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

Summary

Podcast Summary: The Daily Stoic — "These 3 Rules Will Make or Break Your 2026" Featuring Jesse Itzler

Podcast: The Daily Stoic
Host: Ryan Holiday
Guest: Jesse Itzler
Date: December 20, 2025

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Episode Overview

Ryan Holiday interviews entrepreneur, author, and adventurer Jesse Itzler about how to design an exceptional year—specifically, how to approach 2026 with renewed intention, adventure, and personal growth. Jesse breaks down the three rules that have transformed his own life, discusses the importance of intentional planning, building a "life resume," and prioritizing meaningful experiences over routine. The conversation is practical, energizing, and filled with memorable anecdotes and actionable advice for anyone looking to live more deliberately.

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Key Discussion Points & Insights

1. The Challenge and Necessity of Creating "Newness" in Midlife

• Routine vs. Innovation: As we age, it's harder to create newness; you must schedule transformative experiences—they won’t happen by accident.
• Quote:
  "As you get older... it's really hard to create newness. Like, where the hell does newness come from? You have to schedule it."
  — Jesse Itzler (08:16)

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2. Jesse Itzler’s Three Life-Changing Rules

Rule 1: The Year-Defining "Misogi"

• Inspired by a Japanese ritual: each year, pick one big "year-defining thing”—a major challenge or adventure.
• This could be physical (marathon, mountain climb), mental (launching a business, writing a book), or otherwise.
• The impact is both immediate and lasting:
  "If it's truly year-defining, you're going to learn a lot about yourself and grow from it."
  — Jesse (09:41)
• This challenge brings clarity, pride, and acts as a natural filter, forcing you to eliminate less meaningful commitments.
  • Examples: Jesse completed Ultraman, RIM to rim to rim, lived with monks, launched companies.
• Quote:
  "You should be able to look back and be like, '2025? That's the year I did X.'"
  — Jesse (09:29)

Rule 2: Bi-Monthly "Mini-Adventures" (Kevin’s Rule)

• Every other month, intentionally do one thing you normally wouldn’t—adventure, excursion, unique experience.
• Origin: a friend who, every two months, took on a new small adventure for himself or with family.
• The power of compounding these experiences: If you’re 40 and do this until 80, you’ll have 240 mini-adventures and 40 major ones.
• Quote:
  "If you can't take one day out of every eight weeks and do something for yourself… your work-life balance is out of whack."
  — Jesse (12:18)
• Over time, these accumulate into a vibrant “life resume.”
  • Examples: Fishing instead of watching a game, spontaneous city trips, hiking with kids.

Rule 3: Quarterly "Winning Habits"

• Instead of New Year's resolutions (which fail quickly), introduce one specific, positive habit every quarter.
  • E.g., "I'll drink 100oz of water daily," "I'll never be late to a meeting," "Add 10 minutes of meditation."
• Focus on simplicity and sustainability to allow habits to compound.
• Quote:
  "I'm not trying to do 15 things at once. I'm just trying to slowly layer… If you add one habit a quarter, that's four a year. In just a couple years, that’s transformative."
  — Jesse (15:52)
• Build habit momentum and avoid being overwhelmed by radical change.

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3. Practical Strategies for Intentional Living

The Power of Planning & The "Big Ass Calendar" (17:10–18:07; 45:16–46:48)

• Physical, year-long calendar visualizes your entire year, making it easier to fill in and see what actually matters.
• Design life around what matters first (family, health, big challenges), then let work fill in the gaps.
• Quote:
  "Most of us play life on defense... we don't need more time, we need a better system. My calendar is my operating system."
  — Jesse (17:10)

Flipping the Default: Life Before Work (20:15–23:03)

• Most people let work dictate their schedules and fill in personal time with scraps.
• Quote:
  "Work will find a way to fill the cracks for sure. The calendar doesn't lie — you did it all for work and gave the leftovers to your family."
  — Ryan (21:41)

Life by Design and Being "Time Rich" (49:11–52:16)

• Theme: Wealth isn't just money—it's about controlling your time.
• Story of a speed coach who only works as much as he wants because everything is "by design."
• The happiest people are often those in control of their schedules, not necessarily those with the most money.
• Quote:
  "He is insanely time rich... Don't minimize how important 'time rich' is. It's probably the most important thing."
  — Jesse (50:27)

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4. The Significance of Personal "Rules" and Family Wisdom

Naming Rules After Influential People (23:03–25:33)

• Jesse names rules after family and friends (Kevin’s Rule, Mom’s Rule, Charlie’s Rule, Ben’s Dad’s Rule).
• Examples include: Never being too tired for your kids, always taking their hand, or supporting their interests even if they're not yours.
• Quote:
  "The people who've had the biggest impact aren’t necessarily the famous ones. They're people you meet along the way.”
  — Jesse (23:03)
• Wisdom passed down intentionally becomes a life compass.

