If you want a rich life, watch this before 2026
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. 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.
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.
Okay, Jesse, teach me how to plan my year.
Yeah, 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? 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 I had a few events that I thought were pretty awesome. So we, 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 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've, I wouldn't have done it this year. It would've been on my someday list.
Right.
And, 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. You know, like there were some months that just flew by 'cause 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— 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.
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 4 children. I'm married. I had elderly parents I was taking care of. I have friends that I wanna see. I have races that I wanna 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 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 it, why was this year better than last year and this and that. And I, I have this system that I've been using and it, 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. Right. And I'll share it with you and I'll put, I'll walk you through it. And if, you know, will, will help map out your year. And if anyone here is listening, if there's a couple of 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 gonna be very well worth your time. So, so for starters, before you even start anything, you know, here we are in at the end of the year, we're coming into a new year. The first thing that I like to do as I get, as I go into the new year, and I, I call it getting light. I want to come into 2026 fired up, hitting the ground, not playing catch up. Like, oh, I have to do all these emails. I didn't clear 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, the proper way. So the, we have a little jar here, just step 1, getting light. You can see that it's empty 'cause there's gonna be nothing in your jar. When you're done. So getting light starts for me at home. So the first thing that, that I— 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 zero, delete, I mean, I have save, respond like right now.
Forget email. That's how many text messages, unread text messages I have.
I, I don't even know how many. That's 815 last night.
815. So I'm coming into the new year with 815 obligations.
Yeah.
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, uh, 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.
Yeah.
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. 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? Or 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 wanna feel like I have a, 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, 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 to make changes immediately, but I would, 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, 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?
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 7 bags, 7 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. 'Cause 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 had like 7 things to grab, I felt good. Thank you. 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 it sounds ridiculous. Like, how does this fit into planning your year or whatever? It all fits into how you feel, right? You know?
Yes. It's a psychological, it's a psychological momentum win to start. So I love that. So that's which one?
That's jar number 1. Jar number 1. Step 1, get light.
All right, there we go. What's, what's number 2?
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?
Close the books.
They close the books. They have a review session. They think about what worked, what didn't work, et cetera. 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, um, 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 outta 10 on a 1 to 10, it, it's like a multiplier, you know, like it's not gonna multiply the way that it should. It's just, so one, what I like to do is I, 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—
This is a life audit part for you.
Little life audit. It's like, it's, it's, it's a pers— like a business audit. This is my little life audit. And this is what I—
You got to be honest with yourself without beating yourself up too much. 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, but 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 take all the different categories in your life and 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, what would be your number? And you can be honest with me.
Yeah, I think it's an 8.
Okay, so it's an 8.
Yeah.
So what I love about this exercise is you put all this thing in, your brain immediately goes to a 10 and it subtracts the 2 or 3 things that, that bring it down. So what are the, what are the 2 or 3 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 in 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 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. 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 5 years, but I kind of wanted to figure out my next 5 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 it? 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.
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-. Yeah. So B- is good, but not— you don't wanna go through life as a B-. Two, you identified two things that you probably wanna put more energy to in 2026. So like most people are probably gonna have two or three things and it's gonna be usually finance or relationship or health or whatever the main, the main buckets. Those are the things you wanna put a little bit more energy into and as themes. And you're gonna wanna pick 1 or 2 things that are gonna get you excited. 'Cause 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, oh, the energy to repair that and this and that. But you, you know, that's something you have to put energy to.
We gravitate towards what's easy and we're good at it. We get immediate feedback and momentum from it.
Right, right, right. So part of closing out the year is just doing a little bit of self-reflection. I mean, this is a, 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 in work, etc., could be something, could be something that you want to focus on. We'll get to it in a minute in 2026. So I do a little review of what worked, what didn't work. If I have a calendar, obviously I 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, right? 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 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. 'Cause a lot of people forget, oh my God, I forgot that we went, I took this weekend trip, or I went to this.
Yeah, I can't tell you what I did in March. No.
Yeah. 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.
Right.
So I do a little personal audit. I go through my entire year again, takes like 20 minutes.
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 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. 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, right. Hey, Sean, 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. Right. I love sending those out.
