Jesse Itzler

Plan your work around your life, not your life around work

Jesse Itzler's core planning premise: most people play life on defense, letting calendars fill with other people's requests. Flip it: put the life you want on the calendar first, then let work fill in around it.

“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?”

Steal thisBlock the trips, adventures, and big moments you want on next year's calendar first, then schedule work into the gaps that remain.

"Getting light": clear the clutter before you plan the year

Step one of Itzler's system is a fast purge to start the year with no baggage: delete unused apps, cancel dead subscriptions, donate clothes you don't wear, zero out email. He says the whole pass takes about an hour and creates psychological momentum.

“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.”

Steal thisSpend one hour before year-end deleting apps, killing subscriptions, donating clothes, and clearing your inbox to start January with zero baggage.

The blender: rate your whole life on a 1-to-10 happiness score

Itzler's life-audit exercise: dump every life category (finances, fitness, friendships, marriage, family, where you live and work) into a mental blender, then score overall happiness 1-10. Your brain starts at 10 and subtracts the few pillars dragging you down, instantly surfacing what to fix.

“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.”

Steal thisBlend every life category into one 1-10 happiness score; whatever your brain subtracts from 10 is what to work on next year.

Handwritten thank-you letters as a networking edge

Itzler writes 10-25 handwritten thank-you notes at year-end. His reasoning: everyone reads physical mail even though they ignore email and texts, and the effort of stamping and mailing lands differently with the recipient.

“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.”

Steal thisWrite 10-25 handwritten thank-you notes at year-end; physical mail gets read and remembered when email doesn't.

The misogi: one big year-defining thing every year

Borrowing the Japanese term, Itzler does one hard, year-defining challenge annually so each year is instantly recallable. His own list: wrote Living with a SEAL (2015), launched 29029 (2017), Ultraman (2021), biked across America (2023), rim-to-rim-to-rim (2024). Start at 37 and live to 87 and that's 50 monumental accomplishments.

“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.”

Steal thisPick one hard, year-defining challenge for the year and put it on the calendar ASAP so the year is impossible to forget.

Kevin's Rule: one mini-adventure every other month

Every other month Itzler puts something he wouldn't normally do on his calendar (a fishing trip, a concert, a hike) named after his friend Kevin. Over 50 years that's 300 mini-adventures on top of 50 misogis, and most cost nothing (a Polar Plunge, an $18 hike up Mount Washington, a Central Park run).

“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.”

Steal thisSchedule one out-of-routine mini-adventure every other month; six a year, most of them free or nearly free.

One new winning habit per quarter, not resolutions

Itzler rejects resolutions (they fail) in favor of adding one winning habit each quarter: 100oz of water a day, a 10-minute meditation, never being late. Layered over years (4 the first year, 8 the next, 12 after) they compound into a transformed life.

“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.”

Steal thisSkip resolutions; install one new keystone habit each quarter and let them compound year over year.

One new winning habit per quarter, not resolutions

Itzler rejects resolutions (they fail) in favor of adding one winning habit each quarter: 100oz of water a day, a 10-minute meditation, never being late. Layered over years (4 the first year, 8 the next, 12 after) they compound into a transformed life.

“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.”

Steal thisSkip resolutions; install one new keystone habit each quarter and let them compound year over year.

Too many goals is the #1 trap: better is better, not more

Asked what people get wrong, Itzler says they set too many goals. One specific, nailed goal (learn this one piano song) beats a scattershot list (piano plus marathon plus weight loss) where everything suffers and timelines blow out.

“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.”

Itzler did a marathon and Polar Plunge while earning $800 a year

At 22, broke and couch-surfing in NYC making about $800 a year, Itzler still ran the NYC Marathon, did the Polar Plunge at Coney Island, the Staten Island Biathlon, conferences, and a two-week trip. Proof the rich-life system never required money, just intention.

“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.”

