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Jesse Itzler
That is un friggin believable. That made me cry.
Sean
This is Jesse Itzler, and he's got the craziest resume you've ever seen. He sold a private jet company to Warren Buffett. He helped build Zico Coconut Water. And he's the only guy who can say that 50 Cent was his intern. But I don't admire Jesse just because he's rich financially. I admire him because he leads such a rich life. He runs these crazy endurance races. He goes on adventures with his friends. And I've always wondered, how does one guy do so much? As Jesse says, we don't lack time, we lack a system. So that's why I'm here at his house today to learn the exact system that he uses to plan his year.
Jesse Itzler
I feel like I can rule the world. I know I could be what I want to. I put my all in it. Like, no days off on the road. Let's travel.
Sean
Jesse, teach me how to plan my year.
Jesse Itzler
Listen, this is so exciting, man. Thanks for being here. Yeah. I mean, first of all, before we even get started, I think it's just really important to talk about why we're here. I don't take years lightly. You know, we don't get a lot of them and we're all so busy. And I feel like in general, most people plan their life around work. And I think it's really important to plan work around your life. In other words, we tend to play life on defense. Like our calendars fill up with other people's requests for time zoom calls and meetings and weddings and appointments and kids stuff like before you know it, like, what do we have to show for a whole year?
Sean
Right.
Jesse Itzler
So we're sitting right now in December and do you feel like you had a great 2025? Like, what were some of your highlights of 2025?
Sean
So I had a few events that I thought were pretty awesome. So you went to one of them In January, we planned a big event and we did it. It's called Hoop Group. So that's kind of one of my favorite parts of the year. I feel like because of our conversation last year I picked a musogi, which we'll talk about, but like the sort of grand challenge for the year. And I did it. And I'm like, really proud of myself for doing that. And I kind of know that I really would have. I wouldn't have done it this year. It would have been on my someday list.
Jesse Itzler
Right.
Sean
And then there's other things where I kind of procrastinated or, like, you know, I couldn't tell you, like, what happened in April. I have no idea. You know, like, there were some months that just flew by because I wasn't very intentional. So I'd say I did, like, some of the things that I feel really proud of. Like, I started coaching. I told you, I started coaching a high school basketball team. We, you know, launched a new project for. For our work, and we really, like, poured ourselves into that. So there's a few things that I was pretty intentional about, but I would say there were many months that flew by and.
Jesse Itzler
Which is fine.
Sean
Yeah. But I want to be better at it. Like, it showed me that, you know, this is super important. Like, you know, I've always thought of myself as the CEO of my company, but not the CEO of my life.
Jesse Itzler
We tend to play life on defense. Like, our calendars fill up with other people's requests for time zoom calls and meetings and weddings and appointments and kids done, like, before you know it. Like, what do we have to show for a whole year?
Sean
Right.
Jesse Itzler
So we're sitting right now in December, and do you feel like you had a great 2025? Like, what were some of your highlights of 2025?
Sean
So I had a few events that I thought were pretty awesome. So we. You went to one of them in January. We planned a big event, and we. We did it. It's called Hoop Group. So that's kind of one of my favorite parts of the year. I feel like, because of our conversation last year, I picked a musogi, which we'll talk about, but, like, this sort of grand challenge for the year, and I did it, and I'm, like, really proud of myself for doing that. And I kind of know that I really would have. I wouldn't have done it this year. It would have been on my someday list.
Jesse Itzler
Right.
Sean
And I'm just really glad that I made the time because I. Like, I wasn't going to otherwise. And then there's other things where I kind of procrastinated or, like, you know, I couldn't tell you what happened in April. I have no idea. You know, like, there were some months that just flew by because I wasn't very intentional. So I'd say I did, like, some of the things that I feel really proud of. Like, the misogy that I did. I started coaching. I told you. I started coaching a high school basketball team. We, you know, launched a new project for our work, and we really, like, poured ourselves into that. So there's a few things that I was pretty intentional About. But I would say there were many months that flew by and.
Jesse Itzler
Which is fine.
Sean
Yeah. But I want to be better at it. Like, it showed me that, you know, this is super important. Like, you know, I've always thought of myself as the CEO of my company, but not the CEO of my life. And it's like that my life is the only real project.
Jesse Itzler
Yeah.
Sean
Everything else is just like, you know, a footnote or, you know, just a part of that.
Jesse Itzler
Yeah.
Sean
And so I kind of want to think of myself more as, like, the CEO of my life, the architect of my life. And like an architect. I want to have my blueprints that I want to follow. And of course I'll improvise, but I'd like to have a blueprint versus just winging it, just reacting to the latest thing, you know.
Jesse Itzler
Got it. Well, the way this came about, just to give a little bit of background, is my life got very busy. You know, I have multiple businesses. I have four children. I'm married. I had elderly parents I was taking care of. I have friends that I want to see. I have races that I want to do. Like, there was just so much that I wanted to do. I didn't have a system for it. So I would have all these ideas and I would leave, like, the end of the year, I'd be like, oh, I didn't do this. I feel like, you know, unaccomplished and like, all left all this stuff on the table. And I just kept getting older and older, and as more and more stuff came on my plate, I needed a system. I was never taught a system. No one ever said, hey, this is how you map out your year. You know, they just kept throwing more stuff at me. So over the course of the last probably 20 years, an evolution happened. I started to figure out what. Why did. Why was this year better than last year and this and that. And I have this system that I've been using and just in. It's not based on theory. I didn't Google it. I didn't. Like. It's based on trial and error.
Sean
Right.
Jesse Itzler
And I'll share it with you and I'll put. I'll walk you through it, and if, you know, we'll help map out your year. And if anyone here is listening, if there's a couple here things here that have you, you know, help you have a little bit more efficiency next year or get you excited to do something that maybe you wouldn't have done then the next 20 minutes or whatever are going to be very well worth Your time.
Podcast Host / Narrator
So.
