 Mm.

Ryan Holiday 43:01 And the fact that you could is irrelevant. What matters is have you read about this? And, and so just realizing that whether it's parenting or starting a business or, uh, you know, being successful or creating social change, like, people have been through this a long time, and they have really thoughtful things to say about it. And to not avail yourself to that knowledge, to just go, "I'll figure it out on my own," is not only inefficient, but it's irresponsible, right? Like, you could have succeeded earlier. You could have had the impact earlier. You could have saved yourself going down this road or that road, but you didn't because you thought you were too smart. E- Epictetus says, you know, "It's impossible to learn that which you think you already know."

Jay Shetty 43:47 Mm.

Ryan Holiday 43:48 And so part of reading is also the idea of humility, the idea of like, "I don't know about this. I want to know about this. Somebody knows more about me, more about this than me." That's the mindset of a reader that you want to cultivate. And, and we, we think about this with our kids. Like, they'll ask us questions, and we'll, like, kind of know the answer, and we'll start to answer, and then we stop ourselves, and we go, "No, let's go find out about this together. Like, let's look this up." Like, there's this magical thing called Google. We can look it up, right? We can read a Wikipedia page about it. We can buy a book about it. I want to teach them the habit of, "I'm curious about this."

Jay Shetty 44:25 Mm-hmm.

Ryan Holiday 44:25 "I want to go down the rabbit hole and figure it out."

Jay Shetty 44:28 Mm.

Ryan Holiday 44:28 Just guessing or, uh, you know, half-assing it is, is not, is not the mindset that makes you successful. You want to be the person that figures stuff out-

Jay Shetty 44:41 Mm

Ryan Holiday 44:41 ... and is good at, and has the tools and the determination to figure stuff out. That's what you want your kids to have.

Jay Shetty 44:48 Yeah. And are your kids at school now?

Ryan Holiday 44:50 Yes.

Jay Shetty 44:50 Yeah, so how are you ... And they're going to a, like, a, a regular national curriculum. Like, they're learning, they're learning the curriculum that they teach in the US, right?

Ryan Holiday 44:59 Yeah, yeah.

Jay Shetty 44:59 Yeah.

Jay Shetty 45:00 So, like, with that kind of ... Like, how are you ... I guess I find that as parents, it's natural to want to save our kids from the mistakes we made-

Ryan Holiday 45:11 Yeah

Jay Shetty 45:11 ... or protect them from the wrong turns we took. I would love to hear your philosophy or your thoughts or your approach right now, especially with The Daily Dad, on how are you doing that, or are you trying to limit your projection onto them? Like, how do you deal with them as fresh humans, but then also your thoughts around the world and how school works, and how, how do you navigate the fact that you can always think you know what's right for your kids, but most of what you think is what is right for them is based on what you think was wrong for you?

Ryan Holiday 45:40 Yes. Yes. I mean, I, I heard an interview with Brian Grazer once, the movie-

Jay Shetty 45:45 Mm

Ryan Holiday 45:45 ... producer and-

Jay Shetty 45:45 Yeah. He's been on the pod

Ryan Holiday 45:46 ... and he, he's dyslexic, right? And that dyslexia shaped him and formed him into being this brilliant, creative, uh, you know, sort of producer and, uh, cultivator of talent. And so someone asked, like, "Well, would you want your kids to go through it? It was so formative in shaping you." And he was like, "Are you out of your mind?" So there is this sense that the struggles we went through, um, if we can spare our kids them, that's great, and then at the same time, we also understand that if you spare your kids all trouble and all difficulty, they become very fragile. And so it's this kind of tension between, you know, uh, I, I sort of say, like, you want your kid's life to be good but not easy, right? Like, so where you can prevent needless suffering or struggle or pain, you want to, and then at the same time, if you do everything for them, you're actually making life so much harder for them. So that's why I like this idea of like, hey, if they c- they think that they can just come to me for all answers, uh, they're not developing the ability to figure stuff out for themselves. So what I want to do is model. Like, I may already know the answer. I may already think I know the answer, but I want to figure it out with them together. That's what we want to do.

Jay Shetty 47:00 Mm.

Ryan Holiday 47:01 Um, and I, I, I sort of think about that as a general parenting philosophy.

Jay Shetty 47:04 Yeah. I like, I like what you're saying there because I think it applies in coaching. It applies in mentorship. It applies in a relationship. Like, doing things for other people often feels like love.

Ryan Holiday 47:17 Yeah.

Jay Shetty 47:18 But actually it isn't love because it debilitates them from learning how to do it, and therefore-

Ryan Holiday 47:24 Yeah

Jay Shetty 47:24 ... le- doing things with people is better than doing things for people. I.e., if you were to be like, "I don't know how far the moon is from planet Earth," and you went and checked it on your phone and then just told your kid the answer is different to saying, "Hey, let's both sit down on Google, and let's look at the moon, and then let's look at Jupiter and Saturn, and let's look at the entire, you know, solar system," and-

Ryan Holiday 47:45 Totally

Jay Shetty 47:46 ... right? That's what I'm ... Yeah.

Ryan Holiday 47:46 Totally.

Jay Shetty 47:47 Yeah.

Ryan Holiday 47:47 Yeah, you want to show them how to figure it out for themselves.

Jay Shetty 47:50 Yeah.

Ryan Holiday 47:50 You want to equip them with the tools to do it because you're not always gonna be there to do it for them.

Jay Shetty 47:57 Yeah.

