These 3 Rules Will Make or Break Your 2026 | Jesse Itzler

Most people will enter 2026 hoping life just gets better. Jesse Itzler knows that’s not how real change happens. In today’s episode, Jesse breaks down the three simple rules he follows every year to guarantee it doesn’t slip by. He explains why change has to start before January, how locking in the right priorities forces everything else off your calendar, and why more hustle isn’t the answer in 2026. If you want a year that actually feels different — and you want a plan you can stick to — this episode shows you how. Jesse Itzler is an entrepreneur, author, endurance athlete, former rapper, and part-owner of the Atlanta Hawks. He is the author of two books, Living With A Seal https://www.amazon.com/Living-SEAL-Training-Toughest-Planet/dp/1455534684/ref=tmm_pap_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9.wOC5K6swhA9Stl217wUZdaQrlkBSCy7EwQjXJjZO69_GjHj071QN20LucGBJIEps.fae05LC6xnOWR3wHw0tChaTIyR8M4Sj8kLxgC8PX65E&qid=1746533807&sr=1-1 where he lived and trained with David Goggins for 31 days. His other book is Living with the Monks https://www.amazon.com/Living-Monks-Turning-Happiness-Gratitude/dp/1478993421/ref=tmm_hrd_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9. Y8xRwL1kRL2ghdgF3o0-xgWmWAHR_iarie_8o6E39LnGjHj071QN20LucGBJIEps.7dNL7qPspZRahGzsOCQJWg92oqOk8NSK7nPOMMxH8EU&qid=1746046690&sr=8-1where he lived with an isolated religious community in the mountains of upstate New York. He co-founded Marquis Jet, helped build ZICO Coconut Water, and created the viral New Year planning tool called the “Big Ass Calendar” https://thebigasscalendar.com/. Plan 2026 using the Big Ass Calendar that Jesse created: https://thebigasscalendar.com/ Check out Jesse’s books: Living with a SEAL: 31 Days Training With The Toughest Man on the Planet https://www.amazon.com/Living-SEAL-Training-Toughest-Planet/dp/1455534684/ref=tmm_pap_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9.wOC5K6swhA9Stl217wUZdaQrlkBSCy7EwQjXJjZO69_GjHj071QN20LucGBJIEps.fae05LC6xnOWR3wHw0tChaTIyR8M4Sj8kLxgC8PX65E&qid=1746533807&sr=1-1Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus https://www.amazon.com/Living-Monks-Turning-Happiness-Gratitude/dp/1478993421/ref=tmm_hrd_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9. Y8xRwL1kRL2ghdgF3o0-xgWmWAHR_iarie_8o6E39LnGjHj071QN20LucGBJIEps.7dNL7qPspZRahGzsOCQJWg92oqOk8NSK7nPOMMxH8EU&qid=1746046690&sr=8-1 Follow Jesse on Instagram https://www.instagram.com/jesseitzler/?hl=en, YouTube https://www.youtube.com/@jesseitzler4, and X https://x.com/jesseitzler @JesseItzler https://www.instagram.com/jesseitzler/?hl=en Make 2026 the year where you finally bring yourself closer to living your best life. No more waiting. Demand the best for yourself. The Daily Stoic New Year New You https://join.dailystoic.com/nyny26/ challenge begins January 1, 2026. Learn more and sign up today at dailystoic.com/challenge http://dailystoic.com/challenge. 👉 Get The Daily Stoic New Year New You https://join.dailystoic.com/nyny26/ & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life https://dailystoic.com/life/ 🎁 This holiday season, give the gift of Daily Stoic Premium | https://dailystoic.supercast.com/gifts/new 🎥 Watch the video episodes on The Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos: https://www.youtube.com/@DailyStoic/videos https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/, Twitter https://twitter.com/dailystoic, YouTube https://www.youtube.com/@DailyStoic, TikTok https://www.tiktok.com/@daily_stoic?lang=en, and Facebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Ryan Holiday?

  Welcome 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,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. When I was in Seattle a couple of weeks ago, I said, well, another year is in the books, another year is gone. And what a totally normal, uneventful, not stressful, not difficult, not scary or weird year it's been, right? Certainly, there's been no need for Stoicism in the last 12 months, no need for focusing on what you control, no need to be resilient, to turn obstacles into

• 1:33Ryan Holiday?

  opportunities, no need to remain cool while it feels like everything is falling apart and the world is on fire, right? And it probably says something about a year or a moment in time where Stoicism is required, but that's the moment that we're in. 2025 required it, and 2026 will certainly require it. We have no idea what the year has in store for us, but we do know it's going to be challenging, as all years are. And that's where today's guest comes in. I knew Jesse Itzler was going to be in town. We've known each other a long Long time. Actually, we met at Lance Armstrong's house like 10 years ago. It was a very surreal dinner. Gary Vaynerchuk was there. I was sitting next to Bo Jackson.

• 2:18Ryan Holiday?

  Jesse was there. It was a surreal little experience. My son was a couple of days away from being born, so I was nervously checking my phone. My wife said it was fine to go, but she was like, be prepared to be interrupted because I could need to call you at any moment. So that's what I remember from that dinner. What a weird surreal moment that was. And so here we are 10 years later. He's on the show and here we are at the end of a year. And what I wanted to do in this episode is talk about how do we make 2026 an amazing year, right? How do we create newness in our life as we get older? How do we get out of ruts? Jesse told me some of the rules he lives by and what the kind of review process he goes

• 2:59Ryan Holiday?

  through at the end of one year now passed and how he prepares himself to have an awesome new year ahead. And I think that tees up very well the Daily Stoic New Year New You Challenge, which is kicking off in what 10, 11 days. On January 1st, me and thousands of other Stoics all over the world are going to be getting into the Daily Stoic New Year New You Challenge. It's a new one here for 2026. 21 days of Stoic-inspired challenges, one per day, some Q and A's with me, discussion platform, progress tracker, a bunch of awesome stuff. It's gonna be great. I'd love to see you in there. DailyStoic.com/challenge.

• 3:43Ryan Holiday?

  Lock in your spot before it's too late. Don't kick the year off with some procrastination or trying to get out of things. Dive in. I think it'll be awesome. And speaking of progress calendars and trackers, actually Jesse gave me this awesome one. It's called this big ass calendar. It's like the whole year laid out, like literally one giant sort of laminated piece with every day of the year. And you see it there. You're like, oh, 365 slots. What am I gonna put in there? How am I gonna fill this calendar? So I have a real life to show. I have real progress to show. And I thought it's awesome. We actually hung it up. Up in the office. So thanks to Jesse for sending that. Jesse is the author of two books, Living with a Seal, where he lived and trained with David Goggins,

• 4:26Ryan Holiday?

  well before he blew up and became the David Goggins everyone knows. His other book is called Living with Monks, where he lived in an isolated religious community upstate in New York. He's also the co-founder of Marquis Jet. He helped build Zico Coconut Water. And his new year planning tool called the Big Ass Calendar, as I said, is great. You can follow him on Instagram and YouTube and Twitter, at Jesse Itzler. And I think you're really gonna like this interview. I really liked chatting with him. He was great. I thought it was really fun. Then we had a great walkthrough of the bookstore as well. And then I had to run to pick up my kids, but I hope this helps you think about what you're gonna do for the new year. And again, I hope you join me in the 2026 Daily Stoic New Year, New You Challenge.

• 5:10Ryan Holiday?

  It's new. It's awesome. I'm excited about it. I'm ready to get after it this year, and I hope you will too. DailyStoic.com/challenge.

• 5:22Ryan Holiday?

  All right. So I think when people will be listening to this, it'll be basically the new year. And you had this great thing. You were saying like, if you just added these three things in your life, everyone's life would get better. I thought those might be three interesting habits to talk to people about kicking the year off. Do you remember all three of them?

• 5:37Speaker 01

  Yeah, of course.

• 5:37Ryan Holiday?

  What are they?

• 5:38Speaker 01

  Well, I found that like, most people don't want to change a lot of what they're doing. We live in routines. We're creatures of habit or whatever. So for years, I've just been doing these three things without changing much, and it's radically changed my life.

• 5:53Ryan Holiday?

  Okay.

• 5:53Speaker 01

  You know, and let me just preface that by saying that like, I'm 57. As you get older, and maybe you found this too, it's really hard to create newness.

• 6:03Ryan Holiday?

  Sure.

