


11 Oct 2025 · 42m

In this second part of their engaging dialogue, comedian Pete Holmes and host Ryan Holiday discuss topics ranging from success and psychedelics to the deeper meaning of laughter and enlightenment. This episode delves into the philosophical implications of humor and personal success, intertwining Stoic principles with the art of comedy.
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0:00I'm recording this on a Monday, and Monday is our grocery store day in our family. I usually pick my kids up from school and we go over to Whole Foods, get all our groceries for the week. Although here very shortly, we're going to go over there to get our Thanksgiving turkey because they've got a bunch of great options. Turkeys start at$149 a pound if you have Prime with organic birds at$299 a pound. And they only carry no antibiotic ever turkeys that will bring quality to your table at a great price. Whole Foods has great everyday prices on all your Thanksgiving essentials, whether you celebrate with a massive family or just a few close friends.
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1:11Prices higher in Alaska and Hawaii. Check it out at a Sleep Number store or sleepnumber.com today. Look, ads are annoying. They are to be avoided, if at all possible. I understand as a content creator why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like The Daily Stoic going. So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you a ad free version of Daily Stoic.
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2:45Welcome 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.
3:36Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So you probably know this. When guests come out to the bookstore, we record, in the studio, which is next door to the bookstore. And then usually my last question is like, hey, you want to go check out some books? And we walk next door and I sort of give them a tour of the bookstore and I pick out little books for them here or there. Now, most people love this. And then some people struggle because they think I'm just like loading them up with books that maybe they wouldn't have ordinarily bought. And then it's like, am I tricking them into spending a lot of money?
4:10And then there's a camera behind them. So like, they don't want to be rude. And I actually, it took me a while to pick up on this dynamic. Like it was inconceivable to me that I would have made my friends pay for these books in the bookstore that I'm specifically picking out and raving about to them. So like, I couldn't understand that's the vibe I was picking up on. And so finally I did. We have to tell them beforehand, Ryan's going to pick out some books for you after they're free. If you don't like them, you don't have to take them, but like you're not paying for them. Right. And then, um, when I had Pete Holmes, who's my guest today, We had part one of the episode earlier in the week.
4:44Pete was briefed on this in advance and still had very strong opinions about the books. Like, let me play you this clip because I thought it was hilarious. Have you read Outdoor Kids and an Inside World? No. That's good. That might be up your alley. I don't know why, but I immediately am not into it. Is this a cover reaction? I don't like the title. You would disagree with the idea of having an outdoor kid? I don't like it. Okay.
5:13I've never had anyone put some bath. Usually they just hug her me.
5:21Which is so funny because Pete is one of the nicest, sweetest. Like when you think stand-up comics, most people think sort of like acerbic and direct and sarcastic. And Pete is those things, but he's also like just an incredibly sweet, kind human being. So like for Pete Holmes to be the one that pushes back on the books for the first time, I just thought was surprisingly wonderful. We had a great conversation. As I said, I've known Pete a very long time. I first did You Made It Weird, maybe back in 2019 when Stillness is the Key was coming out. He came on virtually back in 2020. You can listen to that episode.
5:59I've done his podcast a couple more times. Always amazing conversations. His podcast is one of my favorites. I listen to it all the time. I download it when I go on trips and I just listen to it when I'm sitting there on the plane and try not to watch TV. But I do like to listen to Pete Holmes. We had a great conversation in part one. In part two, we're talking about books, talking about this phrase he has written in his mirror, talking about having more compassion for others and his relationship with accomplishment and ambition. And then two jokes that are in meditation. So I actually think the Stoics are very funny.
6:31As I said, Pete Holmes had a great show on HBO called Crashing. He's been in a number of stand-up specials. His most recent one, I think, was recorded in Minneapolis. You can watch it on Netflix. It's great. We watched it. We loved it. He has a book called Comedy Sex God. Actually, Comedy Sex God. That's the little play on words there. And he has one of my favorite podcasts, You Made It Weird. You can follow Pete on Instagram and on Twitter, at Pete Holmes. But in the meantime, just get into this interview, because it's great.
7:02When we kill time, time is killing us. So you never get those three hours back. And I'm not saying you have to be like Mark Wahlberg and get a workout in, but I'm just saying like, what are you going to do in that time? Well, this is interesting. Again, for the sake of a lively podcast, I think about this all the time. I alternate between what you're saying. And there are times when I'm really lit up and devouring life. I can get into like what my friends know as a Tony Robbins phase. Yeah. Like I'm like, get up at five and do breath work and cold plunge. I do that stuff even when I don't feel that way, just because I like it.