Ryan Holiday 47:57 Like, they, there's, um, there's helicopter parenting. People know about that. Then there's this also, this one they talk about. It's called snowplow parenting, and snowplow parenting is going ahead of your kid and clearing all obstacles and difficulties out of their path, which again feels like a form of love. And yet it's also quite cruel because eventually you won't be there, and they will have to experience those obstacles. And if they haven't built the skills or the strength or the confidence, the sense of self that says, "I'm a person that knows how to solve problems," they're gonna be in serious trouble.

Jay Shetty 48:36 Yeah, and that's so... That must be so hard. I'm not a parent, so that must be so hard because when you see this innocent, adorable kid, and they're going through some pain or challenge and it- and you want to give them the skills of how to solve their own problems, which I do believe is prob- if we, if we had to debate it out, it's probably the most useful skill of all time-

Ryan Holiday 48:57 Yeah

Jay Shetty 48:57 ... [laughs] is how do you solve any problem?

Ryan Holiday 49:00 Well, I was thinking about this recently. There, the, there's this singer Morgan Wade, and she has this new song and, and there's a lyric in it. She says something like, "All of your dreams are a parent's fears."

Jay Shetty 49:09 Mm.

Ryan Holiday 49:09 And if you think about your own life, right, all of the things that are good in your life came from risks that you took.

Jay Shetty 49:15 Mm-hmm.

Ryan Holiday 49:15 Like, for me, it was dropping out of college. You know, um, my wife and I, you know, we got together super early. We moved in. We, we did things that in retrospect were crazy and people probably thought were bad ideas. Um, I made career decisions that were crazy. I, I did all these risks, and I wouldn't be here without the risks. And so one of the things that's hard as a parent is realizing that, like, more than anything, what you want is for your kid to be safe, right?

Jay Shetty 49:43 Mm-hmm. Mm.

Ryan Holiday 49:44 And so there's almost this c- i- inherent conflict.

Jay Shetty 49:47 Yeah.

Ryan Holiday 49:47 Right? Like, a person wants to be happy and fulfilled and do cool things, and a parent wants nothing bad to happen ever.

Jay Shetty 49:56 Mm-hmm.

Ryan Holiday 49:56 Right? And the ability to, to realize that there is a tension there, that the thing you want more than anything will ultimately smother and deprive them of the thing that they want more than anything, it's all of it. Like, when I dropped out of, out of college, you know, my parents, like, took it really badly. Like, it, it crushed them. You know, they'd worked so hard. I think so much, uh, wrongly of their identity was tied up in my sister and I's success, and they didn't want to be the parents that had a kid that dropped out of college 'cause that's weird at, you know, a party or something-

Jay Shetty 50:29 Mm-hmm

Ryan Holiday 50:29 ... to talk about. And maybe it was a bad decision. Maybe, uh, it ended up working out, but maybe it was a bad decision and, and so I, I did it, but then immediately after, a bunch of really bad stuff happened. Like, it ended up being way harder than I thought for a bunch of reasons, and what I really needed then was parents, right? And so my parents, worried that I was doing this thing that was dangerous, didn't support me doing it.

Jay Shetty 50:54 Mm.

Ryan Holiday 50:54 And then they weren't there-

Jay Shetty 50:56 Mm

Ryan Holiday 50:56 ... when I needed their actual support, right?

Jay Shetty 50:58 Mm.

Ryan Holiday 50:59 And so it's, it's understanding that, like, what you, what you need to do is not, like, be right about stuff or get your way, but to sort of show them that you're there for them whatever happens.

Jay Shetty 51:13 Mm.

Ryan Holiday 51:13 And that maybe that's a way that you cut through this tension of, like, well, you don't want them to do anything that's dangerous, but if your fear of that pushes them away-

Jay Shetty 51:23 Yeah

Ryan Holiday 51:23 ... then when they are in danger, they're not gonna come to you, right?

Jay Shetty 51:26 Yeah.

Ryan Holiday 51:26 And that's what you should fear more than anything.

Jay Shetty 51:28 Yeah.

Ryan Holiday 51:28 I, um, I interviewed this guy. His name was Dave Carey. He was Captain Dave Carey.

Jay Shetty 51:32 Yeah.

Ryan Holiday 51:32 He was a POW in Vietnam, and, um, he said something to me that I think about now all the time as a parent. He said, "The goal of every conversation as a parent is to get to have the next conversation."

Jay Shetty 51:46 Mm.

Ryan Holiday 51:46 Right? And I think about that in life, in business.

Jay Shetty 51:48 Mm.

Ryan Holiday 51:48 It, it should, it's almost like every decision you make. It's, it's am I closing doors here? Am I burning bridges behind me? Am I shutting things down, or am I keeping things open, right?

Jay Shetty 51:59 Mm-hmm.

Ryan Holiday 51:59 Life is about options. How many options do you have? And just, just realizing, like, hey, this conflict, this disagreement, this tension, you know, the main thing that you're gonna want with your kids in the future is that relationship.

Jay Shetty 52:12 Mm-hmm.

Ryan Holiday 52:13 And nothing is more important than that.

Jay Shetty 52:14 Mm-hmm.

Ryan Holiday 52:15 And so I think about that all the time.

Jay Shetty 52:17 Yeah, no, I mean, reflecting on what you're saying, I feel like that was something that was so, like, my parents when, when I did decide to become a monk, it was like that was uncomfortable for them.

Ryan Holiday 52:30 Of course.

Jay Shetty 52:30 I never went to my graduation ceremony. I graduated, but never went to have the picture taken, and that was a big thing-

Ryan Holiday 52:36 Yeah

Jay Shetty 52:36 ... because everyone's house we'd go to, they've had pictures of their kids, you know, with their little scroll and the hat and all the rest of it.

Ryan Holiday 52:43 Yeah.

Jay Shetty 52:43 And but it was the same. It was they didn't support it, and they didn't block me.