Being Present for Children (24:36–27:27)

• Don't let exhaustion or inconvenience lead to missed opportunities with your children; accept invitations into their world as they come.
• Quote:
  "Whenever your child offers their hand, you have to take it... Whenever they're inviting you into their life, you take it."
  — Ryan, referencing Russ Roberts rule (24:37)

Five-Year View for Life Planning (28:44–29:37)

• Think of life in five-year increments; what changes are coming?
• Motivates prioritizing family and meaningful moments in the present, not deferring them for an uncertain future.

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5. How to Close the Year "Light" (33:46–34:47)

• Clean out physical spaces (closet, desk, car), digital spaces (inbox), and eliminate outdated commitments.
• Write 25–50 handwritten thank you notes by year end to close out emotional debts and practice gratitude.
• Quote:
  "I write thank you letters every year... you wrap up the year, you lighten it for yourself by closing it."
  — Jesse (35:12)
• This year-end "audit" mirrors business reviews: balance the personal books.

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6. Additional Habits and Practical Takeaways

Practice Gratitude Actively

• "Gratitude isn't just something you feel, it's something you do." — Ryan (36:31)
• Jesse’s thank-you note story: wrote 3,000 postcards in a year at age 22.

Charlie’s Rule: Taking Compliments Well (36:45–39:13)

• Look someone in the eye, accept compliments graciously, and “hit the tennis ball back.”
• Quote:
  "If someone's giving you a compliment... it's important to look them in the eye and hit the tennis ball back and say 'Thank you so much, that means so much to me.'"
  — Jesse (37:31)

The Value of Enthusiasm and Attitude (41:06–42:29)

• Most traits people desire in colleagues ("enthusiasm, honesty") are attitudes, not skills; anyone can choose to be this way.
• Quote:
  "Enthusiasm isn't a skill. It's a choice. It's an attitude."
  — Jesse (41:35)

Journaling as a Foundational Habit (52:16–53:18)

• Ryan journals daily, using a "one line a day for five years" system to observe trends and the passage of time.
• Quote:
  "If you're gonna pick a new habit for 2026: five minutes of journaling will make most people happier, more self-aware, calmer."
  — Ryan (52:35)

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7. On Purpose, Wealth, and Life Satisfaction

• Designing for Enough: Focus less on chasing more, or “topping” yourself, more on making every day align with your values.
• Control over one's time (being "time rich") and experiences is more valuable and attainable than ever-increasing income.
• Life design is a practice accessible at every stage, not just once a certain level of success is attained.
• Quote:
  "The happiest people are those in control of their schedules, not necessarily with the most money."
  — Jesse (52:11)

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8. Lessons from Extraordinary People: Asking Good Questions (58:45–61:50)

• Jesse became obsessed with learning the habits of ultra-successful individuals, asking them about their routines, not just their achievements.
• Example: A meaningful story about Warren Buffett revealing treasured childhood memories because Jesse asked about meaningful, personal topics (not stock tips).
• Quote:
  "People want to share if you ask them the right questions... If I'd said, 'What stock should I buy?' he'd have turned away, but I asked him something that hit a nerve.”
  — Jesse (61:12)

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Notable Quotes & Moments (with Timestamps)

• "As you get older... it's really hard to create newness. You have to schedule it." — Jesse Itzler (08:16)
• "If you can't take one day out of every eight weeks and do something for yourself… your work-life balance is out of whack." — Jesse (12:18)
• "Enthusiasm isn't a skill. It's a choice. It's an attitude." — Jesse (41:35)
• "Work will fill in the cracks for sure. The calendar doesn't lie — you did it all for work and gave the leftovers to your family." — Ryan (21:41)
• "He is insanely time rich... Don't minimize how important 'time rich' is. It's probably the most important thing." — Jesse (50:27)
• "If someone's giving you a compliment... look them in the eye and hit the tennis ball back and say 'Thank you so much, that means so much to me.'" — Jesse (37:31)
• "Gratitude isn't just something you feel, it's something you do." — Ryan (36:31)
• "You want to see: are you getting closer or further away from the life you're trying to live? Because your life isn't someday in the future. This is your life." — Ryan (53:20)