• 6:03Speaker 01

  Like, where the hell does newness come from? You have to like, schedule it. You know, it doesn't just happen. So I've been doing these three things, and they've really helped me. So the first one is called, it's an old, there's an old Japanese ritual. Took the liberty to tweak it a little bit, but it's called the misogi. And the notion around the misogi is you do one big year-defining thing. Every year.

• 6:24Ryan Holiday?

  Got it.

• 6:24Speaker 01

  So like at the end of 365 days in 2026, we're here, you know, last year, 2025, like, what do you have to show for the year? You worked hard, you had all these Zoom calls, but like, what did you really do that you're proud of?

• 6:36Ryan Holiday?

  And it doesn't really matter, like, if you got it, if you did it in January, you'd still be proud of it in December. You know what I mean?

• 6:43Speaker 01

  You'd be 100%.

• 6:44Ryan Holiday?

  Something, something big enough that it's year defining.

• 6:46Speaker 01

  Year defining. You have, like, you have one big, I always put one big year defining thing on my calendar. And you're not only just proud of it at the end of the year, you're proud of it when you're 80.

• 6:56Ryan Holiday?

  Yes.

• 6:57Speaker 01

  And you should be able to look back, I believe, and be like, so Ryan, what'd you do in 2015? Well, I know I wrote Living with a Seal, and 2017, I launched a new company.

• 7:06Ryan Holiday?

  That's the year I did X.

• 7:07Speaker 01

  Right, that's the year I did X. And that, so that's something that I do. And every year, I think about what that big thing is gonna be. And it should really be something hard, challenging. And if it's really truly year defining, then you're gonna learn a lot about you.

• 7:24Ryan Holiday?

  Yeah.

• 7:25Speaker 01

  And grow a lot from it.

• 7:26Ryan Holiday?

  So this is like, run a marathon, climb a mountain.

• 7:30Speaker 01

  Launch a podcast.

• 7:31Ryan Holiday?

  Yeah.

• 7:32Speaker 01

  You know, it could be physical, it could be mental, but, and by the way, who doesn't want to have something to show for the year that's like mega?

• 7:39Ryan Holiday?

  Yeah.

• 7:39Speaker 01

  So that's the first thing that I do. And I don't even know what it's gonna look like. I actually do know what mine is for 2026. But two years ago, I did a race called Ultraman. I did rim to rim to rim. So I can go back year, every year and pretty much do, do that. But here's the other thing that's great about that. Not only do you have something to show for it, but I find that the more you experience, the more you have to offer.

• 8:03Ryan Holiday?

  Yeah.

• 8:03Speaker 01

  You know? And I found that I'm showing up better as a husband, I'm showing up better at work if I have something I'm really looking forward to, or something I'm training towards or working towards. It also forces me to say no to other things.

• 8:19Ryan Holiday?

  Yeah.

• 8:19Speaker 01

  That don't move the needle. Like, you would think like, whoa, you threw on a marathon? How do you have time to train for that? Well, when you put that on your calendar, you start to weed out the things that like, you don't need to do.

• 8:30Ryan Holiday?

  You put that on your calendar, it takes stuff off your calendar.

• 8:33Speaker 01

  Correct.

• 8:33Ryan Holiday?

  Because you're not gonna be partying, because you gotta be training.

• 8:37Speaker 01

  Correct. Like, people might think that's insignificant, it's insanely significant.

• 8:42Ryan Holiday?

  Yeah.

• 8:42Speaker 01

  Yeah, so I've been doing that.

• 8:43Ryan Holiday?

  Okay.

• 8:44Speaker 01

  The second thing, I actually named this after my friend Kevin. I was on a hiking trip with my nine-year-old at the time, son. And my friend Kevin's nine year old daughter, we were on Mount Washington in the winter. It's like minus 30 with the wind chill. It's ridiculous. And we're camping outside in a minus 40 sleeping bag and we're bundled up. And I'm like, I turned to him like, Kevin, there's eight billion people in the world.

• 9:08Ryan Holiday?

  Yeah.

• 9:09Speaker 01

  We're the only people out here. Like, there's no one near us.

• 9:11Ryan Holiday?

  Yeah, we chose this.

• 9:12Speaker 01

  And we chose this and it was your idea. I'm like, he's a police officer. And I'm like, how often do you do this?

• 9:18Ryan Holiday?

  Yeah.

• 9:19Speaker 01

  And the guy lit up. He's like, oh, man. Ever since I graduated college, every other month, I do one thing that I normally wouldn't have done. I'm like, what are you talking about? He's like, instead of watching like the Georgia football game, I might go fishing. I might come out here to New Hampshire. I might take my kids to a show in New York City. I just do like a little mini adventure. I'm like, why? He's like, if you can't take one day out of every eight weeks, one day.

• 9:46Ryan Holiday?

  Yeah.

• 9:47Speaker 01

  And do something for yourself. He's like, you're really kind of work, life balances out of whack.

• 9:51Ryan Holiday?

  You're pretending like you're gonna get to all those things when you retire or when things calm down or go back to normal.

• 9:57Speaker 01

  Exactly.

• 9:58Ryan Holiday?

  But they aren't.

• 9:59Speaker 01

  No.

• 9:59Ryan Holiday?

  And time doesn't work.

• 10:00Speaker 01

  It doesn't wait for you to do that.

• 10:01Ryan Holiday?

  Sure.

• 10:02Speaker 01

  So, but then, and then he was like, here's the thing. He's like, so I do like six mini adventures a year, like one every other month. So here's why those two things are so important. Let's say one of your listeners is 40 years old, I don't know, and they live to be 80.

• 10:16Ryan Holiday?

  Yeah.

• 10:16Speaker 01

  And they just added from this podcast, those two things did everything the same next year. But they just did that consistently and they live to be 80.

• 10:25Ryan Holiday?

  Yeah.

• 10:26Speaker 01

  You'd have 40 year defining things that you might not have had. You'll have 240 mini adventures.

• 10:33Ryan Holiday?

  Yes.

• 10:33Speaker 01

  So like, you see how that.

• 10:34Ryan Holiday?

  That's a full life right there, almost.

• 10:36Speaker 01

  It's insane. It compounds in an insane value.

• 10:39Ryan Holiday?

  Yeah.

• 10:40Speaker 01

  So, once I started realizing that, God, man, I don't have to like change this 365 days. I'm only carving out like seven or eight of them, you know? Um, but look how this works over time. That really has had, and it's, and it's true for me. Like, you know, being 57, I've been doing this for a long time and I've built like this insane life resume.

• 11:03Ryan Holiday?

  Yeah.

• 11:03Speaker 01

  Of things. I don't even wanna call them accomplishments, cause I don't look at them as accomplishments.

• 11:08Ryan Holiday?

  They're experiences.

• 11:08Speaker 01

  They're experiences that have accumulated. And now at 57, I have this like, you know, I've lived with monks, I've run races, I've traveled. I've watched this, I failed at this, but. Through it all, it's just really been an incredible life, man.

• 11:26Ryan Holiday?

  What's the third one?

• 11:28Speaker 01

  The third thing is I'm not really good at resolutions that they don't. Most people aren't, you know, the statistics show.

• 11:33Ryan Holiday?

  Most of them don't make it even through January.

• 11:35Speaker 01

  But I am good at this, and that's just every quarter I add a new winning habit. So I'm a big believer that we're all products of winning habits, winning routines and a winning mindset. If you can get those three things right. And by simply layering in like a new winning habit a quarter, like I don't drink enough water. I'm gonna drink 100 ounces of water.

• 11:56Ryan Holiday?

  Sure.

• 11:56Speaker 01

  I'm never gonna be late to a meeting. I'm gonna add a 10 minute a day meditation practice to my life. Just slowly continuing to layer in, simple to add on to your everyday habits. And that's really worked out well, too.

• 12:11Ryan Holiday?

  Yeah, cuz I think people, they're like, I wanna become this transformatively different person or live a transformatively different life. But really, you're gonna get there by making as a number of small choices or decisions that, as you said, sort of add up or ultimately compound over time.

• 12:26Speaker 01

  Cuz it's really overwhelming and radical to be like, I'm gonna just transform. Like, it doesn't, for most people, work like that.

• 12:33Ryan Holiday?

  No.

• 12:34Speaker 01

  It works by taking baby steps and getting momentum. And I found like adding one winning habit every quarter, every nine, you know, three months is totally doable.

• 12:43Ryan Holiday?

  So like, I'm gonna start walking, or I'm gonna stop smoking, or I'm gonna like just things you're gonna start or stop doing, basically.