Ryan Holiday 52:50 Yeah.

Jay Shetty 52:50 And then when I failed at it or when it all ended, they were there to catch me.

Ryan Holiday 52:55 Yeah.

Jay Shetty 52:55 I moved back in with them.

Ryan Holiday 52:56 Yeah.

Jay Shetty 52:56 And those two statements you put, two of the chapters in the book are always be a fan and love unconditionally, and I was reflecting on those. And I was like, I think my parents have always loved unconditionally. Like, they've been able to have this relationship with me where, yeah, I, I, I would totally give them credit for that, where they never let me feel like they weren't there for me regardless of even if my choices were totally against theirs, and I respect them a lot for that because it, it, I've made it hard [laughs] many times.

Ryan Holiday 53:31 No, no, it's beautiful, and kids do make it hard, right?

Jay Shetty 53:33 Yeah.

Ryan Holiday 53:33 And it's, it's gonna be a challenge. There's this, there's a story about Jim Valvano, the basketball coach. He realizes at, like, 10 or 12 or 13 or whatever that he wants to be a basketball coach, and he tells his dad. He says, "I'm gonna, I want to be a college basketball coach." And the dad goes, "Okay." And then the next day, his dad calls him in, into his bedroom, and, uh, he says, you know, "What, what's going on?" And the dad says, "See that suitcase?" And the son says, "Yeah," and he says, "It's packed." And, and he says, "Why?" And he says, "It's packed for when you coach in the Final Four." You know, and this idea of, like, your kid has this dream, and you don't judge it. You don't tell him that it's unrealistic. You don't tell him it's crazy. You don't let him know how hard it's gonna be. You also don't take it over and say, "Well, here's what you're gonna need to do." You just go- I'm rooting for you is, is a beautiful thing. And too much of the love that parents have or the support is conditional-

Jay Shetty 54:33 Mm-hmm

Ryan Holiday 54:33 ... on whether it's going well, whether it's socially acceptable, whether it's understandable or not. You know, I think a lot of parents want their kids to be doctors and lawyers because they know what doctors and lawyers are.

Jay Shetty 54:47 Mm-hmm.

Ryan Holiday 54:47 Right? And social media manager sounds made up, right? [laughs] Even if one pays better than the other-

Jay Shetty 54:53 Yeah

Ryan Holiday 54:53 ... even if one is what lights the kid up and the- they hate the other thing more than... They just want it, it... This, this desire to understand, uh, gets in the way of just support, uh, which is really what it comes down to, the sense that, "Hey, these people, these people believe in me."

Jay Shetty 55:12 Yeah.

Ryan Holiday 55:12 Uh, "These people really believe in me."

Jay Shetty 55:14 Yeah, and I feel like with my parents, I, I probably had more of a neutral relationship where I wouldn't say they were believing in me or rooting for me-

Ryan Holiday 55:21 Sure

Jay Shetty 55:21 ... but they weren't putting it down.

Ryan Holiday 55:23 Yes.

Jay Shetty 55:24 And so it was more a bit like sh-

Ryan Holiday 55:25 Let's start there.

Jay Shetty 55:26 Yeah, yeah. [laughs]

Ryan Holiday 55:26 Yeah, yeah.

Jay Shetty 55:27 You make your decisions and-

Ryan Holiday 55:28 Yeah

Jay Shetty 55:28 ... whatever. Like, it's not like we believe in you and it's gonna be great, and we- it's not like we're trying to hold you back. I think a lot of us today, though... And, and I think the difference for me was I had such conviction, and I always have when I've made my choices, and it sounds like you did, too, obviously in the way you described it, where I didn't really care what anyone thought-

Ryan Holiday 55:45 Yeah

Jay Shetty 55:45 ... and I still kind of am that way. Like, I'm like, "Whatever, I'm gonna do what I want anyway." And I think a lot of people, like, want their parents to, like, root for them, and I hear this a lot where they're like, people say to me, like, "Jay, like, my parents don't believe in me, and, like, no one's, like, encouraging me and no one's supporting me. What do I do in that situation?" And so it's interesting because we also have that inbuilt desire for our parents to root for us. But as in your case and as in many others, and even in mine in a different way, your parents aren't gonna be your biggest cheerleaders all the time, and most of us didn't have that experience. So while you're trying to be a dad who is unconditional and a fan, you didn't get that, and majority of people in the world didn't get that. So how-

Ryan Holiday 56:24 No one can screw you up.

Jay Shetty 56:25 Yeah.

Ryan Holiday 56:25 I remember I was, I was in business with someone, and, uh, he was doing something kind of crazy. I forget what it was. But someone brought up, I was like, "Why is he like this?" And he goes, "If you just translate everything he's saying into 'Daddy, Daddy, look at me,' it all makes sense."

Jay Shetty 56:40 Mm-hmm.

Ryan Holiday 56:40 And you realize this person didn't get kind of approval or attention from their parents, and, and it drove them to be successful in business, but it also made them a liability in business because they weren't dealing with the situation at hand. They were dealing with this sort of unfulfilled, unmet desire to get attention, to be recognized, and that's a really, that's a really dangerous thing, you know?

Jay Shetty 57:06 Mm-hmm.

Ryan Holiday 57:07 And I think at the core of it, a, like a good number of men are just motivated by wanting their dad to be proud of them.

Jay Shetty 57:13 Mm-hmm.

Ryan Holiday 57:13 And the sooner you realize that if your dad wasn't proud of you at the beginning, no amount of success is gonna make you feel that later, right?

Jay Shetty 57:23 Yeah.