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Timestamps for Key Segments

• Jesse Introduces the Three Rules: 08:10–16:39
• On Intentional Planning and the Big Ass Calendar: 16:53–18:07 & 45:16–46:48
• Work-Life Balance & Reversing the Default: 20:15–23:03
• Naming and Sharing 'Rules': 23:03–25:33
• Year-End Reflection & Clean Slate Rituals: 33:46–34:47
• Gratitude, Thank You Notes, and Compliments: 35:12–39:13
• Enthusiasm, Attitude, and “Anyone Can Do This”: 41:06–42:29
• Being 'Time Rich' & Life by Design: 49:11–52:16
• Journaling & Reflective Habits: 52:16–53:18
• Asking the Ultra-Successful the Right Questions (Warren Buffett Story): 58:45–61:50

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Final Thoughts

Jesse Itzler's approach urges listeners to actively design their years (and lives), not drift along in routine. His three rules—and the stories and wisdom behind them—make this episode a practical, motivating blueprint for directing your energy, time, and attention toward what matters in 2026 and beyond.

For more info on The Daily Stoic New Year New You Challenge, visit dailystoic.com/challenge.

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Transcript

[Toyota Trucks Narrator]

The world is full of tours.

[Ryan Holiday]

But.

[Toyota Trucks Narrator]

You don't choose a Toyota truck to follow the beaten path. You choose it to find the places.

[Jesse Itzler]

In between.

[Toyota Trucks Narrator]

The detours, where each adventure pulls you toward the next, and wrong turns turn out right. So why would you ever take a tour when you could take a detour? Toyota Trucks.

[Toyota 4Runner Owner]

My family owns a 2023 Toyota 4Runner, and honestly, it's my favorite vehicle that I've ever owned around town. It's smooth and reliable, but where it really shines is on our trips into the backcountry. We've taken it on backpacking adventures to Colorado and New Mexico, loaded up with gear and never had to think twice about whether it could handle the terrain. That's what Toyota trucks are built for. Off road confidence, rugged durability, and the freedom to explore. Toyota has a long history with the outdoor community, and they're committed to helping more people get out there and experience what nature has to offer. From remote trails to scenic byways, Toyota Trucks empowers you to take the detour, roam freely and discover places that still feel wild and untouched. And they're not just making great trucks. They're working to expand access to adventure so more people can connect with the outdoors and pass that passion on to the next generation. Discover your uncharted territory. Learn more at toyota.com trucks/adventure-detours that's toyota.com trucks/adport-detours you know, you don't have to.

[Ryan Holiday]

Let big wireless and your overpriced phone bill suck the joy out of the holidays this year, because right now all of Mint Mobile's Unlimited plans are 50% off. You can get 3, 6 and 12 months of unlimited premium wireless for 15 bucks a month. It's their best deal of the year and it makes it really easy for you to give your expensive wireless bill the Scrooge treatment. All Mint plans come with high speed data and unlimited talk and text at the nation's largest 5G network. Plus you can bring your current phone and number over to Mint. Actually, we just signed up for a Mint Mobile plan to use the social media phone here at the office and we didn't notice any kind of change in the quality of service or network or any of that. Just a whole bunch of savings. Turn your expensive wireless present into a huge wireless savings future by switching to Mint Shop. Mint unlimited [e-mail] 6 that's mintmobile.com 6 Limited time offer upfront payment of $45 for three months, $90 for six months or $180 for 12 months. Plans required $12 per month equivalent taxes and fees Extra initial plan term only greater than 35 gigabytes. May slow when network is busy Capable device required Availability speed very mint mobile.com 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 the 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 is may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. When I was in Seattle a couple 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 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 Itzer was going to be in town. We've known each other a long time. Actually. We met at Lance Armstrong's house, like 10 years ago. It was very sur dinner. Gary Vaynerchuk was there. I was sitting next to Bo Jackson. Jesse was there. It was a surreal little experience. My son was a couple 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 through at the end of one year now past 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 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 youw Challenge. It's a new one here for 2026. 21 days of stoic inspired challenges. One per day, some Q&As 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 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 to 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 his 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 going to put in there? How am I going to 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 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 well before he blew up and became the David Goggins everyone knows. His other book is called Living With Monks where he lived in 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 esseitsler and I think you're really going to 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 going to do for the new year. And again, I hope you join me in the 2026 Daily Stoic New Year New you Challenge. 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 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? What are they?