The 8 boxes: a running life resume of everything you want to do

Itzler keeps a one-page sheet of 8 boxes for his most important life buckets (adventure, marriage, health, kids, business, personal goals, family, finance) and fills each with a running to-do list of experiences. Some get checked off this year, some are long-term; it becomes his blueprint and 'life resume.'

“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.”

Steal thisDraw a one-page grid of your 6-8 core life buckets and keep a running list of experiences you want in each; pull a couple onto the calendar each year.

Itzler read Living with a SEAL 60 times before handing it in

On making one-way-door products great: Itzler read his finished book cover to cover roughly 60 times, editing each pass, because once a book is published it can't be altered. His standard is to hand in the absolute best version he's capable of.

“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.”

Hand in the best version and you're at peace no matter the reviews

Itzler delayed publication two weeks to make Living with a SEAL 10% better. His payoff isn't sales: because it was the best book he could write, even 1-star reviews wouldn't bother him. A half-assed version would have haunted him forever.

“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.”

Run a personal year-end review like a business closes its books

Jesse Itzler treats December as a personal annual review: just as companies do post-mortems on what worked and didn't, he takes inventory of his own year across personal categories and gives himself a grade before planning the next one.

“like any business in America, when we get to the end of the year, they close out the year. They have review sessions, what worked, what didn't work, you know, what was successful, what wasn't successful. They give themselves a grade, et cetera. And I found that, um, a lot of people don't do that in their own personal lives. So I like to take a little inventory in December and just kind of have a little review process around how the year went”

Steal thisEvery December, run a personal year-in-review: grade each life category, note what worked and what to fix, then plan the next year.

Most people play life on defense; the fix is aggressive planning

Itzler argues that as you age, routine kills newness, and the only way to guarantee new experiences is to plan aggressively rather than let your calendar fill with other people's requests.

“So I become a really aggressive planner and I feel like a lot of us play, um, life on defense. Our calendars fill up with other people's requests for time. Like I mentioned, Zoom calls, weddings, appointments, school stuff. And at the end of the year, like you don't have a lot to show for it.”

Write 20-30 handwritten thank-you letters to end the year

Itzler closes every year by sending handwritten letters to the people who impacted him. He says mailed letters break through the digital clutter because people read their mail even if they ignore DMs, texts, and Slacks.

“I write handwritten letters. To the 20 to 30 people that really impacted me or helped me.”

Steal thisWrite 20-30 handwritten thank-you letters each December to the people who helped you; mailed notes break through where DMs and texts don't.

Write 20-30 handwritten thank-you letters to end the year

Itzler closes every year by sending handwritten letters to the people who impacted him. He says mailed letters break through the digital clutter because people read their mail even if they ignore DMs, texts, and Slacks.

“I write handwritten letters. To the 20 to 30 people that really impacted me or helped me.”

Steal thisWrite 20-30 handwritten thank-you letters each December to the people who helped you; mailed notes break through where DMs and texts don't.

You can't outsource soul: the DNA of a business can't be delegated

When Sam asks about services that mail letters for you, Itzler refuses, arguing that soul is the one thing a business owner can't outsource, and customers and friends can feel when something has lost it.

“Yeah, you can't outsource it. You can't outsource it. You know, um, as a business owner, like I've realized that you can't outsource soul, you know, and the DNA of a business is the soul of the business, the heartbeat of a business. You can't outsource that. And customers feel soul and your friends feel soul.”

The blender exercise: rate your whole life 1-10 to surface what to fix

Itzler's diagnostic: mentally throw every life bucket (finances, health, weight, relationships, where you live) into a blender, then rate the result 1-10. Your brain starts at 10, and the two or three things dragging the number down become crystal clear, those are what you work on.

“What I love about that exercise is immediately your brain goes to a 10. And then the 2 or 3 things that are bothering you pop in your head like crystal clear and take that number down. So maybe it was like, oh, my finances aren't there, or like, I hate my job, or things aren't great in my work. Whatever came into your head, those are the things you gotta work on.”

