Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough

2024/9/16

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If you don't have time to do the thing that only you can do, what kind of life is that? He's the host of The Daily Stoic. His books have sold more than 10 million copies. Ryan Holiday, ladies and gentlemen. 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.

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Hey everyone, welcome back to On Purpose, the number one health and wellness podcast in the world. Thanks to each and every one of you that come back every week to become happier, healthier, and more healed. Today's guest is probably our record holder of most times on the podcast, which makes me very happy. I was just saying to him offline that

The doors of On Purpose will always be open to him because when I first kicked off my interviewer journey, I had a show at HuffPost called Follow the Reader. It was on HuffPost Live. I would be on Facebook Live every single day interviewing authors.

I was just starting out, probably had like, I don't know, like 100,000 people who are connected to my work. And he would always come on. And I think I interviewed him twice there. I then interviewed him at NASDAQ when I had a NASDAQ Reads show. Then he came on my podcast when it kicked off. I'm talking about the one and only Ryan Holiday, one of the world's best-selling living philosophers. Ryan's books include The Obstacle of Life,

is the way, ego is the enemy, the daily stoic, discipline is destiny, and the number one New York Times bestseller, stillness is the key, and appear in more than 40 languages and sold more than 6 million copies. Ryan's bookstore, The Painted Porch, which I've not been able to visit yet, but I really want to,

is one of the most incredible projects he's working on. And his new book is The Daily Dad, 365 Meditations on Parenting, Love, and Raising Great Kids. I even matched my t-shirt. That's how much I love this book. Go and grab a copy. If you love Ryan's work, you're going to love this book. And as someone who is preparing and thinking about being a dad at some point in his life, I'm really excited for this conversation. Welcome back to On Purpose, Ryan Holiday. Ryan, thanks for being here.

Yeah, I think about that first interview all the time because I think my voice failed, if I'm remembering correctly. I've been doing interviews for like days and days and then my voice just stopped and there was some sneeze. Someone was like crawling on the floor, giving me water, whatever. But now every time I'm like, I hope that doesn't happen again. You got a good, that's exactly what happened. So we're in this smaller room. We weren't in the studio that day for some reason. So we booked this separate room in the office and

And yes, your throat fell and you were coughing and you felt uncomfortable. And I'm looking at the producer going, get him some water, get him some water. Because there wasn't water for some reason. Here, we have plenty of water today. He brought his own, everyone. That's how much I think about it all the time. And you're spot on. The producer literally crawled to avoid being in the shot.

- Yeah, and people don't, I mean obviously producers serve an unsung role, but like you don't understand all the things that are going on behind the scenes that make it not terrible. And yeah, I think she like crawled under the floor and sneakily handed me the water. - Yeah, Helena, why don't you do that? I've never seen you do that before.

That's because you're well prepared. No, I genuinely meant what I said. I appreciate it. I love talking to you. I've always been a fan of your ideas. And, you know, to have, I've had so many interactions with you. It makes me very grateful. Well, sometimes it's good when like something terrible happens. I just think about it as like crossing it off the list. Like I remember I gave this talk. This is maybe like 15 years ago. I gave a talk at Yale. There's this thing called the master's tea. And you give a talk.

in the house of one of the headmasters at Yale. It's this sort of prestigious thing. It was really cool. I hadn't given many talks and I'm sitting there and you sit on these couches and like a handful of students are invited. And I'm sitting there and I feel something on my shoulder. And then I look over and there's someone leaning on my shoulder. And I was like, what's this? And I realized that one of the students has fallen asleep while I was talking. And so I'm like, you know, it'll never be that bad, right? That's like the worst, you know, sometimes you want to get the terrible things out of the way. And then you're just like,

all right, like it doesn't matter how much I screw up, how bad the podcast goes. It's unlikely my voice will completely abandon me ever again. And now I can rest assured. That's amazing. Yeah, I got to have that. That's crazy. I got to have one of those experiences early, early on in my life. I was like,

seven or eight years old. And we used to do in London school assemblies that were dedicated to people's religious holidays at school. So you'd celebrate everything from Hanukkah to Christmas, to Diwali, et cetera. And so it was Diwali.

