The Cost of Chasing Success | Chris Distefano

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0:38Whether you just got started holiday shopping or you're finishing up, these PCs and accessories make perfect gifts for everyone on your list. Shop now at dell.com slash deals and don't miss out on the best prices of the year. That's dell.com slash deals. I got an amazing night's sleep last night. One, because my six-year-old fell asleep in the car at like six o 'clock and he transferred him from the car seat to the bed and it stuck, which is just magic. So he's in bed way earlier than normal. But I sleep really well every night because I have a 8 Sleep Pod 5 Ultra, which is 8 Sleep's best product.

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2:26Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. we explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring.

3:20Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I was talking in, I think it was Friday's episode, right? About my crazy experience driving to and then back from Dallas, very weather impacted. But it's funny, you know, you think, oh, this was inconvenient for me, my bad luck, we planned this trip, we're going to do all this stuff, and then it doesn't go your way. And then I interviewed someone on the podcast this morning. That's not this episode, but I'll bring you that later. Anyways, he landed in the late evening and ended up spending four hours, he said, stuck on the runway at Bergstrom, the airport here in Austin, got into his hotel at like three in the morning.

3:59Whenever you have a travel horror story, just remember, it's probably not even close to the worst travel horror story. It's probably not even close to your worst travel horror story. I was thinking about this because today's episode, the night before I did this interview, I was stuck on the runway at Austin. We landed fine. We weren't delayed or anything. I think we were actually ahead of schedule when we landed, but then there was like a lightning strike right when we landed. And so all the crew had to get grounded and they have to, the rule in Austin, because they do this at Barton Springs too, it's like, it's got to be like 30 minutes between lightning strikes before, it's a 30 minutes of a long time, right?

4:36So you think, okay, it's 28 minutes, we're clear, two minutes, we're finally, and then boom, another lightning strike. So I spent quite a while on the ground. I ended up getting home late. I thought I was going to get to see my kids before bedtime. I didn't. So on this one, when we're stuck in the car together and it's raining, it's crazy. I go, hey, at least we're together, right? At least we're getting some time together. So I try to always look at these things with perspective. I don't know. Seneca never flew in an airplane, but they would have experienced some crazy travel delays. I mean, imagine just you're sitting in a boat and it can't go because there's no winds or you suffer a shipwreck.

5:10Imagine how delayed Zeno was. It ended up being for the best, as we know, but the point is, you're lucky you're not dead, right? Anyways, today's episode is with someone I've been meaning to have on the podcast for a long time. When I heard him talk about Daily Stoic, I think it was on Rogan, a couple of other things, and then I got a text from people who said, hey, this guy's like a huge fan, you should connect. And I was familiar with his stuff. I'd seen a couple of his comedy specials, and I said, hey, if you're ever in Austin, come by. and he was in Austin to do some gigs and meet some people and he came out to the store.

5:41It was awesome. Chris DiStefano is one of the funniest and most respected standup comedians today. He's released two comedy specials that you should check out. One's Size 38 Waste, which came out in 2019. And then Special Ueshi came out in 2022. And he recently headlined Radio City Music Hall, one of the things we talked about in the episode. You know, you have these goals in your career, in your life, and you do them. What do you feel then? And you thought it was going to mean so much. You thought it was going to make you feel good. But does it? That's the tricky part. So I was really excited to talk to Chris.

6:14He came to the Painted Porch. We talked about balancing comedy and family life, his relationship with his faith, the role that's playing in his life today, success and self-acceptance. And then how do we actually define what that success is so we can achieve it without the ball or the goalposts constantly being moved? And of course, the power of saying no. He's on tour this summer, so you can get tickets to see him live at his website, chrisdcomedy.com. You can follow him on YouTube, Instagram, and Twitter at chrisdcomedy. Very funny guy. I thought this was a great episode, and I can't wait for you to hear it.

6:55Are you like a routine guy? Yeah, I need that because I feel like without that, my anxiety gets out of control. if I don't have my things that I'm sticking to. Yes. I can't, I have too many thoughts. Like, what do you have, like a thousand? Some people have like a thousand thoughts a minute or something. So if I don't know what's coming next sometimes, I mean, I get into this trouble. I get into trouble a lot on podcasting. I constantly have to do a podcast and then deal with whatever I said in the moment, just the repercussions of that. Wait, so do you feel like the routine deals with the anxiety or does the routine create the anxiety?

7:36I feel like it goes both ways with me. I guess it could go both ways. For me specifically, my routine helps with my anxiety. Like the more I just try to wing it and free flow through things, I know that that's calm and I get that. But I, just from experience, I really get into trouble. Like when I just, you know, like yesterday I was on the podcast just saying whatever I wanted. And then I woke up this morning I was like, you're going to really have problems with your family for saying what you said in public. And so I'm like, okay, that was a mistake. But the way I deal with that now is I just say, you know what, man, today's a new day, you'll do better, whatever.

8:16I always think worst case scenario now, that's what helps me so much in my life. I'm just like, you know what, what's the worst possible thing that's going to happen is, okay, maybe that person won't have me on their podcast. I've offended some people. I'm a comedian. But wait, wait, how does routine, it feels like you putting your foot in your mouth is very different than being a creature of routine. Oh, yeah. Oh, yeah. Oh, well, going back to that, then. Yeah. I know sometimes my brain goes, I think for me, if I don't have a routine, what's going to happen then is I'm just going to sit with my own thoughts for too long and with no direction and my anxiety, which I've just now in my life kind of learned how to control it the best way I think I can control it.

8:55I think I'll always be a part of me. But that's the only way that I can be like, hey, when you have these anxious thoughts that are coming up. If you know that at one o 'clock, you know, that's when you normally go to the gym and at, you know, 2.30 is when you pick up your kids and at 11 a.m. is when you try to break your fast and have a meal, I'll know that like, well, I only got 15 minutes till my next thing. So whatever these anxious thoughts, they're going to have to be put to the back burner because I have to do my thing that I always do at that time. Yeah. That's how it is for me. Yeah. Yeah.

9:22Like I'm a big, okay. Yeah. Like this is the eating window. This is when I do this. This is when I start. This is when I finish this. But I find it keeps the anxiety at bay to a degree, but it also creates opportunities for anxiety because now you need things to go a certain way. Right. Like, okay, now, I don't know, your kid had a doctor's appointment or this thing happened. Now the routine's blown apart. So you have to just like, shit, this isn't how I want it to be. But then also it's like, I think a regular person is like, hey, I try to get started around nine o 'clock. But if you're the person who's like, I start at nine o 'clock, then now you've created this thing that has to happen, not just an expectation, but you've created a necessity that you don't actually have control over.

10:05Because traffic, children, other people, all these things can get between you and the thing you have said that if I do this, I will feel soothed. And if I don't do it, I will feel distressed. Now it's like the universe decides whether you get that thing or not. Yeah. Sometimes I feel like that way in therapy. like you know like i know therapy is a good thing for a lot of people i get it and i've been in and out of it for a long time but i recently i've been like you know i was doing good until i had this tuesday 11 15 therapy session and then i'm talking about all these things that i'm kind of making a bigger deal in my head about because i feel like i want to talk to my therapist and have something to talk about yeah and be like this is what's bothering me in my life but it's like i think i just made it i exacerbated my brain for this session what if i would have just not done that and I would have just went to the gym or went for a walk or done whatever is normally in my routine that day, I would have not felt, I like feel worse sometimes after I'm like, but then I start to go like, well, I can't be the only person in the world that doesn't need therapy.

11:06Of course I need it. But I'm like, why is this not making me feel better? For me, it's that. And it's also it's like, now I have this hour thing in the calendar, or if I'm going to do it in person, then I got to drive across town. I got to, you know, I got to leave by a certain time to arrive by a certain So it's like, is the thing helping or not? Because it's now this like thing that my life is pivoting around. Right. So it better be good or else like, not better be good, but like it better be having a positive impact or I'm just stressing myself out for no reason. Yeah, I know. And I'm trying to go now like where I'm like, the thing that gives me the least amount of stress where I am like just stress free is when I'm with my kids.