• 12:51Speaker 01

  Yeah, I mean, even just now, like, one of the things that I'm working on is just like, I'm an interrupter. I'm an interrupter, so I'm like, I'm really like one Mississippi-ing in my head after you stop talking to make sure that I'm not interrupting.

• 13:06Ryan Holiday?

  I'm interviewing you, you should be doing the talk. Look, every once in a while, like, hey, you should really speak up more. But I would say most of us talk too much, not too little.

• 13:13Speaker 01

  Right, right. So, you know, those are things, and I'll just, I'm not trying to do 15 things at once. I'm just trying to slowly layer.

• 13:21Ryan Holiday?

  So that's four a year. You just have that four positive habits a year.

• 13:23Speaker 01

  Right.

• 13:24Ryan Holiday?

  That's big. I mean, that adds up, especially if if you start doing them and then next year you add four more and next year you add four more and you and now some of those habits you're a couple of years into, you that is how you become a transformatively different person.

• 13:39Speaker 01

  Hundred percent. I mean, looking at me, I take I'm trying to fix the things and add habits that really will help me. So for example, I've been notoriously late my whole life, you know?

• 13:50Ryan Holiday?

  Yeah.

• 13:50Speaker 01

  I'm still not great at it, but I'm but that's something that I prioritize. Like this month, man, 2026, I'm not going to be late to a meeting.

• 13:59Ryan Holiday?

  Yeah.

• 13:59Speaker 01

  They're going to look at me like, what? Yeah.

• 14:02Ryan Holiday?

  We were planning on you being late.

• 14:03Speaker 01

  Right. And so those kind of things are what I'm talking about.

• 14:07Ryan Holiday?

  Yeah.

• 14:08Speaker 01

  And then, you know, layering in these little mini adventures and a big, the big kind of year defining thing on my calendar. And then, you know, look, I'm I really, I'm a big believer in planning.

• 14:22Ryan Holiday?

  Yeah.

• 14:22Speaker 01

  And I'm aggressive with my planning. I feel like most of us play life on defense. Our lives fill up with Zoom calls and other people's requests for our time. And I don't think people need more time. I think they need a better system.

• 14:38Ryan Holiday?

  Yeah.

• 14:39Speaker 01

  And if you have a good operating system, I mean, for your personal life.

• 14:42Ryan Holiday?

  Yeah.

• 14:43Speaker 01

  We have it for our business, right? We put systems in place for operating. But if you have a good operating system for your business, for me, that's my calendar, but where you're really following like, you know, you laying out what you want to do. Like my 2026 is baked, fully baked of what I want to do.

• 14:59Ryan Holiday?

  Yes.

• 15:00Speaker 01

  Family trips, vacations, one on one stuff with my wife, with Sarah, you know, the races I want to run, the Masogi, it's all on my calendar. Work's going to fill in around that.

• 15:10Ryan Holiday?

  Yeah.

• 15:11Speaker 01

  But I don't think you can just wake up and wing it like, well, I don't know, man. Now it's all of a sudden it's September and, you know, like, oh, I only got like 90 days left of the year. Like, it doesn't work like that.

• 15:22Ryan Holiday?

  Yeah.

• 15:22Speaker 01

  Especially as you get older and you have more kids. Maybe when you're younger, you could do that. But for me, it does, it just doesn't work.

• 15:40Ryan Holiday?

  There's a famous story you might like about Alexander the Great. So he's trying to conquer this distant country. And obviously, his reputation precedes him. So the rulers of the country sort of get together and they, they call a meeting like a parlay. And they go, hey, we'll just give you this land over here. You let us keep this, we'll give you this land over here. And Alexander the Great goes, you know, I didn't like march across the world to, to take what you're going to give me. He's like, I'm going to take what I'm going to take and you're going to keep what I give you. And, and Seneca tells this story because he said, this is our relationship with sort of self-improvement versus work, pleasure, et cetera, right? He's like, basically what we do is we let work take up all our time and then we, we use the little bit of leftover.

• 16:23Ryan Holiday?

  So I think it's, it's interesting what you just said, that like, if you lay out your calendar and you go, here are the important things that I want to do with my family, that I want to do with my health, that I want to get better at, you're like, work will find a way to fill in all the cracks.

• 16:35Speaker 01

  For sure.

• 16:36Ryan Holiday?

  But most people, most of us do it the exact opposite, right? You're like, the presumption is the work gets up the vast bulk of your week and your year. And then you're like, and then I'll make time here or there for family, friends, et cetera. And then we tell ourselves this lie, of course, we go, and I do it all for my family. And it's like, the calendar doesn't lie. You, you did it all for work and then you gave the scraps. The leftovers is what your family got. It's what you got. It's what, you know, your spiritual health, all these things that you should also be working on. That gets the leftovers and we should probably flip it.

• 17:11Speaker 01

  Yeah, I agree. I mean, that's what I, I mean, one Mississippi. Yes, right. That, that is, um, no, I mean, that, I agree. I mean, I think work's always going to find you, man. And if you think about how much time most people spend laying out their work schedule and reviewing that and that versus how much time they actually invest in planning their own personal life and invent a life of adventure and the things they want to do. You know, I just think it's as important to prioritize and plan your personal life as it is your business.

• 17:43Ryan Holiday?

  Yeah, to be intentional about. What you want to do as opposed to what most of us do, which is look, work is paying me money. And if I don't do it, the bill collectors will yell at me or my boss will yell at me or my clients will yell at me. So that gets all the the focus and then you're like, the rest of the stuff I'll figure out. I'll wing it or I'll get the leftovers and like your kids aren't going to yell at you now for it. But they'll resent you for it later or you'll you'll look back and go, hey, here's all the things that I missed that I can't do again. Or, you know, it doesn't manifest itself in the day to day, the same way that it does professionally. But you find out when the divorce papers come through or or the health, the doctor gives you the diagnosis for some preventable thing.

• 18:29Speaker 01

  It's funny because I mentioned that I had me, I named that Kevin's rule, you know, that that kind of principle. But I've been naming it's the people that have had the biggest impact on my life for the most part. And I've had a lot that have really impacted me, but the people that are the biggest impact aren't the people that have like necessarily millions of followers. They're people in my regular day life that I've come across friends or associates or whatever. And throughout my journey, I've been naming like tips. Yeah, Kevin's rule, I have my mom's, I have all these different rules. And you were just talking about your kids or children in general, and it reminded me of like, one of the rules that I had that I learned from a guy at a basketball camp I was at.

• 19:11Speaker 01

  Is that he said, he said to me and just talking is like, you know, I have a rule that I'm never too tired for my kids.

• 19:16Ryan Holiday?

  Sure.

• 19:17Speaker 01

  And I love that. And I've it stuck with me. So I have like probably 20 of these rules I've named after people. Maybe some, one day someone will name a rule after me, but I love that. And I think about it all the time. Like if I come home from a trip and my kids want to have a baseball catch.

• 19:32Ryan Holiday?

  Yeah.

• 19:33Speaker 01

  And I'm like, oh, I'm too tired, you know, like something is wrong, you know? So.

• 19:38Ryan Holiday?

  Think about that, like I try to remind myself, the pool is never too cold.

• 19:42Speaker 01

  Yeah.

• 19:42Ryan Holiday?

  It doesn't matter that I just got dressed.

• 19:45Speaker 01

  Ryan's rule.

• 19:45Ryan Holiday?

  I just got dressed. It's like when they want you to jump in the pool, you jump in the pool. And I don't always do it, you know, it's a rule that I don't always fault, but I certainly feel guilty every time I don't. It's like, what, what am I prioritizing over this? And it's not a request, it's like an invitation.

• 20:02Speaker 01

  Yes.

• 20:02Ryan Holiday?

  You know, that that's a rule I I got from someone's name is Russ Roberts. His rule is whenever your child offers their hand, you have to take it. Obviously, literally, if your kid wants to hold your hand, you take it. But I think what he really means is like, when they're like, hey dad, do you want to play video games? Or they're like, hey, I need to go to the store. Can you take me? It's basically whenever they are inviting you into their life or to do something with them, you take it.

• 20:29Speaker 01

  Yeah, I have a similar rule. It's Ben's dad's rule. My friend Ben told me this about his dad growing up. And he said that, so for me as a parent, I find myself encouraging my kids to do the things that I love to do. You know, so I'm like, oh, let's go play basketball. I love playing basketball. They might not want to do that.

