Sometimes all it takes is a single quote or idea to suddenly shift my entire perspective on life. I had one of those moments when I went down the rabbit hole listening to Jesse Itzler.

DON’T LOOK AT HOW MUCH TIME YOU HAVE LEFT.

INSTEAD LOOK AT HOW MANY TIMES YOU HAVE LEFT.

– Jesse Itzler

“I’m fifty years old,” says Itzler. “The average American lives to seventy-eight. That means if I’m average, I have twenty-eight years left. How old are your parents? How many times a year do you see them? Let’s say they’re seventy-years-old, and average. If you see them twice a year, you don’t have eight more years with them, you’ve got sixteen more times with them. Once I started to look at time this way, my visits with them became insanely valuable. Now, the television is off; I’m present. I fundamentally shifted the way I look at life. It created urgency to not put stuff off.”

Wow, I thought. My mind was blown. Brains had exploded out the left side of my head, and Jesse Itzler was holding a freshly fired pistol to the right.

My mind immediately shot to thoughts of my German friend, Daniel, who I met in Seoul, Korea in Spring of 2005, while studying abroad. We were roommates in the international dormitory at Yonsei University. I was twenty-four, and it was my first time out of the country. Daniel, on the other hand, was impressively well-traveled for a twenty-four-year-old (during high school he had even been to, of all places, Tennessee, which is why he could understand my deep southern drawl acquired from growing up in Virginia Beach, Virginia). During that semester, we spent an inordinate amount of time together. We studied a little; we explored a lot; we partied to excess; however, most importantly though, we experienced.

At the end of the semester, we jetted to Singapore to begin an impromptu backpacking trip through Southeast Asia. We had discussed nothing but the bare bones of the trip. We booked nothing in advance. We planned nothing. I wish I could say we were geniuses, but the truth is that we were lazy, procrastinating college students. Little did we know that our lack of planning was an invitation to serendipity. It gave us freedom to stay longer in places we enjoyed, and quickly depart places that bored us. We spent the next few weeks making our way through Malaysia, Thailand, and China, at our own leisure, getting into trouble, short-lived romances, and adventures. The details are for another time, but suffice it to say that the experience still provides sustenance to my soul all these years later.

Since 2005, I’ve seen Daniel five times in sixteen years. Sobering. There was: (1) Miami, in Spring 2009 (he came to visit me while I was in law school at the University of Miami); (2) New York City, in January 2010 (he was there for work and I was there for a law school trial competition); (3) Maastricht, Holland, in Summer 2010 (he worked there as an economics professor and I had an internship with a law firm in Amsterdam); (4) Seoul, in Fall 2014 (I quit my first law job, which I hated anyway, and flew out on five days notice when I found out he was visiting Korea); and lastly (5) London, in Fall 2019 (a long overdue rendezvous).

Five times in sixteen years. At this rate, I have maybe twelve times left with my good friend, not thirty-seven years. Looking at it this way creates scarcity, which creates value, which creates urgency, which motivates action. My first gut instinct is to schedule a trip right now, something memorable, something worthy. My soul tells me to be urgently intentional. The question is will I listen.

THE LATER YEARS ARE DIFFERENT THAN NOW.

– Jesse Itzler

“My seventies are going to look different from my forties, fifties, and sixties,” says Itzler. “I have maybe twenty quality years left. I just went wakeboarding. There were no seventy-year-olds out there. I just went climbing Mt. Washington. There were no seventy-year-olds up there either.”

Again, I flashed back to my backpacking trip with Daniel, specifically our visit to the Great Wall of China. At the Wall’s base were tourist groups full of senior citizens preparing to cross an item off their bucket list. I watched them struggle to walk the first of the many stairs that would be required to get to the summit. At the top, I didn’t see any of those seventy-year-olds. Not a one. I made it, however, even having been sick with food poisoning for two days at that point. While at the top, I thought about those seniors struggling with each step. I admit I both pitied them and judged them. Old age had robbed them, and they were complicit. Daniel and I had energy; we had vitality and youth; we were doing life right. I realized at that moment that experiences and adventures should not be put off for later, certainly not for the end.  

REMEMBER TOMORROW.

– Jesse Itzler

“The only way to get a win against Father Time is by taking action now to prevent a regret in the future,” says Itzler. “I just ask myself, ‘will I regret this in the future?’ If the answer is yes, then I prevent it. It’s really that simple. If you look at life as a novel, you’ll see that most people don’t seriously focus on the end of the story. Instead they spend their time thinking about the beginning (the past) and living in the middle (the present). That’s fine if you’re merely reading a novel, letting it carry you whichever way the author intends. However, if life is a novel, it’s not meant to be read by you; it’s meant to be written by you. You’re the author, so you should be thinking about the end as you’re writing the current chapter, shouldn’t you?”

I realize the truth of what Itzler is saying here because, personally, about a decade ago, I got a huge win over Father Time, and I’ve been talking trash in Father Time’s ear about it ever since. In 2008, I had begun law school at the University of Miami. My girlfriend at the time had moved from Virginia to Miami with me. During my first semester, I learned of an opportunity to participate in a study-abroad program in Tokyo that would cost half the tuition compared to staying in Miami for that same semester. Financially, it was a no-brainer. I knew it was a once-in-a-lifetime experience. My girlfriend, however, saw things a little differently. She issued an ultimatum: if I went to Tokyo, our relationship was over. She explained that there would always be time for Tokyo; I countered by asking when that time would be, and positing the following life trajectory: after law school came a law job, then came kids, then it would take over twenty years to raise the kids, and then we would be sixty years old. ‘When exactly did the time for Tokyo fall into place?’ I asked. ‘After I’m retired?’ With a face straighter than a champion poker player, she paused before flatly answering,…’yes’. So I broke up with her. Tokyo was amazing.