11:46So like, I'm just like two places when I'm with my kids and when I'm on stage doing standup, I feel like zero anxiety. All my anxiety about standup is the moments before and the time after is just about what did I just do? Why did I say that? And then leading up to, oh my God, what am I going to do? What am I going to say? But when I'm actually saying it and doing it, it is truly zero. As calm as I could ever be in my life is when I'm on stage. And then I feel that same calmness with my kids. so I'm trying I'm not the dad that like flips out about anything I'm just like I love my their kids my response is always their kids I don't care I love them so I'm trying to think of ways where it's like how much like because I know my kids are going to get older and then they're not going to want to be with me as much and I get that so I'm like how do I I'm trying to just figure out ways to be home to still feel fulfilled in my career and be home as much as possible because in my career you know the guys who go on and make you know 50 million dollars are all on world tours.

12:43Like you have to go away and leave your house. For long periods. And I don't want to do that, but yet I want to be successful. So I'm trying to figure out that balance of doing it. And right now I'm at a point where it's like, you're watching some of my peers like really blow up and I'm not being like, well, I could do that too. I'm saying, well, good for them, but I try to put myself in their shoes where I'm like, but do I want to go? Do I really want to go tour Australia? Is that what I want to do? I have to be away from my family for a month because they're not coming with me. they have school.

13:12So I'm like, I love Australia, but I'm just going to be like, I'd rather just do shows in New York and Boston so I could get home at night. And it's a weird thing because my agent is like, I've never had a client like you, that you have an opportunity to do all these big things. And you're telling me, no, I don't kind of don't want to do them. And the reason is because you want to pick your kids up from school. He's like, which is fine. I get it. He's like, but you have like major opportunity here. And you just look at me in the face and be like, No, I don't want to do it. So I don't know if it's self-sabotage or not.

13:41No, no. I think about that too. Like, are you actually doing it for the right reasons? Or is it this kind of weird imposter syndrome, ego thing? Because like, when I'm home, am I actually home? Do you know what I mean? Like, it'll be like, okay, yeah, I don't, I got offered to do this thing, but I have to fly over here to do it. I don't want to do that. I don't want to be gone. Or they wanted to add an extra thing. So I'd be gone an extra day or whatever. and then then i'm home and it's like well i got all the stuff i want to do it's not like i'm sitting around all day just being a parent right right and so like when you look at it like actually comparing apples to apples so okay i was gone for 24 hours but i was home but how many of the 24 hours was i home and then how many of the 24 hours was i home for was i actually present for the numbers start to be less uh you're the greatest dad in the world do you know what i mean got it And then so going like, actually, probably the way to do it is to like accept a good chunk of the things and be gone when you're gone and then be home when you're home.

14:43Not just patting yourself on the back for physically not being away. Yes. It's a good point because I think you had said once that Jerry Seinfeld had said like he wants the garbage time with his kids. So like I kind of, when I heard that, I was like, there have been times where I would really beat myself up about that exact thing. I'd be like, you know, where I'm home. I said no to this thing to be home, but now we're all like on our devices or we're all like watching a movie or my kids don't even want to talk to me or there was an argument, but I'm like, but all this is time with them. That's true.

15:12I'm just saying it's like, okay, so for me, I try to measure like when I'm traveling, I measure it in how many bedtimes am I gone? So like, that's like to me, so like last night was tough because I was supposed to get home by like eight, but I got home at like 10. So you missed the bedtime. So it's like, I might as well have just been, I might as well have just taken a later flight, you know? But so anyways, I measure in terms of bedtime, but then like sometimes I'll catch myself during a bedtime and I'm like, am I here for this or am I trying to wrap this up? Do you know what I mean? Like I turned down a work thing for this and then what am I doing?

15:43I'm trying to rush through this to do a less important work thing in the other room when it's done, you know? So it's this kind of like wallflower thing. I don't know if you had this when you were a kid where you're sort of like, well, I could be doing that. I could be over with the popular kids, but I'm choosing not to. And I think you can end up making some career and life decisions. You're telling yourself that you're doing this harder, more principled thing, but really you're just afraid, or you're just not putting yourself out there. And by not putting yourself out there, you're not having to deal with, oh yeah, I agreed to go on the Australian tour and now ticket sales are light or whatever.

16:21By opting out, you kind of get both. You go, I could have, but I'm not having to take the risk of doing it. And that's a new part. I never thought of it that way until very recently where I've been like, hey, man, are you using your kids actually as a cop out? Because when you're like, oh, I'm not doing as well as so-and-so because I'm a dad. It's like, no, you asshole. Yes. It's a cop out. I'm going to be 40 in a few months, which I know people like that's not really that much different than 39. But there's something about like that number in our society where it's like, oh, now you're 40. I think it's because when our parents were 40, like 40 was old.

16:55And now it's not old. Like you mentioned several. You look at George Costanza, like he's supposed to be young, but like people who looked older sooner. Yeah. So 40 was like old to us. Whereas like now, you know, it's not right. There's, it feels like a benchmark is really not that much. But I've gone to this where I used to be a lot, very much, you know, I mentioned a lot, like say something on a pod or my stand up. Yeah, it seems to be a problem for you. And then people are like, and then I'm like, oh shit. Like, why did I say that? Like, you know, like my family's going to be upset. That was nuts, whatever.

17:27But now I'm at a point where I'm like, hey, man, the career that I have, you know, takes care of multiple people in my family, which I'm very proud of. So I'm kind of like, I am who I am in the moment. And that's just what I do. I can't do it any other way. My brain is just I'm kind of always been this way. I've always been like, I'm a guy that thinks after even when I was playing sports. My coach would always be like, there's some people that think before diving on the floor into the stands. And some people think after you are the guy that thinks after and you always have been. And that's just your brain.

17:55And I guess I'm getting to the age where I'm like, kind of like having this energy where I'm like, you know, either accept me as me, as I accept you for you, or don't accept me at all. You can't just accept like one part of me type thing. And so I'm getting better at just, you know, liking me. Because for a while there was like people would say, oh, I like you. Your comedy helps me so much. It helped me with this and that, which is nice. But I would literally in my head be like, I cannot imagine why you would like me at all. What you would think is funny about me at all. I would never say that to them because that's too much.

18:27But you would internalize it. I would internalize it. Defect the compliment. Always. Well, now I'm just going to say, you know what, Chris? Now it's like, dude, you're better off just saying thanks. I appreciate that I can help you. Just say that because the rest of the stuff is just like your own thoughts just sucking you in. It's like you are who you are. You're going to have to like accept you. I was like, I can't live another 40 years being like, I don't know really who I am. It's like, dude, you know who you are. Just be that guy. Well, there's some ego too. It's like, you somehow know better than this person.

18:57Like, they're saying that they liked you. Right. Right? And you're like, no, you don't. Like, I know better. Yeah. I'm actually a piece of shit. And you couldn't possibly enjoy what I'm doing. There's like, there's just this sort of self-absorption that runs through on both ends of the spectrum. There's the ego of like, oh, I'm better than everyone. And then there's this ego of like, I suck and I know better than everyone. even though there is tangible and demonstrable proof to the contrary that you are good at what you do. Well, it's this interesting, it's this kind of a paradox because I believe the big reason why I am that way, I am that way, which I don't love about myself, is the Catholic guilt.

19:30I was hardcore Northeast, you know, New York Catholic, Catholic parents, like whatever. And then so I went away from Catholicism for a long time, but now I'm back. Now I'm back in to religion. Now I'm back just saying I fully, you know, believe, and it's just my ideas. Whatever anybody else wants to do is up to them. I'm just like, I'm back, and I'm looking at Catholicism as the thing that I think made me this way that I don't like, but also the thing that's helping me be better and be more accepting of who I am as a human being. Do you actually believe it, or is it just like comfortable, the rhythms of it?