• 20:48Ryan Holiday?

  Right.

• 20:48Speaker 01

  Ben told me that his father would find out what it is his kids like to do. Like, let's say maybe his son liked to bake, you know? He would then take baking lessons.

• 20:58Ryan Holiday?

  Wow.

• 20:59Speaker 01

  And he would do, oh man, it was like, I was like crying when he told me this, man. It was like, I loved it. And his dad would sign up for all these things that his dad had no interest in doing.

• 21:10Ryan Holiday?

  Right.

• 21:10Speaker 01

  But his kids were interested in it.

• 21:12Ryan Holiday?

  I almost broke down. I was in a car once. I was in San Diego going to a talk. And the driver picks me up and I was wearing a Metallica shirt or something. And he goes, oh, do you like Metallica, some heavy metal band? And I go, yeah, I do. I was like, do you? You know, and he was like, well, I didn't. And I was like, what do you mean? And he's like, you know, my son is really into heavy metal. And he's like, so every year I would take him to one heavy metal concert. So he's like, I've seen this band and this band and this band. And he was like, I never liked it. But after, you know, 20 years of this, like, I've seen all of them and I am a fan. I loved it so much, not just because it was sweet, but like, it tends to be with music or any kind of like cultural stuff that parents have the exact opposite reaction, right?

• 21:55Ryan Holiday?

  It's like, you like rap music and your parents are like, you can't listen to that. It's not appropriate. Or like, turn that shit off. Like, it's not just that parents tend to not be interested. They're anti-interested. They're like trying to crush that interest. And here, this dad with a thing, and this would have been quite some time ago. So the music would have been more controversial than it is now. He's going like, no, no, you're interested in it. Therefore, I'm interested in it. Therefore, we're doing something together about it. And it was, whenever you hear stuff like that, it's just the sweetest thing in the world.

• 22:26Speaker 01

  Oh, my God, yeah.

• 22:27Ryan Holiday?

  You gotta do that.

• 22:28Speaker 01

  Yeah, especially because like, you know, it all goes by so fast, which everybody knows. But, you know, you think you're gonna be the age you are forever.

• 22:37Ryan Holiday?

  Sure.

• 22:38Speaker 01

  And like, it's getting harder to do something like, you know, like I'm 57. But like, how many more relevant years do I like? I was on my, I have a lake house and I was taking the kids water skiing over the summer. I didn't see any 70 year olds water skiing.

• 22:51Ryan Holiday?

  Yeah, sure.

• 22:52Speaker 01

  When I was on Mount Washington and it got a little busier the second time we went, I didn't see these 70 year olds going. I'm sure there are, but like, I didn't see it like.

• 23:00Ryan Holiday?

  Well, that's the lie people tell themselves about travel and stuff, right? Peter Attia talks about this, like you're gonna, you think you're gonna do this when you stop working. Nobody's having fun traipsing around Italy when they're 75. They can't do most of the things. It's, it's painful.

• 23:15Speaker 01

  No.

• 23:15Ryan Holiday?

  And so you got, the whole point is you should do it now, not just because you might not be able to do it later. Cause you could die, but it just won't be as good later.

• 23:22Speaker 01

  Yeah, you won't enjoy it as much. Yeah, I know. So I mean, like, that's basically how I live my life. I mean, I'm trying to, I'm almost living like ma- in a manic, like, trying to do as much as I can now. I don't want to say in a crazy way, but in a designed way, I would say, you know, like, cause I'm very aware of that. You know, I was very aware, like when my parents were getting older and they lived in Florida and I lived in Atlanta. I wasn't seeing them that often. Maybe I'd see them like four or five times a year. Recognizing like, man, if they live another 10 years, like, I'm only seeing them two or three times a year. Like, I don't have 10 years, I have 20 visits.

• 23:59Ryan Holiday?

  Right.

• 23:59Speaker 01

  When I started to like, look at things like that, and now I'm looking at that with my kids too. You know, it's changing. Yep, I like to look at things in five year increments.

• 24:09Ryan Holiday?

  Okay.

• 24:10Speaker 01

  So my son now is a sophomore in high school. So in five years from now.

• 24:16Ryan Holiday?

  He's in a totally different phase of life.

• 24:17Speaker 01

  Yeah, in five years from now, my whole life looks different. So right now, everything's great. All my kids are home. Sarah's parents are alive. You know, I lost my parents within the last five years. I lost both my parents. But in five years from now, all my other kids are in high school. My oldest is out of the house. I'm almost an empty nester.

• 24:37Ryan Holiday?

  Yeah.

• 24:38Speaker 01

  Parents, Sarah's parents and those that are older and they're 80, they're now in their 90s. It's a whole different chapter.

• 24:44Ryan Holiday?

  Sure.

• 24:45Speaker 01

  You know, so you gotta think about that. And that, and that will help you think about, at least in my case, how I want to live out this year, 2026. And beyond, you know, that really dictates, do I want to go on that trip or do I want, my son's only here for two more years?

• 25:02Ryan Holiday?

  Right.

• 25:03Speaker 01

  Is this gonna, am I back by six o'clock? Like those decisions, they're like magnified and multiplied. And it's a really important lens to look through life versus like, oh yeah, I'll just do it tomorrow and.

• 25:16Ryan Holiday?

  No, I had one of those where I was like, you know what, like I get to pick my own schedule. Like I was like, you know what, maybe I'm just like not going to come into the office one day a week. And then I'll just spend more time with my kids. And I kind of like, I'd been thinking about it and my wife and I've been talking about it was like a plan. And then I was like, you know what, like this year I'm going to do it. And then I, and then I was like, wait, like I missed it. Like me not going to the office on Friday doesn't do anything because I still have to take them to school. Like I might as well go into the office after I drop them off from school. Like there was a time when that would have been really powerful and important. And this is, I think a lesson just beyond parenting is like, as you're, as you're making these plans, actually the value of those plans is often disappearing or the ROI is, is diminishing as you go.

• 26:01Ryan Holiday?

  Like, I could have been there, you know, this time, but they, they're like, what are you doing here? You know, like, what did you do all day? Like, because I, I could have, like that little thing is gone. That opportunity to just where they're at home all day. They're not at home all day. And by the way, they want to do stuff that doesn't involve me. You know, on Friday, like that, that's what's always changing. So you're always telling yourself, hey, I'm going to get to it later. But that's something else that Seneca talks about. He says, the one thing all fools have in common is they're always getting ready to start. So you're making the plan, you say you're going to do it, but like, the whole point is you gotta fucking do it now. Cause now is when the math on it actually works, not two years from now.

• 26:43Speaker 01

  Yeah. The last three years I've taken trips with a group of friends. There's about 10 guys and, and we rode our bike across America. We went to Finland to tour the best saunas in the world. We went on a sauna tour of Finland. We did rim to rim to rim at the Grand Canyon.

• 26:57Ryan Holiday?

  Did you do that one where you jump in the actual, like through the hole in the ice?

• 27:00Speaker 01

  Yeah. And the Baltic, we did, we did it all. And when I first sent out the email, hey, guys, I'm, we're going to go to Finland. You know, I literally wrote like, I know you're gonna say like, it's, I don't have the time.

• 27:12Ryan Holiday?

  Yeah, it's impractical.

• 27:13Speaker 01

  Put this down.

• 27:14Ryan Holiday?

  Yeah.

• 27:15Speaker 01

  And build around it. We're going to Finland, you know?

• 27:18Ryan Holiday?

  Mm hmm.

• 27:18Speaker 01

  And we've done it. And for the last three years, we've, it was never the right, two weeks to bike across America. You're never gonna have, everyone's got jobs.

• 27:26Ryan Holiday?

  That's inconvenient whenever you do it.

• 27:27Speaker 01

  It's never gonna be the right time.

• 27:28Ryan Holiday?

  Yeah.

• 27:29Speaker 01

  You know, so let's just do it.

• 27:30Ryan Holiday?

  Yes.

• 27:31Speaker 01

  And we, and we're so glad we did it. And here's the interesting thing about that. This is crazy, but of the 10 guys that did these trips with me, I only knew one of them 10 years ago. So I got this new friend group.

• 27:45Ryan Holiday?

  From the.

• 27:46Speaker 01

  From doing these things like, and, and that didn't exist in my life, like 10 years ago. And I think a lot of people, as they get older, think like, where's my tribe? Or, you know, I, I, I don't know, or like.

• 27:59Ryan Holiday?

  No one's gonna give you one.