Jesse Itzler
So for starters, before you even start anything, you know, here we are at the end of the year, we're coming into a new year. The first thing that I like to do is I get as I go into the new year and I call it getting light. I want to come into 20, 26 fired up, hitting the ground, not playing catch up, like, oh, I have to do all these emails. I didn't clean my clock. I want to be ready to go. No baggage, no baggage. Light. And I literally, I want to feel light. I even like the term getting light, right? So getting light means closing out the year, you know, the proper way. So the. We have a little jar here. Just step one, getting light. You can see that it's empty because there's going to be nothing in your jar when you're done. So getting light starts for me at home. So the first thing that, that getting light means getting rid of all the apps on your phone that you don't use. Getting rid of, canceling all the subscriptions that you don't use that you're paying, you know, stuff, going to your closet and donating all the clothing that you don't wear. Now that might sound insignificant. It's very significant. It's a sign that like of newness. It's a sign of like I'm coming into the year getting rid of stuff that I don't need anymore. It's your desk coming in and not having clutter everywhere. It's your filing cabinet, it's your car. Is your car messy? Do you have your insurance in your car? Is there like getting everything tight? And by the way, that whole process to me could take like an hour, right? It's not like I'm talking about like, oh, I need a week. It's like your emails, I get my emails to 0delete.
Sean
I mean I save, respond like right now, forget email. That's how many text message unread text messages I have.
Jesse Itzler
I don't even know how many. That's 815.
Sean
815. So I'm coming into the new year with 815 obligations, 815 guilt trips that I, you know, mistakes that I've made basically if I don't clear that out. So you, you told me before this, you said, hey, step one is get light. I can't do that here. Cause I'm at your house. And so I did it and I couple things that I learned right away. First of all, just doing the simplest action gave me momentum. Cause planning my year felt big and heavy. It's like, oh, God, I gotta know what I want in life. And it's like, dude, I haven't known that for 37 years. Am I sure today's the day I could do this? Versus what I did was I went to my car and, like, you know, the cup holder area, Like, I got little kids, so that is like, nom. That is popcorn, everything. I don't know. There's a whole history of, like, life in that little cup holder. So I just cleaned out the cup holder, the simplest possible action. And right away, I was, like. Felt a little lighter, right? Like, one layer off my back. And then I did it to my desk. I did it to my subscriptions. I canceled $1,300 of monthly subscriptions of just random apps and software that we've been signed up for. So I already started to get light and feel pretty amazing. I cleaned up my home gym.
Jesse Itzler
Yeah.
Sean
Which was like, I didn't have to. You know, nobody else works out there, but I do. And, like, those are places I go every day. My car, my gym, my desk.
Jesse Itzler
I think it's highly significant. It's the. You're describing momentum, and momentum is not to be underestimated. You know, if you start the first week, you come back from the holidays, and, like, everything's a mess, and, like, you gotta play catch up. You're going through 815 texts. Is that a good way to start the year? Would you rather, like, do all that now in this little cleanup period that we're in now? You know, get it all done and then come in, like, ready to. I'm in attack mode. You know, I don't want to feel like I have a knapsack of weight on me. I want to come in attack mode. So if you're listening to this, I highly encourage you to spend a little bit of time and get organized, get light, get rid of things. And I would think about also part of that, just mentally, like, subtraction, like, what's heavy in your life? You know what I mean? Like, what relationships are heavy, you know, what obligations and commitments can you cut down just to get a little bit more lighter? And doesn't mean it to make changes immediately, but I would. I would put a little bit of thought in. Into that.
Sean
Let's take a quick break. We're covering a lot of information in this episode. So the team at HubSpot did something really cool. They took my notes from talking with Jesse, and they turned it into a guide on how to plan a massive 2026 in less than 60 minutes. If you want those notes, you can get them right now in the link in the description. Now back to the episode.
Jesse Itzler
So that's the first step. And you know, like I said, I go through. I go through everything from my closet to my emails, to my subscriptions, to my car, to my.
Sean
Where do you start? What's your closet?
Jesse Itzler
I start in the closet. And by the way, if you went up to my closet right now, maybe you guys can film it on the way out. I have seven bags. Seven bags of donate. I have a very simple rule. If there's a jump ball, 50, 50, like, should I keep this or not? Then I just say, someone needs it more than me. Right? And it's easy to part because sometimes it's hard to part with stuff. Maybe it's sentimental or I'll take a picture of it. If I don't wear it, I'll just keep it or I'll throw it in a box. It's like a sentimental box. But I don't want a zillion things hanging in my closet. I never wear. Right, how about this? When I walked in my closet this morning and I had all these little hangers with nothing on it and I like seven things to grab, I felt good. No, I'm not kidding. Like I felt good. Like I didn't feel like I was wasting clothing or space or time. I know, sounds ridiculous. Like, how is this fit into planning your year or whatever? It all fits into how you feel, right? You know? Yeah.
Sean
So psychological. It's a psychological momentum win to start. So love that. So that's which one? That's jar.
Jesse Itzler
Number one. Jar number one. Step one, get light.
Sean
All right, there we go. What's. What's number two?
Jesse Itzler
Closing out your year. So every good business. And so after you get light, you know, what does every good business do at the end of the year?
Sean
Close the books.
Jesse Itzler
Close the books. They have a review session. They think about what worked, what didn't work, etc. So I like to close out my year. So that process for me is pretty simple. The first thing that I do is I take inventory on me. So if you planned the best year in the world and you had the most unbelievable things happen, but you had several things in your life that were broken. Maybe it was your marriage or your relationship, maybe it's your finance, your health. I don't know. Even if you had this windfall of money or whatever, if a couple of the key pillars are operating at a 5 out of 10 and a 1 to 10, it's like a multiplier, you know, like, it's not going to multiply the way that it should. Just so one, what I like to do is I like to identify, like, where are my weaknesses? Okay. What are the things I have to fix next year? So what I do is the life audit part. Life audit. It's a person, like a business audit. This is my little life audit. And this is what I.
Sean
You gotta be honest with yourself without beating yourself up too much. Like, what's the psychology around this? Right? Cause I want to be, you know, like, I'll tell you one right now, right? So like, I want. I'm actually going to do this, by the way. This is not like theory. So I think we should actually fill this out for me at least. So this is fitness.