[Jesse Itzler]

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 routine, 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, 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. Like, where the hell does newness come from? Yet, 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 misogy. And the notion around the misogy is you do one big year defining thing every year.

[Ryan Holiday]

Got it.

[Jesse Itzler]

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?

[Ryan 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, like, you'd be something big enough that it's year defining.

[Jesse Itzler]

If you're defining, you have, like, you have one big Year. 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.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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

[Ryan Holiday]

That's the year I did X.

[Jesse Itzler]

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 going to be and it should really be something hard, challenging. And if it's truly year defining, then you're going to learn a lot about you.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

And grow a lot from it.

[Ryan Holiday]

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

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

So that's the first thing that I do and I don't even know what it's going to look like. I actually do know what my 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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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 that don't move the needle like you would think. Like, whoa. You throwing 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.

[Ryan Holiday]

You put that on your calendar, it takes stuff off your calendar because you're not going to be partying because you got training.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

Yeah. So I've been doing that.

[Ryan Holiday]

Okay.

[Jesse Itzler]

The second thing, I actually named this after my friend Kevin. I was on a hiking trip with my 9 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 like, Kevin, there's 8 billion people in the world. We're the only people out here, there's no one near us.

[Ryan Holiday]

Yeah. We chose this and we chose this.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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. To New Hampshire. I might take my kids to a show in New York City. I just took 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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

You're pretending like you're going to get to all those things when you retire or when things calm down or go back to normal, but they aren't.

[Jesse Itzler]

No. And it kind of doesn't work. It doesn't wait for you to do that.

[Ryan Holiday]

Sure. So.

[Jesse Itzler]

But then, and then he was like, here's the thing. She'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. 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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yes.

[Jesse Itzler]

So like, you see how that, that's.

[Ryan Holiday]

A full life right there, almost.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

So once I started realizing that, God, man, I don't have to like change. There's 365 days. I'm only carving out like seven or eight of them, you know, but look how this works over time. That really has had. And, 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 of things. I don't even want to call them accomplishments because I don't look at them as accomplishments. 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 launched this. I failed at this. But through it all, it's just really been an incredible life, man.

[Ryan Holiday]

You know, what's the third one?

[Jesse Itzler]

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

[Ryan Holiday]

Statistics show don't make it even through January.

[Jesse Itzler]

But I am good at this. And that's just every quarter I had a new winning habit. So I'm, 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 of quarterly. I don't drink enough water. I'm going to drink 100 ounces of water.

[Ryan Holiday]

Sure.

[Jesse Itzler]

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

[Ryan Holiday]

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

[Jesse Itzler]

Because it's really overwhelming and radical to be like, I'm going to just transform. And like, it doesn't for most people work like that. No, 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.

[Ryan Holiday]

So like I'm going to start walking or I'm going to stop smoking or I'm going to like just things you're going to start or stop doing. Basically.

[Jesse Itzler]

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 in my head after you stop talking to make sure that I'm not interrupting.

[Ryan 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.

[Jesse Itzler]

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.

[Ryan Holiday]

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

[Jesse Itzler]

Right.

[Ryan Holiday]

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

[Jesse Itzler]

100%. I mean, looking at me, 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. I'm still not great at it, but. But that's something that I prioritize. Like this month, man, 2026, I'm not going to be late to a meeting. They're going to look at me like, what?

[Ryan Holiday]

Yeah, we were planning on you being late. Right.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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 really, I'm a big believer in planning.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

And if you have a good operating system, I mean, for your personal life. Yeah, 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're laying out what you want to do. Like my 2026 is baked, fully baked of what I want to do.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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' like that.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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.

[Ryan Holiday]

Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastrop 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. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it 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. Learn [e-mail] Trucks Adventure detours the world.

