Chapter 1: What is Jesse Itzler's system for planning a successful year?
That is un-friggin'-believable. That made me cry. 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.
Chapter 2: How can you prepare for a productive 2026 by getting light?
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.
Chapter 3: What does it mean to close the books on your past year?
So that's why I'm here at his house today to learn the exact system that he uses to plan his year. I feel like I could rule the world. I know I could be what I want to. Okay, Jesse, teach me how to plan my year. 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 kid stuff.
Chapter 4: How should you effectively plan your year?
Like before you know it, like what do we have to show for a whole year? Right. 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? So we 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 Misogi, 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.
And then there's other things that were, I kind of procrastinated or like, you know, I couldn't tell you, Like what happened in April? I have no idea.
Chapter 5: What are the eight boxes in Jesse's planning system?
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 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- Which is fine. 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. We tend to play life on defense.
Chapter 6: How can you implement a life audit for better personal growth?
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? Right. 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?
So we 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 Misogi, 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. And I'm just really glad that I made the time because I wasn't going to otherwise. And then there's other things that were, 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 Misogi that I did, I started coaching. I told you, I started coaching a high school basketball team. We launched a new project for our work, and we really 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. Which is fine. Yeah, but I want to be better at it. It showed me that this is super important. 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, my life is the only real project.
Everything else is just like, you know, a footnote or, you know, just a part of that. 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?
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, you know, unaccomplished, and, like, I 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.
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 why was this year better than last year and this and that. And I have this system that I've been using. And it's not based on theory. I didn't Google it. It's based on trial and error. and I'll share it with you and I'll walk you through it.
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Chapter 7: What is the significance of setting a Misogi for the year?
That's how many text messages, unread text messages I have. I don't even know how many. That's 815 by the way. 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 told me before this, you said, hey, step one is get light. I can't do that here because I'm at your house. And so I did it.
And a couple of things that I learned right away. First of all, just doing the simplest action gave me momentum. Because planning my year felt big and heavy. It's like, oh God, I got to 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, 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. I think it's highly significant. 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 got to 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. I don't wanna feel like I have a knapsack of weight on me. I wanna 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 it doesn't mean you have to make changes immediately, but I would put a little bit of thought into that. 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. So that's the first step.
And you know, like I said, I go through everything from my closet to my emails, to my subscriptions, to my car, to my- Where do you start? What's your- Closet. 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.
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Chapter 8: How can you create a meaningful life checklist for personal fulfillment?
Like what's the psychology around this, right? Because 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. 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. Yeah. We're making a Sean smoothie. I want you to look at 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, et cetera.
Where you live, where you work, put everything in the blender and then shake it all up. And now on a one to 10, with 10 being the best score and one 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.
Yeah, I think it's an eight. Okay, so it's an eight. Yeah. So what I love about this exercise is you put all this thing and your brain immediately goes to a 10 and it subtracts the two or three things that bring it down. So what are the two or three things if you don't mind sharing? 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 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 nine 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. Right. And what was the other? 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 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 channel them towards something that's cool and interesting and matters to me that I'll be proud of years from now as it develops? So a couple of quick thoughts. So for starters, an eight is an 80. If my kid comes home with an 80 on a test, that's a B minus. So B minus is good, but you don't want to go through life as a B minus.
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