20:00I believe, after I read Case for Christ, that book by Lee Strobel, I do, I am actually, I'm a big historical facts guy, and I do believe that there was enough evidence in there for me to be like, this is enough that I feel like I should believe what I was told by the priests and nuns when I was little. This is what I should—they weren't all wrong. Yeah, there's stories and they get a little crazy, but I'm like, if you're telling me that these accounts were writing about Jesus' resurrection and his existence within some of the earliest accounts within five years of his death, I'm like, all right, I'll go for it.

20:35i'll believe because i feel like the problem with me for a while was i was half-assing it i had two one foot in one foot out so it's like just go all in and my thing now is like look if when i die i was so wrong i'd be like that's fine i'll just pascal's wager do you know what that is pascal's wager no i've heard it wagers basically is like should you follow these ideas if you're if you're wrong and it doesn't exist then you were just a good person your whole life works out pretty nice yeah uh if you're right that's also great right the the wager is like it's it's better to follow these ideas yeah and turn out it was all nonsense right then to not follow the ideas and it turns out it was true yeah because i feel like that's exactly what i'm doing i feel like i've a lot of my problems come from one foot in one foot out a lot of you know even when you're on social media or today's world it's like there's always one thing and then there's they can disprove it so i'm like you know what i'd rather do you know it's going to just make me feel better it's just to make a choice and just say, I'm believing it.

21:35And that's just what I want to do. And if people, I'm never, ever, ever going to be like, you should believe too. I'm just like, this is just what I do. It makes me feel better. Once a week, I know I'm going to have an hour to listen to good things, meditate, kind of get off my phone. Maybe my kids will come. Maybe they won't. I will never make them come. My mom was like, that's a problem. My mom was like trying to shove Catholicism down my throat and i was like also just the logistics i was like why did we spend every sunday like let's start sunday off with a loss we're all mad at each other and fighting no and coordinating this thing yeah i tell my eight-year-old you know the the three-year-old you know she'll come or not come but i tell my eight-year-old how do you feel today do you want to come do you want to go sit there and then we'll go to the park after and if she says no then it's no then i said all right i'll be back in an hour and then we'll go to the park i will never where i grew up you are you real what What are you going to do?

22:27She would be like, Chris, you're not going to come to church. What are you going to stay here and masturbate? I'd be like, yes, that's what I'm going to do. You know, the angels are crying when you do that. I was Catholic growing up and then we moved across town and then we weren't Catholic anymore. Interesting. Because my parents didn't want to... They went to a more convenient, different church. I like your parents. So I was like, oh, it's not that serious then, huh? Yeah. Well, I think really nothing's that serious, right? Our thoughts are, I'm making up my life with my thoughts. Like even I'm, you know, I'm creating problems that don't exist at all.

23:00And I know that. So I try to remember that. I forget it sometimes, but I try to as much as I can just remind my kids that things are not that big, even being late for school. It's like we're striving to be on time. I want us to be on time. But if we're 10 minutes late, it's genuinely, it's okay. It's truly okay. No, we talk about that in our, it's like, look, it's better to be on time. and at the same time, acting dangerously to get there on time is not an improvement. No. Do you know what I mean? Like, I'm not gonna, first off, rush. I'm not gonna rush putting you in your car seat. I'm not gonna rush driving so we can get there on time.

23:34But I struggle with that because this is like, I think back to the routine thing. I'm like, okay, I like to start writing at nine. That's like when I start doing. That's the routine that we're on now. And so this is just a thing I made up, right? This is like nine is the time. but why am I stressing about because you know there was a spider in the car and now I got there at 905 like why in my head is that a huge deal there's a because there's the discipline of doing the thing you get really rigid you create rules like this is how much I write every day this is this how many times I go up each week right you come up with your things and you understand that the person who makes lots of excuses is never going to end up doing it because once you start making excuses, you make an endless amount of excuses.

24:15But the flip side of that is not such rigidity that you, one, have anxiety, and two, you have no room for spontaneity or just the reality of life not being in your control. So I'm trying to remind myself, hey, this is a book, first, I've been working on this series of books I'm doing for five years, and I'm not like, there's still another year plus in this cycle. So this isn't a thing that's being measured in five minute increments. So the idea of whether I showed up today is it. And then I go, okay, I'm rushing through school drop-off so I can get there by, I can have an extra five minutes. But then conversely, if some business opportunity comes along and I have to be gone for two days to do a talk or whatever, I'm like, sure.

24:59You know what I mean? Like I'll accept that because there's a monetary amount attached to it. But then here, my kid needing five more minutes, I'm like, let's move this along. The discipline can become like, not a problem, but it's like this thing that once you flip on, it's hard to flip off. Yeah. My father always would say, I'm sure you've heard it before. We said, listen, if it's not going to matter in five months, don't give it more than five minutes. Just do not even stress yourself out with these things that you won't care about. Like road rage. My dad would always say like road rage was the dumbest thing because you will literally, you can change the course of your life for something you won't remember in an hour you will it is so in the moment thing and so i constantly i try to remind myself of that where i'm like you know like we're getting so bent out of shape because we're three minutes late for school it's like dude tomorrow and i we won't who cares like yeah you aggressively pass someone you do some slightly dangerous maneuver to get a yeah ahead of someone who's going like 10 miles below the spiel and then you're both caught at the same light yeah five minutes later and you're like okay that was a big gamble for literally no gain there's this sort of, the Buddhists call it like willful will.

26:04Like you're trying to make things a certain way. And I think people think that's what stoicism is, right? Because stoicism is this sort of self control, self command, but it's also this like toughness and discipline and systems. But like, it's really, it can make you very, not just miserable, it can also make you like stupid because you're like needing things to be a certain way. And you're not asking, does it actually need to be this way in this situation? Yeah. Like sometimes I think, is this stoicism, right? Because my dad is just like old school, like new york guys like sometimes they say they make you think about things we're like that was pretty stupid but it's also kind of smart and and so like i remember this wasn't stupid this was actually a lesson where i'm like okay i i get that it was helpful i saw we were in brooklyn right and uh meter made you know like a guy who got a ticket from like his meter was and you know it's like you know greaseball italian guy came out he was like are you fucking kidding me to the meter made he was like i'll bash your head in you're gonna give me a ticket like going crazy and my dad and i are across the street we're just listening and my dad's like you see these what how stupid is that and i was like he was like that guy's mad at the meter maid he goes but the guy has a mercedes benz right he goes i know he owns that cafe he's wearing a twenty thousand dollar chain he goes does he want to switch places with the meter maid sure the meter maid doesn't want to give the ticket that's just what he is he had he came here he probably came from another country he was like what i would do if i was that guy is that 20 whatever that hundred dollar ticket is just a reminder that i don't have to do that and i and i have money i got life i got life by the balls and this guy's getting so bent out of shape over a hundred dollar ticket to him this guy's a multi-millionaire what is it it's nothing he's a drop in the bucket he's screaming at this guy doesn't want to do that and i was like that's actually a good way of looking at it like he said to me he was like so never get mad at the meter maid chris because you don't have to do that And I was like, interesting.

27:55There's a thing from Seneca that says we should pay the taxes of life gladly. So it doesn't just mean like, hey, look, every year your tax bill comes due and it is what it is. You got to pay it. But I think he's saying like, look, delays are attacks on travel. You know, like critics are attack on being successful. Like rumors and gossip are an attack on or attacks on, you know, doing things. Annoying people are attacks on living in a city. Like there's taxes to everything, right? And you just pay them because that's what they are. Being mad about them doesn't make them any less. You might be able to skirt one or two here or there, but in the end, you pay a lot of taxes in life and just accept it.

28:31And I just try to think about that. When you start to be successful, your literal tax bill goes up and up and up, right? It starts to be very large.

28:47You probably heard the headlines about all the different cuts to foreign aid and food benefits. This is having a profound impact on the world's poorest people and the world's poorest communities. But, you know, just hearing about that, that's not what stoicism is about. Stoicism is, to me, what you're going to do about it. And that's where GiveWell comes in. GiveWell is trusted by tens of thousands of donors each year because they provide free and independent research that helps you understand how to have a big impact. GiveWell has spent the last 18 years researching global health and poverty alleviation, and they direct funding to the highest impact opportunities.