Jesse Itzler
Let me put you through it. So I want you to just imagine you had a blender. So anyone here could do this. Imagine you had a blender. You're making a smoothie or making a Sean smoothie. I want you to all the different categories in your life and don't rate them, but just in general, think about what you have. So you have finances. That's a big part. It goes in your blender. Fitness, your health and wellness goes in the blender. Friendships, marriage, family, etc. Where you live, where you work, put everything in the blender and then shake it all up. And now on a 1 to 10, with 10 being the best score and 1 being rock bottom. Rock bottom. And you put all these in together, what do you think your overall happiness number is? Because at the end of the day, we want to feel good. What would be your number? And you can be honest with me.
Sean
Yeah, I think it's an eight.
Jesse Itzler
Okay, so it's an eight.
Sean
Yeah.
Jesse Itzler
So what I love about this exercise is you put all this thing in your brain immediately goes to a 10, and it subtracts two or three things that, that bring it down. So what are the two or three things, if you don't mind sharing?
Sean
Yeah, so it would be the fitness one. So I had a goal with my fitness, which was, this is it. This is going to be the year I'm going to get the best shape of my life. And I was like, I'm going to build these healthy habits to where by default, I got to be in the best shape of my life. That was the goal. And if I'm honest with myself, I made some progress, but not at the proportion of how important it is to me. It wasn't some important. It was really important. But. But I only Got some progress, not a lot of progress. And so that was the one where that was like, go from a 10 to a 9 right away because I didn't get as far along there. I'm not as proud of myself as I would be if I had done this the way I intended to.
Jesse Itzler
Right. And what was the other?
Sean
The other one is in the work category. So I had a great year financially, but my goal this year was to actually find another project to pour my creative energy into. So the podcast has been this amazing thing over the last five years, but I kind of wanted to figure out my next five years, what that would be. And I wandered around for a little bit trying to, is it this? Is it that? And I ultimately landed on this book project and I started on it, but, like, I didn't get as far as I thought I would. And if I'm honest, even now I wander a little bit of like, is that. Is that the right. Am I making the right decision? So there's some uncertainty there of like, am I going to use my talents the way that I want to use them? Am I going to put channel them towards something that's cool and interesting and matters to me that I'll be proud of, you know, years from now as it develops.
Jesse Itzler
So a couple quick thoughts. So for starters, an 80, you know, an 8 is an 80. 80. If my kid comes home with an 80 on a test, that's a B minus.
Sean
Yeah.
Jesse Itzler
So B minus is good, but not. You don't want to go through life as a b minus 2. You identify two things that you probably want to put more energy to in 2026. So like, most people are probably going to have two or three things and it's going to be usually finance or relationship or health or whatever. The main, the main buckets, those are the things you want to put a little bit more energy into and as themes. And you're going to want to pick one or two things that are going to get you excited because no one wants to work on their weaknesses. You know, like, if you're having a bad marriage or something, like, that's hard to, like the energy to repair that and this and that. But, you know, that's something you have.
Sean
To put energy, which we gravitate towards what's easy and we're good at it. We get immediate feedback and momentum from it.
Jesse Itzler
Right, right. So part of closing out the year is just doing a little bit of self reflection. I mean, this is a deep dive and like a little bit personal, but identifying, like, what are the things I got to work on going forward. And what am I going to put a little energy in. So for you, fitness, coming up with some newness and work, et cetera. Could be something. Could be something that you want to focus. And we'll get to it in a minute, in 20, 26. So I do a little review of what worked, what didn't work. If I have a calendar, obviously have my big ass calendar. What I like to do is I like to go through my phone and I'll write down all the highlights. My calendar is my highlight reel.
Podcast Host / Narrator
Right.
Jesse Itzler
I like to write down all the highlights. Maybe it's my kid's football game or maybe it was a concert I went to. And just make sure that I have a full, full recap of the year so I can look at it on one piece of paper. It's the best exercise. I can look at it on one piece of paper, see where my gaps were, see what I accomplished. Because a lot of people forget. Oh my God, I forgot that we went. I took this weekend trip or I went to this.
Podcast Host / Narrator
Yeah.
Sean
I can't tell you what I did in March.
Jesse Itzler
So. So do a thorough review on one big piece of paper. Go back through your phone. And then, by the way, now you have a great time capsule too, of 2025. So I do a little personal audit. I go through my entire year again. Takes like 20 minutes.
Sean
So like I have one from this, like in November, it was my first basketball practice as a coach. I had one weekend where we just went on like, AI and made songs. So it was like we just basically became musicians for a weekend. And we. And we had a demo, like on Monday where we all played our tracks for each other. And so I put that in there. Then I was like two, like, books that I read or an interesting thing that I read and a conversation I had with my buddy Trevor about, you know, about fear and the stuff he's learned in his research. And so I just try to, like, write those now so that I kind of have it. I have it, you know, more at my fingertips.
Jesse Itzler
Yeah, yeah, I love it. And then one thing that I love to do is I write handwritten letters. I love to spend a little bit of time and write thank you letters to people that like, hey, Shawn, you know what? There's 8 billion people in the world. You chose me to be on your podcast. There's 8 billion people. Thank you so much for the opportunity to address your audience. I love sending those out.
Sean
So you. So I brought some. Cause I want to Actually do it this year. So when I. I'll even do, you know, a couple of them today.
Podcast Host / Narrator
But.
Sean
But I'll do. Do some more after we. We wrap up. But the thing that I was gonna ask you is like, how do you. Like when I sat down to do this, I was like, where do I start with this? And what am I saying? So are you using the review to basically be like, oh, my friend who helped teach my son how to drive, you know, is that kind of how it's all feeding one into the next?
Jesse Itzler
My kids, football coaches, people that had tutors, anyone that had an impact on me, podcasts that I was on, friends that I did races with. Some. It could be someone from afar like, Sean, you don't even realize this, but your podcast had a big impact on me. I'm a fan. I'm just. This, this, this ch checks several boxes for me. Selfishly, it's a great networking tool because everybody reads their mail. Not everybody reads their email or their text, but everybody reads their mail. And there's a different energy that goes into a handwritten letter. Writing it, getting a stamp, licking it, taking it to the mailbox. Someone receives that differently than da da da da send.
Podcast Host / Narrator
Right.
Jesse Itzler
So there's a different energy.
Sean
And you're not outsourcing this. You're not giving this to an assistant somewhere?