And coming from an Indian background and a Hindu background, I was, my mom had volunteered for me to perform a piece in my, not even native language, but scriptural language, dressed up as an ancient Indian prince king vibe. And so I go out there, the clothes are not flattering, like it's not looking right. And there's parts of my body showing, it's almost like a toga, like an Indian toga. And-

I have to read this thing, which I'm not very familiar with. And I have to sing it too. And I have a terrible singing voice. I can't sing to save my life. And I start singing and all my friends are in the audience and they burst out laughing.

And then I'm getting really nervous and everyone's laughing so much that I start crying. Yeah. And then I forget the lines because I'm so nervous. So I look down to read them and I can't read them because my tears have smudged the words on the page. And then all of a sudden, this is the most embarrassing part, my teacher comes on, puts her arm around me and walks me off stage. Oof.

And I didn't live that down. That was my first day for experience in public speaking. So yeah, it's probably not gonna be worse than that. No, no, I hope not. I hope not now, but you know, I'm really excited to talk to you about this because you just asked me a question and I, you know, we were just talking about this and I said, let's start recording because it's a good, uh, good conversation. You asked me if I'm thinking about being a parent and I was saying that me and my wife have always wanted to have kids and

But it's really interesting because we'd set up a life that we thought we were going to 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, 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 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 going to change our life 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. I think what you said at the beginning, though, is interesting because 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 a marriage. Like 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 want to make more money. They want to accomplish all these things. And then parenting is kind of this thing that we just hope that we get right. We just win it, right? And that's a tragic thing.

skewed sense of priorities, I think. 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. Yeah. Like there's that kind of, the idea of what you just said of flipping the script of like, when should we have kids? Do I want to 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. You can go the other way or I'll never be qualified to have kids. Yeah, the comedian Tom Segura has this bit where he goes, you know, people say that having kids changes you. And he goes, that's not quite right.

it's that having kids should change you. Right? So like, if you're not ready to be changed, that's one of the things when people ask me to go, I'm thinking about having kids, 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 going to be opened up

emotionally, physically, spiritually, in all of these ways that if you're resistant to, because you liked the way things were before, you're not only doing your kids a disservice, but I think you're doing yourself a disservice. Because this is a profound 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. Were you this conscious person?

about being a parent before you were a parent? Or is it something that came from the process? No, it definitely came from the process. Like you think you know, and you have ideas, but it's not until this thing happens to you that you go, oh, all these other things aren't as important to me anymore, right? I think 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 write a best-selling book, you sell a screenplay, you know, you have some number in your mind, and then maybe it's winning a gold medal. You do something, and then you get it, and you go, oh, this is like nothing, right? This didn't change anything.

what I thought it would change. It didn't transform me in the way that I thought it transformed me. I feel lucky that I'd done a bunch of those things before I had kids because then

I was already wrestling with the, not the emptiness, but I was wrestling with 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. What do you think it does do then? Like, what does it do in any goal? And of course, some goals are

have a different scale to others, but the idea of becoming a bestselling 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 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, um,

I actually, A, never believed it would be big 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 because I get joy out of that act in and of itself. Like the act of studying, researching and simplifying brings me joy. Sure. 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 every week for hours every day. 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 having a goal achieve and what type of goal should we set? 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 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 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 bonus success of the rewards or the royalties or whatever.

So I think you want to root what you're trying to do as much as possible in what is up to you. So if you only enter competitions

where winning is up to you, you will always be a winner, right? And so if your goal is to beat this other person, right, to be more than this other person, this other type of person. I remember I talked to this author once and he was working on this book and he said, I said, what's your goal? And he said, oh, I want to sell like 2 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 what I have found is that 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 comes as early as possible in the process. That doesn't mean that once you figure it out, you stop doing it. You do stop. You can keep doing it. But you've just – you've broken the connection between –

like your sense of self and these external things that are not up to you. Yeah. Yeah. That resonates. I feel like for me, growing and learning are just such integral components of being alive 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. 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? 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. 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. And they might only ever be able to afford one time to watch me play. And I don't want to let them down. And that's how he played through injury. It wasn't that he wanted the championship more or that he wanted the ring more. It was that I want to be there for my fans who are showing up for me. I want to hear your thoughts on that. Yeah. I mean, you have my book, Conspiracy, right there, which I saw when I came in. And that's my worst selling book.