So you, you, so I brought some because I want to actually do it this year. So when I, I'll even do, you know, a couple of them today, but, but I'll do, do some more after we wrap up. But the thing that I was going to 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 it, is that kind of how it's all feeding one into the next?
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 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, right? Writing it, getting a stamp, licking it, taking it to the mailbox. Someone receives that differently than da da da da, send.
Right.
So there's a different energy.
And you're not outsourcing this, you're not giving this to, to an assistant somewhere.
No. So part of it's selfish. I'm planting seeds as a networking tool and it's just a thank you note. Like, you know, we built a relationship and this is part of that process too. 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, right? You know, I'll write it to the, 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—
I'm a goal-oriented monkey. What's a number I should shoot for?
Even 10 is amazing. 10 to 25. You can do 'em on the plane. You can do 'em while you're watching a football game. Probably takes about 3 minutes per.
Oh, that's perfect. 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 out into the world.
There's no rule to it, but I think getting 25 out— 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?
I remember I got one from Joe.
There you go. Yeah, that's it. I didn't write you one yet for— No.
Okay.
It's coming.
Well, I have a separate list for people that don't write me. Thank you.
That's what— 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. Right. And, and, and that's an ink stain in your brain. You probably never forget it, you know?
So ink stain in the brain.
I like that. Yeah. So that, that's another strategy of closing out the year. Part of my process.
So I already have one. I have one for Haley. Haley. Shout out to Haley. Haley is what I call my food girlfriend. She's my nutritionist who will call me. She calls me every morning, 8:00 AM, 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 that 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 2 days in a row. I go dark for 3 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.
You know, step 1, I'm trying to get light coming into the year with energy. Step 2, 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 of 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 3 pain points that are going to suck you down no matter how much energy you put into the year, right? You got to fix the pain points.
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 going to 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 a resolution? Uh, this. And it's a, it's a should do. It's not I'm going to 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. So I like this.
Can I just jump in for one second? I think that anybody can have a good year. Like things are gonna happen. I'm gonna get an invitation to something. There's gonna be a highlight. Like to have an okay year, you could do it. Who the fuck 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 it, right? I can have a good year. Maybe a couple of people invite me on a great trip. I get someone says, we gonna go to the Super Bowl. That's amazing. Or I can sit down and say, what's gonna 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 it— this doesn't say I'm not working. This is not— I'm just planning me before my work. Work's always gonna be there. I'm gonna have a, I'm gonna work a lot more hours than I'm gonna do this. But that's different. I'm talking about the stuff that like at the end of the day, Your 6-year-old kid, your young, you know, your kids are gonna like, you're, you're gonna 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 gonna show you how to do it right now. Our goal is to get you excited about this, right? It's not to 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 have to do, 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 3 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 gonna play aggressive.
Okay.
We're gonna plan aggressive. We're gonna think about the things that we love to do that we wanna put our energy into. We only have a limited amount of energy. We wanna 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 3 very simple things. 2 of 'em are planning and 1 of 'em is more habit. You talked about resolutions, but I, 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 misogi 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've been like, man, I launched this insane 3-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'd you do in 2015? I wrote Living with a SEAL. 2017, I launched 29029, a business that I had. 2021, I did a race called Ultraman. 2023, I rode 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?
I'm 37.
So if you can do that from— if you started now and you had one big year-defining goal and you lived to be 87, you'd have 50 monumental things that you've accomplished in your life. That's a heck of a ride. Heck of a ride. So the first thing I encourage people to do is think about in 2026, 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 gonna like, you win. You win. What's the one thing you wanna 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, it's a really important, and I don't think it should be something like, it's gotta be hard and big, right? You truly, you're defining, not like, oh, I took a trip to Italy. That's a trip to Italy.
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So we put down the Big Mistogi. 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's Rule after my friend Kevin kind of taught me about this. But every other month I do something I want. 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 co— 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 6 weeks to do something for yourself. Like, what are we doing? So if you do plan like 6 little mini adventures, whatever they are, you put 'em 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, year-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 Road Runners Club or, you know, there, 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 gonna take my kids learning how to drive. I'm gonna carve out these days. You know, what are the big memories I wanna 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 goes around it. Those are very fundamentally different approaches. And so those big rocks go on the calendar first.