7:41But there's another thing, and I think you're going to agree, if I get a three-hour delay, which I often do, not often, but as much as the next, you could walk and read and achieve and all that sort of stuff. But there's also just, well, we could do it right now. If it's not in the moment, where is it? No, I'm not saying you have to productively use the time. I'm just saying, am I going to spend this time angry? Am I going to spend this time watching the seconds tick by? Right, right, right. Like if I sat there and meditated for three hours, that would also be great. Yeah, yeah, yeah. Or if I was just chill and had a delightful conversation with the person sitting next to me.
8:18The point is just to be there and to be alive as opposed to what if you're an anxious person, which I am, or if you're a person who needs to be in control all the time. To file it as wasted. Like, I'm going to kill this time by, like, I just go, okay, I'm going to go do something else. Yeah, yeah, yeah. And it could be, like, I've always wanted to watch this movie, and now I'm going to watch this movie. Like, that's something to show for it if you enjoyed the movie. Right, right, right. You know? Yep, I'm with you. I didn't think we were disagreeing as much as I'm, like, a delayed flight, I think of them very fondly.
8:51Yeah. I sometimes remember the names of people that I talk to. Because it's a really unique situation. You're in the same boat. Yeah. You're in the same plane as all these people. and everybody's having different reactions. I think travel is one of those humbling experiences where you really are out of control. And I thrive in those. I do worse when I'm late to the airport. If it was my car departing at the wrong time, that's harder for me to be chill. But if a flight is delayed, the thing that I was getting at was like, in the moment, which I think is our little snapshot of eternity. I think what we call the present, again, this is everything I'm saying is pretty much Rupert or Eckhart or Ram Dass or all these people.
9:35But so it's just going to be a soup. I'll do footnotes at the end. But it's like the present moment isn't like one frame of film with an infinite amount of past behind it and an infinite amount of future in front of it. That's not really our experience. It's the only thing there is. It's eternity. Yeah. It's how, and then the mind interprets that. How much time, one time I was on ketamine and I kept laughing going, and I go, how much time was there between that which is and that which never was? How long is the present moment? Is the present moment a moment? Is it a second? Is it a year? But also as soon as the clap is gone, it wasn't.
10:19Yeah. It makes a lot more sense on drugs. But where that gets useful is if you are delayed and you can sit down. Jesus tells a lot of parables about this, trying to explain how precious. Also, Eckhart Tolle, if you have church trauma like I do, a lot of people tell that story about the beggar sitting on the box and he's asking for change. And finally, someone says, what's in the box? And he looks in the box and it's filled with gold. Look to the New Testament for dozens of other parables that are like just trying to say it's already here. You already have it. He's like, tomorrow will take care of itself.
10:53Yeah. But what are we talking about? Yeah. What we might say in the modern day is like, tomorrow doesn't exist. You know, what are you talking about? Show me tomorrow. Yeah. And show me the you that's worried about that tomorrow. We're getting a little heady, but in the airport, what I was going to say was you can sit and again, you could do it right now. We have the hum of the air conditioner. One of the most helpful meditations or just kind of practices is going like, hear the sound of the air conditioning and like, try to, this is again, Rupert, try to put like an imaginary hand and touch what is the sound made of?
11:28Like, what is it? What makes a sound? You can do it with your eyes open. What makes the sight of Ryan? What makes the feelings in my body? And they're all made of the knowing of them. And a delay at the airport is a really good opportunity to trip out and listen to the commotion and the sort of the white noise of an airport and just go, this is me. This is made of me. I flew into Newark yesterday. I know, sorry, last week. I flew into Newark last week and I was walking out and I realized, oh, I slept, right? Like I spent, I had a flight that was supposed to take off at 10 and we took off at 4 or 5 a.m.
12:09Like five years ago. And I walked by it and I was like, I slept right there. And I had a fond feeling about it that I certainly did not have in that moment. That realizing, okay, five years later, all I can think of is like, remember when I spent the night at the airport? That was crazy. And actually I was coming home to close on this whole building. And so like, I thought I was going to miss the signing, which in retrospect, it's so silly. Like they don't, like you miss the signings don't matter. Now, the pandemic revealed, you can just do them in DocuSign. But it was like, I got to get to this meeting.
12:41If I don't get to this meeting, this thing won't happen. It's a little ceremony. Yeah. It's a stupid thing. And then they slide the keys across the table. Again, all of this can happen asynchronously, but it just didn't then. But I tortured myself through that eight hours at the airport in a way that I didn't need to. Yeah. That now, in retrospect, I clearly think of fondly. Why couldn't I have given myself more of that gift now? Well, that was in my book. There are a couple ideas that I uncovered for myself in my book. I'm sure you have dozens and dozens. I have one book. I meant to bring it.