It is not that it hasn't sold well. It's not that it's bad. It's just all my books, it's not sold well. But it's the one that without question, if people ask me what book I'm most proud of, it's that one. And that's because I grew the most writing. 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. You love all the projects that you do, but that one was just different. It was just different in so many ways. If you can find a way, when the Stokes are saying, if you only enter things that were winning, it's up to you, you always win. What they're saying is that 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 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 crap if if you love all of that then everything else is extra and you got you got to 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've had to do work on that. 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 going to 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 yeah.

ideally most of the success is off the table just from having done it. 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 you've picked all the fruit that's up to you to pick. 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. Yeah. 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. Yeah. 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.

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not having time to do what you like to do in said 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.

Now those things might be lucrative, those things might be fun, those things might be rewarding in their own ways, but the main thing is like what got you into this, right? And if you don't have the time to do that, 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 going to be administrative things and obligations and business? Of course. But if you don't have time to do the thing that only you can do, like what kind of life is that?

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But I want to go back to when you were there. 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 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 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 where I would get to bring in speakers to help people be more curious and excited. And I remember we had Salim Ismail who wrote Exponential Organizations come in one day and my mind was blown because I was like,

I'm going 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. 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. Well, it's funny We did have very similar past I remember so I I don't believe in this idea that you have to like quit your job blow up your life to pursue Some sort of thing. I wrote three books while I was a full-time employee at a large fashion brand and

If you are good at what you do, you can get leverage at that company to pursue these other things. But I remember this would have been like the summer of 2014. So I'd written a couple books and I had gone back to American Apparel where I was sort of consulting in the turnaround of the company. I was getting this huge consulting fee. I was making great money. And I remember I was running in the morning and I got this like alert on my phone that I had a meeting, like I had a staff meeting.

And something hit me. 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 want to do to help you 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 idea was as long as my sort of corporate work was supporting and facilitating me doing the other stuff, it was great. And then as soon as they were fighting for the same resources, I made that shift. But I think some people think that 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. Right.

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. 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 summer of 2012. I didn't hit the New York Times bestseller list for another five years after that. It takes a long time. 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. Right? Like, it's going to take way longer than you thought. And so if you quit in this sort of dramatic gesture, you know, you're not going to have the runway to pull it off. Right? You need, like, a lot of runway, a lot of time. And so...

That was certainly my path. It took a lot longer than I thought. Yeah, 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 so true when it comes to anything in life. And for me, 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. 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, for no fame, 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 that I told you about 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 repetition. Yeah.

Yeah, you need a lot of reps. You need way more reps than you think that you do. And the amazing thing about what social media and 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? 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 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 spin stuff off. It takes like a long, a long time. - Yeah. - 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 has 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 suddenly do get the audience, you're actually ready for it. Like if I had gotten the audience ready

that I thought I wanted or deserved when I wanted it, it would have been preposterous. Yeah, I was actually just thinking about this because I was just doing the marketing for Daily Dad and I was in New York and I did The Daily Show and I did CBS Sunday Morning and I did a bunch of shows. And I remember thinking back when my first book came out in 2012, 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 as I wasn't ready and the 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. And so you think you want it when you want it, but-

You don't. I heard something about the early days of Google where they were like, eventually everyone's going to try our product. But

If they all try it now, we won't be able to deliver for them. 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 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 because you're getting better every single day. Yeah. And so I think about that, of course, with having kids too. Like if I'd had kids when I, earlier, I wouldn't have been emotionally ready. You know, like, so it's, it's patience is, is, is all. 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 want to dive into that with you. And then the other side of it is the mentality of, well, no, I'm going to be patient and I'll be better when I get it. Yeah. 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 kind of 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,

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, 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 live every day and no one 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 and

Well, yeah, 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 have been very excited to get them in 2019 or 2020 or six months ago. But you're better now, right? So you think that you want it when you want it. But...

it's better to get it later because you'll be better later. Yeah. 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 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. 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 an idea in a moment in time that I can't even conceive of yet. Like, you know, Michael Lewis, the author, he'd probably written 15 books before the big short came out, right? When the markets melded down in 2008, he had written dozens of popular books about

about finance, about sports, about 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, right? And I think Churchill said something about like, there comes this time in everyone's life where 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 so just the sense that like every day I get a little bit better. I work on it all the time. I'm putting in my reps. I'm following my process. I'm, you know, putting in the hours and I have this, maybe it's 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. Yeah. And that kind of keeps me going. What a beautiful way to live. That's spectacular. 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 had quite a fascinating life because of something that his dad did and everything.