[Toyota Trucks Narrator]

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[Ryan 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 gonna take what I'm gonna take and you're gonna keep what I give you. And. And Seneca tells this story because he 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 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 for sure. 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 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 your spiritual health, all these things that you should also be working on that gets the leftovers. And we should probably flip it.

[Jesse Itzler]

Yeah, I agree. I mean, that's what I've. I mean, one Mississippi. Yes, that, that is. 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 versus how much time they actually invest in planning their own personal life and event, 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.

[Ryan 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 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 your kids aren't going to yell at you now for it, but they'll resent you for it later. Or you'll look back and go, hey, here's all the things that I missed that I can't do again. Or 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 the doctor gives you the diagnosis for some preventable thing.

[Jesse Itzler]

It's funny because I mentioned that 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 have 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, like Kevin's rule. I have my mom's rule. 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 is that he said. He said to me in just talking, he's like, you know, I have a rule that I'm never too tired from my kids.

[Ryan Holiday]

Sure.

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

And I'm like, oh, I'm too tired, you know, like, something's wrong, you know?

[Ryan Holiday]

So I think about that. Like, I try to remind myself the pool is never too cold.

[Jesse Itzler]

Yeah.

[Ryan Holiday]

It doesn't matter that I just.

[Jesse Itzler]

Ryan's rule.

[Ryan Holiday]

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 fall, 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.

[Jesse Itzler]

Yes.

[Ryan Holiday]

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

[Jesse Itzler]

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, right. 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.

[Ryan Holiday]

Wow.

[Jesse Itzler]

And he would do. Oh, man, it was like a mo. 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.

[Ryan Holiday]

Right.

[Jesse Itzler]

But his kids were interested in it.

[Ryan Holiday]

I. I almost broke down. I was in a car once it. 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. So he's like, I've seen this band and this band and this band. And he was like. And 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 cause 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? 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.

[Jesse Itzler]

Oh my God.

[Ryan Holiday]

Yeah, you got to do that.

[Jesse Itzler]

Yeah. Especially because, like, you know, it all goes by so fast, which everybody knows. But you know, you think you're going to be the Age you are forever.

[Ryan Holiday]

Sure.

[Jesse Itzler]

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 have? Like I was on my lake, 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.

[Ryan Holiday]

Yeah, sure.

[Jesse Itzler]

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.

[Ryan 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 and nobody's having fun traipsing around Italy when they're 75. They can't do most of the things, it's painful. And so you got. The whole point is you should do it now, not just. Cause you might not be able to do it later. Cause you could die, but it just won't be as good later.

[Jesse Itzler]

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 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, because 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. Right 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, yet I like to look at things in five year increments.

[Ryan Holiday]

Okay.

[Jesse Itzler]

So my son now is a sophomore in high school. So in five years from now, he's.

[Ryan Holiday]

In a totally different phase of life.

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Sure.

[Jesse Itzler]

You know, so you got to think about that. And that will help you think about, at least in my case, how I want to live out this year, 20, 26 and beyond, you know, and that really dictates do I want to go on that trip or do I want. My son's only here for two more years.

[Ryan Holiday]

Right.

[Jesse Itzler]

Is this going to. Am I back by 6:00'?

[Ryan Holiday]

Clock?

[Jesse Itzler]

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.

[Ryan Holiday]

And 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 had been talking about it. It was like a plan. And then I was like, you know what? Like, this year I'm gonna 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. Cause 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. Like, yep, I could have been there, you know, this time. But 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 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'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 got to fucking do it now, because now is when the math on it actually works. Not two years from now.

[Jesse Itzler]

Yeah. The last three years, I've taken trips with a group of friends. There's about 10 guys, 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.

[Ryan Holiday]

That one where you jump in the actual. Like, through the hole in the ice.

[Jesse Itzler]

Yeah. In the Baltic.

[Ryan Holiday]

We did.

[Jesse Itzler]

We did it all. And when I first sent out the email, hey, guys, we're going to go to Finland. You know, I literally wrote, like. I know you're going to say, like, it's. I don't know the time or practical. Put this down.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

And build around it. We're going to Finland, you know, 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 the. Everyone's got jobs.

[Ryan Holiday]

That's inconvenient whenever you do it.

[Jesse Itzler]

It's never gonna be the right time.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

You know, so let's just do it.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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 have did these trips with me, I only knew one of them 10 years ago. So I got this new friend group from the. 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 don't know. Or like, no one's gonna give you one. No. No, they're not. You gotta go and make an effort. And not everybody wants that, you know, but it's been amazing.