13:17I was looking for it in my office. Oh, no, please. It's right here. Just kidding. But you know the feeling. It's like you write a whole book and then, or I do a whole hour of stand-up, and there's a couple things that you're like, or you do a million podcasts, and you're like, there's a couple moments. One of the ones in my book that, you know, if I asked chat GPT to summarize my book, I would hope it would include this. I actually did and it did a great job, but it didn't include this. Is good episode is the idea that when we watch television, we want stuff to happen and we want stuff to go wrong.
13:47And then the trick is to, cause I know exactly what you're talking about. Every time I'm at, I think it was O 'Hare. It is O 'Hare. One time it snowed so much, I had to sleep at O 'Hare. And when I'm there in O 'Hare, I look around and I'm like, that's where I slept. And it was a good episode. So we talked about this once, you and I. I was like, is this a good book title? Because I'm fascinated with book titles. Nostalgia for the Present. And I was like, that's all right. It sounds like a guy trying to sell a book, to be honest. But Nostalgia for the Present is a real idea. It's like, can we nudge that up?
14:20In real time, can you say good episode while it's happening? The way you would title that book now, especially if you wanted it to be like a Mel Robbins book or something, you'd call it like, you'll love this later. You'll love this later. That's what I would title that book. You'll love this later. Did she write Let Them? Yeah. I just started reading it in a coffee shop. And you ever read, look, I don't know anything about Mel Robbins. I just, I saw the title. I assumed it was like fluff. It is light. I don't find it to be like dense. And I'm like, oh, god damn it. Yeah. You know what I mean?
14:52And I was like, good for you. Thank you, Mel. There are certain self-help books that are like men, and then there are certain that are sort of universal, like for everyone. And I've just been on these planes. I've seen so many women reading Mel Robbins books, who I like. And I was just like, that's how you would make that book seem like, oh, yeah, I'm going on vacation. I don't read a lot. I'll read this. You'll love this later. You'll love this later. And my books have benefited from this. You want like a little mantra or expression that even if you don't read the whole thing, and you're like, okay, I get the basic point, which is like, hey, if you're gonna - The Body Keeps the Score.
15:24Yeah, which is like the densest, most fucked up book you could ever read. It's about like generational trauma. Yeah, but you call it The Body Keeps the Score and you're like, that's a secret. I need to know that. Yeah. You'll love this later. Can I have that? Go for it. It's a great idea. I'll just email it to myself. Most of my emails are to myself. Yes. I also thought about calling one yes, thank you. I don't know how Malcolm Gladwell does it. He writes a book called Blink and everyone buys it. Malcolm Gladwell is a legacy. That's like, he's like a rock band from the 80s. Like he was in a different world when there were multiple book chains and books got covered.
16:02He writes for the New Yorker. It's a different thing. There used to be a thing called the big idea book. And you could just, it could be called like strategy or it could be called like Blink or it could be like the wake up effect or, you know, like some made up like concept and people would be like, I'll read that. And now people are too busy. And also there's most of those books can be summarized in a 60 second TikTok. Right. So like you have to now it just has to be a different thing. Books play a different role in the culture and in dissemination of ideas. And so you just I mean, some people can do it like Robert Greene's doing a book on the sublime.
16:38Yeah. You know, like have a first time author take a crack at that. Right. And see if they can watch it sell six copies. Right. You know, and Roberts will sell a million. You just sort of broke my heart, though, because one of the things I don't like, and by the way, I paid$40 for the Let Them audiobook. So, like, I'm in, Mel. This isn't shade. I've even done it. I was with my manager last night, and he was kind of being my manager. And I thought, let him. Let him kind of, meaning, you know, he just kind of talks. And I'm like, maybe it gets a little fluffy. I'm like, yeah. And that job, and like, so there's this passage at the beginning of meditations from Mark Strelitz, it goes like, today you're going to meet people who like suck and are dishonest and shitty and all this stuff.
17:20He's basically saying, but then it seems like depressing and cynical, but what he's basically saying is like, that's their job. What's your job? Your job is to not be like that. Count yourself lucky that you didn't get the shit job. You didn't get the shit part in the play. You're the good guy, not the villain. Let them do their thing. And yeah, sometimes I go, this is just not just like this is their job, like literally your manager or whatever, but it's like, this is a long winded person. Yeah. This is a person who has to make light of everything. This is an extremely sensitive person. Right.
17:50This is them doing what they do. Right. What am I going to do? Yeah. And also I could try to make them not do that and probably have zero chance of success. Or, you know, like I feel like I'm pretty good when I talk to old people being like, this is, they're going to tell me this story again. You know, like, or they're going to forget where they're going and it's going to go into this other thing. And that's what I signed up for when I agreed to have this conversation. Not in a negative way. Yeah, yeah, yeah. Like, you're doing you and I sought you out. Why am I trying to bring you back to this point as if we're going to win this conversation?