he used to just as a kid be following his, the Daily Dad, like following his dad around. And he was taking on crazy adventures and experiences as a little kid just because his dad had a crazy job. Sure. 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 or it wasn't like, oh, and then I became invited. It was just, he had a great set of stories he was sharing. And I realized that at one point I realized that collecting experiences and

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 because my parents forced me to go, not knowing that. I never said, oh, I really want to be a public speaker 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 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. 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 we'd connect and support each other. You've supported my books.

But it's that you're just collecting that connection and relationship, if that makes sense. Yeah, one of my mentors, the writer Robert Greene, he said one of the great things about being a writer is that it's all material, that everything that happens to you is material.

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 going to choose it as I'm going to 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 say that the obstacle is the way, it's not that, hey, this thing happened and

And now as a result, your business is 10 X better off, right? Like it.

sometimes just shit happens bad shit happens but you learned from it or it it forced you to grow in some way just the sheer hanging on this of it made you stronger 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 yeah it's that

The stuff that happens is shaping you and forming you and giving you opportunities to evolve as a human being. That's what that idea is. And so 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 into the work. And what a great way to live knowing that your best work is still ahead of you. Yeah, I hope so. I mean, maybe not, right? Maybe not. I believe it. I believe it for you. I believe for me. I think that's a great way to live and think.

Yeah, I mean, your best work doesn't have to be your most successful work. Of course. That's what I mean. Yeah, yeah. I'm just saying that's, that's how I get up every day 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 like to think that it's all building towards something.

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of in-stock trucks, including the ultra-rugged new Tacoma and heavy-duty half-ton Tundra. You can experience the legacy of Toyota for yourself. Visit BuyAToyota.com, the official website for deals to find out more. Toyota, let's go places. Yeah, yeah. And I feel like when I look 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. Yeah. But no one really knew about it. So no one would really visit. But today...

500 to 1,000 years later, pilgrims visit these places. And they did that believing and knowing that one day this place will be of significance, but not maybe in my lifetime. 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 no it's it's kind of beautiful to go through life and go like hey somebody planted this tree 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 the note. Like all of us are the lucky recipients of investments that people made a long time ago.

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 what is it 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 we consume works of art that were totally obscure or unappreciated in their own time that we came back around to.

And so the idea of owing the future something, I think is a really beautiful idea. There's that quote like, "The world is great when old men plant trees "in whose shade they'll never know." And what about you, right? Like what have you planted? What are you contributing?

what are you giving away is is a is a way to measure your own life yeah yeah one of the chapters that stuck out from your book that i loved uh is called wait yeah i wanted to pick it up oh yeah raise a reader yeah and it's and it stuck with me because i was a kid who never liked reading until 14 and now i consider myself a like a voracious reader i absolutely 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. And then you'd read Roald Dahl 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

David Beckham's autobiography, Dwayne "The Rock" Johnson when he was a wrestler's autobiography, and then the biography of 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? 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. And 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. There's all these awesome things that would actually reach them and speak to them that could sort of inculcate that identity of being a reader. And so like 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 because he's obsessed with video games. And like to me, this is like barely a book. But to him, it's a way to learn more about this thing that he's interested in, which is what reading is. And they've done this interesting study of kids reading. Like if you remember as a kid, you'd have to read some like essay or short story or whatever. And this is how they would test your reading comprehension. Right.

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, 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. You see this even in publishing where like physical books are—

are considered higher than audiobooks and ebooks. And I personally don't read audiobooks and I don't like reading ebooks. I'm a physical book person. 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. And so just meeting people where they are to me is the main way that you raise readers. And it's, we just get in our own way on these things. Like I've read so many books, even since I've gotten older, like about where I grew up.