“No man ever steps in the same river twice, for it is not the same river and he is not the same man.”

– Heraclitus, Greek Philosopher

At sixty, Tokyo would not be the same, and neither would I. I’d be one of those senior citizens at the base of the Great Wall. By remembering the end of my story and reverse engineering my decision, I got a win over Father Time.

You don’t need to be a trained psychologist to understand that people on their deathbeds regret things not done much more than mistakes made. I’ve found that it takes little effort to envision the regrets that I will have in my last moments. Remembering the future and thinking backwards has been an invaluable tool for me.  

ELIMINATE THE UNIMPORTANT AND IRRELEVANT.

– Jesse Itzler

“I realized how much time I spent needlessly worrying about things that are irrelevant,” says Itzler. “When I released my mind from these things, I got insanely creative and gained so much energy. Thoughts and worry are exhausting. One little hack I have is that I keep a ‘to-do’ notepad on me at all times, and anytime I think of something I need to do tomorrow, I write it down. No more mental energy goes into it. I’m back focused on today. I’m also an avid sports fan. But when I audited how much time I spend watching sports, I had to eliminate a lot of it. I realized that I just don’t care about who won the championship two years ago, or what happened in the first round of March Madness. What I do care about are the experiences I had with good friends.”

Itzler is saying two very important things here. First, don’t spend more mental energy worrying about tomorrow than necessary. I implemented the simple, yet effective daily to-do list on my iPhone, and it took away those nights where I would spend my last waking moments worrying about the next day, the anxiety sometimes reaching a fever pitch which kept me me awake.

Second, identify what is unimportant, then eliminate it. There is immense value in knowing what is not important. When you spend time on something unimportant, you pay an opportunity cost. When I was a teenager, I was obsessed with basketball; I played it all the time; I watched it all the time; I studied it. It was important to me, then. But, even though I stopped playing seriously when I was twenty-five, I continued to watch it. My interest in it had waned but I still spent time on it, maybe out of habit, maybe out of a need to fit in, maybe to have something to talk about with other guys. Wanting to relate to others and participate in small talk is not an invalid reason to do something, but for me, I am no longer spending time watching sports I really don’t care about. Instead, I am maximizing the time spent on things that are actually important to me, and I’m loving it.

BREAK ROUTINE. CREATE NEW EXPERIENCES.

– Jesse Itzler

“When you live in routine, the clock goes fast,” says Itzler. “Every other month I take a trip I normally would not have taken. If I can’t take at least one day every two months to create an experience, then I’m out of whack. But if I can do this for the next thirty years, then I’ve created one hundred fifty moments that otherwise would not have existed. Creating newness is hard because it takes work. Routine, on the other hand, is easy. As you get older there is no newness, only routine. I calendar newness. I already know the trips I’m going to take next year, and so does everyone in my life, too, because it’s scheduled, it’s built into my life, into my calendar, and I’ve trained those around me that it’s part of what I do and who I am.” 

Itzler’s wisdom of building intentional newness into life is undeniable, and I need to be better about it. The ocean of daily tasks can very easily throw me into a routine. Some routines turn into ruts. However, I’ve found that ruts are easy to recognize because they are like hitting rock-bottom for an addict, which makes breaking free from them easier than breaking free from a non-rut routine, much less a routine I actually enjoy. The non-rut routines create the greatest obstacles to newness. Not every novel respite from routine needs to be akin to climbing Everest or a bucket-list trip planned months in advance. I’ve injected lots of valuable newness by simply engaging in a conversation I normally would not have, or attending an event that pops up on my radar. Sometimes these simple moments of newness have completely altered my life’s trajectory.

STOP CARING WHAT OTHERS THINK. RIP UP THE PARADIGM. TRY THINGS DIFFERENTLY.

– Jesse Itzler

“I’m so aware of my mortality,” Itzler says, “that I don’t fear what others think. In one hundred sixty years, no one currently on the planet will be alive. In fact, Stephen Hawking, who is one of the greatest minds of our time, predicted that due to war, disease, and famine, there will be no human life on Earth even one hundred years from now. If you knew that to be true, absolutely true, are you seriously telling me that you wouldn’t take a chance at doing life differently? That’s the way I look at it. Why not take a chance? We have one life; one shot at this. We don’t get a do-over.”

Itzler uses the story of NBA legend Rick Barry to illustrate how people’s concern about embarrassment holds them back. Rick Barry was famous for shooting his free throws underhanded, and also famous for being one of the greatest free throw shooters ever, averaging 89.31% for his career. Over three thousand players have played in the NBA since Rick Barry, but not a single one has adopted his underhanded shooting style. For example, Shaquille O’Neal, although he was the most dominant player the league has ever seen, was a notoriously poor free throw shooter–a dismal 52.7% for his career–so bad that opponents would purposely foul him the entire game to make him shoot free throws. However, Shaq said “I’d rather shoot 0% than shoot underhand. I’m too cool for that.” But why, Barry asked, would a player prefer to be ridiculed for being a bad shooter rather than be a great shooter who does it differently? Shaq let fear of embarrassment stop him from potentially becoming the absolute greatest player of all time.

Itzler is right. Fear of ridicule or embarrassment should never stop someone from taking a chance at doing life the way they want. I’m surely not going to let it anymore. Life is a quest, an adventure; not a mission to live like everyone else, not a mission to avert risk. I’m ripping up the paradigm foisted upon me by my culture, the media, my parents, and my own delusional fear of risk. And maybe, just maybe, if I stop caring about what other people think, and instead strive for my own definition of success rather than avert risk, then maybe, just maybe, I’ll get a huge win on Father Time. All I know is that playing it safe is playing to lose.

Thank you, Mr. Itzler.

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