Ryan Holiday 57:23 I do think there, there's this great quote from Marcus Aurelius that, that is a really important piece of parenting advice that I try to think about. He says, you know, "Things are not asking to be judged by you." And he says, "Remember you always have the power of having no opinion." So being a fan, being a supporter, being a cheerleader, that's, that's where you want to get as a parent. But what if you just started by not having an opinion?

Jay Shetty 57:47 Mm-hmm.

Ryan Holiday 57:48 Like, your kid is your kid, and they're gonna do what they want to do, and they're gonna be who they are. The fewer opinions you have about that, the better your relationship is gonna be.

Jay Shetty 58:00 Absolutely.

Ryan Holiday 58:01 You think back with your relationship with your parents, and you think about the arguments that you had, the things you fought about, and how, in retrospect, how small those things seem and how little they mattered, uh, because what matters now is that there is the relationship, right?

Jay Shetty 58:17 Yeah.

Ryan Holiday 58:17 What matters is that there's still the affection and the feeling and that you spend time together, and yet there were moments where it seemed like they were willing to trade that to enforce some arbitrary rule or some cultural norm or s- you know, force you into some box that they had for you. And, and the fewer opinions you have, the better-

Jay Shetty 58:39 Yeah

Ryan Holiday 58:39 ... I think as a-

Jay Shetty 58:40 Yeah

Ryan Holiday 58:40 ... as a parent. Like, your kid likes this video game. The fact that you think video games are dumb is an opinion you don't need to have.

Jay Shetty 58:48 Yeah. Keep it to yourself.

Ryan Holiday 58:49 Yeah. [laughs]

Jay Shetty 58:49 Yeah.

Jay Shetty 58:50 And how do you deal with it on the other side? Like, I find that I'm sure a lot of people listening, they're like, "I wish my parents had that mindset," right?

Ryan Holiday 58:58 Yeah.

Jay Shetty 58:58 Because they didn't. But then how do you still live a meaningful, fulfilling life because so much of who we are is wrapped up in this entire relationship? And you find, as you said, we are like, "I'm gonna do my own thing because I want to control my life," but we're still controlled by the expectation of being successful because our parents want us to be successful, so we're still trying to prove them wrong or right. And so how do you kind of... What, what do you do in that scenario where someone's lived a life and they're like, "Well, I'm kind of like you, Ryan, where my parents weren't my number one fan. I didn't have unconditional love. They don't support me, and I still find myself trying to impress them all the time"?

Ryan Holiday 59:38 Yeah. Yeah. It's, it's, it's realizing that if you didn't get it, you're never gonna get it.

Jay Shetty 59:43 [laughs]

Ryan Holiday 59:44 And, and, and, and to, to try to, to try to continue to get a thing that you're never gonna get is a fool's errand, right? And that you have to figure out why you want to do what you want to do and what, what's important to you, right? And that... Have you ever done any inner child work?

Jay Shetty 1:00:03 Yeah.

Ryan Holiday 1:00:03 Yeah. You realize, oh, hey, like, my parents weren't what I needed to be, uh, to this 14-year-old, but I need to be what I- what that 14-year-old needed, or I'm gonna go through the world as a 14-year-old.

Jay Shetty 1:00:17 Mm-hmm.

Ryan Holiday 1:00:18 And it's not appropriate for a 14-year-old to be in this meeting or in this conversation or to be, you know, operating at this level. You know, you have to re- s- sort of re-parent that inner child, or it's gonna pop out at totally inappropriate times and places. And I think one of the beautiful things about having kids is it does give you a sense of- ... who you were, right? You, you don't really remember what it's like to be four, and then you have a four-year-old and you go, "Oh, this is what I needed as a four-year-old."

Jay Shetty 1:00:48 Yeah.

Ryan Holiday 1:00:49 And so I can't go back in time and give that to, to, to my four-year-old self, but I can do a better job for this four-year-old. We, we dropped my four-year-old off at, at camp yesterday, and he really didn't wanna go. He was really struggling. He was really upset, and he was sort of having this anxiety attack, and he was struggling, and he was crying. And, um, and, and so ultimately after like 30 minutes, this had dragged on, and 30 minutes, 45 minutes is going, and he's getting more and more upset. And then we, m- without even talking about it, we just decided he didn't need to go. And a- as, as my wife got back in the car and we're driving him back to our house and we're gonna, you know, just have a fun day or whatever, uh, all I said was, "I think we both know that our parents would've handled this differently."

Jay Shetty 1:01:34 Mm.

Ryan Holiday 1:01:35 And, you know, they would've forced it, right? And, and the idea that, hey, it's an opportunity to do things differently-

Jay Shetty 1:01:44 Mm

Ryan Holiday 1:01:44 ... to stop certain cycles, right, to turn over a new leaves, to just, to just do it a better way.

Jay Shetty 1:01:51 Yeah.

Ryan Holiday 1:01:51 And that that, that is not only your obligation, but it's also healing for yourself.

Jay Shetty 1:01:56 Mm.

Ryan Holiday 1:01:57 To go, "Oh, this is what I needed then." And you can't go back in time, but you can write a

Ryan Holiday 1:02:04 better future.

Jay Shetty 1:02:05 What gave you the intuition in that moment for you specifically to know whether to push them to go to camp or were you were like, "No, actually..." Because I, I remember as a kid, I used to get a lot of those anxiety attacks as, as a young kid. And I remember even when I was going to high sc- I had to take exams to get into certain high schools that my parents wanted me to go to, and I remember, like, just being so stressed at that time with, like, going to these entrance examinations. You don't know anyone there, and you're sitting in this hall, and you're doing exams at 11 years old, 10 years old to get into this 11-plus school and whatever. And I remember feeling that when there were times when my parents were like, "It's okay," and there were times-

Ryan Holiday 1:02:44 Yeah

Jay Shetty 1:02:44 ... when I was pushed through. And-

Ryan Holiday 1:02:45 Sure

Jay Shetty 1:02:45 ... obviously, I o- I only personally remember the ones where I was pushed through that worked out.