And I'm like, why didn't anyone tell me? Like Joan Didion is from the same town that I grew up in. And nobody told me that, right? I had to read these other novels.

that didn't resonate with me. But if this lady was from where I'm from, that would have resonated with me at such a deeper level, right? And I try to think about what does the person wanna learn? What do they have a problem with? How do we find a book that solves that problem? Because 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 up. And then maybe you'll go read something that's purely artistic. It doesn't have any of that, but you really got to find where the book does something for someone. I'm so glad you brought that up because I think a lot of people ask me like, Jay, what should I read? Like,

and my number one question to them is what are you struggling with? Like that's the question I love to ask back. And I say, I can 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 for reading. We've been trained to look for in terms of entertainment, which is great. And I have nothing against that. Or we've been trained to be like, oh, it's the smart thing to do. Or like, that's 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. Yeah.

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. 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 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. It's important to realize that pretty much anything you're going through, someone has gone through before and written a book about. Maybe 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. General Mattis was a four-star general in the Marines. He was Secretary of Defense. Sort of this, he's known as this kind of warrior monk because he's not just this warfighter, but he's also this deeply thoughtful sort of student of his craft. And he pointed out, he points this out to like young soldiers. He says like, hey, people have been fighting

battlefields for as long as humans have existed and the earliest literature is about this right, you know, we were 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 has this great quote I think about all the time. He says, if you haven't read hundreds of books about 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. And it's the same thing, right? If you haven't read it,

You don't know about it. And the fact that you could is irrelevant. What matters is have you read about this? And so just realizing that whether it's parenting or starting a business or, 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.

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. Epictetus says, you know, it's impossible to learn that which you think you already know. 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 we think about this with our kids. They'll ask us questions and we'll 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. Let's look this up. There's this magical thing called Google. We can look it up. 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. I want to go down the rabbit hole and figure it out. Just guessing or, you know, half-assing it is not the mindset that makes you. You want to be the person that figures stuff out and is good. It has the tools and the determination to figure stuff out. That's what you want your kids to have.

Yeah. And are your kids at school now? Yes. Yeah. So how are you, and they go into a, like a regular national curriculum, like they're learning, they're learning the curriculum that they teach in the US. Yeah. Yeah. 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 or protect them from the wrong turns we took.

Yeah.

Yes. Yes. I mean, I heard an interview with Brian Grazier once, the movie producer. Yeah. He's been on the pod. He's dyslexic, right? And that dyslexia shaped him and formed him into being this brilliant, creative, you know, sort of producer and 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, 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, 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 think that they can just come to me for all answers,

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. And I sort of think about that as a general parenting philosophy. Yeah, 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. Yeah. But actually it isn't love because it debilitates them from learning how to do it. And therefore doing things with people is better than doing things for people. I, 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 solar system. Totally. Yeah, you want to show them how to figure it out for themselves. You want to equip them with the tools.

To do it because you're not always gonna be there to do it for them Yeah, like they there's this helicopter parenting people know about that and 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, well, they're going to be in serious trouble. Yeah. And that's, 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 you want to give them the skills of how to solve their own problems, which I do believe is

if we had to debate it out, it's probably the most useful skill of all time is how do you solve any problem? Well, I was thinking about this recently. There's this singer, Morgan Wade, and she has this new song and there's a lyric in it. She says something like, all of your dreams are a parent's fears. 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. Like for me, it was dropping out of college, you know,

My wife and I, you know, we got together super early. We moved in. We did things that in retrospect were crazy and people probably thought were bad ideas. I made career decisions that were crazy. 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? And so there's almost this inherent conflict, right? Like a person wants to be happy and fulfilled and do cool things. And a parent wants nothing bad to happen ever, right? And the ability 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 college, my parents took it really badly. Like it crushed them. They'd worked so hard. I think so much wrongly of their identity was tied up in my sister and I's success. And they didn't wanna be the parents that had a kid that dropped out of college. 'Cause that's weird at a party or something to talk about.

And maybe it was a bad decision. Maybe it ended up working out, but maybe it was a bad decision. And so 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. And then they weren't there when I needed their actual support, right? And so it's understanding that like,

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. And that maybe that's a way that you cut through this tension of like, we don't want them to do anything that's dangerous.

But if your fear of that pushes them away, then when they are in danger, they're not going to come to you, right? And that's what you should fear more than anything. I interviewed this guy. His name was Dave Carey. He's Captain Dave Carey. He was a POW in Vietnam. And 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. Mm-hmm.