18:23Winning the conversation is that I'm talking to an 80-year-old. Let's hear some 80-year-old. Let's hear an 80-year-old. Yeah. That's what we ordered. Yes. Here it is. Yeah. Yes. Thank you. The stones go, why are you expecting figs in winter? That's their expression. Don't go to the hardware store for milk. Yeah. You've known this person your whole life. You know that as good as they are, they're extremely fragile or they, in the end, they'll do the selfish thing or what, like this is them for better or for worse. Well, I, okay. So one of the things written on my mirror is don't get mad learning something you already knew.
18:56Yes. And that's true. And we can hold that. And then the great thing about having this somatic embodied emotionally brilliant wife is she goes and don't be mad at yourself for being mad at learning something you already knew so you have to that that grace that you extend to your parents for disappointing you in the same way you can extend to yourself and be like that's also okay because there's something still not fully cooked that i get mad like it's tricky like parental approval does seem to mean more, even though you can go like, but I have plenty of approval. Like that's the oldest story in the book.
19:35There's one person not standing up for the standing ovation. And you're like, right. So it's, unfortunately, you can't think your way through that. You kind of have to. No, that's true. It's like, hey, it's reasonable that way. And it's reasonable that you are reacting this way. There's kind of this higher lower self and you can accept the lower self and still aspire to the higher self, but just not kick yourself for not always being there. Yeah. Accept it and accept yourself when you can't accept it.
20:07Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin, and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in.
20:52We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory.
21:34Learn more at toyota.com slash trucks slash adventure dash detours. We just took our kids to an outdoor performance at the Nutcracker. They had a snow cone, and then they went insane in the car ride home. And one of the things I try to remind myself when that's happening is that I don't control my kids' behavior, especially when they're too far gone like that, but I do control how I respond, right? That's stoicism, but it's also what Dr. Becky talks about. Dr. Becky is a clinical psychologist and a best-selling author, and she founded Good Inside, which is there to give parents practical, actionable tools for handling those everyday challenges with confidence.
22:15My wife introduced me to Dr. Becky's books. I love them. I've recommended them a million times. I've had her on the podcast. And as it happens, Dr. Becky is hosting two live Q &A events for good inside members. I am one of them. She signed me up for it about a year and a half ago. I've loved it ever since. On December 1st, you can join Dr. Becky for her How Not to Raise Assholes event, which is about avoiding entitlement and raising kind, empathetic kids. And on December 15th, she's hosting her How Not to Lose It over the holidays event, which I'm sure we could all use. As I said, I'm a big fan of Dr.
22:52Becky. She's been a great influence for me as a parent and just as a human being. And Daily Stoic listeners can join for 15 % off with code STOIC15. You just got to head over to goodinside.com to catch the events.
23:13Every book I'm looking at, like the abs diet, there's no way. And this is one of the crises, I guess you could say, that we're facing is like the abs diet, without a doubt, could be summarized by ChatGPT. Yeah. And might even be better. Like stop eating this, this, and this, and this, and do this and this and this. I did that with the glucose revolution. Will you just tell me what I should do? Oh, take, eat fiber before you eat. Thank you. What is being lost though, and this is being lost in myself, like I was saying once in defensive TikTok in the 90s or the 2000s, if we wanted to know, is it more fuel efficient to drive with the AC on or with the windows down, like aerodynamics on a road trip, we'd watch Mythbusters.
24:01It was a 60 minute show and it's 30 % commercials or more. They're just stringing you along, not getting to the fucking point. And now it's a TikTok and someone goes, I don't know the answer, but it's like, it's this. Yes. The problem is, and I think we're starting to infuse this into our experience, is like sometimes it's just fun to watch Mythbusters. And sometimes it's fun to read the abs diet because how you are and what happens to your heart rate and the feeling of allowing someone else's consciousness to take over yours, it feels better than just knowing you should stop eating carbs. Just reading is good.
24:39Reading is good. There may be a story in that book. And by the way, most of these books are rejects. There's a company called Books by the Foot. Well, there's an L. Ron Hubbard right by your head, which I thought is really a funny choice. So there's a company called Books by the Foot, and they just sell books for things like this. Some of these are books for my friends. Some of them my publisher sent me a bunch. But most of these are like you're buying them literally by the cubic foot. Fast Food Nation. I thought of that last night. To fill them up. So these are not my books, and they can't come out.
25:05So this is just a set. But yeah, also like some of the most interesting things I've ever learned that I think about all the time were in books that that was a tangent. Yeah. And so the idea of just distilling it, just give me the nut of this thing. And it's like, that's not why we're reading. ChatGPT won't know what would grab you. Like I've read so many books and I'm sure what stuck with me for 40 years might have been, would certainly have been left out of the summary. Yes. Yeah, for sure. Yeah. And also just reading in and of itself is good. But to bring it into what I do, going to a comedy show is good.