Ryan Holiday 1:02:50 Yeah.

Jay Shetty 1:02:50 Uh, but naturally, there are lots of kids in the world who only remember the times when their parents should have let them pull out and they didn't.

Ryan Holiday 1:02:56 Yeah.

Jay Shetty 1:02:56 So how did you, at least for yourself, reconcile that in a moment like that? Because I'm sure sometimes you're like, "No, pushing through is good," and, you know, you're not-

Ryan Holiday 1:03:04 You know, the, the Stoics say one of the most dangerous things we can do is extrapolate, right? 'Cause it takes us out of the moment we're in, and then we're thinking, "Well, what if it happens again?"

Jay Shetty 1:03:12 Mm.

Ryan Holiday 1:03:12 "And what if it happens again? And what if it happens again?" And then all of a sudden you're living in this future where if you let this thing happen over and over and over again, your kid is utterly incapable of doing anything for themselves. And just going, "Hey, what does one day of camp actually matter," right? What is, uh, what, what is w- what is actually at stake here?

Jay Shetty 1:03:31 Yeah.

Ryan Holiday 1:03:31 And you realize that almost nothing is at stake.

Jay Shetty 1:03:33 [laughs]

Ryan Holiday 1:03:34 Right?

Jay Shetty 1:03:34 Great answer. Yeah, I like that.

Ryan Holiday 1:03:35 You know? Like, your kid's throwing a temper tantrum, and you go, "This is not an appropriate way to act. I don't wanna raise a kid that throws temper tantrums. I don't wanna raise a kid that can't ha-" And, and you realize that you're not even thinking about your kid anymore. You're thinking about you.

Jay Shetty 1:03:47 Mm-hmm.

Ryan Holiday 1:03:48 And, and what you should be thinking about is, "Oh, wait, we forgot to have lunch," right? [laughs] Or, "Oh, wait, they're tired. Oh, wait, they're coming down with something." And you realize, oh, this is an individual instance. It is not a reflection of the, their trajectory as a human being. And, and being able to do that to anyone in life is really pow- It's an incredible gift to be able to look at the moment you're in as not much more than a moment that you are in is, is an incredible thing to do for yourself and them. I, I struggle with that even as a writer. Obviously, discipline is important. Commitment is important. S- routine is important. But then you have kids, and you're in this world of unavoidable reality, and you have to go, "I can't do what I wanted to do today." That doesn't mean the wheels are gonna come off and everything is gonna collapse. You have to be, "Okay," you know?

Jay Shetty 1:04:41 Mm-hmm.

Ryan Holiday 1:04:41 And, and just that sort of acceptance-

Jay Shetty 1:04:43 Yeah

Ryan Holiday 1:04:43 ... a- and to go, "This is a singular instance, no more, no less. I'm just gonna do what we need to do." And, and, and when I think about things that have gone really haywire with our kids or in my life, it's because I wasn't in that moment. I was in whatever I was extrapolating that moment to mean if it happened over and over and over again.

Jay Shetty 1:05:05 It's a brilliant answer. I love that. That, that resonates so strongly with me because I think we... You're so right. We just take one moment to be so predictive-

Ryan Holiday 1:05:13 Yeah

Jay Shetty 1:05:14 ... of their [laughs] entire future. Like, "If I let him quit camp today, then he's gonna quit this," and-

Ryan Holiday 1:05:19 If I let people-

Jay Shetty 1:05:20 Yeah

Ryan Holiday 1:05:20 ... talk to me this way-

Jay Shetty 1:05:21 Yeah

Ryan Holiday 1:05:21 ... then I'm just gonna be this person that gets pushed around.

Jay Shetty 1:05:24 Yeah.

Ryan Holiday 1:05:24 And you're like, this is a one poorly written email. This-

Jay Shetty 1:05:28 Yeah, yeah, yeah

Ryan Holiday 1:05:28 ... it, it doesn't mean anything more than that.

Jay Shetty 1:05:30 Yeah.

Ryan Holiday 1:05:30 And, and that you can just let, like, let it go.

Jay Shetty 1:05:33 Yeah.

Ryan Holiday 1:05:33 Now, obviously, if you're doing that all the time for everything, you can get in trouble too, but, but just going, "Yeah, this is, this is not that big a deal."

Jay Shetty 1:05:40 Mm-hmm.

Ryan Holiday 1:05:40 I, I... That's a question I try to ask myself all the time: Does this actually matter, or do I just think that it matters? Is my, I- is, is what other people think, you know, informing whether I think this matters or not? Do I actually care about this? And then that just turns down the volume-

Jay Shetty 1:05:57 Yeah

Ryan Holiday 1:05:57 ... which is really what you need the most. You just need to turn down the volume.

Jay Shetty 1:06:01 Yeah. That's my favorite one, disconnecting

Jay Shetty 1:06:03 from... If I ever get worked up about something or riled up about something, it's because I've let the opinions of others become-

Ryan Holiday 1:06:09 Yeah

Jay Shetty 1:06:09 ... a lens through which I'm seeing the significance of something.

Ryan Holiday 1:06:13 Well, one of the really screwed up parts about having a kid, and I was just talking to someone who has a, like, a six-week-old. So you get your kid, take them home from the hospital, and then you have to take them to their first pediatrician visit, and then you do this a bunch of times in their first year. And you take them to the pediatrician, and the first thing they do is they weigh them, and they measure them, right? And then they give you these numbers. They go, "Your kid is 80th percentile in height and 40th percentile in weight," and they, a- and their head size is the 16th percenti- They... The first thing that happens when you have a kid- Is they tell you mathematically where your kid measures up against other kids, and it's like this the whole way.