And I think about that in life, in business. It's almost like every decision you make. 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? Life is about options. How many options do you have? And just realizing, okay, this conflict, this disagreement, this tension, you know, the main thing that you're going to want with your kids in the future is that relationship. And nothing is more important than that. And so I think about that all the time. 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 of course i never went to my graduation ceremony i graduated but never went to have the picture taken and that was a big thing 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 and but it was the same it was they didn't

support it and they didn't block me yeah and then when I failed at it or when it all ended they were there to catch me I moved back in with them yeah 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 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 I've made it hard. No, it's beautiful. And kids do make it hard. Right. And it's, it's going to be a challenge. There's this, there's a story about Jim Volvano, the basketball coach. He realizes that like 10 or 12 or 13 or whatever, they wants to be a basketball coach. And he tells his dad, he says, I'm going to, I want to be a college basketball coach. And then the next day, his dad calls him in into his bedroom and,

And he says, "What's going on?" And the dad says, "See that suitcase?" And the son says, "Yeah." And he says, "It's packed." And he says, "Why?" And he says, "It's packed for when you coach in the Final Four."

And this idea of like your kid has this dream and you don't judge it. You don't tell them that it's unrealistic. You don't tell them it's crazy. You don't let them know how hard it's going to be. You also don't take it over and say, well, here's what you're going to need to do. You just go, I'm rooting for you is a beautiful thing. And

too much of the love that parents have or the support is conditional on whether it's going well, whether it's socially acceptable, whether it's understandable or not.

I think a lot of parents want their kids to be doctors and lawyers because they know what doctors and lawyers are, right? And social media manager sounds made up, right? Even if one pays better than the other, even if one is what lights the kid up and they hate the other thing more than... They just want... This desire to understand gets in the way of just support, which is really what it comes down to. This sense that, hey, these people...

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Yeah. And I feel like with my parents, I probably had more of a neutral relationship where I wouldn't say they were believing in me or rooting for me, but they weren't putting it down. Yes. And so it was more a bit like, let's start there. Yeah. Yeah. You make your decisions and whatever. Like, it's not like we believe in you and it's going to be great. And we, it's not like we're trying to hold you back. I think a lot of us today though,

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. And I still kind of am that way. Like, I'm like, whatever, I'm going to 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 on supporting me. What do I do in that situation? And so I'm

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 going to 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... No, it can screw you up. I remember I was in business with someone and 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. And you realize this person didn't get kind of approval or attention from their parents 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 dangerous thing. And I think at the core of it, a good...

number of men are just motivated by wanting their dad to be proud of them. And the sooner you realize that if your dad wasn't proud of you at the beginning, no amount of success is going to make you feel that later. Right. I do think there's this great quote from Marcus Realist 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 where you want to get as a parent. But what if you just started by not having an opinion? Like your kid is your kid and they're going to do what they want to do and they're going to be who they are.

The fewer opinions you have about that, the better your relationship is going to be. Absolutely. 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.

Because what matters now is that there is the relationship, right? 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, you know, force you into some box that they had for you. And the fewer opinions you have, the better, I think, as a parent. Yeah.

Your kid likes this video game. The fact that you think video games are dumb is an opinion you don't need to have. Yeah, keep it to yourself. Yeah. 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? 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 going to 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 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. Yeah. Yeah.

Yeah, it's realizing that if you didn't get it, you're never going to get it. And to try to continue to get a thing that you're never going to get is a fool's errand, right? And you have to figure out why you want to do what you want to do and what's important to you,

And that, have you ever done any inner child work? - Yeah. - Yeah, you realize, oh, hey, like my parents weren't what I needed to be to this 14 year old, but I need to be what that 14 year old needed, or I'm gonna go through the world as a 14 year old.

And it's not appropriate for a 14-year-old to be in this meeting or in this conversation or to be operating at this level. You have to sort of reparent that inner child or it's going to 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 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. And so I can't go back in time and give that to my four-year-old self, but I can do a better job for this four-year-old. We dropped my four-year-old off at camp yesterday and he really didn't want to go. He was really struggling. He was really upset. And he was sort of having this anxiety attack and he was struggling, he was crying. And, um,

And so ultimately, after like 30 minutes, this is dragged on and 30 minutes, 45 minutes going and he's getting more and more upset. And then we without even talking about it, we just decided he didn't need to go. And as as my wife got back in the car and we're driving him back to our house and we're going to, you know, just have a fun day or whatever. All I said was, I think we both know that.

that our parents would have handled this differently. And they would have forced it, right? And the idea that, hey, it's an opportunity to do things differently, to stop certain cycles, right? To turn over new leaves, to just do it a better way. And that that is not only your obligation, but it's also healing for yourself to go, oh, this is what I needed then.