25:42Laughing for an hour is good. Syncing up not just with me, but with an audience is good. And, you know, you can also watch clips of me on TikTok and that will be the momentary little thing. That's fine, I suppose. But it's, but, you know, the big picture thing is better. I just think, for instance, speed reading is one of the most nonsensical things that I've ever heard. First off, it's not real. I think it's a giant scam. But the idea of nobody's like, let me show you how to have sex faster. Or here's how you can scarf your food down and barely taste it, but you'll still get all the nutrients.
26:21It is a pleasurable, beneficial, historically proven way to stretch your empathy, stretch your understanding of the world, learn things, decompress, disconnect. It is a thing you should enjoy doing. Now, if you don't enjoy doing it, you don't need to do it. There's other ways you can learn things. But the idea of like, I love reading so much, I want to fast forward through it is ridiculous. Like you're missing the point. Let's have sex faster. You're right. And we all know, it turns out these things take practice though. We know cooking a meal is like great for digestion and stuff. You're going to appreciate it so much more.
27:06We are now just post-mating. Chelsea Peretti has this great joke I love where she goes, what happened that every meal I'm like, what would a king eat? And I'm like, we're figuring out slowly that what we want isn't obviously what we need. It's not even what we really want. And I'm one of these completely, I have no evidence to back this up other than my inherent optimism. I think we're going to start figuring that out. I think AI, I think all this stuff is going to help us realize that all the donuts in the world isn't the answer. And there'll still be this yearning and it'll help us see it more clearly.
27:42It's not quite a bit, but I feel like we don't talk enough about how bringing donuts to something is actually rude. You're like, here, eat this thing you shouldn't eat that no one feels better after eating. I feel like it's a microaggression. Microaggression is not using the wrong pronoun. Microaggression is bringing... It'd be like just giving out cigarettes. Like, why are you doing this? We shouldn't do it. We know we shouldn't do it. It's a crash. Yeah, exactly. That's very funny. I'm with you. it's not quite a bit because if anything about stand-up trends, I mean, that's a huge part. I don't spend a lot of time thinking about that.
28:18But if you want to write a joke about how you should bring donuts to everything, there's your mailbook. That's the bit. Like you can't fill an arena saying, don't bring donuts. You can take it from me. You can fill a small theater.
28:37but if you want to say why are we only bringing donuts to sad things yeah bring donuts to everything i mean sold out yeah it's like when you're telling people what they wanted to do already that's that's exponential and when you're challenging them and so like i think it's so funny people be like because my stuff has done well they go oh she just he just did this for the money you know and it's like yeah i picked this obscure school of ancient philosophy because i I thought it was my rocket ship to the top. Like I couldn't have picked a less attractive thing. Yeah, yeah, yeah. And like, so sometimes people will be like, oh, they're just selling out.
29:11It's like, do you know how hard they're working to get people? Like, I think you think I have a headwind or a tailwind. And I don't think you realize how, what a headwind this person is actually working with. No, it's true. It's funny that I also wrote down the book, You'll Love This Later. That is me trying to be like, is this what you want? But yeah, who cares? Maybe it was when you were interviewing Taylor Tomlinson, you said something that caught me and that I thought about a lot since she said something and then you were like, no, I am one of the greats. Oh, wow. And you had this interesting discussion about it.
29:43But I think if people hear someone going like, I'm one of the best, I'm one of the best to ever do what I do, or I'm one of the greats, that feels like immediately egotistical. It's horrible. I mean, out of context, I'm like, I don't know. Right, right. I don't know about that. But the discussion you ended up having was fascinating. I think you're like, because you get to do what you do. You get to do the thing professionally and 99 % of people don't get to do it. So, so statistically you already, I think that's how you were saying. And then also I think that you enjoy it, that you're the best version of yourself.
30:15I can defend it. Certainly. I would say that if I didn't think I was one of the greats, meaning in this context, I'm like, obviously there's these incredible outlying savants. I think that the perspective of I'm one of the greats is a measuring of the degree to which I'm doing the comedy that I would like to see. Yes. And when I think, and I'm the only one that can gauge that. So I can't even listen if you say I'm one of the greats or if you say I'm not one of the greats. I'm going like, if I was in the audience, and I mean this very firmly, this is exactly what I would want the show to be. Yes.