• 28:00Speaker 01

  No, no, they're not. You gotta go and, and make an effort.

• 28:04Ryan Holiday?

  Yeah.

• 28:05Speaker 01

  And not everybody wants that, you know? But it's been amazing, you know?

• 28:10Ryan Holiday?

  I think there's something about like the Masogi thing, like doing challenges, like so for, for Daily Stoic, we do this thing called New Year, New Year. It's 21 days of like challenges. And the whole point is they're like fucking hard. Like, how do you spend the first 21 days of the year doing something challenging? And like, some of them are more challenging than others. Some are physical, some are mental, some are spiritual, whatever. But I do think there's something about like doing hard stuff that's really good for you. And like, there's big hard stuff, like I'm gonna bike across America. And there's also big hard stuff, like, you know what? I'm gonna clean out that drawer in the kitchen that has become a doom bin of just everything. Like, I'm gonna do this thing that I don't wanna do, so I can be the person who did it.

• 28:49Speaker 01

  That drawer's so hard, I can't even do it.

• 28:51Ryan Holiday?

  Exactly.

• 28:52Speaker 01

  I can't even do that.

• 28:53Ryan Holiday?

  Right. It's easier to run 100 miles than clean out that drawer.

• 28:56Speaker 01

  Yeah.

• 28:56Ryan Holiday?

  Or like, mine is like, I'm usually more of like an inbox zero person, but it's like, I'm gonna like declare email bankruptcy and wipe. I'm gonna start with zero emails on January. That's like one of my goals.

• 29:07Speaker 01

  Oh, I nuke my emails in December. I go to zero.

• 29:09Ryan Holiday?

  Yeah.

• 29:10Speaker 01

  Delete all.

• 29:10Ryan Holiday?

  Yes.

• 29:11Speaker 01

  Every year. Yeah, I mean, a big thing for me is coming into the new year light. That's like a theme, like I want to come into the new year as light as possible. I don't want to carry a lot of stuff over, so that there's a process that I do.

• 29:25Ryan Holiday?

  Yeah.

• 29:25Speaker 01

  The first thing that I do is I clean out my closet. That might sound ridiculous.

• 29:29Ryan Holiday?

  Yeah.

• 29:29Speaker 01

  But I don't want to go into a closet with 8,000 things I don't wear.

• 29:33Ryan Holiday?

  Yes.

• 29:33Speaker 01

  So I just have a very simple rule. If I look at something and I'm like, should I keep it or not? That I always say someone needs it more than me and it goes in the donate box.

• 29:41Ryan Holiday?

  Yes.

• 29:41Speaker 01

  So I come in, I take care of my closet, I get it as lean as possible. Then I go to my desk. I get rid of all the papers, everything around that car, everything gets cleaned. Emails, done. Subscriptions I don't need, gone, deleted. Like, I literally spent, what does every business do at the end of the year?

• 30:00Ryan Holiday?

  They balance the books.

• 30:01Speaker 01

  They balance the books, they do an audit, they do a review.

• 30:04Ryan Holiday?

  Sure.

• 30:04Speaker 01

  I do the same thing with my life and I'm, I'm going through, I haven't started yet this year, but I'll start to do that in, um, this is, this is airing in January.

• 30:12Ryan Holiday?

  In December, yeah, January, December, yeah.

• 30:14Speaker 01

  But I, I will have done that by the time this airs, I will go through all of that stuff. Cleaning everything out and email is a part of it. And I want to come into it like, I don't want to be cheap, I don't want to come into January behind.

• 30:28Ryan Holiday?

  Yeah.

• 30:28Speaker 01

  I want to attack January, like clean, light, and I just call it coming in light, you know? And it's a process. I write thank you letters every year.

• 30:37Ryan Holiday?

  Yeah, I read that, that, that seems like a good foundational habit. You, you wrap up the year, right? How many people do you write thank you notes to?

• 30:44Speaker 01

  Anywhere from 25 to 50 normally.

• 30:47Ryan Holiday?

  Handwritten?

• 30:47Speaker 01

  Handwritten, oh, of course, yeah. Yeah, handwritten, handwritten notes hit so much harder.

• 30:53Ryan Holiday?

  And then that, that lightens it for you because you're like closing.

• 30:56Speaker 01

  Closing it up.

• 30:57Ryan Holiday?

  You're, you're balancing your debts or you're, you're canceling out your debts or whatever.

• 31:00Speaker 01

  A little bit, it's also a habit that I, when I was 22, so like between the ages of 18 to 22, I slept on 18 different friends' couches. They were putting me up, trying to figure out how I'd be as an entrepreneur and, you know, trying to make it as an entrepreneur and I failed in everything, so I needed couches. And I had, I didn't have a lot of money, but um, my entire marketing campaign and networking campaign at that time was to write handwritten letters. I wrote 10 a day. I wrote 3,000 in one year, literally. I'm not kidding. Postcards, I'd send them to everybody. And it stuck with me because people would like, remember them, you know, like, not everyone checks their emails or their DM. Everyone reads their mail.

• 31:40Ryan Holiday?

  Especially now, getting a handwritten card is like even more out of the

• 31:45Speaker 01

  Yeah.

• 31:45Ryan Holiday?

  The blue.

• 31:46Speaker 01

  You'll get one. I write into people whose podcasts I was on. Usually I write like, there's 8 billion people in the world and you chose me to be on your podcast.

• 31:53Ryan Holiday?

  Sure.

• 31:54Speaker 01

  Thank you.

• 31:55Ryan Holiday?

  Yeah.

• 31:55Speaker 01

  Thank you so much.

• 31:56Ryan Holiday?

  That's another one. Like people want, they're like, I'd like to be more grateful. I want to practice gratitude. But it's like, it's not a thing you are, it's a thing you do. Like you, you, you, it's not just this feeling. It's like, are you expressing it?

• 32:10Speaker 01

  Well, I have a rule. Can I share a rule?

• 32:11Ryan Holiday?

  Please.

• 32:12Speaker 01

  So, um, I have

• 32:13Ryan Holiday?

  Is this Jesse's rule?

• 32:14Speaker 01

  It's Charlie's rule. Okay. That's my son.

• 32:16Ryan Holiday?

  All right.

• 32:17Speaker 01

  So my son at nine ran a full marathon.

• 32:20Ryan Holiday?

  Whoa.

• 32:21Speaker 01

  So he was getting a lot of attention from it and I didn't even know he was doing it. By the way, I didn't know to mile 20. I was, we were running the same race and then I was like, what are you doing?

• 32:30Ryan Holiday?

  Yeah.

• 32:30Speaker 01

  It's like, I got six more miles left. I'm like, I'll run it with you. After that, he was getting a lot of attention. People like, you know, Charlie, that was unbelievable. And he didn't really know how to handle that. So he would kind of like would look away when people congratulated him. He was like kind of shrugging and be like, mm, thanks. And I sat all our kids down at dinner one night and I've said, Charlie, listen, if someone's giving you a compliment, you know, and I realized like, I don't really take compliments well either.

• 32:56Ryan Holiday?

  It's uncomfortable.

• 32:56Speaker 01

  It's uncomfortable. But if someone's giving you a compliment, they're putting the energy out to recognize anything that any of you kids have done.

• 33:03Ryan Holiday?

  Yeah.

• 33:04Speaker 01

  It's important, you know, to look them in the eye and hit the tennis ball back and say, thank you so much. That means so much to me. Versus shrugging your shoulder and say, thanks, makes them feel uncomfortable, almost awkward where they're going out of their way to recognize you. Now it's really important that you guys just, you know, just try it and watch how they light up.

• 33:25Ryan Holiday?

  Sure.

• 33:26Speaker 01

  When you do that, you know? And I was teaching a program, like a coaching course, and I was telling this story to a bunch of people and explaining how like, then I realized like, I don't take compliments. Compliments well.

• 33:36Ryan Holiday?

  Yes.

• 33:37Speaker 01

  And I went through the, you know, we all practiced it. And I walked over to one of the ladies that was there a couple of minutes later. And I said to her, I was like, Melissa, I heard that you got an Airbnb and you rented this Airbnb the night before the event. All the people came and they had dinner at your house. I'm like, that's unbelievable that you took the time and energy to do that. And she looked at me and she shrugged and she went, thanks. And I'm like, Melissa, I just spent 30 minutes. And I realized that people really don't know how to take a compliment and how important that is for your own personal brand.

• 34:14Ryan Holiday?