Jay Shetty 1:06:52 Yeah.

Ryan Holiday 1:06:52 They should be walking by this age, they should be, uh, reading by this age, riding a bike by this age. And so you have this data, like if, if you didn't know how other people were doing, you wouldn't care. But because they told you, then you, you wanna win that game, and the game is the size of your kid's head-

Jay Shetty 1:07:12 [laughs]

Ryan Holiday 1:07:12 ... which you have no ability to influence whatsoever. I mean, yeah, you wanna know, hey, your kid is dangerously un- you know, uh, underweight and maybe malnourished, but it's usually it's like, oh, they're 87% in weight and not 94? You know? Like, and all of a sudden you're thinking as a kid, you're thinking back to when you were a kid and you're like, "Well, I wanna get an A-"

Jay Shetty 1:07:33 Yeah

Ryan Holiday 1:07:33 ... "and so anything above 90," you know? And, and so it's, it starts at the very beginning, this sort of comparison game, and the less, if you knew less, you would be much more relaxed and much more kind to them and yourself. And it's important to remember that you're not raising an average kid.

Jay Shetty 1:07:54 Mm.

Ryan Holiday 1:07:54 You're raising your kid. You're not raising, uh, a kid on a spectrum. You're raising this person that you were gettin- you were given that has a unique set of DNA and a unique set of circumstances that you have some control over and a lot of things you don't have control over. And I think the more you can kind of tune out what other people are doing... Like, my wife and I were, like, concerned that this kid we know who was born like the same day as my son, like he's riding a bike, and m- my son can't ride a bike, and we're like, "Are we screwing up? Are we holding him back? Are we bad as parents?" And then we were talking to them, and they were concerned that their son couldn't swim, and ours can swim like a fish, and you just realize, oh yeah, it's all, it probably has nothing to do with anyone. It's just one of them is naturally disposed to swimming, and the other has some brain that makes biking easy. And if we didn't know that, that some kids were doing this and some kids were doing this, we would just be like-

Jay Shetty 1:08:54 Yeah

Ryan Holiday 1:08:54 ... "Well, they'll learn it eventually," right? And so I think, of course you do, it is important to benchmark and know generally when stuff's supposed to happen, but just so much of this information, it's only there to make you feel inferior or insecure or alarmed, and that's not gonna make you a better parent.

Jay Shetty 1:09:13 Mm-mm. Mm. Absolutely. I mean, I'm so glad you went there because I feel like that's the exact thing that's on everyone's mind, and I think it applies to everything from having kids, to getting married, to being engaged, to moving in, to dating, to friends, to how much money you should have made by what age. Like, it, it just goes across the board.

Jay Shetty 1:09:36 I wonder, I've spoken to a lot of people on the podcast about mom guilt-

Ryan Holiday 1:09:40 Yeah

Jay Shetty 1:09:40 ... to mothers. Dad guilt's a thing too, and you know, as someone like you who you said you've had a lot of successes before you became a dad, but at the same time, you're an ambitious, driven individual. I'm sure you know other dads who became dads before and after they've had success. Let's paint the scenario, which I think is a common scenario. Someone's trying to put food on the table. They're trying to take care of their family. They don't get to be there for bedtime every night. They don't get to go to the football game on the weekend. Like, they can't show up at all these places because of genuine reasons. How does that person be a present, loving dad, or what does it look like for that scenario?

Ryan Holiday 1:10:20 I do find moms are way harder on themselves than dads.

Jay Shetty 1:10:23 Yeah.

Ryan Holiday 1:10:23 And, and part of that is 'cause dads, I think historically, have been judged on a much, uh, more generous or slide-

Jay Shetty 1:10:32 Abs-

Ryan Holiday 1:10:32 ... sliding scale, right?

Jay Shetty 1:10:33 For sure.

Ryan Holiday 1:10:34 And so the fact that there is some dad guilt is, is in, in a sense a sign of progress, right? That like, "Oh, hey, this is something that I am, uh, expected to be good at, to take seriously, and that if I'm not good at it, someone's not just gonna handle it for me," right? I think the reason moms feel guilty is they, they're like, "There's no safety net." Like, "I'm the final line of defense," right? And so I do feel dad guilt sometimes, and, and I, I see that as a sign that, like, I'm, I'm caring about it, right? 'Cause you know who-- Like, it's like, um, it would be wonderful if all parents were concerned that they weren't doing a good enough job, but the, the fact is there's a lot of parents that aren't thinking about it at all. They're either not thinking about it 'cause they're so convinced they're perfect, and they're not, or they just don't care that much. So it's good that you're, it's good that you're insecure, that you're questioning yourself, and then just realize that other than that, other than the indicator of, of prioritization, it's not actually helping you be a better parent, right?

Jay Shetty 1:11:37 Mm-hmm.

Ryan Holiday 1:11:37 Whipping yourself, like I, I joke like your kids are gonna hit you enough.

Jay Shetty 1:11:40 [laughs]

Ryan Holiday 1:11:41 Like, you don't need to whip yourself on top of it, right?

Jay Shetty 1:11:43 Yeah.

Ryan Holiday 1:11:44 Um, be kind to yourself, and that, that's a, a great line from Seneca. He says the, the, "The sign that f- that philosophy is working in your life is that you're becoming a better friend to yourself."

Jay Shetty 1:11:55 Yeah.