30:58without blemish. Yeah. Exactly what I want. And in that sense, I agree with myself. No, I'm not asking you to defend it because I was defending it for fun. Yeah, it was great. Like, I was like, oh, that's a really interesting way to think about it because one of the things that Stokes talks about, that Stokes talk about is like, if you want to win, pick a race that only you can win. If you're like, no, no, I have to be the best. And by that, I mean, I have to beat everyone. Then like, you better hope you're the most genetically gifted. You better hope that the actual fastest person is sick that day.
31:28You better hope a bunch of things go right. And sometimes you get it. And even if you do get it, you only get it briefly. But if you're like, no, no, no, winning for me is like, you set up your own set of standards. You set up your own definition. Then it's much more likely you're going to have that. And then you are one of one and you are truly one of the only people to do it that way. And that's an even better explanation of what I'm saying. It's like, in being Pete, I'm the best at that that's ever been. And that's a Bill Hicks thing. He goes, if you're being 100 % yourself, you'll be the only one that can do that.
32:04And you'll have supply and demand covered. It's also been something that I've been thinking about. I don't do a lot of psychedelics, but I think I thought of this when I was on psychedelics. I know the guy that clearly does a lot. That's not true. I don't. But it's also written on my bathroom mirror. It says flawless, meaning Pete is being Pete flawlessly. And I picture myself winning an Oscar. Let's say I am mad that the flight is delayed. And I picture like Barbara Walters interviewing me and being like, how did you know to eat that entire pizza to make yourself feel better? And I'm like, I just did what came naturally.
32:41And like, if you think about like a beautiful Philip Seymour Hoffman movie where you like, like think about somebody watching you. Yeah. And then let's say my mother does something that upsets me. I picture my mom winning an Oscar. It's like at the end of your life, you're brought out on stage and it's the Academy Awards and everyone's giving you a standing ovation. And they just couldn't believe. And I do like doing it with like, how did you know it would be so uniquely disappointing to your son when you said that? And it's like, I just did what? It was my instinct. Like every great actor. But that's kind of a cheeky way to make fun of my mom.
33:18But really, it's really helpful to go, you're doing this flawlessly. Yeah. And apparently we need you to be this because I believe that everybody is a response of a system. My mom is not an isolated individual. She is a part of this mosaic. That's perfect. That's the other, I'm trying to work it out. I already did this like meaning of life slash God slash whatever joke has been something that is really thrilling to me that people like when I do it. because that's what I've always wanted to do. And I'm like, okay, I have this one. It's what I'm going to do tonight. But then I need to write the next one.
33:58And I'm like, well, maybe I'll move away from using words like God and stuff. Because the thing I really want to say is kind of what we're saying here. And I've said it before, but it's, if I were you, I'd be you. And maybe you've heard me say that. I find that just incredibly powerful. It's like somebody that you really disagree with. You're like, it's the most obvious thing in the world. If you grew up in their body, with their genetics, with their parents, with their school, with their trauma, if everything that had happened to them happened to you, you would be them. Yeah. And there's something really like, that's compassion.
34:34Yeah. It's also self-compassion. If I were me, I'd be me. It's like, yeah, everything that happened to me, every trauma, every experience, every heartbreak made me into me. And then you start to see how everybody and everything is unfolding lawfully. Yeah. That doesn't mean logically or fairly. Or fun. Or fun or good. It's just, it's another way of saying yes, thank you. Yeah. And no, I just was really struck by that conversation because there's also this thing where it's like, look, you've got a show on HBO, you tour, you've done all these things. Like how elite does this definition have to be?
35:09And why do we make it? Why do we continue to move it out of reach so we can feel shitty? Yes. And there's also just some level of like, how many people would kill. I think about it. I've said this to someone, I was talking to someone and they're like, not only would they kill to be you, they would kill to have gone to high school with you. Like they would be telling people, oh, I know that person. Right, right, right. Like that's a gratitude exercise you're trying to get. Yeah. And then we're like feeling insecure. We go, I'm not enough. Yeah. Well, that's the seeking and resisting. Yes. The ego would rather be miserable than stop existing.
35:44And if, you know, if you said I've done enough, you sort of vanish, you know, and, and people that's intolerable. So you, you move the goalposts and you go, yeah, but I don't have an EGOT. Compared to so-and-so, it's nothing. Just, just stop it. Just stop it.
36:13All right. So in your podcast, you always ask people when they laugh the hardest. Yes. Can I add one thing to what we just said? I don't know why, but I feel like you'll like this. We've been talking about the top of the mountain. I'm going to come down to the earth and just say something fun. Sometimes people go like, there's no such thing as making it. I'm like, yes, there is. Like there is. Of course there is. And it's fun. Yeah. And it doesn't have to be where I am. There's a lot of people below me that have also made it. but you get this sense of like, one day you wake up and you're just like, I'm doing it.