Jesse Itzler
No. So part of it selfish. I'm planting seeds as a networking tool and as just a thank you note, like, you know, we built a relationship and this is part of that process. Two, like, the recipient feels great about it. Like, oh, my God, this guy took enough time to handwrite me a letter. Like, it's that that makes them feel good. I've been doing this since I'm 21 years old. Even this year, I'll write 25 letters. You know, I'll write it to some of my partners at the Atlanta Hawks. Hey, guys, great year. Thank you, guys. You know, people that have stepped in for me. Someone offered to do a speech when I was sick for me, like, just unbelievable gestures. I recognize them. I recognize them.
Sean
I'm a goal oriented monkey. What's a number I should shoot for?
Jesse Itzler
Even 10 is amazing. 10 to 25. You can do them on the plane. You can do them while you're watching a football game. Probably takes about three minutes per. Oh, that's perfect.
Sean
I'll do this on my flight back. Yeah, I can either watch a shitty airplane movie or I can just like kind of flood myself with, you know, being grateful and spreading some good karma.
Jesse Itzler
Out into the World, there's no rule to it, but I think getting 25, look, you do it for 10 years, you send 250 thank you notes, handwritten letters to people like, how many are you doing? How many have you gotten? How many handwritten letters did you get last year thanking you.
Sean
I remember I got one from Joe.
Jesse Itzler
There you go. Yeah, that's it. I didn't write you one yet for no. Okay, it's coming.
Sean
Well, I have a separate list for people that don't write me that.
Jesse Itzler
You remember Joe? Yeah, this is what I'm saying. Like, you know, like, you don't have to be a genius or a bazillionaire to write a handwritten letter. And. And. And that's an ink stain in your brain to probably never forget it, you know, so.
Sean
Ink stain in the brain. I like that.
Jesse Itzler
Yeah. So that. That's another strategy of closing out the year, part of my process.
Sean
So I already have one. I have one for Haley. Haley. Shout out to Hayley. Haley is what I call my food girlfriend. She's my nutritionist who will call me. She calls me every morning, 8am and she says, you know, what's the plan for today? How'd you do yesterday? And we. She's like a food therapist, basically talking through more of the psychology versus a meal plan. And, you know, thank you to. I already know for her is like, thank you for sticking with me. Like, I know I pay you for this, but, like, sometimes I flake out on the calls for two days in a row. I go dark for three days. Sometimes I say I'm gonna do something I don't. But I feel like she always shows up with, like, full faith, not just, like, doing an obligation. And I really, like, I appreciate that. You know, like, it takes a lot. Like, she's. She believes in me, and I think that's one of the best gifts you can give someone. She gave me that, so I'll use that as my Hailey note.
Jesse Itzler
You know, step one, I'm. I'm trying to get light coming into the year with energy. Step two, I'm closing out the year. And by the way, you can use your own strategy if you don't want to write a handwritten letter. I'm just telling you what I do, right? I want to get light, whatever that looks like for you. I want to close out my year. This is how I do it. But however you want to do it again, summarizing your year, closing the book on it, memorializing it, reviewing it like you would as CEO of your Business really important and super fun. That might be like, oh my God, I didn't do shit this year. Well, okay, good wake up call. We got a whole new year to attack, you know. So it's just an honest assessment and identifying with the blender what it is I really need to spend a little bit time on. That doesn't mean that's my goal for next year. That it's just like being aware of the pain points, right? Because you're not going to be a 9.9 if you have three pain points that are going to suck you down no matter how much energy you put into the year. Right. So you gotta fix the pain points.
Sean
So this is cool because it's kind of like a measure twice, cut once type of deal where we haven't even got to the thing I'm gonna do next year, right? Like, I think that's how I would typically have done this. Was resolutions, you know, the end of the year, what's resolution this? And it's a, it's a should do. It's not. I'm gonna do. I don't put a date on it. I don't really use the momentum from getting light and reviewing my year and taking account of what's going on to make that plan. I just kind of jump into it.
Jesse Itzler
So I like this can jump in for one second. I think that anybody can have a good year. Like things are going to happen. I'm going to get an invitation to something. There's going to be a highlight like to have an okay year. You could do it. Who the wants to have an okay year? You don't get a lot of years, right? You're not hoping for a great year. I can have, right? I can have a good year. Maybe a couple of people invite me on a great trip. I get someone says we go to the super bowl. That's amazing. Or I can sit down and say what's going to light me up that I'm so excited about this year that like I wake up and I have no pressure. I know that if I execute this and this isn't saying I'm not working, this is not. I'm just planning me before my work. Work's always going to be there. I'm going to have a, I'm going to work a lot more hours than I'm going to do this. But that's different. I'm talking about the stuff that like at the end of the day, your six year old kid, you're young, you know, your kids are going to like you, you're going to have a photo book like that. There's no zoom calls in my book. There's no picture of me on zoom on in that book. That's stuff that I did that like immediately made me smile. That's what this is. I'm going to show you how to do it. Right now. Our goal is to get you excited about this, right? It's not the plan, a perfect year or whatever. It's to make sure that 2026 doesn't fall through your fingertips, right? And we have a lot to show for it. So at the end, and this is exciting to me, there's a lot of days in here to. You don't do everything every day. We got a lot of time to accomplish the things that you want to accomplish. All right, that's just, just for starters, it's a big long Runway that we have. So I do three things every year as the backbone of my planning. And this is where I start. Now, again, the key is to plan my life first so my work comes around it. Not what most people do, which is their work fills up and then whatever gaps they try to fill in, we flip that script upside down. We're going to play aggressive, we're going to plan aggressive. We're going to think about the things that we love to do that we want to put our energy into. We only have a limited amount of energy. We want to put our energy into the things that excite us or move the needle in the buckets that matter. So to ensure that, for me, I do three very simple things. Two of them are planning, and one of them is more habit. You talked about resolutions, but I like something that I do better than resolutions. So there's an old Japanese ritual called the misogi. You know, the term and the notion around a misogy is you do one big year defining thing every year. This is really important. At the end of the year, you want to have something to show for it. Last year for you, it might have been like, man, I launched this insane three day basketball camp with billionaires. I launched that in 2025. Maybe it was I, you know, wrote, I'm launching a book. Whatever it is you want to have a podcast, whatever, one big, really big year defining thing that you have. To the point that if I were to say to you right now, what'd you do in 20? If you asked me, what did you do in 20? 2015, I wrote living with a seal. 2017, I launched 29 or 29, a business that I had 2021, I did a race called Ultraman. 2023, I rolled my bike across America. 2024, I did rim to rim to rim. 2025. Every year you should be able to, you know, and if you can do that. How old are you?