[Ryan Holiday]

You know, I think there's something about, like, the Masogi thing, like, doing challenges. Like, so for. For Daily Stoke, we do this thing called New Year new you. 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 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 that.

[Jesse Itzler]

Draws so hard I can't even do it.

[Ryan Holiday]

Exactly. I can't even do that. Right. Yeah. It's easier to run a hundred miles and clean out that drawer.

[Jesse Itzler]

Yeah.

[Ryan Holiday]

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

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

Delete all.

[Ryan Holiday]

Yes.

[Jesse Itzler]

Every year.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yes.

[Jesse Itzler]

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.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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 clean. Emails done, subscriptions I don't need gone, deleted. Like, I literally spent. What does every business do at the end of the year?

[Ryan Holiday]

They balance the books.

[Jesse Itzler]

They balance the books. They do an audit, they do a review. I do the same thing with my life. And I'm going through. I haven't started yet this year, but I'll start to do that in. This is. This is airing in January.

[Ryan Holiday]

December. Yeah, January. Yeah.

[Jesse Itzler]

But 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. I don't want to come into January behind.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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.

[Ryan Holiday]

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

[Jesse Itzler]

Anywhere from 25 to 50. Normally. Handwritten. Oh, of course, yeah, yeah. Hand. Handwritten notes hit so much harder, and then that.

[Ryan Holiday]

That lightens it for you because you're like, closing.

[Jesse Itzler]

Closing it up.

[Ryan Holiday]

You're. You're balancing your debt or you're. You're canceling out your debts or whatever a little bit.

[Jesse Itzler]

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 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, no, not everyone checks their emails or their dm. Everyone reads their mail.

[Ryan Holiday]

Well, especially now. Getting a handwritten card is, like, even more out of the. Yeah, the blue.

[Jesse Itzler]

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

[Ryan 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 this feeling. It's like, are you expressing it? Well, I have a couple points.

[Jesse Itzler]

Can I share a rule, please? So I have this Jesse's rule. It's Charlie's rule, named after my son.

[Ryan Holiday]

All right.

[Jesse Itzler]

So my son, at 9, ran a full marathon.

[Ryan Holiday]

Whoa.

[Jesse Itzler]

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.

[Ryan Holiday]

I was.

[Jesse Itzler]

We were running the same race, and then I was like, what are you doing? Yeah, 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 kind of like, Would look away when people congratulate him. He was like, kind of shrug and be like, thanks. And I sat all our kids down at dinner one night, and I said, charlie, listen, if someone's giving you a compliment, you know, and I realized, like, I don't really take compliments well either.

[Ryan Holiday]

It's uncomfortable.

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

It's important, you know, to look him 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. It's really important that you guys just, you know, just try it and watch how they light up.

[Ryan Holiday]

Sure.

[Jesse Itzler]

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 well.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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 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, and 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. 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, and the.

[Ryan Holiday]

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

[Jesse Itzler]

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.

[Ryan 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?

[Jesse Itzler]

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.

[Ryan Holiday]

I'd be like, just. Don't just change the subject. Be like, yeah, cool.

[Jesse Itzler]

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

[Ryan Holiday]

Well, the other thing you can do, by the way, this is 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 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 meeting that person's interest and curiosity and acknowledgement with those things back.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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.

[Ryan Holiday]

Sure.

[Jesse Itzler]

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 am 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' so many better entrepreneurs.

[Ryan 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.

[Jesse Itzler]

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 hardworking 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.

[Ryan Holiday]

Yes.

[Jesse Itzler]

Enthusiasm isn't a skill. Yeah, it's a choice. It's a choice. Like, sure, it's an attitude. I mean, you don't go to school to become enthusiastic.

[Ryan Holiday]

Right.

[Jesse Itzler]

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 role is, like, 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.

[Ryan Holiday]

Yes.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

You know, make a decision. Like, I always tell my kids, like, you guys want to play and be. 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. That you can drop the ball, make it. But anyone can do that.

[Ryan 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, a contractor or something, you know, like those trades that are just incredibly frustrating whenever you're dealing with something, like around your house or whatever, all the time, 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. And then I go, you know what the actual lesson here is? I could learn how to lay floors, right? So whatever happens in my life, I could figure out this actual trait. Not to say that it's easy to do, but you could figure it out. It's not rocket science, but 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 service. All those Things are the things that most domains and fields are desperately lacking in.