36:46And that's worth, this is sort of in defense of achieving. As much as I like to say like, oh, just surrender and surrender. I'm also like, no, it's fun to chalk up your hands and fucking climb the structure. And when people are like, there's no making it. It's always the next thing. I'm like, no, there's a difference. I've been at a lot of different, and I'm not even talking about hotels or flights or anything like, or fancy food or knowing celebrities. there's a feeling where you go i answered the call yeah you're like did you make it into the league or not like there's a certain number of people in the nba at one time and when you when you're there and then if you make it long enough you you like most of the professional sports if you there's a certain number of years you play and then you qualify for like a pension right like that like to do that is an incredible achievement and just because you didn't win a championship doesn't mean you're a fucking loser.
37:39Like you fucking did it and you did it at the highest level for an extended period of time. That's great. And it's funny, I was talking to someone the other day who was like, they identified as a professional athlete, but they'd only played like minor league baseball. And like, there was a part of me that was like, that doesn't count. And I was like, wait, no, you were getting paid to play baseball. The amount of people in the world that would be desperate to just do that for one pitch is like incredible. And you did it. You fucking did it. You earned the thing. give it to yourself it can be your version of making it yes but i'm like you'll know yeah and it's nice like when can you call yourself a writer right or like an actor when do they get to say i'm a writer director or sorry i'm an actor director right it's like yes on some level there's no like club and you have to like qualify or whatever like a millionaires do you have a one million dollars and one dollar.
38:34But at the same time, like, you'll know, like, you'll know it's, there's people who are posing and then there's people who are writers because they write professionally and people consume their writing. It's not a black and white thing, but you'll know. Yes, you'll know. That's the same with comics for sure. Like I'm an entrepreneur. No, you're not. Like it's a pretty big club and welcome. When you do the thing, you can be in the club. Yeah, yeah, yeah. And if we weren't keeping you out of the club, it wouldn't be a club worth being in because it'll feel so nice. If it wasn't hard, if it wasn't discouraging, everyone would do it and it would be worthless.
39:10Yeah, yeah, yeah. Like there's a reason that it's... Scarcity and difficulty create the value that you then seek. That's right. That's right. So anyways, on your show, you always ask people when they laugh the hardest. And so whenever I interview comedians, I tell them that there's this stoic named Chrysippus who dies of laughter. Oh, wow. And we're told he's sitting on his - The ultimate compliment. He's on the list of unusual deaths on Wikipedia. Oh, wow. Which is quite an accomplishment, I would say. So he's sitting on his porch and we're told that a donkey walks up and starts eating figs out of his garden.
39:45And he says to the person who runs up to the, like, I'm so sorry with my donkey. And he says, you should give that donkey some wine to wash down those figs. And then he starts laughing at his joke so hard that he dies. And so my endless search is to find out what the fuck this joke means. Yeah. And then also I just enjoy, it's not just that he died of laughter. It's that he died of laughter at his own joke. At his own joke. At his own bad joke. Yes. There's something sage-like about that. Yeah. That's a guy realized. I mean, like the ultimate joke, I hope I'm not forcing this. This is what it made me think, is that God split into multiple things.
40:27That's a joke. So that's the cosmic joke, is that I appear to be over here and you appear to be over there. If you think of this as God's dream, that's a joke. We're all made of the mind of God. So it's funny that I think I'm over here and I'm worried that I'm going to die and you're worried that you're going to die and we're all talking about making it. That is funny. So he might have been dipping into like that donkey eating figs and drinking wine is the same as me eating figs and drinking wine. We're all asses. We're all asses and it's all, it's again, a very stereotypical, like psychedelic experience is like anything is everything.
41:02And he's like, anything is everything. This donkey. And that could click in such a way that it would be an enlightened kind of laugh. It reminds me of your thing about like, if you think that we're all monkeys on a rock in space, everything is funny. Everything's funny. Everything is funny. Like somebody made all this. We stacked these things on top of each other. We all had to be in the same place at the same time. And then we go and watch movies. And like, it's all so dumb and ridiculous. Like Seinfeld has that joke about how he's like, horses, they're like big riding dogs. They're big riding dogs.
41:37It's great. And you're just like, yeah, everything is ridiculous. Yeah. Like, I just think of the seriousness of people getting on horses for hundreds of years. Yes. They're big riding dogs. And then you watch like sci-fi movies and they get on worms. And you're just like, they're taking this seriously as a mode of transportation. Like you're just on the back of this wild animal. So dumb. I just think of the silliness of life. Maybe that's what he's laughing at. For sure. I mean, this came to mind. It's like, I've never done this on stage. I don't think it's that funny. But, you know, back when it was new that you couldn't bring water on a plane, a TSA agent, this is only slightly true, but I'm going to tell it the slightly true better way.