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31:42One of the things you realize when you pay a lot of taxes is that you're paying a lot of taxes because you have a lot of income, right? Like even the most in America, you're paying like 40%, right? Which it used to be like 95%. So the point is you can remind yourself when you pay a large tax bill. And I'm not saying you don't have an accountant that tries to minimize your tax. Of course you do, but you go, I'm paying a lot of taxes because I'm making a lot of money, right? And when you're paying taxes, like yesterday, I'm sitting on the runway and we're just sitting there. We had to wait like 30 minutes or whatever because of a thunderstorm.

32:14That sucks. But I also flew from Washington, D.C. to Austin in three hours. That's a miracle. You know, like and planes don't crash that much. Right. And they don't crash that much because there's rules that force them to be overly cautious about that. Like these are just the taxes of life. Right. And you pay them gladly because they're the one thing that never goes away. And in fact, the more you do, the more people you meet, the better things go, the more there's going to be these things. And the ability to be like, shit, I got a ticket. That sucks. But it's an inconsequential amount of money to me is a much better place to come at it from than or let's say you don't have a lot.

32:55I'm alive. And that's why I'm getting this ticket is much better than the alternative. and deciding to be a dick to a person who's just doing a job, even if they are the tip of the spear of an unjust or fucked up system. Again, it's better than the alternative. It's better than the alternative. And I think too, a lot of times I equate money and time as like time having much more value than money to me now. And like in September, I did, you know, Radio City is like one of the biggest things, right? In New York, right? The next step is you go to master square garden so we did a show at radio city and it sold out like it like you know a few days it took right so it was it was great and so my i'm telling my dad and i was like dad you know radio city sold out four months before the show whatever it is he goes great he goes don't add anything else i know that that's what you're talking to me that's what you're going to ask me and i was like or like to add another date he was like yeah don't add another date and i was like uh i was like no but it's we have four months and this one sold out already goes yeah no I know but I know you're going to ask me do I think you should add a second show and I'm telling you no you already sold out you did the thing why do you want to go through all that pressure again you you set out you told me what your goal was was to sell out Radio City and you did that he was like you know if you if you add a show you'll make more money but then we can't do the after party as a family we can't celebrate any of this stuff with you we're then going to have to you'll we'll come to your first show yeah and then we're going to go home because we're not going to stay for your second show yeah that's all about you what she was like obviously you know i'm my advice is to not do it even though your agents are going to tell you it's good twice the money it's hot right now i don't think you should do it you should sell out so i did it and uh you didn't listen i didn't listen i was gonna ask this that's the the kind of very sage yeah wonderful advice that almost immediately gets ignored immediately i didn't add it that night i added a second show the next night.

34:45Okay. And so I thought it wasn't as bad. I thought it was like, I was like, okay, dad, I figured out a way that we can both be happy. We could still have the after party at Radio City after the show and we can be together as a family. But then I'm going to do a show at the theater at Madison Square Garden, you know, down the road the next night. And he was like, I think, again, that was a mistake because you've, yes, maybe you've solved one problem, but you've now, now the first one sold out quick. So if the second one doesn't sell it like that, you're going to think you're a failure and i was like no i promise i won't and then that second show didn't sell out to a day before the show and i felt like you were nervous the whole time well not only was i nervous the entire you know team that i had around me that was so excited about radio city within two weeks they were like man why isn't this other show selling what did we make a mistake it became negative right away when if i would have just said hey i gotta win you know it's like i would have been happier for longer and so i guess just being older my father being older again you know kind of having some health issues he's like i'm telling you when you get to the end you're not going to care if you did that second show that night where you're going to care about it's like oh i had a great night with my family and that night actually did wind up well radio city because we had a little you know drinks and food with my family but then i was in bed with my girl and kids at 11 p.m i was in bed right with them watching uh we're watching ace ventura and we all fell asleep before midnight so like this whole like rock star thing you think is going to happen like what people always say well what'd you do after radio city did you go to rainbow room did you guys go to what did you do and i'm like dude i was in i was literally in bed and i i don't have like any fomo about that i was like oh that was the right choice but i do regret not listening to my dad and i do listen to him a lot more now where i'm like you know what man there's no end to up it's like yeah if you sell out quick and keep adding and adding and adding but really what you're doing is just adding stress and pressure you're not you're not kind of taking your foot off the gas where i think sometimes in life you have to even if that means you're going to sacrifice some money did you feel i i'm curious because like we have these things that we like strive for our whole life like for an author it's like i want to hit the bestseller list or you know for a comedian it's like i want to sell at madison square garden or radio city music hall you do the thing right you're there you win the gold medal or the award or whatever and uh how does it feel is it actually what you thought it would be do you feel good enough in that moment and what how did you actually feel?

37:07I felt good. I felt great. People said, oh, you got to take it in. It's going to be a moment, you know, try to like slow it down. I don't really remember much of being on stage other than walking out. Then it was kind of like just in the moment. What I will say though, which is interesting, which is my Jasmine, my girlfriend was like, this is, you know, I've noticed this about you is I'm doing the best I've ever done in my career now. Like I've financially the best, had the most accolades, have the most things going on. For the first time ever in my career, it's like the industry's, I want to say coming to me, but they're, I'm not auditioning for things.

37:43They're like, hey, we have things for you. Like you have a vehicle, but I feel like the most disconnected from comedy. And I feel almost as far as what I am as a comedian, kind of the least power that I've ever had in my career. And Jasmine was like, you know, I think it's because what you, what's happened to you is, cause she's been with me for, you know, 12 years, 10 years. She's like, so she's seen when we had truly nothing. She was like, you got used to being successful. So you always chase, you're a chaser. You're always chasing the adrenaline rush. But what's the next big thing? And you're like, you're getting these things.

38:17And like, you kind of forget that, like how much, like, even when you're saying, oh man, that show is only 70 % sold out, but it's still like over a thousand tickets. She was like, do you remember like when you used to go away in 2016 and you wouldn't sell, you wouldn't sell 40 tickets over the course of a weekend anywhere. You just couldn't sell. And so she was the one that told me, she's like, I think you should go back to like your roots, go back to like even doing some of like the open mics, even though, you know, you know, you're past that. Like go back to like what drove you to be like love comedy because all these goals that you have written, you've gotten most of them.

38:49And now you're like kind of like, oh, I'm kind of not doing so well now. And she's like, what the fuck are you talking about? Like, look at our life. You're doing great. So I deal with, I'm dealing with that, but I'm aware of it. So I'm hoping that I'll be able to correct it. You think there's going to be this moment where you feel like you arrived? Like you would think you could leave Radio City Music Hall feeling like a made guy. Like I made it. And I don't feel like I made it now. No matter what you tell me or don't, I don't know what that, like, I'll look at Kevin Hart and be like, oh, he made it, you know?

39:19But do you think he feels like he made it? I don't know. I don't, I wonder. Because I wonder if it just, if it just never stops. Like, you know, like I heard George Carlin talk once about how George Carlin is, you know, to a comic, one of the greatest comedians ever, absolutely on the Mount Rushmore, 14 HBO comedy specials. It's an insane thing to do. One HBO special, he did 14, just genius. And he, I heard him at the end of his life, I think it was on Larry King, talking about how he always felt like he wasn't shit because of Richard Pryor. Richard Pryor was the guy. And he just was like, I, if Richard Pryor didn't live in my time, I would feel good about myself.

39:53but you wonder if like, even if Richard Pryor didn't live, you still wouldn't feel good about yourself. You'd find another reason. Well, I remember thinking like, if I could write one book, that would be a thing. Like not even like how many copies it sold or did it hit a bestseller list or whatever it did. But I was like, if I could write a book, that would be cool. I've literally written so many books. I don't know how many. Like I always get the number wrong. So like, you'd think you'd be like, you did it. You feel, but no, you don't, right? So you feel the same as me at times. I mean, yeah, I think there's a good part about it and a bad part.