Steal thisPut every life bucket in a mental blender, rate it 1-10, and work on the 2-3 things your brain instantly flags as dragging the score down.

The Misogi: one big year-defining challenge per year

Itzler adapts the Japanese misogi ritual into doing one big, hard, year-defining thing annually, riding a bike across America, running your first marathon, launching a podcast. Having it on the calendar makes you show up differently and gives you a built-in reason to say no.

“the concept around a misogi is every year you do one big year-defining thing. So again, at the end of the, the year, even though you're busy with all this stuff, you have one year-defining thing that to really show for your time over the 365 days.”

Steal thisPick one big, hard, year-defining challenge each year and put it on the calendar; it reshapes how you show up and lets you say no to distractions.

Kevin's Rule: do one out-of-routine thing every 8 weeks

Named after Itzler's friend Kevin, the rule is to take one day or weekend every eight weeks to do something you normally wouldn't, fishing, a trip, visiting old friends, yielding six mini-adventures a year. Over a 50-year horizon that compounds into 300 mini-adventures.

“every other month I do something one day or one weekend that I normally wouldn't have done. I'm like, what are you talking about? He's like, oh, instead of like watching the Georgia football game, I'll take my kids fishing. I'll come to Mount Washington. I'll go visit my college friends.”

Steal thisBlock one day every 8 weeks for something off-routine; that's six mini-adventures a year, 300 over a lifetime.

Adventure costs a subway token: rich-with-adventure while broke in his 20s

Itzler counters the idea that adventure requires money: in his broke 20s he did the Coney Island Polar Plunge for a subway token and took his kids to Mount Washington for $18 in parking. America's parks, rivers, and mountains let you fill a year with adventure for under $400.

“Every year I would go to the Coney Island Polar Plunge on New Year's. You know what it costs? A subway token. Subway token. You know what it costs to do the trip to Mount Washington with my kids? $18 to park. We live in a country that offers the most insane rivers, mountains, national parks, oceans, hikes, streams.”

Add one winning habit every quarter instead of New Year's resolutions

Rather than setting goals he can't hit, Itzler layers in one new winning habit each quarter, drinking 100 oz of water, never being late, a 10-minute meditation. Over five years that's 20 compounding habits.

“rather than doing all these goals and stuff, which I, that could never accomplish. Um, I very simply, every quarter I add a winning habit to my life. For, so for example, like I, I don't drink enough water. I'm gonna drink 100 ounces of water, you know, um, as a new habit. I'm never gonna be late to a meeting. I'm gonna add a 10-minute-a-day meditation practice.”

Steal thisDrop resolutions; add exactly one new winning habit each quarter so it compounds into ~20 habits over five years.

A wealthy mentor's rule: take 3 cumulative hours a day for yourself

Running MarqueeJet at 30, Itzler interrogated wealthy clients about how they lived. One, 'James,' said he takes three hours a day for himself, cumulative across a morning sauna, a lunchtime read, a walk, so he shows up better as a parent, spouse, and boss without resenting anyone.

“One thing that he said to me, one thing he said to me, he goes, and I take 3 hours a day for myself. And I'm like, I can never do that. Well, he goes, oh no, it's cumulative. I'm like, well, what does that look like for you, James? He's like, oh, I might take a 30-minute sauna in the morning. I might take a little time at lunch to read, go for a walk, work out, da da da da. At the end of the day, it's about 3 hours a day for myself.”

Steal thisCarve out 3 cumulative hours a day for yourself (sauna, read, walk, train) so you show up better for everyone else without resentment.

Daily vitamins: do 2-3 of your favorite energizing activities every day

Itzler keeps a list of ~10 things he loves that make him strong (sauna, cold plunge, running, breathwork, walks with his wife) and treats them like a daily multivitamin, doing two or three each day so he shows up fully present.