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 going to make time for this, then I realize I'm limited by my own imagination. It's like, I don't even really know what, what would I do? Because I'm just not practiced at Well, having these unscripted days, having these misogynes, it's almost hard, like, to think of them. So I guess, like, is it hard for you too? And also, like, how do you get better at that?
Well, first of all, just being aware 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, you're just looking at the world differently. Like, oh, Taylor did this race. That would be in— 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 wanna 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, and you, 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 so— imagine if you took that same energy into planning the most important thing, your life. You'd look at the world differently. You'd start to like, fill up stuff with like, you know what, I do wanna go to the Georgia football game. I do wanna go, you know, jump in the water or whatever. You— I, I've never been in a sauna. Let me go to one of these sauna places and see what everybody's— 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, you 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 op— man, just to be— are your parents alive?
Yeah.
Are your kids healthy? Knock on wood. Yeah. 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, um, 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 Masogi's rule down, I put my Kevin's rule stuff as they come. And I get inspiration. Here are ideas. I'm gonna go visit a college friend. I wanna go see my parents. I'm gonna take a family trip. I'm gonna take my kids out from school and take 'em to lunch one day and surprise them. It doesn't have to be, but you just wanna start lighting shit up. And then you put all your other rocks. So you have your Kevin's Rule, your misogi, 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, on my calendar, is I don't believe in resolutions. They've never worked for me. Most resolutions fail.
Right.
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 gonna be in a great spot. So you wanna do things that, that towards that. So for me, adding one new win— winning habit a quarter, that could be like, I don't drink enough water, I'm gonna drink 100 ounces a day. I'm gonna learn a 10, a 10-minute, add 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 8 next year, 12 the year after, like, you just keep layering it in and adding this stuff and do everything the same, you're gonna 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 gonna have a better year, and it's gonna jumpstart a whole new process for you. Two other things I wanna 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? 'Cause you're gonna 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 outta balance. Like, sweetie, I'm not gonna be around. I'm 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 gonna do today? Like, The competition's too good. The night before, lay out your thing. 7:00, I'm gonna work out. 8:00, I'm taking my kids to school. 9:00 to 2:00, I have this. 2:00, 1:00, 4:00, I shut down, like, and follow the script, you know, and just to create some more, more efficiencies. So that's sort of how I plan my year. Musogi. Then I put my Kevin's Rule down. Then I put all my little rocks down, the things that I wanna do. I think about where I wanna 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. 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, a common trap. What's a common trap?
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 friggin 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 4-month journey became a 1-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.
Do you already have your misogi for Next year or not yet?
Yes.
What is it?
I am going— so I like to do physical things. I'm gonna do a 29, 20, an Ev— I'm calling it the Everesting Triathlon. So I'm gonna swim 29,029 feet, which is 5.5 miles, then bike 29,029 feet, the equivalent of Everest in elevation gain on a bike, which is really, really hard. And then I'm going to do a 29er/29er event, which is you climb the equivalent of Mount Everest. All in a triathlon format.
So like back to back to back, 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 going to be super hard. Like the bike alone will take— will probably take me like 30 hours. The swim will take 5 hours and the hike will take 30 hours. That's 70 hours roughly. Jeez, I can't wait.
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 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. Uh, after asking a few founders what they were using, I found out about Mercury.. And so now my payroll is 2 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, Call M&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 could do whatever you want. And then people will self-limit because they say, well, that's not me, so I guess I can't. Yeah. And so, like, what say you?
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 $250,000. But, you know, at the time was—
that's all, that's all the money.
I was making like $800 a year, you know. But at the end of the year, I did the 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 2-week trip. Like, I've been doing this since I had zero. I just didn't formalize 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, blah. Like, what's going on? I'm like, I don't know. I've 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's gonna fill up and other people are gonna determine where your energy goes. If you choose where you wanna put your energy, da da da da da da da da, like you just did, then you're gonna have an amazing year. It's a decision. I really wholeheartedly believe that it's a system. So the last thing I wanna 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, and not everything needs to resonate, right? We just wanna 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, uh, 8 boxes.
Okay.