42:17She goes, you can't bring that water on the plane. And I'm like, yes, I can. And then I drank it. The water is still on the plane. Yes.
42:29I know that's dumb, but that is give that donkey some wine. Yes. I also, you know, he's tapping into like, some comedians don't like dissecting what a joke is. I think it's helpful. It's an incongruity. It's incongruous. It's ridiculous. To give a donkey wine. So that's a joke. It's absolutely a joke. I just also love like, I can't, that's gotta be close to the best. What if I die laughing now? Twice that joke killed somebody. Well, yeah, why is irony funny? Why are coincidences funny? It's just because it's unexpected and weird. But also I just love the idea of that's like the best way to go, right?
43:06Like you laugh so hard you die. Yeah, I think, I mean, having a heart attack and laughing, it seemed very similar to me. There's like a lot of wheezing. I bet he was very red, veins in the neck. Like, it doesn't sound that... Because then what's happening, it's like choking on your favorite food. Yes. You know what I mean? You're still choking. Right. Yeah, yeah. I guess I'm imagining he's just laughing and then dead. Yeah. You're right. Like, he's laughed so hard he gives himself a brain aneurysm and then is gone. As opposed to this, like... Exfixiation. Yes. Yes. You laugh and you dislodge something and you die.
43:41That sounds pretty good. Yes. Going out like that. I mean, I think about this a lot. I love that. I was just talking to somebody about the oldest joke they've ever found. And it was, you know, probably Babylon or something or Samaria. And they found it on a scroll and it was like, and it's about something awful because the past was awful. And they go, this guy buys a slave from a slave trader. And a week later, the slave dies. So the man goes back to the slave trader and says, hey, that slave you sold me died. And the slave trader says, that's weird. He never did anything like that when I had him.
44:14That's the oldest joke we have. And it's so funny that like, it's obviously unsuccessfully, but it's trying to soften a horror. Yes. It speaks to kind of like a... They both know this is bad. Like the, what the, at some level, what they're doing fucking sucks. I'm telling you, dude, it's everything I do. I do for my family. Like to me, a good joke, a good comedy, good art. And I'm not, I like Marc Maron. I'm not Marc Maron going up and being curmudgeon and trying to tear down systems or, or Jeanine Garofalo. or I'm not going at it that way. And I like all of those people. I'm just saying like offensive comedy to me is comedy where you come in thinking that food is great, sex is great, winning is great.
44:59And someone tells you food is great, sex is great and winning is great. And you leave. Does it question none of your assumptions? What a missed opportunity to talk about, that joke is talking about the horrors of slavery in their unconscious. And when I'm talking about Mark Wahlberg says, everything I do is for my family, not to toot my own, but in the way that I'm doing what I want to be doing is I'm saying it actually, I'm a very sensitive person and it really hurts my feelings when people say things like that. It makes me very, very sad. And I think it makes you sad too. I don't mean you. I just mean, I think it makes us sad.
45:40So if we could like dislodge the rock in the river and like it while we're doing it, that's why I've tried to write jokes about a lot of like just unconscious delusions that we have. And don't think, I don't think I have those. I'm built on leaky buckets from here. Well, there's, there's two jokes in meditations one is intentional one isn't and i think one is one is offensive for like offensive reasons and then the other is offensive i think because of what it challenges so the the offensive one he he's cribbing someone else but there was an an old joke even then that was um this guy is so rich uh has so much stuff that he has no place to shit he's like joking about the rich man who's so rich he has no place to shit that his house is just filled with stuff he has no place to shit so it's got a curse word in it.
46:31It's whatever. I think it's mildly funny. My favorite joke in meditations, which I think he's deadly serious when he's saying, he goes, ask yourself, am I afraid of death because I won't be able to do this anymore? And this implying whatever dumb shit you're doing. Oh, that's funny. You're like, I'm afraid. I don't want to die. I want to live forever. And you're currently at the DMV. Yeah, you hate it. And life actually sucks in some way or your life sucks. Yeah. And then you're like, but immortality is the key. And he's questioning whether this thing that you prize is actually so worth prizing.
47:08It's brilliant.
47:14Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.
47:29Thank you.
Comedian Pete Holmes is back for Part 2 and in full philosopher mode. He and Ryan dive into success, psychedelics, and why it’s not egotistical to say you’re “one of the greats.” They talk about how to find peace when life feels out of control, why laughter might be the highest form of enlightenment, and what it really means to “make it.”
Pete Holmes is an American actor, comedian, writer, producer, and podcaster. He first gained recognition in the early 2010s as a stand-up comic, and also released his first comedy special and worked as a television writer and actor. He is the host of the podcast You Made It Weird, author of Comedy Sex God, and the creator of the HBO show Crashing.
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