“let's say I have 10 of those things on my list. Okay. Those are my vitamins. Those are the things that make me strong that I need every day. I try to do 2 or take 2 or 3 of those vitamins. I can't do them all, but I try to do 2 or 3.”

Steal thisList ~10 activities that energize you and take 2-3 of these 'daily vitamins' every day so you show up at your best.

Offered $10k for 10% of everything he'd ever make — and almost took it

Broke and couch-surfing at 22, Itzler was offered $10,000 by a music manager in exchange for 10% of his lifetime earnings. He thought it was the deal of the century until his host's father, a successful entrepreneur, intervened.

“But I want to own you for the rest of your life, basically 10% of anything you make. And I was like, I'll take it because I needed the money to go in the studio. I thought it was a deal of the century. You're going to give me 10 grand and all I'm going to do is pay you if I make it.”

Will vs. Can: stop asking if you can, ask if you will

A mentor told a young Jesse Itzler that the question isn't whether you CAN make a business work, it's whether you WILL. Anyone can start a podcast or run a marathon; the deciding variable is willingness to do it.

“He said, Jesse, you know, will you make this business work without the 10 grand? I said, Lou, I'm onto something. I know I can make it work. There's a, I know I can. And he, he took his notebook and he literally threw it on the ground and he said, I didn't ask you that. I didn't ask you, can you? I said, will you? Hmm. There's a big difference between can and will.”

Steal thisWhen you say 'I can do that' about a goal, replace it with 'will I or won't I?' and commit.

Take a marquee client at a loss to build a calling card

Itzler delivered a Knicks theme song for $4,000 even though it cost him $4,800 to produce. Landing the Knicks as a named customer made every subsequent sales call to other pro teams easy.

“And by the time I paid the studio, the engineer, the lawyer that I had, the singer, the producer, it cost me $4,800 to actually deliver the song. That they were paying me $4,000 for. And when I look back on it, you know, for most people they'd be like, that's a terrible business model. It was the best business model in the world for me because when you start out, you know, people buy into stories, momentum, and people very often more than the products.”

Steal thisLand one marquee logo at break-even or a loss, then use it as a reference to win everyone else.

Walk the market into the room instead of pitching a slide

Re-pitching NetJets, Itzler skipped the PowerPoint and brought eight real prospects into the lobby who each stood up and said they'd buy a 25-hour jet card but never a fractional plane. Live demand beat any chart.

“We brought in our own focus group. We had 8 people in the lobby. Mm-hmm. And they walked in one by one and they stood up and said that they would never buy a fraction of an airplane, what NetJets was selling, but they would buy a 25-hour jet card. And at the end of the meeting, they literally said, if you guys raise money or put up your own money, if you can figure it out, we'll give you a shot.”

Steal thisInstead of a market-size slide, bring real prospects who say 'I'd buy this' to the decision-maker's face.

Marquis Jet's average customer spent ~$250k/year

Itzler explains that Marquis Jet's roughly $200M first-year sales weren't membership dues — the average customer spent around $235k-$250k a year on flight time.

“No, because our average— our average customer spent close— I think it was $250,000 or $235,000 a year.”

Cornered the muffin supply at TED to land his first jet customer

To break into the credential-gated TED conference, Itzler bought out every muffin in Monterey, then used the only available muffin to start a conversation with Josh Kopelman of Half.com — his first Marquis Jet sale.

“So the next morning I got up at 5 and I bought all the muffins from this. I controlled all the muffin inventory. In Monterey, California. And I literally just waited. And this is a true story, by the way, and it's, it's been verified.”

Do what everyone would do, then 30% more — earn the referral

Itzler kept his first jet customer by over-servicing: returning every call like anyone would, but also vetting pediatricians for his trips and pre-booking dinners. The unexpected extras earned referrals he rinsed and repeated for five years.