  Yeah.

• 34:14Speaker 01

  You know what I mean? Especially at a young age, like we want to get a reputation of being, you know, vibrant or personable or whatever. So I named the Charlie's Rule after, and I'm super aware now.

• 34:27Ryan Holiday?

  And the rule is you gotta take the compliment and then hit the tennis ball back.

• 34:30Speaker 01

  Yeah, thank you so much. I really appreciate it. You know, they're going out of their way to recognize you. You have to make sure you go out of your way to thank them.

• 34:38Ryan Holiday?

  So if you send me a thank you card, do I have to send you a thank you card back for the thank you card? And then we just go back an endless amount or?

• 34:44Speaker 01

  No, but if I say, Ryan, this is an insane studio and this must have taken a lot of time to like physically do this. And if you guys put all these books here by yourself, that must have been an amazing. I'm proud of you, man, because this is a really cool environment. It would be nice for you to look back.

• 35:00Ryan Holiday?

  Yeah, be like, just don't just change the subject. Yeah, cool.

• 35:03Speaker 01

  I've truly recognized how unbelievable this is. And by the way, it is friggin amazing. It would be nice for you to return that to me.

• 35:13Ryan Holiday?

  Well, the other thing you can do, by the way, as pertaining to this is like, if it makes you uncomfortable, be like, it's great. Let me tell you about who actually did it. Right? Cause like, I didn't do any of this. This kid named Brayden Wood, who's this, this kid came to my house. He was 16. He was like, hey, can I like do odd jobs or whatever? And he's now 24 and he does incredible stuff like this. You, you can hit the compliment back by explaining and articulating. What you put into it, what it means, how it happened. You don't have to, you know, you're not dodging it. But what you're doing is, is meeting that person's interest and curiosity and acknowledgement with those things back.

• 35:51Speaker 01

  I just think there's a lot of things like that, that anyone can do.

• 35:54Ryan Holiday?

  Yeah.

• 35:54Speaker 01

  That make a big difference in, I'm a 980 on my SAT guy. I've sold five companies. I've had five exits. I've had a lot of egg on my face, too. But it's certainly not because I'm the smartest person.

• 36:06Ryan Holiday?

  Sure.

• 36:06Speaker 01

  But it is because I've been writing letters and I've been communicating and I've been following up and I've been doing things that anyone can do. I'm so back of the pack as an entrepreneur. I don't even like to say, when people introduce me as an entrepreneur, I don't even like it because there's so many better entrepreneurs.

• 36:24Ryan Holiday?

  It's like being a writer. It's just, it's not something you should be describing yourself by. It's, it's, it's better for other people, but it can still be a little.

• 36:31Speaker 01

  I feel like I'm really good at living, at living life and designing life. But, you know, if, if I was going to say to you, what would you look for? What would be the things you'd be looking for if you were built, hiring a CEO or building a team? What would be the, some of the, some of the traits? And you'd be like, oh, I want them to be, you know, enthusiastic and honest and hard working and, you know, you could even make a list. And every word that you threw at me, I guarantee they would all be attitudes and not skills.

• 36:59Ryan Holiday?

  Yes.

• 37:00Speaker 01

  Enthusiasm isn't a skill.

• 37:02Ryan Holiday?

  Yeah.

• 37:02Speaker 01

  It's a choice. It's a choice.

• 37:04Ryan Holiday?

  Sure.

• 37:05Speaker 01

  It's an attitude. I'm, you don't go to school to become enthusiastic.

• 37:09Ryan Holiday?

  Right.

• 37:10Speaker 01

  A skill, you can go to skill to become a painter. That's a skill. School to be, you know, learn a skill, a trade or whatever. And so Charlie's rule is, plays into that a little bit. It's like, you know, the things that anyone can do, why not do, why not choose to do those great?

• 37:29Ryan Holiday?

  Yes.

• 37:30Speaker 01

  Like choose to pour your soul into everything you, choose to care the most.

• 37:34Ryan Holiday?

  Yeah.

• 37:34Speaker 01

  You know, like make a decision like, I always tell my kids like, You guys want to play and be the best team? Yesterday, I was dropping my son off at football and literally when he was going out of the car, I was like, be a leader. Hit everyone in the helmet, pick them up, great play. Like, stand out for that. You can drop the ball, but anyone can do that.

• 37:54Ryan Holiday?

  Well, that's the thing is whatever you end up doing in life, someone can probably teach you the skill of doing the thing. But they can't teach you to want the skill. They can't teach you to show up on time. They can't teach you to not be fucking nuts. You know, like, they can't teach you, to be honest, like, most. I think about that all the time. Whenever you're dealing with like contractor or something, you know, like those trades that are just incredibly frustrating whenever you're dealing with something like around your house.

• 38:18Speaker 01

  All the time.

• 38:19Ryan Holiday?

  And you go, I just go like, at first I'm frustrated. He's like, they're not coming back on time. They're doing this, that, you know? And then I go, you know what? The actual lesson here is I could learn how to lay floors. Right? Like, so whatever happens in my life, I could figure out this actual trade. Not to, not to say that it's easy to do, but you could figure it out. It's not rocket science.

• 38:39Speaker 01

  Right.

• 38:40Ryan Holiday?

  But like, apparently, it is hard to have some of these other skills, like being dependable, being honest, you know? Getting things done quickly, having a sense of urgency. Like, you go, oh, okay, like, this is frustrating. But what it is showing me is that if whatever happens in my life, there's a lot of rungs you can fall and still be reasonably successful. Because the rare things in life are what you're saying. Enthusiasm and creativity and, you know, connection and serve. All those things are the things that most domains and fields are desperately lacking in.

• 39:19Speaker 01

  And you can't outsource it. Like, you can't outsource enthusiasm or soul, or you can't outsource, you know?

• 39:25Ryan Holiday?

  Personality.

• 39:26Speaker 01

  No, I mean, it's like, those are things that, they're more like decisions. And I think that, you know, they don't teach those things at school.

• 39:33Ryan Holiday?

  Yeah.

• 39:33Speaker 01

  But everyone, everyone has those, everyone listening to. And if you don't have the other stuff and you overcompensate by, thank you so much, that means so much, and writing letters and doing all these things that like. To me, I never took a business class. My dad owned the plumbing supply house. We never talked about business. I'd rely on things that were intuitive to me. Like, writing a note was intuitive. Like, I don't know, people are gonna get that. Felt like the right thing to do. My dad wrote me letters when I went to camp. Sleepaway camp as a boy, every day. I'm like, I loved it. People are gonna love it. And I think that those, those things, you know, especially if you're on a downtick. Because one way to put like a little stop plug in the downtick is to build momentum.

• 40:14Ryan Holiday?

  Mm-hmm.

• 40:14Speaker 01

  So if you're doing things like that that make you feel good and make other people feel good, you can kind of very often stop the momentum, which is really important. Anyway, I don't know how we started talking about this, but I think that's, it's an important thing to, to think about. You know, because anyone can do it.

• 40:29Ryan Holiday?

  Well, yeah.

• 40:30Speaker 01

  I could never play in the NBA.

• 40:32Ryan Holiday?

  Yeah.

• 40:32Speaker 01

  You could, you could teach me how to dribble this and that. I'll never be able to play in the NBA. But I can play in this field at a high level, doing things that anyone can do.

• 40:41Ryan Holiday?

  Okay, so you sent me your big ass calendar thing.

• 40:43Speaker 01

  Mm-hmm.

• 40:44Ryan Holiday?

  There is something to be said, like, I, like, my book, the book I'm working on right now, is laid out on my wall in my office. There's something to be said, I think, especially in a world where everything is an app or it's tech-driven for like, just old school pen and paper and physical representation of things. Like, to go to your point about, hey, do one big activity, do eight or 16, you know, mini experiences. When you see a calendar with 365 squares on it, you go, oh, 16 experiences is nothing.

• 41:19Speaker 01

  Right.

• 41:19Ryan Holiday?

  You know, like, it's, it's half of one month. And, and you, you realize, oh, I can definitely make time for this. There's something about seeing it all laid out that's very empowering.

• 41:29Speaker 01

  Yeah, I couldn't operate without seeing my whole, the calendar, our calendar's 365 days, the big ass calendar on one piece of paper. And I couldn't operate without seeing and tracking.

• 41:42Speaker 01

  Towards my goals, seeing where there's gaps in my time and laying out the whole year. Like I, first of all, I'm visual. We all are. We think in stories and we remember in stories. So I don't get that on my phone when I'm scrolling. I don't see the whole.