40:21The good part about it is you're always starting at zero. And that's what keeps you sort of hungry and humble about it, right? Because like, it doesn't matter if you're Kevin Hart or the greatest person who ever did what you think you did, you're still waking up and facing like a blank page. You have to come up with a new hour. You still have to go up in front of an audience and do your thing, even if you've done it hundreds of times. So the fact that the thing is hard and by definition, you always have to keep doing it in a new way, that prevents you from ever feeling like, I've made it, I'm the best, I'm perfect.

40:53Right. So that keeps you hungry and good in a positive way. Right. The other part of it is because it is hard and then because other people around you are doing great, there's this part of you that's not looking at your success relatively, like where you were a couple of years ago, or just what is your potential. Right. And then you're comparing, so you're not looking there because you would feel objectively that you've done a lot and you've arrived, you're looking at other people. And I have to remind myself, I chose to write about an obscure school of ancient philosophy. There's a fucking ceiling on that.

41:26Do you know what I mean? To sell millions of that is insane in and of itself. But that you chose to be a classical musician. You know what I mean? You chose to be a Christian musician. Whatever you chose to do, you didn't choose to be a pop star. You can be really big at this thing and you can redefine what big in that thing is. But by choosing this thing, you were unchoosing other things and you have to accept that. And so I try to remind myself, you're really running your own race. And it's not helpful to go, well, this person sold 5X. Right. It's like, okay, but did they face the same constraints as you?

42:08And also did all these other random things outside of our control, the moment of time it came out, what their market, all this other stuff. So you would like to think that not just accomplishing things, but far surpassing whatever your wildest expectations for what those accomplishments would be would make one feel good. Right. And the reason you don't is that you were trying to fix an internal thing with external achievements. and that's fundamentally impossible. And then that's why, you know, what you do is you just do the work. It's like, if I'm just doing, you really start to feel bad about yourself when you're like, I'm in this career and I'm not doing the work.

42:44Or good work. And then you're like, you know, why am I not getting all these things? And because the last thing sometimes, sometimes, you know, we'll say is, well, I'm the problem. I'm the one who's not putting out good work. But for me, I think as long as I'm just every day trying specifically for me, trying to write a new bit, then I'm doing the work and then eventually it'll pour out of me like I just have faith at this point that it always will. But I think I start to get in my head when I'm not realizing, Chris, the reason why you're feeling disconnected is really just because you're not writing the way you used to write.

43:17And you're saying, oh, you basically gave yourself a break. You basically gave yourself a pat on the back when you shouldn't have. Even though you don't announce it that way, you're carrying that pat on the back energy. So I think that's why Jasmine was saying it without saying. You should go back to the open mics. You were always gone at open mics. She's like, you know, our routine was always to put the kids to bed by eight o 'clock and then I'm out the door at nine. That's how our life was. And now I don't do that. Now it'll be like, oh, put the kids to bed. I'm like, I did two podcasts today.

43:45I got to get into the city at 930. I'll go tomorrow. Right. I'll write at home in the morning. And then I don't do that because I'm like, oh, I'll make up an excuse. Like, you know what, man, maybe I'll watch a documentary on history to research about a bit I want to do about the Revolutionary War. And then you start to become that. So I think just kind of always checking yourself. And just, I think one of the Stoics was talked about like, kind of like not worrying about like, maybe it was the third thing. Yeah. That type of thing, where it's like, don't worry about, like that's trying to get recognition for everything you do is the problem thing.

44:19Just do the thing because you want to do it and then it helps someone. Yeah. Mark Cerilla says, you do someone a good turn and they receive the good turn. don't ask for the he says like an idiot you ask for the third thing which is recognition of that thing so yeah just just doing doing the work doing your best it's of course it's wonderful if it's well received if you're well compensated for it and more often than not you are but that yeah the it's it's wanting the well that was your best work or that was amazing or the odd you know you want that thing one of the things that i think that's good about writing and also comedy well it's it's a double-edged sword so you get good at the thing and then the reward or the expectation in the industry is to stop doing that thing right so writers write a couple books and then they become consultants or they go give talks or whatever and then the hard part of sitting down and writing they don't do that much anymore or they do it every once in a while and then comedy like yeah going up multiple times a night uh and then you can get past a point where you have to do that.

45:21Or you could keep doing standup and then like they want to put you in a sitcom, which takes you away from standup. Yeah. And it's the actual craft part of it, the doing the thing that keeps you, I think, humble, but also fulfilled because you're getting this sort of daily rewards of like, of doing the thing that attracted you to the space to begin with. Like I didn't become a writer as a means to an end because what I really wanted was a podcast or talks or going to conferences. Like that wasn't like, I'll do that if I'm compensated for it. But the thing I wanted to do was be a writer. And my friend Austin Kleon says, it's like, you have to do the verb, not be the noun, right?

46:02Like, are you a writer or are you writing? Right. You know what I mean? Like, are you doing comedy or are you just identified as a comedian? Yes. And if you're doing the thing on a daily basis, I think it keeps you more in the headspace that you want to be in. Yeah. Do you know Colin Quinn? I mean, I know his work. Colin Quinn, yeah, is like a mentor of mine, like New York legend. Sure. Actually, he was just, he's in Austin as well. We just had breakfast and, you know, we talk a lot and he's a great guy to have because he's like that old school guy that is just about the comedy, just about the art.

46:40Like he does not like that comedians have become like arena acts. He's like, that is fundamentally not what this was about. This is an intimate art form. You know, like I am about the comedy. He's the guy, like, even if you have like a joke that went viral, he'll be like, you know that that's hacky bullshit that you're doing. And you know that that was an easy punchline and it went viral because people don't know what we know and you're better than that and things like that. But then if you have something that's good that went viral, he's very appreciative. He's like, that's the art. That's what you do.

47:07And so what I love about him is because he's content in who he is because he said, he's like, dude, he's like, you know, he's, I've been doing comedy 30, he's been doing comedy 35 years. He's like, I've never sold half the tickets in New York that you've ever sold. I never have. He goes, but I'm happy at this point in my life because I do the work every day. Every day I'm writing, I'm trying to push myself forward. And he was like, you know, he's like, I'm going on, he's going on a tour right now. And he's like, you know, I got dates all over in Seattle and Vancouver. I'm going to be away. He's like, and I know that the shows aren't sold out.

47:38He's like, I make one little joke about it to the crowd, and then I go on and I do my thing because I love to be present with the audience and do my comedy. He was like, I think you young guys, you can get so famous so quick because of the internet and sell so many tickets so quick because of the internet, but then you forget that's not what comedy was supposed to be about. You're not supposed to be judged on your likes or your ticket sales. He was like, does your comedy feel urgent? Is it so urgent that I need to tell the audience tonight this bit that's going to be cathartic for me? that's what it is he was like so don't forget that don't get wrapped up in oh well you know you were comedian of the year this year and now i'm not comedian of the year next year it's like that's it's so dumb he was like we have such a subjective art form people are going to love you people are going to hate you this is not the nba you don't make the team or not make the team you're just doing comedy because you love it or you're not doing comedy that's that's who it is yeah i've tried to get to a place where like speaking of the nba i'm like i'm in the league that's what matters.

48:34I don't have to be the number one person in the league. What matters is, are you in the league or not? Are you one of the people that's able to do the thing? But how do you justify being in the league? Because you make a living doing writing? I mean, obviously, you're very successful, but how do you do it? How do I know that I'm in the league? Yeah. It's a somewhat subjective measure, but I mean, I'm published by the largest publisher in the world. If I have an idea, someone will buy it. And then the other part for me, as I was designing my career, is like what I really hated was like coming up with something and then somebody else getting to decide whether it got seen or not.