Sean
I'm 37.
Jesse Itzler
So if you can do that from. If you started now and you had one big year defining goal, you live to be 87. You'd have 50 monumental things that you've accomplished in your life. That's a heck of a ride, right? Heck of a ride. So the first thing I encourage people to do is think about in 2026, at the, in, at the end of the year, in December, by the way, if you didn't even do anything else but you just did this, right? You're going to, like, you win, you win. What's the, what's the one thing you want to look back on and be like, you know, I did this this year. And you might not know what that is now, but when it is, put that down on the damn calendar asap. Because that is, it's a really important. And I don't think it should be something like, it's got to be hard and big, right? Truly, you're defining, not like, oh, I took a trip to Italy. That's a trip to Italy.
Sean
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Jesse Itzler
Put down the big mistogee. That's one step. The second thing that I do is every other month I put something on my calendar that I normally wouldn't have done. I named this Kevin, Kevin's Rule, after my friend Kevin kind of taught me about this. But every other month, I do something. So, like, instead of watching the Georgia football game, I might take my kids fishing, we might go to a concert, I might go visit my car. I have a little mini adventure because it's the same multiplier. If every other month you do one thing you normally wouldn't have done, this is critical mission Critical. If you can't do that, you're really out of balance. Like, you can't take one day out of every six weeks to do something for yourself. Like, what are we doing? So if you do plan, like six little mini adventures, whatever they are, you put them on on your calendar and, you know, I could show you mine in a second. Well, same thing if you're 37 and you live to be 87. So you'd have 50. I just learned how to play the piano. Moments, you're defining things. But now you'd have 300 mini adventures on top. Like, just think about that, man. 50 year defining things and 300 mini adventures you wouldn't have had. That is who's doing that, right? You know, And I'm not talking, oh, I need a lot of money. I don't own my own. It's easy for you to say, no. Anybody can go to the Polar Plunge, that's free. Anybody can go to Mount Washington that costs $18 to park and hike. Anybody can do a Central park run, you know, enjoy the New York Roadrunners Club or, you know, there's just so much that this country offers if you prioritize it. So the way you prioritize piano. So I do those two things. So that already is, you know, filling up my calendar with some adventure. And then I do what you do. I think about, what are the other big things? What are the other rocks that are important to me? Maybe they're my kids football games, or maybe they're a college visit, or I'm going to take my kids learning how to drive. I'm going to carve out these days, you know, what are the big memories I want to have and moments, they go on my calendar first. Again, the goal is to schedule your life so work fills in around it first work and your life fills around it. Those are very fundamentally different approaches. And so those big rocks go on the calendar first.
Sean
So, I mean, I might just be kind of bad at this, but I guess for me, I almost feel like, you know, going in, I feel like I'm limited by time. And then as soon as I say, no, no, I'm gonna make time for this, then I realize I'm limited by my own imagination. It's like, I don't even really know what would I do? Because I'm just not practiced at having these unscripted days at having these masogas. It's almost hard, like, to think of them. So I guess, like, is it hard for you to. And also, like, how do you get better at that.
Jesse Itzler
Well, first of all, just being aware of that. I want to put stuff on my calendar that's meaningful to me, gives you a different awareness into what other people do. So instead of approaching things like, oh, I could never do that, you know, which is like, what I thought before I saw you play the piano. By looking at what other people are doing, that should be inspiration, you know, so you're just looking at the world differently. Like, oh, Taylor did this race. That would be. I never thought about that. What would it look like? Sarah just said to me she wants to run the Disney half Marathon. We've been married for 20 years almost. I've never seen her run once in my life. You want to run the Disney Half Marathon? She just told me now she wants to learn the dance from what? You get inspiration from other people. And so, you know, it's a process. No one's ever taught anyone to think or look at the world like that. We look at the world that, like, oh, I have a zoom call. And like, think about how much energy you put into scheduling your work meet all staff meetings, zoom calls, reviews, board meetings, investor meetings, looking at pitch decks, you know, like, conference calls, travel, like, we spend. Imagine if you took that same energy into planning the most important thing, your life. You look at the world differently. You'd start to, like, fill up stuff with, like, you know what? I do want to go to the Georgia football game. I do want to go, you know, jump in the water or whatever. I've never been in a sauna. Let me go to one of these sauna places and see what everybody. What is this thing that's going on? You know, you'd start to, like. And it becomes contagious, infectious, you know, addictive, when you start to have this kind of enthusiasm and excitement. So, you know, we don't get taught that in school. We don't get taught that by our. By anybody. You know, you get taught it by being inspired to say, you know what? I don't want to be an 80. I don't want to be an 8. I want to be a 9. You know, take it in your own hands and say, like, I want this year to be my highlight reel. You know, another step that we should be in here is just being excited to have the app, man. Just to be. Are your parents alive? Yeah. Are your kids healthy? Knock on wood. You're 37 years old. Both your parents are alive. All your kids are healthy. How does life get better than that? Like, no, seriously, like, just being excited about, like, Jesus, man. I'm in this position where I can go visit my parents while they're healthy. I can take my kids to something. Don't blow that opportunity. Don't blow that opportunity, you know? So this isn't about planning the most perfect year at all. It's about planning something that you're excited about, that you feel good about at the end of the year. And you're not just like, if it moves the needle this much for a listener, they're like, God, I want to be really intentional on how doing more things that are important to me, learning something, spending more time with my family, you know, like it's going to be worth it. So I do those two things. I put my misogy's rule down, I put my Kevin's rule stuff as they come and I get inspiration here, ideas. I'm going to go visit a college friend, I want to go see my parents, I'm going to take a family trip. I'm going to take my kids out from school and take them to lunch one day and surprise them. It doesn't have to be, but you just want to start lighting shit up. And then you put all your other rocks so you have your Kevin's rule, your misogy, and then these big rocks, these other moments, whatever