[Jesse Itzler]

And you can't outsource it. Like you can't outsource enthusiasm or soul or you can't outsource, you know, personality. 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. Yeah, 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 a plumbing supply house. We never talked about business. I rely on things that were intuitive to me. Like writing a note was intuitive. Like, I don't know, people are going to 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 going to 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. 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 start talking about this, but I think that's a, it's an important thing to think about, you know, because anyone can do it. Well, yeah, I could never play in the NBA.

[Ryan Holiday]

Yeah, you could.

[Jesse Itzler]

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.

[Ryan Holiday]

Okay, so you sent me your big ass calendar thing. There is something to be said. 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 just old school pen and paper and physical representation of things. To go to your point about, hey, do one big activity, do 8 or 16 mini experiences. When you see a calendar with 365 squares on it, you go, oh, 16 experiences is nothing.

[Jesse Itzler]

Right?

[Ryan Holiday]

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

[Jesse Itzler]

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

[Ryan Holiday]

It's not a big enough picture.

[Jesse Itzler]

It's not a big enough picture.

[Ryan Holiday]

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.

[Jesse Itzler]

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.

[Ryan Holiday]

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[Jesse Itzler]

I hired a speed coach to work with one of my boys on, on their speed. And the guy came over and he must have 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 the 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, 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. So I, I moved to an online platform training kids how to run faster by videos. This is, I 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 rule. Yeah, I left that. And I'm like, I want to live my life by design.

[Ryan Holiday]

Yeah, sure.

[Jesse Itzler]

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

[Ryan Holiday]

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

[Jesse Itzler]

Well, no, you know what? He is insanely time rich.

[Ryan Holiday]

Maybe.

[Jesse Itzler]

I may be financially, sure 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.

[Ryan Holiday]

Yeah. How many powerful people have no power over their schedule? A lot. They wake up and somebody is telling them what they are doing all fudgeing day. And how many of those things do they actually want to do? So how powerful?

[Jesse Itzler]

Right.

[Ryan Holiday]

Really?

[Jesse Itzler]

Are they 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 the. 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.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Dirt, you know, he doesn't live in a penthouse.

[Jesse Itzler]

This guy was not living on Park Avenue.

[Ryan Holiday]

Yeah. All right.

[Jesse Itzler]

And he was friendly and happy and every week and greeting people and fishing. And I was like, fuck, yeah. I'm grinding my ass off.

[Ryan Holiday]

Right.

[Jesse Itzler]

Making X amount of dollars. Probably making, like 90 grand and spending 130.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

More time than I have.

[Ryan Holiday]

Right.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah. I have these. I do this journal. And you. 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. I'm almost done with my second one, so I'm on the fifth line.

[Jesse Itzler]

Do you journal every day?

[Ryan Holiday]

I do. It's one of my favorite habits. That's a good habit. If you're like, hey, I'm gonna pick a new habit for 20, 26. Just, like, I'm gonna 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 gonna do that five minutes a day. That would be, I think, foundational habit. That would make most people happier, more self aware, calmer. And you do it all at one.

[Jesse Itzler]

Time in one book. You keep it in the same book.

[Ryan 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. Oh, yeah, because most of the time you're journaling and then you finish the journal and you start a new one.

[Jesse Itzler]

It's a true autobiography of your time.

[Ryan Holiday]

Yeah, you're see, 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 want to see, like, hey, are you getting closer or further away from the life you're trying to live? Because 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 because now you're, you're deferring and hoping that a bunch of things happen a certain way instead of just doing it.

[Jesse Itzler]

What don't you have that you want?

[Ryan Holiday]

Yeah, there's not that much, like, you know, that's a question you probably get all the time. People like, what are you working on next? And you're like, I like what I do this. I'm. 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 got to do this new thing to top what I did before, or I need to do this very different things. I don't like what I'm doing. 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. I worked really hard to get in that position. Why am I going to try to get out of it?

[Jesse Itzler]

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

[Ryan Holiday]

Yeah, okay.

[Jesse Itzler]

Libra's Rule. I got offered. I'm like, no money in my 20s. 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.