• 41:55Ryan Holiday?

  It's not a big enough picture. I can look at my week laid out on my phone, but I can't, you can't, a month is not, is too, that's too many little things on, on one iPhone.

• 42:04Speaker 01

  When you start to see what you're actually doing in a year over the course of 365 days, and like only a couple of those squares are filled up, you're like, whoa.

• 42:13Ryan Holiday?

  Yeah. You tell yourself, I worked on this for eight years, but actually you worked on it like eight days for eight consecutive years, which isn't that many.

• 42:33Speaker 01

  I hired a speed coach to work with one of my boys on, on their speed. And the guy came over and he must've drove an hour away. First, he, first he called me, couldn't get me on the schedule for like six weeks. So six weeks go by, he shows up in a car, we do a session. I thank him so much for, for coming out. And I said, you know, wow, you know, six weeks, like we, I want to set up another, another session, but like this took six weeks. You must be so busy. And he's like, busy? He's like, no, I'm not busy. I just got back from four weeks of fishing or whatever the hell he was doing. I go, what? He goes, oh, no, no, it's by design. I said, what do you mean? He said, well, like I realized that if I had to do all these sessions, it would take up all my time.

• 43:17Speaker 01

  So I, I moved to an online platform, training kids how to run faster by videos. This is just doing this as a favor. I follow you on social, whatever he's like, but that's all by design. And I left that. It's coach's role.

• 43:30Ryan Holiday?

  Yeah.

• 43:30Speaker 01

  I left that and I'm like, I want to live my life by design.

• 43:34Ryan Holiday?

  Yeah, sure.

• 43:35Speaker 01

  I want to design the life that I want to live. How many times I go away with my kids or what I do.

• 43:41Ryan Holiday?

  Like almost certainly that guy makes less money than you, but you're not taking four weeks off.

• 43:45Speaker 01

  Exactly. Well, no, you know what he is insanely time rich.

• 43:50Ryan Holiday?

  Yeah.

• 43:50Speaker 01

  Maybe I may be financially.

• 43:51Ryan Holiday?

  Sure.

• 43:52Speaker 01

  Wealthier than him, but he's time rich. And let me, let me tell you something. Don't minimize how important time rich is. It's probably the most, who cares if you have all this money and you're not like taking the time to do what you want to do.

• 44:05Ryan Holiday?

  Yeah, how many powerful people have no power over their schedule?

• 44:08Speaker 01

  A lot.

• 44:09Ryan Holiday?

  They wake up and somebody is telling them what they are doing all fucking day. And how many of those things do they actually want to do? So how powerful.

• 44:17Speaker 01

  Right.

• 44:17Ryan Holiday?

  Really are they?

• 44:18Speaker 01

  Right, no, this guy was the happiest guy. It reminds me of like, I'll never, like the certain things you think about in your life. I was running when I was 23 years old. I lived in New York City. I was on the west side and I went up to on the water up to like Harlem. You know, I was like in like a hundred or whatever. And there was a guy I ran by all this every Sunday. And he had this little fishing rod. I'll never forget this, man. And he was fishing over the side into the Hudson River. He had a little boombox, like a little like lunch, construction lunch pail. And he looked like the happiest guy I've ever seen in my life.

• 44:53Ryan Holiday?

  Yeah.

• 44:54Speaker 01

  This guy, like his kids were running around. He had a little dog and you could, I don't want to judge, but like based on the look of everything, the shoes, the rips, the holes, the whole dirt.

• 45:04Ryan Holiday?

  He doesn't live in a penthouse.

• 45:05Speaker 01

  This guy was not living on Park Avenue.

• 45:07Ryan Holiday?

  Yeah.

• 45:07Speaker 01

  All right. And he was friendly and happy and every week and greeting people and fishing. And I was like, fuck.

• 45:14Ryan Holiday?

  Yeah.

• 45:15Speaker 01

  I'm grinding my ass off, making X amount of dollars. I'm probably making like 90 grand and spending 130.

• 45:23Ryan Holiday?

  Yeah.

• 45:24Speaker 01

  You know, and this guy's probably like, you know, like probably saved more money than I had.

• 45:28Ryan Holiday?

  Yeah.

• 45:29Speaker 01

  More time than I have.

• 45:30Ryan Holiday?

  Right.

• 45:31Speaker 01

  And I'm like, geez, but it's stuck in my head.

• 45:33Ryan Holiday?

  Yeah.

• 45:34Speaker 01

  And time rich is important, but the life by design also hit me hard.

• 45:39Ryan Holiday?

  Yeah.

• 45:39Speaker 01

  And that's what the calendar is. It allows me to design the things that I want to do first and fill everything in around that.

• 45:45Ryan Holiday?

  Yeah, I have these, I do this journal and you write one line a day for five years. And it's very weird, like, you know, the first year it's whatever, but like, I'm almost done with my second one. So I'm on the fifth line.

• 45:56Speaker 01

  So you journal every day?

• 45:57Ryan Holiday?

  I do. It's one of my favorite habits. That's a good, if you're like, hey, I want to pick a new habit for 2026, just like, I'm going to carve out five minutes to do some journaling, ideally on paper, just to process my thoughts, like to get them out of here and onto the page. I'm going to do that five minutes a day. That would be, I think, a foundational habit that would make most people happier, more self-aware, calmer, and you definitely have the time.

• 46:23Speaker 01

  In one book? You keep it in the same book?

• 46:25Ryan Holiday?

  So, so this one, the journal I love, I do a couple, but this one is, is one line a day for five years. So you're like, okay, here's where I was last year, the year before, the year before. It's very helpful to see the passage of time that way.

• 46:38Speaker 01

  Oh, yeah.

• 46:38Ryan Holiday?

  Cause most of the time you're journaling and then you finish the journal, you start a new one.

• 46:41Speaker 01

  It's a true autobiography of your time.

• 46:43Ryan Holiday?

  Yeah, and you're like, oh, I've been, sometimes you're like, oh, I'm good. I'm consistent with this thing. And then other things you're like, oh, I started this and then it fell off. But there is something about you, you want to see like, hey, are you getting closer or further away from the life you're trying to live? Cause most of us are saying, well, yeah, I'm doing all this so that someday X, Y, or Z will happen. But like, your life isn't someday in the future. This is your life. And so I do try to think about how close is the life that I want to the one that I have right now. And if it's too far, then, you know, it's not great. That's, that's not great. Cause now you're, you're deferring and hoping that a bunch of things happen a certain way instead of just doing it.

• 47:25Speaker 01

  What don't you have that you want?

• 47:27Ryan Holiday?

  Yeah, there's not that much. Like, you know, that's a question you probably get all the time. People are like, what are you working on next? And you're like, I like what I do. This, I want to do more of this. That's my, like, the idea should be that you're not. There'd definitely be things like, I want to run this race, or I want to try this. But like, the idea of like, well, I gotta do this new thing to top what I did before, or I need to do this very different thing because I don't like what I'm doing. I like, I like writing, and so if I can wake, if the majority of my days are I get to wake up and do that thing, that's success. I'm not trying to get away from that. I'm trying to do that. That was the whole, that's, I worked really hard to get in that position. Why am I going to try to get out of it?

• 48:06Speaker 01

  Right, right. Yeah. It reminded me of another rule.

• 48:10Ryan Holiday?

  Yeah, okay.

• 48:11Speaker 01

  Lieber's rule. I got offered, I had like no money in my twenties, so someone had offered me $10,000 for 10% of my life going forward. And I was like, it was this guy, Steve Lieber, and I almost took it because I needed the 10 grand. By the way, 10 grand at that, I'm Elon Musk.

• 48:29Ryan Holiday?

  Equity is expensive.

• 48:30Speaker 01

  You give me 10 grand, I'm Elon Musk at 21.

• 48:33Ryan Holiday?

  Sure.

• 48:34Speaker 01

  But, um.

• 48:35Ryan Holiday?

  I remember the first time I made $10,000, I was like, what am I gonna do with all this money?

• 48:38Speaker 01

  Yeah. He told me, he was telling me about his life, and he was, and he was a manager. And he came to a point in his life where he would rather make 25 cents working for himself than a dollar working with the guys that, he was making a ton of money, but he wanted, he was willing to take that.

• 48:58Ryan Holiday?

  To have control and be in charge of his own destiny.