these moments are. And then the third thing that I do after all that stuff is on my calendar is I don't believe in resolutions. They've never worked for me. Most resolutions fail. But what does work for me, it's not a planning thing, but it's a really good strategy as we go into the next year, is to create one winning habit, a quarter. We're all a product of winning habits, winning routines, and a winning mindset. If you get your habits right, your mind right and your routines right, you're going to be in a great spot. So you want to do things that towards that. So for me, adding one new winning habit, a quarter, that could be like, I don't drink enough water, I'm going to drink 100 ounces a day. I'm going to learn at a 10 minute a day meditation practice. I'll never be late for another meeting. But if you start layering in winning habits again, cumulatively for this year now you have eight, next year, 12 the year after. Like you just keep layering it in and adding this stuff and do everything the same. You're going to have a great year, better year, just by definition, if you add, you learn how to play the piano, you go on these trips, you have some winning habits, you're going to have a better year and it's going to jump start a whole new process for you. Two other things I want to talk about, I think balance is something that you hear a lot of and I think that balance isn't something that happens day to day. It's something that you should look at over the course of a year, you know what I mean? Because you're going to be in and out. We talked about seasons when you first got here, when you're learning how to play the piano or maybe you have a big pitch meeting or whatever, you're out of balance, like sweetie, I'm not going to be around working late, whatever. But then you go into a season of recovery or, you know, action or whatever. So the balance over the course of the year is going to going to come into play where it could level out, but there's going to be times where it's day to day way out of whack. So you can't look at that on a day to day level. I would look at it more over the course of a year. The second thing that I would say is on a daily basis or even a weekly basis, I think it's important to think about where do you want to put your energy? What are the things that you want to put your energy into? Usually to me it's the stuff that's on my calendar. And what do you want to, what don't you want to put your energy towards? Because we only have a limited amount of energy. So think about your themes for 2026. You know, like for you it might be fitness, it might be, you know, trying something new at work, a new, launching a new project or whatever. You know, that would be a good clue of like where you want to put your energy into and especially on a daily basis. So for me, I like to look at my weeks on a Sunday night and look through what's going on on a week at a glance basis to see if like I don't really need to do this now. That's not super important. I have more important things to do right now than, than that. And even on a daily basis I like to write out the night before what my day looks like. People talk about morning routines, but I'm a much bigger believer in evening routines because I feel like you can't just wake up and wing it. Oh, am I going to do today? Like the competition's too good the night before. Lay out your thing. Seven o', clock, I'm going to work out. Eight o', clock. I'm taking my kids to school nine to two. I have this two one, four. I shut down like and follow the script, you know, just to create some more, more efficiencies. So that's sort of how I plan my year. Masogi. Then I put my Kevin's rule down. Then I put all my little rocks down. The things that I want to do, I think about where I want to put my energy. I look at my balance more on like the year versus day to day. I don't beat myself up that oh my God, I'm, I'm not home today, you know. And then on a day to day level, starting the night before. Yeah.
Sean
What do you think most people get wrong when they do this process? Like they, they mean well, they're trying, but they fall into like a common trap. What's a common trap?
Jesse Itzler
A common trap is having too many goals. More isn't better. Better is better. So like you had one specific goal. I'm gonna learn how to play the piano this year. This song, you know, that's a really great goal and you freaking nailed it. Versus I'm learning the piano. I'm gonna run a marathon. Like now you're like all over the place and like you're missing lessons and now your four month journey became a one year journey and everything suffers. So I think a lot of people say I'm going to lose weight, I'm going to do this. I'm going to like change my whole life, every area of everything. I think it's too much like that.
Sean
Do you already have your musogi for next year or not yet?
Jesse Itzler
Yes.
Sean
What is it?
Jesse Itzler
I am going. So I like to do physical things. I'm going to do a 2020, an EV. I'm calling it the Everesting Triathlon. So I'm going to swim 29,029ft which is 5.5 miles, then bike 29,029ft, the equivalent of Everest in elevation gain on a bike, which is really, really hard. And then I'm going to do a 29 or 29 event which is you climb the equivalent of Mount Everest all in a triathlon format.
Sean
So like back to back to back.
Jesse Itzler
Back to back to back to back. I'll sleep because we'll do it like stages. But back to back to back to back, it's me super hard. Like the bike alone will take will probably take me like 30 hours. The swim will take five hours and the, the hike will take 30 hours. That's 70 hours roughly. Geez, I can't wait.
Sean
All right, let's take a quick break because I gotta tell you a story. Let me tell you about the first time I tried to run payroll for my team. I was using a traditional bank. And you know the type. It's got a janky interface, it's built like a 2002 tax form. And, and it was open only during business hours. And I hit send and it froze. They flagged the transaction, they locked my account, they put me on hold for 45 minutes, and then they told me I gotta visit my local branch. And that was the day I started looking for a new banking solution. After asking a few founders what they were using, I found out about Mercury. And so now my payroll is two clicks. I can wire money, I can pay invoices, I can reimburse the team all from one clean dashboard. That's why I use it for all of my companies and so do 200,000 other startup founders. And so if you're looking to level up your banking, head to mercury.com and apply in minutes. Mercury is a financial technology company, not a bank. Banking services are provided through Choice Financial Group, column A and Evolve bank and Trust members, fdic. And I'm sure you get a lot of like, easy for you to say, you're rich, you're free, you have all the time you want, you have all the money you want, you can do whatever you want. And then people will self limit because they say, well, that's not me. So I guess I can't.
Jesse Itzler
Yeah.
Sean
And so like what say you?
Jesse Itzler
When I was 22 years old, I was sleeping on my friend's couch in New York City. I was bouncing couch to couch to couch. And I had a friend that was one of the guys that I was staying with, was working and making a ton of money, like quarter million dollars. But you know, at the time was.
Sean
That'S all, that's all the money.