And you can't go back in time, but you can write a better future. What gave you the intuition in that moment for you specifically to know whether to push them to go to camp or where you were like, no, actually, because I remember as a kid, I used to get...

A lot of those anxiety attacks as a young kid. And I remember even when I was going to high school, 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 when I was pushed through. And obviously I only personally remember the ones that I was pushed through that worked out. 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. 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

- 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? 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 actually at stake here? And you realize that almost nothing is at stake, right? You know, like your kid's throwing a temper tantrum and you go, this is not an appropriate way to act. I don't want to raise a kid that throws temper tantrums. I don't want to raise a kid that can't. And you realize that you're not even thinking about your kid anymore. You're thinking about you. And what you should be thinking about is,

oh, wait, we forgot to have lunch, right? 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 their trajectory as a human being. And being able to do that to anyone in life is really powerful. 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 an incredible thing to do for yourself and them. I struggle with that even as a writer. Obviously, discipline is important. Commitment is important. 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 going to come off and everything is going to collapse. You have to go, okay. You know, and just that sort of acceptance. Yeah. And to go, this is a singular instance, no more, no less.

I'm just gonna do what we need to do. 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. - That's a brilliant answer. I love that. That resonates so strongly with me because

I think we, you're so right. We just take one moment to be so predictive of their entire future. Like if I let him quit camp today, then he's going to quit this. If I let people talk to me this way, then I'm just going to be this person that gets pushed around. And you're like, this is...

one poorly written email. It doesn't mean anything more than that. And that you can just let it go. Now, obviously, if you're doing that all the time for everything, you can get in trouble too. But just going, yeah, this is not that big a deal. 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 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, which is really what you need the most. You just need to turn down the volume. Yeah, that's my favorite one, disconnecting 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 a lens through which I'm seeing the significance of something. Well, one of the really screwed up parts about having a kid, and I was just talking to someone who has 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 their head size is the 16th percentile. The first thing that happens when you have a kid

They tell you mathematically where your kid measures up against other kids. And it's like this the whole way. They should be walking by this age. They should be reading by this age, riding a bike by this age. And so you have this data. Like if you didn't know how other people were doing, you wouldn't care. But because they told you, then you –

you want to win that game. And the game is the size of your kid's head, which you have no ability to influence whatsoever. I mean, yeah, you want to know, hey, your kid is dangerously underweight and maybe malnourished, but it's usually it's like, oh, they're 87% in weight and not 94, you know? 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 want to get an A 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.

It's important to remember that you're not raising an average kid. You're raising your kid. You're not raising a kid on a spectrum. You're raising this person that 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. I think the more you can kind of tune out what other people are doing, like my wife and I were concerned that

This kid we know who was born like the same day as my son, like he's riding a bike and my son can't ride a bike. And we're like, are we screwing up? Are we holding 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

And if we didn't know that some kids were doing this and some kids were doing this, we would just be like, 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 going to make you a better parent. 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 just goes across the board. I wonder, I've spoken to a lot of people on the podcast about mom guilt to mothers and

Dad guilt's a thing too. And as someone like you, 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, but

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, right?

How does that person be a present loving dad or what does it look like for that scenario? I do find moms are way harder on themselves than dads. And, and part of that is because dads, I think historically have been judged on a much more generous or sliding scale. Right. And so the fact that there is some dad guilt is, is in a sense, a sign of progress, right? That like,

oh, hey, this is something that I am expected to be good at, to take seriously. And that if I'm not good at it, someone's not just going to handle it for me, right? I think the reason moms feel guilty is 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 I see that as a sign that like, I'm caring about it, right? Because you know who, like, it's like,

It would be wonderful if all parents were concerned that they weren't doing a good enough job. But the fact is there's a lot of parents that aren't thinking about it at all. They're either not thinking about it because 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 insecure, that you're questioning yourself.