• 49:01Speaker 01

  And like, as a 20, you know, like, again, like, that makes a lot of sense now, but like, when you're 21, you're like, I never heard anyone talk like that, ever, you know? That was a pivotal moment in my life.

• 49:13Ryan Holiday?

  Yeah, because most people are, their vision of success, if you actually talk to the people that have that, they're all trying to get out of it.

• 49:19Speaker 01

  Yeah, exactly.

• 49:19Ryan Holiday?

  You haven't actually thought about what it would be like to, you know, then you're like the dog that caught the car. Like, it's actually a miserable, I remember Peter Thiel told me that once, he went to Stanford, and then went to Stanford Law, and he got into like, one of the biggest law firms, and then he realized, he'd spent his whole life trying to get into a place, and he talked to the people at the place, and they were all talking about getting out. And that's, I think that's more, that's true more often than people think it is.

• 49:44Speaker 01

  Yeah. Oh, for sure.

• 49:45Ryan Holiday?

  Like you talk to people in politics, which, so a lot of people seems like it would be so cool. And then they all just talk about how fucking much they hate it.

• 49:54Speaker 01

  Well, go talk to someone that's, that, you know, sells their company. Very often, like they go through, you know, they built up the stuff for this one day. Yeah. That they're going to exit and sell their company and then they sell it. And very often, if it's a founder, they're really miserable.

• 50:08Ryan Holiday?

  Tragedy of their life.

• 50:09Speaker 01

  Yeah.

• 50:09Ryan Holiday?

  And then what do they do? They go start another company.

• 50:11Speaker 01

  I know.

• 50:12Ryan Holiday?

  It's like, you already did it.

• 50:13Speaker 01

  I know.

• 50:13Ryan Holiday?

  You could have just stayed, stayed there.

• 50:15Speaker 01

  Yeah.

• 50:16Ryan Holiday?

  Yeah. We are really good at coming up with ideas for exiting or getting to a place as opposed to how do we develop something sustainable, like it's same, same truth. We're good at planning vacations for like visiting places we want to go. As opposed to designing a life that we like living in and don't desperately need an escape from.

• 50:36Speaker 01

  Yeah. Coach's rule. You gotta, you gotta, you know, design life by design.

• 50:40Ryan Holiday?

  Yes.

• 50:41Speaker 01

  I feel like my dad had that. I think it's real, and I think it's just so important, man, like. And I understand, I recognize that people don't have, you know, people have to work, obviously.

• 50:51Ryan Holiday?

  Of course.

• 50:52Speaker 01

  And not everyone is, you know, it's, it's easier, easier for you to say, you know, I get all that. But my life at 21, when I look back at it, was very similar to my life now. I was still running marathons. I was going to the polar plunge in Koh-i-Island that was free. I was going to all these speeches and offerings around New York City that like didn't cost a lot of money. I was, I'm doing on a bigger scale now, but I'm still doing the same kind of things that I love to do. I just have more brown rice on my plate. You know what I mean? Like, so I was lucky enough to kind of recognize a lot of that stuff. Early on.

• 51:24Ryan Holiday?

  Yeah.

• 51:25Speaker 01

  You know? And when I started Marquis Jet, which was a big deal for me.

• 51:30Ryan Holiday?

  Yeah.

• 51:30Speaker 01

  I was 28, 29 years old. I started this private jet company with my partner. We grew it from nothing to $5 billion in sales and we sold it to Warren Buffett's net jets. Berkshire Hathaway's net jets. And the gift wasn't like. The money, which was definitely a big deal for me at that time. Forget it. I'm not gonna, but I'm 30 years old and we're flying the who's who of CEOs, athletes, entertainers, pop culture, and I'm getting to meet all these people and I'm fucking young.

• 52:00Ryan Holiday?

  Yeah.

• 52:00Speaker 01

  Single. I don't know anything about anything, you know? And I was obsessed with their habits.

• 52:08Ryan Holiday?

  Yeah.

• 52:08Speaker 01

  And so any chance I got a chance to meet someone at the airport or at, at one of our events or whatever, I'd ask them a million questions like, where do you vacation? Do you, how many newspapers do you, by the time you go to bed?

• 52:19Ryan Holiday?

  Yeah.

• 52:20Speaker 01

  You know, like, what do you do with your money? Like anything? And they were willing to share, you know?

• 52:24Ryan Holiday?

  You would think people would ask more than they do.

• 52:27Speaker 01

  Right. And you'd be surprised how people want to help people.

• 52:30Ryan Holiday?

  Yeah.

• 52:30Speaker 01

  So when you ask, you get people like-

• 52:32Ryan Holiday?

  Because it's something they spent a lot of time thinking about and they, there's not that many people to share it with.

• 52:36Speaker 01

  Dying for people to ask them. They want to share all this stuff, you know, like, especially if you toot a little ego, like, you know, like Ryan, you're the best in the world. You're the best author I ever met. How, what's the key to like, oh, well, first of all, thank you.

• 52:49Ryan Holiday?

  Right. I really admire how you do this and you're picking some tiny thing they, they don't get to talk about a lot.

• 52:56Speaker 01

  Right.

• 52:56Ryan Holiday?

  And they're like, yeah, how much time do you have?

• 52:59Speaker 01

  Anyway, back to that. So I was obsessed with people's habits and I, I started to pick up and try some of them, you know, like, I'm a product after 30 years ago of trial and error of all these different-

• 53:11Ryan Holiday?

  Right.

• 53:12Speaker 01

  habits people were talking about, you know, like, oh, I read six newspapers. I read this and this. I, I get seven hours of sleep. I get up early. Like I would try all the different things because that's how you, you know, you learn. I was at a conference and my wife's become really good friends with Warren Buffett over the years. And very often he'll ask to sit next to Sarah so they can get caught up or whatever. And like, sometimes it's uncomfortable for me because I'm the plus one, which is fine.

• 53:37Ryan Holiday?

  Yeah.

• 53:37Speaker 01

  But I'm just sitting there while they're having this conversation and like, no one really wants to talk to me. They want to talk to Sarah. And it's like weird, but it's like, we go to this event and this time I'm sitting next to Warren. And we're at the same table, but somehow Sarah, and I know Warren well too, but we're not-

• 53:54Ryan Holiday?

  You sold them your company.

• 53:55Speaker 01

  Yeah. But, so I just, I asked him. Out of nowhere about his dad. And I said, I said, Warren, can I ask you a crazy question? You know, this is a guy that's been asked about the yen and dollars and stocks for seven years. No one's ever asked him anything like this.

• 54:13Ryan Holiday?

  Yes.

• 54:14Speaker 01

  I said, I got four kids. Did your dad ever take you on a one-on-one trip when you were growing up? Three and a half hours later, we're still talking about this.

• 54:25Ryan Holiday?

  Yeah.

• 54:26Speaker 01

  Three and a half hours later. The host of the conference was coming. They thought I was hogging him like from everybody else, like the line of people.

• 54:34Ryan Holiday?

  Do we have to save Warren?

• 54:35Speaker 01

  He's shooing people away. He's like, no, no, no, no. He's like, and he told me the most unbelievable, never shared before stories about his relationship with his dad. How he took him to the Lionel Train Company in New York and they went to the Goldman Sachs and the CEO came out and shook his hand when he was 11 years old and they went to a baseball game. They saw the longest baseball game in the history of baseball at Wrigley Field at that time. And now he had one mitt that his dad got him and the whole neighborhood shared the mitt. Like it was unbelievable. But to your point, people want to share.

• 55:10Ryan Holiday?

  Yeah.

• 55:11Speaker 01

  If you ask them the right questions.

• 55:13Ryan Holiday?

  Yeah, that's the power of a good question.

• 55:14Speaker 01

  If I would have said to him, hey, Warren, what stock should I buy? He would have been like turned away from me.

• 55:19Ryan Holiday?

  Yeah.

• 55:19Speaker 01

  But I asked him something that hit a nerve.

• 55:22Ryan Holiday?

  Yes. There's nothing in it for you in that question.

• 55:24Speaker 01

  No.

• 55:25Ryan Holiday?

  There's no agenda in that question. It's just, it's just about connection.

• 55:29Speaker 01

  Yeah. And people want to connect.

• 55:31Ryan Holiday?

  Yeah.

• 55:32Speaker 01

  People want to connect.

• 55:33Ryan Holiday?

  Speaking of which, I want to connect you with some books. So let's go next story.

• 55:35Speaker 01

  Let's do it.

• 55:41Ryan Holiday?

  Thanks 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.