Jesse Itzler
I was making like $800 a year, you know. But at the end of the year, I did the Polar plea. Polar Plunge in Coney Island, I ran the New York City Marathon, I did the Staten island biathlon, I went to multiple conferences, I went on a two week trip like my. I've been doing this since I had zero. I just informalized it, I didn't even understand it. But what happened is when I got into my 40s and 50s and I was like, God, this guy wrote a book, this guy sold the business, this guy ran an ironman, this guy did a marathon, this guy goes in saunas, this guy did blah Blah, blah, like, what's going on? I'm like, I don't know. I just been, like, it adds up. I've just been doing all these things. And then I realized this is what I've been doing. I just do it on a bigger platform now. So it doesn't mean, like I said, you don't have to climb Mount Everest to have a great year. You have to do things that make you feel good and they don't just happen. You need a system. If you wait, your calendar is going to fill up and other people are going to determine where your energy goes. If you choose where you want to put your energy like you just did, then you're going to have an amazing year. It's a decision. I really wholeheartedly believe that it's a system. So the last thing I want to say real quick is another thing that I do. And again, like, I'm just talking about things that have been really helpful for me, trying to just share as much as I can. And not everything needs to resonate, right? We just want to inspire people to have a program and a plan that makes them have an efficient year. We'll take you through your year is. I call it the eight boxes.
Sean
Okay?
Jesse Itzler
And this is something that has really been helpful for me. I take a piece of paper and I make eight boxes and I pick the categories. And maybe yours is six. Some might be four. For me, it was eight. I think about what are the buckets that are the most important buckets in my life. The things that I do want to put the energy into. And for me, it was. It's adventure. I love going on adventures. Travel, trips, marriage, obviously is super important. Health and fitness, my children, kids, my business, my personal goals and stuff like this. My family and my personal finance. And we talked about this off camera. I love the way you. You meant, you talked about it. But what I do is I put down all the things it's like a running life to do list, almost checklist. Now, some of this stuff is for this year, some of. And I might even put a little dot, but some of it's long term. For example, in adventure, I put everything I want to do in those buckets in here. So I. This is a snapshot of where I'm going from now till the end of the journey. Some of this stuff will get checked off. For example, I wanted to do a sauna tour of Finland. Always wanted to do it. I did it last year. Check it off. But now I have a new thing I want to do. This race called the three. This thing called the three. I had it. So it's like a running list. And what I love about this is it's like it's out of my head and it lives. It doesn't live. It lives on a. On a piece of paper that I can refer to. And it gives me a blueprint for where I'm going. So, like, if you don't know what you want to do, if you don't have a vision, if you don't have a dream, you know, like one of these things is write a book. It doesn't mean I'm going to do it right now, but I have a specific book I want to write. It goes on this sheet, and I refer to this all the time. Now, some of these things are going on my calendar for 20, 26. Some of them are going on my calendar for 20. Some of them are just long term, and it's a work in progress.
Sean
So you, you basically are collecting throughout the years interesting ideas of what a great life might look like. What are some of the things I want to do before, you know, the clock strikes zero and this whole thing's over. And then in a given year, you might pull one two things and put it on the calendar.
Jesse Itzler
That's exactly.
Sean
And then you see the momentum in the checklist. And this is the.
Podcast Host / Narrator
You.
Sean
I think you call it the life resume. Right? Like, you know, you have a work resume.
Jesse Itzler
I put some examples of it up here, but yeah, perfect. So, like, for example, Sarah just. We were just talking to my wife, and she's like, I want to learn the Thriller dance. Okay, well, that's going to go in my personal bucket. We're going to learn the Thriller dance. Now, does that mean that has to happen this week? No, but I'm. Now it's like, it's exciting. I have. Like you were saying, where do you get the ideas from? Well, when you get an idea, put it down, right? You know, let it bring it to life. Don't let it just marinate. Like, put it down.
Podcast Host / Narrator
So.
Jesse Itzler
And man, it feels good when I check these off. And every year I have like, you know, five or six things that I've done and I've added new stuff.
Sean
Have you ever heard of the idea of a reticular activating system that's part of your brain?
Jesse Itzler
No.
Sean
So there's like this phenomenon. If you ever go car shopping and you start thinking, oh, maybe I'm gonna buy a BMW, all of a sudden when you're out on the road, you'll be seeing BMW. BMW?
Jesse Itzler
Oh, that's the 3 Series.
Sean
That's the one he was saying it comes in blue.
Jesse Itzler
Yes.
Sean
Did all those just appear? No, they've been there the whole time. But your brain, you told your brain, you said, hey, brain. And brain's normally filtering out 99% of things. The RAs, the reticular activating system. So once you switch that on, you've basically told your brain, hey, start to pay attention for this. So, like, you know, you could do it for, for BMWs when you're car shopping, but you could do the same thing for life. So, you know, once you realize, oh, I've got a, like a life bucket list here to, to fill out this sort of menu of things I want to. I want to do in my life, it's kind of like turns on the brain to start looking for possibilities. What might be in that? Like, I don't know, you know, you told me about the three, you know, the Polar Plunge or the 300 Club. If I, you know, now that I'm looking to fill mine up, I'll start to think to myself, hey, would that be one? Would that be one? Is that the one I want? Is that the one I want? And now it'll become easier for me, I think.
Jesse Itzler
Yeah, that's what I was saying about, like, coming up with Misogi's and Kevin's rule. It's in your RAs now, you know, like you're thinking about it. I'm also really lucky. I live with. I have a friend group that also is driven in thinks like this. So when we get together, it's like, any good ideas? You guys, you guys heard any races or what do you guys think about this year? Anything cool you think we should be doing? And, you know, that's how ideas we listen. Because of that, we rode our bike across the country. The same group did Rim to Rim to Rim. The same group went to Finland. The same group, you know, this year is doing the 300 Club at the South Pole. The same group, you know, is. Continues to do these things. So that's not easy to find a group of people that would do that. In fact, I didn't even find that until I was in my 50s. I didn't have that in my 20s, 30s, and 40s.
Sean
You found them by doing these or.
Jesse Itzler
You found by doing them by putting myself out and saying, hey, I'd love to do that with you. You know, sharing it. Social media has helped, right, Bring us together. But of the 10 guys that I've done these adventures with over the last seven years, I only probably knew one of them 10 years ago.
Sean
There's like, that's pretty inspiring because I, I saw you had that group. I've watched some of your videos and when you see it and you see how close you guys are to do these adventures, you sort of just assume, I guess these are just his college buddies that like, I guess I missed it. But you saying I did it, I'm not even 50. So like, what's my excuse to start, you know, now, like, it's not too.