[Ryan Holiday]

Equity is expensive.

[Jesse Itzler]

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

[Ryan Holiday]

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

[Jesse Itzler]

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 was willing to take that.

[Ryan Holiday]

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

[Jesse Itzler]

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.

[Ryan Holiday]

Yeah. Cause 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, you know.

[Jesse Itzler]

Exactly.

[Ryan 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.

[Jesse Itzler]

Yeah.

[Ryan Holiday]

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

[Jesse Itzler]

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 that they're going to exit and sell Their company, and then they sell it. And very often, if it's a founder.

[Ryan Holiday]

They'Re really the tragedy of their life. And then what do they do? They go start another company. When it's like, you already did it. I know you could have just stayed. Stayed there.

[Jesse Itzler]

Yeah, yeah.

[Ryan Holiday]

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, same. True. 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.

[Jesse Itzler]

Yeah. Coaches rule. You gotta. You gotta, you know, design life by design.

[Ryan Holiday]

Yes.

[Jesse Itzler]

I feel like my dad had that. I think it's real, and I think it's just so important, man. Like, and I recognize that people don't have, you know, people have to work, obviously, and everyone is. You know, it's. It's easier. Easy 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 Coney island that was free. I was going to all these speeches and offerings around New York City that didn't cost a lot of money. 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? So I was lucky enough to kind of recognize a lot of that stuff early on.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

You know, and when I started Marquee Jet, which was a big deal for me, you know, 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 NetJets, 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.

[Ryan Holiday]

I'm not gonna.

[Jesse Itzler]

The butt. 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 young, yeah. Single, I don't know anything about anything, you know, And I was obsessed with their habits.

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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 have any Newspapers do you read? What time you go to bed?

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

You know, you would think people would ask more than they do.

[Jesse Itzler]

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

[Ryan Holiday]

Yeah.

[Jesse Itzler]

So when you ask, you get people.

[Ryan Holiday]

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

[Jesse Itzler]

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. What's the key to, like, oh, well, first of all, thank you.

[Ryan Holiday]

I really admire how you do this. And you're picking some tiny thing they, they don't get to talk about a lot. Can you tell? And they're like, yeah, how much time do you have?

[Jesse Itzler]

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 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 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 Sara so they can get caught up or whatever. And sometimes it's uncomfortable for me because I'm the plus one, which is fine, but I'm just sitting there while they're having this conversation, and no one really wants to talk to me. They want to talk to Sarah. And it's weird, but it's like we go to this event and. And this time I'm sitting next to Warren and some. We're at the same table. But somehow Sarah and I know Warren well, too, but we're not.

[Ryan Holiday]

Sold them your company.

[Jesse Itzler]

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? And now this is a guy that's been asked about the yen and dollars and stocks for 70 years. No one's ever asked him anything like this. Yes, 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?

[Ryan Holiday]

Yeah.

[Jesse Itzler]

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

[Ryan Holiday]

Did we have to save Warren from shooing people away?

[Jesse Itzler]

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 if you ask them the right questions.

[Ryan Holiday]

Yeah. That's the power of a good question.

[Jesse Itzler]

If I would have said to him, hey, Warren, what stock should I buy? He would have been like, turned away from me. But I asked him something that hit a nerve.

[Ryan Holiday]

Yes. There's nothing in it for you in that question. There's no hidden agenda in that question. It's just about connection.

[Jesse Itzler]

Yeah. And people want to connect. People want to connect.

[Ryan Holiday]

Speaking of which, I want to connect you with some books. So let's go next. Let's do it. 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. Foreign. Save over $200 when you book weekly. Stays with VRBO this winter. If you haven't seen your college besties since, well, college, you need a week to catch up in a snowy cabin. Take a week long vacation and save over $200. Book [e-mail].

[Jesse Itzler]

And Doug, here we have the Limu emu in its natural habitat helping people customize their car insurance and save hundreds with Liberty Mutual.

[Ryan Holiday]

Fascinating.

[Jesse Itzler]

It's accompanied by his natural ally, Doug Limu. Is that guy with the binoculars watching us?

[Ryan Holiday]

Cut the camera.

[Jesse Itzler]

They see us. Only pay for what you [e-mail] Liberty Liberty, Liberty. Liberty Savings Ferry unwritten by Liberty Mutual Insurance company and affiliates. Excludes Massachusetts.