And This is something that has really been helpful for me. I take a piece of paper and I make 8 boxes and I pick the categories. And maybe yours is 6, some might be 4. For me it was 8. I think about what are the buckets that are the most important buckets in my life, the things that I do wanna put the energy into. And for me it was, it's adventure. I love going on adventures, travel trips. Marriage obviously is, 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, uh, we talked about this off camera. I love the way you, you, you meant, you talked about it. Uh, um, but what I do is I put down all the things. This is like a running life to-do list, almost checklist. Now, some of this stuff is for this year, some of it, 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. I did it last year, check it off. But now I have a new thing. I want to do this race called the 3— this thing called the 3. I add it. So it's like a running list. And what I love about this is it's like it's outta my head and it, it lives, it doesn't live, it lives on a, on a piece of paper, right? 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 wanna do, if you don't have a vision, if you don't have, uh, a dream, you know, like one of these things is write a book. It doesn't mean I'm gonna do it right now. But I have a specific book I wanna 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 2026. Some of them are going on my calendar for 2023. Some of them are just long-term and it's a work in progress.
So you, you basically are collecting throughout the years in interesting ideas of what a great life might look like. What are some of the things I wanna do before, you know, clock strikes zero and this whole thing's over. And then on a given year, you might pull 1, 2 things and put it on the calendar.
That's exactly right.
And then you see the momentum in the checklist. And this is the, you, I think you call it the life resume, right? Like, you know, you have a work resume.
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 wanna learn the Thriller dance. Okay, well that's gonna go in my personal bucket. Right. We're gonna 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. So, and, and man, it feels good when I check these off. And every year I have like, you know, 5 or 6 things that I've done and I've added new stuff.
Have you ever heard of the idea of a reticular activating system as part of your brain?
No.
What's that called?
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 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 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 3, 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.
Yeah. And 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 and 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? 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, right? 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. You found them by doing these, or you found them 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. Um, but of the 10 guys that I've done these adventures with over the last 7 years, I only probably knew one of them 10 years ago. 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 that, I'm not even 50. So like what's my excuse to start, you know, now? Like it's not too late.
Well, 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. Right. You wanna do a 3-day? Now everyone's gonna put their hand up. It's like you sort of have it.
Right.
You just have to now take action into like beyond basketball. Right. Right. And that, that's sort of what we, what I did.
That might be one of my things I put on here is like build a crew to do these things with.
And you know, those, those things for you could also be learning experiences. Like for you, you know, maybe it's not like you said, you don't wanna go scale a mountain in Antarctica, but you might wanna take an intensive, you know, um, memory course with a, a guy that never forgets a name.
Right.
You could take a 4-day thing. And, and 'cause I'm not—
a big one for me is creative projects. So I've created like a creative bucket list. It's like, oh, Oh man, in my lifetime, I wanna 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 this song in a car. I wanna have like a board game that I make. I want, and so I just made a list of things I'd like to make in my life.
You just gave, see that?
Yeah.
Just gave me one.
And so 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 wanna go do in my lifetime. Like, I wanna make a movie. Why not?
I have a song that I wrote 15 years ago that I still think is a hit that I wanna put out.
It's just been marinating.
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, it comes in waves, you know? And even if it takes 15 years, it comes in waves. And the same thing with this book.
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.
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 gonna put out a product like a book or a song or something that's gonna 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 it, you want my, people probably push back on this, but for me, I found that I wanna make the best version that I can make, right? Then I wanna wait a second and then I wanna try to make it 10% better when I think it's done. Like when I did Living with a SEAL, I handed the book in, I read it 600 times. 600, I'm not kidding. 600 times I read that 5-hour book. Maybe not 600. Let's, let's say I read it 60. That's a big difference. But let's say I read it 60, which I probably did cover to cover. Do I like it? Edit it, writing notes or whatever. I finally hand the book in. I have a deadline. They like, we gotta get this out. The public, the 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 call my publisher the next day and I'm like, I need 2 more weeks. She's like, what? I'm like, I, 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 you know what that meant? No matter what happened, I felt good about it. If it got 1-star reviews and sold 18 copies, I don't care. You're at peace. 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 kind of—
those kind of one-way door projects. Yeah, that's awesome. Jesse, thank you so much for doing this.
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. Never looking back.
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