Jesse Itzler
Late, you know, In a way you've done it. You've brought together this group through the basketball tournament that you host. And I'm pretty sure you could call Hayes or any of the guys that we've met and say, hey, I got an idea. I want to go take a survival class in Montana in the winter. I want to do a three day. Everyone's going to put their hand up. It's like you sort of have it right. You just have to now take action into like beyond basketball.
Sean
Right.
Jesse Itzler
And that's sort of what we. What I did.
Sean
That might be one of my things I put on here is like build a crew to do these things with.
Jesse Itzler
And you know, those things for you could also be learning experiences. Like for you. You know, maybe it's not like you said, you don't want to go scale a mountain in Antarctica, but you might want to take an intensive, you know, memory course with a guy that never forgets a name.
Sean
Right.
Jesse Itzler
You could take a four day thing and. Cause I'm not going.
Sean
A big one for me is creative projects. So I've created like a creative bucket list. It's like, oh man. In my lifetime, I want to, I want to make a song that's just a catchy, just banger that just, you know, it gets out there in the world and other people are, you know, bopping to the song in a car. I want to have like a board game that I make. And so I just made a list of things I'd like to make in my life.
Jesse Itzler
You just gape. See that? Yeah, me one.
Sean
And so I'm. I have this like creative bucket list. So for me, one of my. Probably where you have adventure for me would be, you know, creative projects that I want to go do in my lifetime. Like, I want to make a movie. Why not?
Jesse Itzler
I have a song that I wrote 15 years ago that I still think is a hit that I want to put out.
Sean
I've just been marinating.
Jesse Itzler
It's just. Yeah, I don't feel pressure to like, you know, for projects, you know, like that process, that creative process, like it comes in waves, you know, and even if it takes 15 years, it comes in waves. And the same thing with this book.
Sean
How do you balance the like, I want to do so much without you. Don't give off, I feel rushed energy. It's like, it's very rare for me to find somebody who's got both of those right. There's some people who just want to stay in place. They're content, they don't feel that rushed. Most people I know who are the achiever types that have more ideas than they have time, they have this almost like nervous energy and it's almost like, oh, they're almost not enjoying it because they just always feel like I should be doing more.
Jesse Itzler
I have, I have both genes. I have the like, ready, fire, aim. And then I have, I've learned that like if you're going to put out a product like a book or a song or something that's going to live out in the world and it's in its form that can't be altered, right? Like, we can always improve on our products, but like a book, once it's written, it kind of can't be altered. You want to, you want. My people probably push back on this, but for me, I found that I want to make the best version that I can make right? Then I want to wait a second and then I want to try to make it 10% better when I think it's done. Like when I did Living with the Seal, I handed the book in. I read it 600 times. Six. I'm not kidding. 600 hundred times. I read that five hour book. Maybe not 600. Let's, let's say I read a 60. That's a big difference. But let's say I read 60, which I probably did, cover to cover. Do I like it, edit it, writing notes or whatever. I finally hand the book and I have a deadline. They like, we got to get this out the public. You know, Amazon needs it, all this. I hand it in, they're like, great. This is the best. We love it. Thank you. Blah, blah, blah. I go home, I read it 61 the 61st time. I called my publisher the next day and I'm like, I need two more weeks. She's like, what? I'm like, I can make this 10% better. This is the only book. I wanted this to be the best ver like, and I handed in the best book that I could write. I could not write a better that was it. That was the absolute best version of that book that I could write and would know what that meant. No matter what happened, I felt good about it. If it got one star reviews and sold 18 copies, I don't care.
Sean
You're at peace.
Jesse Itzler
That's the best book I could write. But if I wrote a half assed version of that book, I would have beaten myself up forever. So that's how I feel about those kinds.
Sean
Those kind of one way door projects.
Jesse Itzler
Yeah.
Sean
That's awesome. Jesse, thank you so much for doing this.
Jesse Itzler
Oh thank you. I loved it. I feel like I could rule the world. I know I could be what I want to. I put my all in it. Like no days off on the road. Let's travel to never looking back.
Podcast Host / Narrator
Alright everyone, if you're listening to mfm, you probably want to make more money. Well, I want to tell you about a podcast you might want to check out. It's called the Sales Evangelist and it's hosted by Donald Kelly. Each week, Donald interviews the world's best sales experts who share their strategies to succeed in sales. They share actionable insights and stories that will encourage, challenge and motivate you to hustle your way to the top. If you're someone looking to raise your income level, check out the Sales Evangelist. You can find it wherever you get your podcasts.
Date: December 31, 2025
Hosts: Sam Parr and Shaan Puri
Guest: Jesse Itzler
Main Theme:
How to design and live a "rich" life—one defined by memorable experiences and personal intention—by implementing Jesse Itzler’s practical system for planning your year, balancing ambition with fulfillment, and moving from reactive living to proactive, meaningful action.
In this energized, idea-packed episode, Shaan Puri sits down with serial entrepreneur and adventurer Jesse Itzler at Jesse's house to uncover Jesse’s step-by-step system for planning a remarkable year. Jesse, famed for selling a jet company to Warren Buffett, co-founding Zico Coconut Water, and living an epic, adventure-filled life, shares candid advice and tools to help anyone intentionally craft a richer, more memorable life in 2026. The conversation covers confronting the time-suck of daily obligations, clearing physical and mental clutter, annual self-audits, planning signature adventures (the Japanese “misogi”), the power of handwritten thank-you notes, and surrounding yourself with like-minded people.
Jesse’s system—rooted in trial, error, and lived experience—puts adventure, intentionality, and connection above mere busyness. “Richness” comes from designing your year around purposefully chosen milestones, relationships, and new habits, then letting your work and obligations fill in around them. No matter your resources or stage of life, the essence is to act, review, and play aggressively—because nobody wants to look back and realize they lived a “B minus life.”
Takeaway:
If you want a richer, more intentional year, get light, close out your year with reflection and gratitude, proactively schedule big challenges and mini-adventures, and create living systems—on paper and in habits—that make this possible. “You need a system. If you wait, your calendar is going to fill up and other people are going to determine where your energy goes.” (Jesse, 41:24)
Listen to this episode for the full energy, stories, and practical examples that can turn your 2026 into a year you’ll never forget.