49:13Got it. Right. Like something I wanted the audience, like I needed people to know who I was, but it was like, I wanted to have, when I had something to say, I could be like, here's what I have to say. And there would be people listening. Right. And so like when I built out Daily Sto, I mean like, uh, Daily Sto goes out to a million people every day yeah and so it's like i don't really need anything because like i have an audience and that's who i talk to every day like every day i wake up and i have a thing that i say to a million people right and like that's that's being in the league do you know what i mean like i don't need to know does someone have two million does someone have five million did this person only has 50 000 but they're getting covered in the press all the time they're getting invited like i have an audience far bigger than i ever would have dreamed of having and that's an insane number to write to every day that's larger than the subscription of many newspapers yeah like that's it that's the i have an audience and i get paid to speak to that audience that's being a professional writer 100 yeah i agree because i think it's similar with comedy where it's like we kind of have to though like tell ourselves out because like you know you're either on the knicks or you're not right you're either in on an nb one of those contract to yeah so that's how so you can i can objectively say, even though I'm sitting at the end of the bench for the New York Knicks, the LA Clippers, I am in the NBA and that's what I am.

50:30For us, it's like, you know, obviously you're in the league, of course, but you know, you feel like, you know, somebody five rungs lower than you. It's like, are they, could they also justify it and say, well, so it's like, that's why I think the imposter syndrome kind of comes in sometimes with these types of careers we have, because there is no objective measure to say what you have to decide if you've made it or not. So just, you know, That's what I think sometimes gets complicated.

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52:47Were you always able to say, I am a comedian, or did you feel like you had to earn it? Like, what do you do? Like someone asks you to go, like, I'm a writer. Sometimes I think probably what compels people to want to be famous or successful is to not have to answer that question, just people recognize you. But I think early on in my career, I was always very insecure when people would say, what do you do? And I'd be like, oh, I'm in marketing. I would just say something to end the conversation because I hated the part where they would go, like, what do you do? and I'd be like, I'm a writer. And they go, oh, have you written anything I've heard of?

53:17And then I'd have to be like, probably not. You know, like this, that like, there was clearly some insecurity in me that wasn't able to identify it. And then I would also be driven nuts when like someone who was a straight poser, like definitely not doing it, would be like, I'm a writer. And it's like, no, you're not. You work at a restaurant. You know what I mean? Like, but so like, I think sometimes when you're insecure about it, it bothers you that other people are secure about it. when really, yeah, you identify. You either identify with it or you don't. It's a self-assignment. Yes, yeah, I used to, when I first came a comedian, was out there working just as a comic, when I'm going to get into a city, you rent a car, they would say, what are you in town for?

53:58I would say, oh, I'm a comedian. And then it would be all the same questions and tell me a joke and I've never heard of you. And I started just saying, I'm just in town for work. I would never, ever, ever tell you I'm a comedian, never. And then it got to the point where, you know start to get a little bit more recognizable and somebody would stop me and be like oh can we take a pic and then the person they you know they're with their friend the person would say i don't know who you are yeah i'm gonna take a pic so you're like okay up and down you're like i didn't ask for this you know and my response would be you know what to be honest i don't know who you are either i didn't ask for this your friend did i'm we're all strangers yeah and then it became you know social media you know you get recognized people would say oh i know you from tiktok yeah and that would hurt me initially because i'd be like no no i'm not a tiktoker i do real stand-up but then you start to realize well that's just the mode where they're consuming stuff now it's like the sitcom from back in the day it's like now they see you on tiktok that's that's what it's so all these levels of acceptance where now i'm just got to the point where i'm like if you recognize me i'll give you my time i'll always you know i'm so appreciative and if you don't recognize me or say something slick like that i never even get mad i just i'm like buddy we're all blessed and then i keep moving i just tell people i own a bookstore yeah and uh because it's like a nice thing like it doesn't you know if you're like i'm you don't say it's like this whole other awkward conversation so i just pick something like oh whatever and then uh it's also weird for me because i live in this small town so there's this like weird sort of fishbowlness of like being a public figure and living in a small town and sometimes i can't tell do they know me for my work or do they know me because i live in this small town you know what i mean yeah and uh it's like it's it's weird but it's better i think just not to think about it and to just do the thing yeah it's better just to do the just a thing because no matter what you know no matter whether you're in entertainment working for amazon whatever your job is i mean our life is ticking by every day so it's like you might as well just be in the present as much as you can and enjoy everything because i mean i know you know this after how many books do you read how many videos do you see when they interview people in their 90s and hundreds on their death but they're always saying the same thing i don't care about money i don't care i would give all the money in the world back to have time back and to be present and close with my family that's what they want relate they say like relationships i was just watching this video all these elderly people were saying is truly about relationships that's what life is it's not about money at all how are your relationships with others you know don't be lonely have like a community around you and you know like you chase all these things i think somebody said i definitely heard you say it i'm not sure what stoic said it paraphrasing but like if the money is not buying you freedom what's good is the money yes type thing so like i i think a lot about that i'll see some of my peers going on these never-ending tours and i'm like you're just making more money but you're not free you're like always on to the next thing like when do you get freedom from the financial gains you've made i remember like this was a long time ago but like uh i was listening to some morning radio show and then they interviewed bill clinton and i was just like the fucking president is on morning radio do you know what i mean like i was like the thirst of that he was like promoting a book or something yeah and i was like this dude had control of nuclear weapons and then here he is like hawking a book like on a show I've been on.

56:58You know what I mean? Like you, you realize that you think that these people are so powerful and so free. I think about that. Like Mark Theroux is the most powerful man in the world. And yet he wasn't that powerful because like people told him where he had to go and what he had to do. And he had to like, like when Lincoln became president, it used to be like literally anyone could go to the white house. You would just like go and they'd get an appointment. And then you could be like, Mr. President, I want to be the head, the customs officer in new Orleans. Like you would like pitch the president for like these piddly little federal job.

57:32And so Lincoln gets elected. He's in the middle of the civil war. And he would just talk. He's like, I had to meet all these fucking people every day. It was like this line that snakes. Who's the president that got assassinated? Not Chester A. Arthur. And not Garfield. Was it Garfield? One of the president, McKinley. McKinley gets assassinated by some dude he just like spurned for a job. Yeah, yeah. So again, you think it's this incredibly powerful thing. and like actually their assistant is the powerful person because they're deciding what's going in the calendar or not yeah and like you you'll meet them and they'll be like sorry i have seven minutes yeah it's like you think that success is going to give you autonomy and control of your life but for a lot of people it doesn't and i would argue that that's not really success no it's not and i think like to be honest with you especially in today's world the best way to be is somebody like you, you have your specific fan base.

58:24But other than that, you're not like world famous, like everyone knows who you are when you walk in like Oprah, right? You're not Taylor Swift, but yet you have full control of, you know, of what you can say or do. You have fans that love you, that'll go to the end of the earth for you. Your family has whatever they want. You have whatever they want, but yet you can maintain relative, you know, you're recognizable, but like, again relative anonymity where it's like okay three out of ten people know you and they love you but it's like if you went and did something that was crazy nobody would really i mean your fans would be like no we love ryan he's our guy and we stay with you whereas sometimes i think like being like this world conqueror thing it's like that is not all it's cracked up to be it's like dude do you really want to be an a-list famous person do you know what life is like you can't do anything ever in today's world well the other way i think about it is like we you look at like really, really rich people.

59:15And you see how it like destroys their family. You watch succession or whatever, right? Like you see how it's just an impossible amount of pressure and temptation and control. It's not good, right? It's not good to have like truly like gratuitous wealth, right? But what are most, we know that intellectually. And then what are most people doing? They're hoping to get to like some extra level. Like no one's like, hey, I hope my startup is like medium level success yeah they're like i hope i get i hope i get uh purchased for a billion dollars right even though you you're just reading a story about a billionaire whose life fell apart right like every every family that's ever been on a reality show has like totally been torn apart yeah like the the spouses get divorced the kids have drug problems they one of them ends up going to jail like it never ends like but if someone called you right now and you're like chris we're thinking about doing your family seems interesting would you like to do a reality show about your life like this happened to me on multiple occasions and i'm i know this and then i'm like well let's have a conversation about it you know what i like you should be able to click not interested in it at all uh it never goes well and then uh you're like but maybe i'm different Maybe it'll go differently for me.