And then just realize that other than that, other than the indicator of prioritization, it's not actually helping you be a better parent, right? Whipping yourself. Like I joke, like your kids are going to hit you enough. Like you don't need to whip yourself on top of it, right? Be kind to yourself. And that's a great line from Seneck. He says the...

The sign that philosophy is working in your life is that you're becoming a better friend to yourself. Yeah. And so you should be 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? Yeah.

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 think like, hey, the thing 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? - Both, both. - But when they think back to their childhood, they're not gonna go, "Oh, I did have a lot of cool stuff." Like, "I never saw my parents, but I had a lot of cool stuff. It worked out for me." They want you.

And so how do you find that balance? I mean, when we talk about work-life balance, the reason that's so hard is we're talking about trade-offs, like that you can't have it all. And you're going to have to say no to some things.

One of the things 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, right? 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 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, right? You feel that more. The opportunity costs were always there. You just didn't feel it because it wasn't,

personified in a in a heartbroken three-year-old so it's helpful it can it can be really really powerful I have I have this sign in the wall in my office and just as no and it's it's between two pictures of my kids and it's a reminder that what I'm saying yes what I'm saying no to is a and B and when I'm saying no I'm saying yes to a and B

And realizing that your fear of being rude or hurting someone's feelings, well, you better get comfortable with that because 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 say you say families the the most important thing to you, but what is your calendar show? Mm-hmm

I couldn't agree more. I always say the way you spend your money, the way you spend your time and the way you spend your energy shows your values and priorities far more than what you say or think. Yeah. Because what you spend money on is showing what you care about. What you do to make money shows what you care about. But what is your...

Biggest fear or worst quality in you that you are so scared of projecting onto your kids. Are you aware of that you? 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 It's overwhelming

The other day my son was in the car and he's sort of yelling and he's really upset. So I look back and I'm like, what's happening? And my other son goes, you know, I think Jonesy's just really overstimulated right now. And I was like, wow, that's like amazing. You know, like I was like, I wish I like, first off I was proud because he obviously picked that up from us. But I was like, I wish I could have that kind of awareness. Because all I was thinking about is like, what is this noise, right? And he's thinking, well, why is that person making that noise?

And so, yeah, the things that you get upset with your kids about when you lose your temper, like 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 something could have happened and you kind of need to get that across. But most of the time it's nothing that matters. 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 for me, it's about temper. And how do you tame that? How do you keep it from exploding onto the people that you love? That's the struggle. - What have you discovered in that path?

- 'Cause it's hard, like you said, it's hard. - It's really hard, 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? Or why don't you just let this go? You know what I mean?

Does it actually matter that pajamas get on by a certain time? Like, why are you forcing this thing? And I think oftentimes the frustration comes from when things are being forced. And so stepping back 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, right?

but I'm owning it now. And it didn't say anything about you.

And so the ability to, if you can 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, sort through them in therapy 20 years later. Ryan, thank you so much for coming back on the show. 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 one thing you said that is going to stay with me for a long time was, if you don't reparent your 14-year-old self, you're still a 14-year-old. 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 child or that teenager or whatever age it was. And that's something we all need to recommit to. Yeah. I mean, one of the struggles of being a parent, 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 the obligation is to try to do a little bit better, right? To try to give them the things that you felt that you needed or wanted. That's the goal, right? But yeah, you opened this, you said, you're trying to heal. If you leave those things unexplored or unaddressed, you're just passing them along. And there has to be some point where you go, this stops with me, right? Like this...

There's a beautiful Seneca line he talks about how we can't choose our parents, but we can choose whose children we would like to be. 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 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 I can give that to my kids. That's a beautiful thing. 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. Please go and follow him across all platforms. Ryan, anything else you want to share with the community over here? No, thanks for having me. Yeah, thanks for coming back, man. We look forward to every time. So thank you. If you love this episode, you'll love my interview with Dr. Gabor Mate on understanding your trauma and how to heal emotional wounds to start moving on from the past.

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Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough

On Purpose with Jay Shetty

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Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough 01:29:21 Share

On Purpose with Jay Shetty

Shownotes Transcript

Ryan Holiday: Why You Need to Reparent Your 14-Year-Old Self & How to Overcome the Fear of Not Being Good Enough