Ryan Holiday 1:11:55 And, and so-

Jay Shetty 1:11:57 Love it

Ryan Holiday 1:11:57 ... you should be a, a good friend and parent to yourself. But there is this sense, I think, with dads that, like, your job is to provide, and you go, "I'm doing this all for my family." If you never see your family, are you really doing it for them, you know? Um, or, or are you using your kids as an excuse to do this thing that you want to do, right? I'm not saying that providing isn't important and that you shouldn't try to be successful at work. I just, I just think, like, hey, uh, the thing your, your kids want more than anything is you, right? That's what-- Your family wants you, and so if you go, "Oh, I'm doing this for you-" Did they want a new mountain bike or did they want to see their dad during daylight hours, right?

Jay Shetty 1:12:46 Both. Both.

Ryan Holiday 1:12:47 Yeah. [laughs]

Jay Shetty 1:12:47 [laughs] Yeah.

Ryan Holiday 1:12:48 Um, but, but when they think back to their childhood, they're not gonna go, "Oh, I did have a lot of cool stuff."

Jay Shetty 1:12:54 Mm-hmm.

Ryan Holiday 1:12:54 Right?

Jay Shetty 1:12:55 Mm-hmm.

Ryan Holiday 1:12:55 Like, "I never saw my parents, but I had a lot of cool stuff," right? "Uh, it worked out for me." They want you.

Jay Shetty 1:13:01 Mm-hmm.

Ryan Holiday 1:13:01 And, and so how do you, how do you find that balance? I mean, what... Th- when we talk about work-life balance, what we're talk- the reason that's so hard is we're talking about trade-offs.

Jay Shetty 1:13:12 Mm.

Ryan Holiday 1:13:12 Like, that you can't have it all, and, um, you're gonna have to say no to some things. One of the things that, that having kids changed for me is that it made it easier for me to say no, because it illustrated the opportunity cost much more vividly.

Jay Shetty 1:13:28 Mm.

Ryan Holiday 1:13:29 Right?

Jay Shetty 1:13:29 Mm.

Ryan Holiday 1:13:29 Like, if I didn't have kids, if it was just me and my wife or just me, you know, I could always squeeze more stuff in, and I'd, I'd, I'd, I couldn't calculate or necessarily feel what it was costing me. But when you've promised your time to this little person who wants to wrestle or go in the swimming pool or play Legos, and then you're not able to be home because you agreed to some dumb conference call or you let someone pick your brain, you feel that more.

Jay Shetty 1:14:02 Yeah.

Ryan Holiday 1:14:03 Right? You feel that more. The opportunity costs were always there.

Jay Shetty 1:14:06 Mm.

Ryan Holiday 1:14:06 You just didn't feel it, because it wasn't personified in a, in a heartbroken three-year-old.

Jay Shetty 1:14:13 Mm.

Ryan Holiday 1:14:14 So it's helpful. It, it can, it can be really, really powerful. I have, I have this sign on the, on the wall in my office and it just says "No".

Jay Shetty 1:14:21 [laughs]

Ryan Holiday 1:14:21 And it's, it's between two pictures of my kids, and it's a reminder that when I'm saying yes, what I'm saying no to is-

Jay Shetty 1:14:29 To them

Ryan Holiday 1:14:29 ... A and B. And when I'm saying, uh, no, I'm saying yes to A and B. And realizing that, that your fear of being rude or hurting someone's feelings, well, you better get comfortable with that, 'cause you're gonna hurt- you're gonna... You're being rude to someone. You're letting somebody down. You're hurting someone's feelings. And should it be this stranger or should it be this person that you promised, you know, you were gonna be there for, or that you said is the most important thing in the world to you? Like, the calendar doesn't lie. You s- w- you say family's the, the most important thing to you.

Jay Shetty 1:15:09 Mm.

Ryan Holiday 1:15:09 But what does your calendar show?

Jay Shetty 1:15:11 Mm-hmm. I, I, I couldn't, couldn't agree more. I always, I always say the way you spend your money, the way you spend, spend your time, and the way you spend your energy shows your values and priorities far more than what you say or think.

Ryan Holiday 1:15:23 Yeah.

Jay Shetty 1:15:23 Because your ba- like, what you spend money on is showing what you care about. What you do to make money shows what you care about. But

Jay Shetty 1:15:30 what is your biggest fear or worst quality in you that you are so scared of projecting onto your kids?

Ryan Holiday 1:15:38 Ooh.

Jay Shetty 1:15:38 Are you aware of that? Are you-

Ryan Holiday 1:15:40 Yeah. I mean, I think you have to be. I think, I think... I've never been glad that I lost my temper. It's never made anything better. And so, you know, kids are frustrating. Uh, it's overwhelming. Um, [laughs] the other, the other day my s- my son was, uh, in the car, and he started yelling and, and he's really upset. So I look back and I'm like, "What's happening?" And my, my other son goes, "You know, I think Jones is just really overstimulated right now."

Jay Shetty 1:16:08 [laughs]

Ryan Holiday 1:16:09 And I was like, "Wow, that's, like, amazing."

Jay Shetty 1:16:11 Yeah.

Ryan Holiday 1:16:11 You know? Like, I was like, "I wish I..." Like, first off, I was proud, 'cause he obviously picked that up from us. But I was like, "I wish I could have that kind of awareness." 'Cause all I was thinking about is like, "What is this noise?" Right? And he's thinking, "Well, why is that person making that noise?" Um, and, and so, yeah, the things that you get upset with your kids about, uh, when you lose your temper, like, it's, it's never stuff that you're like, "That was..." Okay, 1% of the time it's like they ran away from you in a parking lot and you're so scared that something could've happened, uh, and, and you kind of need to get that across. But most of the time it's, it's nothing that matters.

Jay Shetty 1:16:49 Mm.