1:00:38Right. And it won't. It will not go differently. So then what do you think is one of the, what is to like maintain that like happiness then? And like, what do you think we have to do? Like just be smart enough to know what to say no to type thing? Yeah. You have to be able to say no. Like I try to think, one of my rules is I try to think if I accept this, when I'm looking back at why I got divorced, is this the answer? Interesting. You know what I mean? Not that every marriage lasts forever and you know, I could end up, who knows, right? Right. But I try to go like, you know, I try to not make decisions where I go, looking back, it was all that.

1:01:12You know, it all began there. I remember in 2016, I got an offer to be a press secretary for one of the members of Trump's cabinet. And I'm not a Trump fan, so I was like surprised to be asked. And I almost certainly wouldn't have made it like through the vetting process. but it was like, I felt very clearly like this was like a crossroads moment where like my books were doing well and I had this, but like, I was like, oh, this is, this is the path where if I take it and it does work out, this is like sort of the Washington power broker path where you have a different kind of life and a different kind of career.

1:01:47And it might be really exciting. You might do a bunch of things, but I'm like, it's definitely tearing my family apart because like I live here and that is in DC. And either we do some complicated splitting thing, or I would uproot everyone to pursue something that was basically just a feather in my cap extra for me. And that also would be insane hour. And I've had other ones where it's like, especially when I was in marketing, hey, do you want to come do six months here in this sort of turnaround job? Do you want to be the head of this at this company. And they were always lots of money and would have taken me in a very different direction in my life and could have been interesting.

1:02:31But I would always go like, well, first off, what did I want to do? What was the dream? The dream was to be a writer. So why am I accepting these things that are not that thing? And then what is the cost of that thing going to be. So often I think people take things because they're cool, because other people in their life say they should do them, because everyone accepts when offered to do this thing. And to not do it feels crazy. But in a couple of years, it will feel crazy that you did it. That you did it. That's why that power of no. It's very, very difficult to do it. But in the moment, I can't imagine why anyone would want to actively be president.

1:03:14No matter what side you're on, your life is going to get torn apart by the other side. And with social media, it will get really torn apart and you're going to cause major problems for people that you say you love. So why are you even in a position to do that? And I never, I was like, do they not think it? Or do we have different brains and they are just that power hungry? What is it? Yeah. I mean, it's funny, like going back to the Stoics, that ambition, that lust for more and more and more is like the most timeless part of the human experience. Why is Elon Musk starting more companies you know what i mean yeah he says it's for humanity but it's not it's for him like he he is addicted to chaos and drama and wants things always to be his way right and so he can't when he has an idea he can't be like someone else could do a good job of that you know or like that he that's his thing and so that's probably good for humanity in some way right like uh if the europeans were like, yeah, Europe is pretty big.

1:04:13Let's just chill here. You know, then the rest of the world wouldn't look the way that it does. So now I'm not saying that that was good for humanity because obviously it wasn't so great in other ways. But the point is like, if people didn't have this desire to always see what's on the next side of the hill or to always achieve more or grow more, if Jeff Bezos was happy running a$10 million company, it wouldn't have become a trillion dollar company. So like evolutionarily and economically, it's good to harness that energy, but it's probably bad for the individual. There's this line from this novelist, Stefan Zweig, I think where he says, no conqueror has ever been surfeited or satisfied by conquests.

1:04:53Never in the history of the world has a Napoleon type been like, I fucking did it, man. Alexander gets basically as far east as a human has ever gotten. He's the most powerful man in the world and his army's like well we did it we're ready to go home right and he says all right you go home and you tell your families that you left me here to conquer the rest of the world wow and then he fucking died like a whore he got a disease and he died a horrible death or the other the other uh theory is that his men killed him so they could go home right and so like that's the thing that makes you do that thing right as we're talking about is an extremely hard thing to turn off, even when you are so past the point.

1:05:40So do you think there's anyone in history or anyone that you know that has figured it out on how to just balance that the right way? Or do you think it is part of our human DNA, as you mentioned, survival mechanism where we just have to know about it and try to limit it as much as we can, but it will never fully go away? Yeah, I think it's hard to point at a specific person and be like, they crushed it because Because you don't know a person and you don't know what their family... But what I would say is that it's rarer to be the person who goes like, I've got two rings, I'm good, than to be Tom Brady who needs to go for one more and then it comes at a cost.

1:06:19In some ways, the person who is really great but doesn't need or thirst for one more or whatever is rarer. Right. That's the harder thing. Like the Stoics say, the greatest empire is command of oneself. So there's lots of people who have commanded big empires or big armies, but it's rarer to find a person who got really far at what they were good at. Like, you know, again, there's the person who does nothing and they go, oh, it's because I've conquered all my desires and needs. Sure you have. You know, you just never got asked. But like, I think to be great, to achieve a level of mastery or success at your thing and be good with it is the most impressive thing.

1:07:03Like Seneca talks about how there's the poverty of having too little, like because you're actually poor. And then there's the poverty of wanting more. And to get to a place where you're like, I took this as far as it could reasonably or somewhat unreasonably be taken. And now I'm gonna retire with dignity. Like how many boxers retired at the right time? Like basically zero. Rocky is like basically the only one. He turned down like a million dollars for his final fight in like 1950s money or whatever, when it was actually a lot. And they just don't do it. They always go for one more. And then that's when they get Parkinson's.

1:07:41Right. You know, like there's one more job. Right. You know, just one more job and then I'm out is when the bank robber gets caught. Yeah, because it's almost like in our culture where it's like, if you have success one year, but not the next, then you're unsuccessful. It's like people forget about what you did last year. It's like you have to somehow keep this up and keep this up. and that's like that rat race that you want to try to get out of but it's tough right because you're like you know like you know the player that that doesn't that just retires at the top of their career then they're all over espn getting you know just destroyed by everyone and they've let the fans down and how selfish are they when they're like oh yeah andrew luck andrew luck just made like a hundred million dollars and he was like i'm good i don't want to get hit in the head anymore and people were like what the fuck is wrong with you yeah like which is crazy because it's like, and that's an example of a guy who on paper is like, oh, well, he's actually figured it out, right?

1:08:32He made all the money. If you blow through$100 million, that's on you. You know, like you shouldn't be, even in today's economy with inflation, you should not be able to blow through$100 million. You should be good. That's a generational wealth. Your kids should be good. Everything should be good. Just, you know, just put that in, let it earn interest. Don't even touch it. And so, you know, I think like something like that, but it's very ballsy, right? I mean, And that was probably scarier for Andrew Luck than him getting sacked by the biggest NFL linebacker in history. That's probably scarier for Andrew to be like, I'm going to tell the fans that I'm retiring when I don't really need to retire.

1:09:08My body can do it. I just don't want to get hit in the head anymore. In a way, it's almost more courageous than being like, I'm going to try and try and try to win one more or to win the highest. It could be like, hey, I didn't win a Super Bowl, but I was a starting NFL quarterback. and how many people can ever fucking say that and i'm good yeah uh that's that's pretty yeah that's pretty insane that's pretty or or to be great at the thing and not be a monster elsewhere that's i think also very rare right they're probably related to each other but it's very rare that you find someone who's extremely good at the thing and then like they can turn it off and go home and not be like the main character.

1:09:50I always, my mom always told me a big thing that she always wanted me to remember. And I do, is I've actually let, I had a pretty good accountant a few years ago and I let him go. He did this thing that my mom said, always watch out for that. My mom was like, always like, I want you to always like look for people that you can tell a lot about a person, how they treat the people they think they don't need. Yeah. So I always want you to look for that in human beings. Like, and I had this accountant, who was just being so unnecessarily mean to our waitress at this lunch we were having. Wow. And I was just like, even though he's excellent at what he does, I was like, I actually just don't want, you are treating that person because you don't think you need her, you only need her in this moment, like she doesn't exist.