“I serviced the hell out of him. I did what everybody listening would do, but I did 30% more. So when he went to Mexico, he expected me to return his call and every DM and all that. Of course I did what everyone here would do. But he went to Mexico. He didn't expect the list of pediatricians that I vetted in case his kids got sick.”

Steal thisDeliver the expected service, then add the 30% no one asked for — that's what generates referrals.

Named Matt Damon as 'my partner' mid-pitch to save the Coke deal

With his Coca-Cola coconut-water pitch going badly, Itzler casually dropped that Matt Damon was his partner, then got Damon to film a 35-second coconut video addressed to Coke's CEO. The deal closed and Coke bought Zico two years later.

“I just turned to the president, the guy at Coke, and I'm like, you know, my partner Matt Damon and I, and the guy went, Matt Damon's your partner? I said, I didn't mention that. What are you talking about? We go all the way to the 1-yard line. I leave and I call Matt. I'm like, Matt, I need a favor.”

High-aggravation, high-reward? Pass. Even on friends.

Itzler's filter at 55: more isn't better, better is better. He turns down anything high-aggravation regardless of the payoff — money, projects, even friendships — and is actively on 'friend reduction.'

“I have this thing at this point in my life, if it's high aggravation for high reward, I'm not doing it. If it's— and that goes for anything, money, friends. I don't want high aggravating friends. I'm on friend reduction right now. I'm on friend reduction, man. I want low aggravation.”

Pickles: a $billions category with zero brand marketing

Itzler argues pickles are a marketing problem waiting to be solved: 75% of Americans eat them, the average American eats ~10 lbs a year (more than cereal), yet of the 7 best-tasting pickles he could name only one company.

“So I'm like, if I only know one of this top 7 best tasting pickles, there's a problem in the marketing of pickles. It's a marketing problem and I'm a good marketer. So, and it, that's where it started. And I'm like, This is a category with no innovation, no fun. You know, 75% of Americans eat pickles. The average American eats like 10 pounds a year. That's more than cereal.”

Steal thisHunt for huge consumption categories with no recognizable brand — that's an unbranded marketing opportunity.

Roll up liquor-store countertops and rent them to CPG brands

Itzler's freestyle idea: liquor stores have the only uncluttered checkout countertops in retail and are a fragmented mom-and-pop market. Roll them up, control 10,000 countertops, then sell that prime impulse-buy space to big CPG brands.

“Do a roll-up, go pay someone for, go rent the countertops of all the liquor stores and then go to Nabisco or one of the big boys and be like, hey, guess what? I own 10,000 countertops. You want to put your widget there? You want to put your fucking widget there? Keep the money warm, Sean.”

Steal thisAggregate fragmented physical shelf space (liquor-store counters) and resell it to brands that crave impulse placement.

3 minutes a day: compliment, congratulate, console

Itzler's relationship-building system is sending short notes daily under three buckets — compliment, congratulate, console. Three a day for a year is ~1,000 'permission slips' that earn the right to reconnect later.

“So I was like, okay, if I did 3 of those a day and just took 3 minutes and just started hitting friends, suppliers, manufacturers, influ— whatever, over the course of a year, I'll send 1,000. I will plant 1,000 permission slips all over the country and world, 3 minutes a day.”

Steal thisSpend 3 minutes daily sending notes that compliment, congratulate, or console people in your network.

The Misogi: one big year-defining thing every year

Borrowed from a Japanese ritual, Itzler's Misogi rule is to put one hard, year-defining challenge on the calendar annually (a book, a race, living on a monastery). Over a lifetime that's ~50 things on your 'life resume.'

“So there's an old Japanese ritual called the misogi, and we took the liberty to kind of create our own version of what that means. But basically it means that every year you do one, or the way I've interpreted it is you do one big year-defining thing. And you had, you should have something to show for it every year.”

Steal thisSchedule one hard, memorable, year-defining challenge for next year and put it on the calendar now.