Ryan Holiday 1:16:49 And yet you are telling them that it matters, and you are telling them that they don't matter in a way that you would never want, right? And so I think, I think for me it's, it's about temper. Um, and, and, you know, how do you tame that? How do you keep it from exploding onto the people that you love? To- that's, that's the struggle.

Jay Shetty 1:17:09 Mm. What have, what have you discovered in that path?

Ryan Holiday 1:17:12 Uh, I-

Jay Shetty 1:17:14 'Cause it's hard, like you said.

Ryan Holiday 1:17:15 Yeah.

Jay Shetty 1:17:15 It's hard.

Ryan Holiday 1:17:15 It's really hard.

Jay Shetty 1:17:16 Yeah.

Ryan Holiday 1:17:16 It's really hard. My wife and I try to get good at going like, "You're having trouble handling this right now. Why don't you step outside? Why don't you go for a walk?" Like, or, "Why don't you just let this go?" You know what I mean? Like, why... Is it act- does it actually matter that pajamas get on by a certain time?

Jay Shetty 1:17:34 Mm.

Ryan Holiday 1:17:34 Like, why are you forcing this thing? And I think oftentimes the frustration comes from when things are, are being forced.

Jay Shetty 1:17:41 Mm.

Ryan Holiday 1:17:42 And so stepping back is, is usually the best way to do it. And then I also think like, look, people lose their temper. It's a fact of life. My parents lost their temper at me quite a bit. I don't ever remember them apologizing for it, right? Which is something I try to do a lot. I try to go, "Hey, it's stressful for me at the airport. I'm trying to make sure that we all get to the place that we need to get by a certain time so we can go on the vacation that, by the way, you want to go to more than me," right? "But I was just, I was stressed earlier. Like, I wasn't in control of myself earlier, and I'm not proud of that. I don't like that, and that wasn't good."

Jay Shetty 1:18:23 Mm-hmm.

Ryan Holiday 1:18:23 "But I'm owning it now."

Jay Shetty 1:18:25 Mm-hmm.

Ryan Holiday 1:18:25 "And it didn't say anything about you."

Jay Shetty 1:18:28 Yeah.

Ryan Holiday 1:18:28 Right? And so the ability to, if you can't in the moment go, "Hey, I'm overstimulated or I'm stressed," can you do it later at least? If you can do it later, it's not as good, but it's still an improvement. And then can you take responsibility for your emotions, as opposed to dumping those emotions on someone else and then making them filter, uh, you know, sort through them in therapy 20 years later?

Jay Shetty 1:18:49 Ryan, thank you so much for coming back on the show, man.

Ryan Holiday 1:18:51 Oh, this is a pleasure.

Jay Shetty 1:18:51 Today's been... It's so great. It's so great. I feel like what I wanted to do today was talk about parenting, but also being a kid of parents who didn't read The Daily Dad and what that feels like as an experience because you're trying to be a parent without having had parenting training. And

Jay Shetty 1:19:11 one thing you said that is gonna stay with me for a long time was, "If you don't re-parent your 14-year-old self, you're still a 14-year-old."

Ryan Holiday 1:19:19 Yeah.

Jay Shetty 1:19:19 And I think a lot of us can resonate with that statement very deeply, that there's an age that we feel we lived our toughest, worst year, and no one took care of that-

Ryan Holiday 1:19:33 Yeah

Jay Shetty 1:19:33 ... child or that teenager or whatever age it was, and that's something we all need to recommit to.

Ryan Holiday 1:19:39 Yeah. I mean, one of the struggles of, of being a parent is you're trying to give stuff that you didn't necessarily get, right? And it's even harder for people who didn't have, you know, a dad or a mom, or, you know, their dad or mom was an alcoholic. Or you're trying to give things that you didn't get, but that's, that's the obligation is to try to do a little bit better, right?

Jay Shetty 1:19:59 Mm-hmm.

Ryan Holiday 1:19:59 To try to give them the things that you felt that you needed or wanted. That's the goal, right?

Jay Shetty 1:20:05 Mm-hmm.

Ryan Holiday 1:20:05 Um, but yeah, you opened this, you said, you know, you're, you're, you're trying to heal. I, I do... If you leave those things unexplored or unaddressed, you're just passing them along, and that's... There has to be some point where you go, "This stops with me."

Jay Shetty 1:20:20 Mm-hmm.

Ryan Holiday 1:20:20 Right? Like, this... There's a beautiful Seneca line. He, he talks about how we can't choose our parents, but we can choose whose children we would like to be.

Jay Shetty 1:20:29 Mm-hmm.

Ryan Holiday 1:20:30 And the idea that, like, biology doesn't have to be destiny, that it doesn't have to keep going the direction that it always went, that you can do it differently, that you can decide, "Hey, no, my, my parenting heroes are these people, that I can borrow from these parents that had different tools than my parents, that had more patience or wisdom or insight or empathy than my parents, and that, that I can, I can give that to my kids," that's, that's a beautiful thing.

Jay Shetty 1:21:00 The book is called The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids by Ryan Holiday. If you don't already follow Ryan on Instagram, on YouTube, across social media, his podcast, of course we named all the books earlier, uh, please go and follow him across all platforms. Ryan, anything else you wanna share with the community over here?

Ryan Holiday 1:21:21 No. Thanks for having me.

Jay Shetty 1:21:22 Yeah. Thanks for coming back, man. We look forward to it every time, so thank you. If you loved this episode, you'll love my interview with Dr. Gabor Maté on understanding your trauma and how to heal emotional wounds to start moving on from the past.

Speaker 1:21:37 Everything in nature grows only where it's vulnerable. So a, a tree doesn't grow where it's hard and thick, does it? It grows where it's soft and green and vulnerable