1:10:33And I just don't like that about you. I was honest with him. I was like, I don't like that about you at all. And I think you're excellent at what you do with the numbers. But even if I can find an account who's not as good as you, but is a better person, I'm just going to go with them. And then he was like, you're going to be broke. Then he started attacking me. I was like, oh, this guy really sucks. Because then - Well, you got a glimpse into character. Yeah. There's a story about the Emperor Hadrian. So Hadrian has this, it's this remarkable, unprecedented moment in history. So Hadrian is the emperor of Rome, and he doesn't have any children.

1:11:05So he has to choose a male heir. And so he chooses this guy, Antoninus Pius. He wants to choose Marcus Aurelius, but Marcus Aurelius is like a teenager. So he's like, That's the worst thing that could happen to a teenager. So he's like, I need an intermediary. So he chooses this Roman senator named Antoninus Pius, who has to, in turn, adopt Marcus Aurelius. So he sets up this—that's how Marcus Aurelius becomes the emperor of Rome. So the question has been, what did Hadrian see in Marcus Aurelius? We don't really know. And what did he see in Antoninus Pius? It was just then known as Antoninus. Pius is the name he gets because he's so wonderful.

1:11:39But how, because if you pick a lot of people in that time, you pick, you're like, okay, look, here's this defenseless boy and I'm going to die. You're going to become emperor. And then you have to give it to him later. I mean, the first thing that guy's going to do is kill that person. Of course. Yeah, that's what I was thinking. Yeah. Yeah. And that doesn't happen. So the story is that Hadrian is heading into the Roman Forum one day and he sees Antoninus helping his elderly father-in-law up a flight of stairs. No one's watching, and he doesn't know that Hadrian can see him. And he just sees him helping like an old man who is not like even a blood relative.

1:12:15He's just helping his wife's father up a flight of stairs. The idea is that this glimpse of kindness and decency and softness is the confirmation that he already knew he had the political skills and the leadership skills. He had the ruthlessness to do it. But did he have too much of those things to possibly be the guardian of this person? And it's an incredible story because, you know, they thought Antoninus would live for a couple of years. He lives for 20 years. Wow. So he grooms Mark Cerullus for success for 20 years. And they become like father and son, but had no relation to each other whatsoever.

1:12:52It's like, how did it happen? And this glimpse, this moment of character is what I think, you know, seals it up for him. And conversely, we have these moments of character where you see someone and you're like, oh, you're like a dick. Like you fundamentally see other people as expendable or worth less than you or whatever. And that's like a glimpse into probably how if some push came to shove, there was some problem, he would treat you that way. The accountant would treat you that way. Right. That's why. Yeah. Like I have a thing going on right now where I was fortunate enough, I sold a sitcom idea in the room to two major networks just last week in LA.

1:13:27It's like a cool, like, you know, like it's just cool. I'm like, this is like, you know, big networks. And my agent was like, listen, the offers came in and they are pretty much like exactly the same. And what do you want to do? And I literally am going to go with the network that treated me just as human beings in the present moment when I was with them. I just felt like they were like nicer. They were both nice. But like one group was just like they were looking me in the eye when they were talking to me. I felt like they really wanted to work with me. And the way networks work is those people who bought my show can all be gone in three months.

1:14:03And the other network would have given me the better chance. But I don't know any of that information in the future. Just in the present, I go by my mom's rule. I was like, these people seem like the people that, and maybe I'm wrong, but again, I can only go by my gut. I'm like, they seem like the people who would, you know, treat people that they think they don't need with kindness. And I'm like, so I'll go with them. And I feel good about that decision where I had this opportunity like eight years ago. and I went with, I did all these things like, this calculation will get this show. It was a sitcom for CBS.

1:14:34I was like, we'll go there because this is going to happen and all these things. And then it didn't go. It didn't get picked up. And I was like, oh man, I should have just went with like a gut thing. I should have made a better, should have made the decision in the present and not worried about the future because I thought all these calculations would get me to the answer in the future. And I was wrong. But just like you ignored your dad's advice, How much higher would the other offer have had to be for you to go with the not as kind people? There's obviously a number, right? Yeah, I guess there is a number.

1:15:05Well, I would say this. Twice? Twice. I would say this. If I felt that that number, if we got to in success, would literally buy me like a year of freedom that I wouldn't have to do anything I didn't want to for money, I would take them. But if it was just, you know, no. Because I'd be like, that's still not going to change my life, you know? And one of them agreed to film in New York, one didn't. So for me, it's like, if you're filming in New York, and I don't have to get on a plane, I mean, even if you tell me there's a less likely chance of success, because I know now the big, big lesson that I learned, I learned actually a really valuable lesson when I had the CBS sitcom pilot in 2016, and it didn't go.

1:15:45It gave a year of my life. My daughter was one, and it was this whole thing. We shoot the pilot, you know, it's like crazy, like amazing. on the LA lot with, you know, CBS Radford, like this crate, you know, Chaz Pimentarius playing my dad, Annie Potts playing my mom. It's like this whole thing. And I'm like, wow, like, you know, my family, I gave all this. And then what happened was, is I was on a plane, right? Coming from San Francisco back to New York. And it was the day that they were making the announcements on, yeah, you shoot, you know, they shoot 10 pilots, right? They're going to pick up five to go on the air that you as the consumer will see, right?

1:16:22So I see on my phone, an article comes out, CBS picks up their fall lineup and my show wasn't on it. So I text my manager, I'm like, damn, dude, like, you know, I just saw it, like, you know, whatever. And he was like, no, no, no. He was like, I was just gonna call you. Yes, those four have been picked up for fall, but it's between your show and another show on which one is gonna be the winter pickup. There's gonna pick up one more show that's gonna start in January and it's between your show and another show that I think the show was about a talking dog. So they're like, I'm like, okay. So the plane is like taking off, like, you know, like accelerating to like take off.

1:16:59And I was sitting in the front and the first, the lady was like, the flight attendant was like, you need to put your phone away. Cause I'm like texting, whatever. She's like, put an airplane mode. And then I'm like, all right, I'm, you know, whatever. We're like literally like taking off and I'm going to put an airplane and my fingers going like this. And a text comes from the top of my screen from my manager saying they went with the other show. Sorry. and I was like oh shit and then like I hit an airplane mode and like my head went back into the headrest and I just for like two hours was like in like this fog that has never happened since for me but it was like this thing where I was like fully disconnected from reality where I was like not even in my body like what am I gonna do now and then whatever started to slowly get back into my body I land I you know my family didn't know I tell them and I tell uh you know they're like oh sad whatever and i tell my one-year-old daughter i'm like you know that big show that daddy was working on like it's not gonna happen and i'm sorry i like and she goes she was like oh so can we not go to the park then and i was like no of course we can go to the park she was like oh so then why are you saying you're sorry yeah and i was like oh shit yes i was making this all about me my family my daughter doesn't care at all she's like just push me in in the swing.

1:18:12And then I learned that it was never about the end result. It was always about, like my father would always say, it's not about the outcome. It's about the output. I want to see your output. I don't care if you win or lose. It's never about that. It's about your effort, right? And I realized the relationships I, like, yes, my pilot didn't get to air, but I still made those relationships. I still got those opportunities. I still was in the present every day getting this opportunity. and I always kind of regretted all these years of being like, I didn't enjoy that process as much. It was outcome dependent for you.

1:18:44Yes, where now I don't feel that way. Now I'm like, maybe it will only just be a pilot again, but now I'm like, oh, I'm getting like a second chance to be like, live this thing the right way now. Like enjoy these moments the right way and understand maybe your show gets on the air, maybe it's not about that. It's about these possible relationships you're going to make, this kind of new thing to look forward to each day. That's what life's about. It's amazing. Yeah. You want to go check out some books? Yes. Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it.

1:19:18We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything. I just wanted to say thank you.

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