Month: April 2022

I like to gamble. Not to the extent where I’m tempted to take my monthly mortgage payment and leverage it into an Aston Martin. But all the same, I enjoy the lights, the noise, the smell, and the seedy company of a gambling house. And I’ve been found to revel in the thrill of a wager won, and even the despair of a wager lost.

But whether in the loving embrace of lady luck or in the deathly grips of misfortune, I’ve found there’s a lot to learn from throwing the dice, turning the cards, or spinning the wheel.

The most important lesson learned was the analysis of the “gut feeling”. And what I’ve learned about that gut feeling is that there’s no such thing. Often times when people bet big or bet on a long shot, and it pays off, they immediately credit a gut feeling, or sense of the divine intervening on their behalf, as motivation behind the risky wager. But, the reality is there was no gut feeling, and there was no divine intervention. No amount of praying was going to fix those dice or change the face of that card.

But instead what I’ve learned that inexplicable feeling to be, is “hope”. Flashes of hope occur within us all the time, but never are your senses more alive to these flashes than when hanging on the edge of a die, or the flip of a card. Gambling heightens our sense of awareness to flashes of hope to the extent that we will make quick and seemingly irrational decisions based on it.

Now let’s leave the gambling house and travel somewhere a little more productive. Maybe the office, or the field of play, or even the bedside of sick loved one. Have you ever been the champion of irrational hope in those environments? Ever been irrationally optimistic about your team’s chances of landing that contract? Ever been the teammate spurring your fellow members toward victory in a seemingly impossible match? Ever sat face-to-face with someone you love and told them that you’ll get through this together? And meant it? If you have, then you’ve been a victim to these flashes of hope. And what a great victim to be, because these flashes, when shared with those feeling less than optimistic, can be exactly what the team needs to hear in order to take the next step.

When rowing 3,000 miles across the ocean, these flashes aren’t just helpful, they’re vital. Each member of both my teams, at multiple points in the crossing, showed signs of ridiculous, irrational, absurd signs of optimism. Flashes of hope that seemed so out of place, and so at odds with what we were up against, they become hard to justify. But let me tell you, when one of those flashes hit one of my teammates, the others were desperate to be led by them. Flashes of hope leverage human emotion in a way that makes the impossible possible. It allows us to gamble on ourselves against the longest of odds, only this time we’re not reliant on a die to tell us our fate. We rely on one another.

So stay sensitive to those flashes of hope, and when they come, go all in, gamble on yourself, gamble on each other, and watch as it pays off.

Do we all know the theory of entropy? The theory of entropy states that all things in this world, or even in the universe go from a level of low entropy, highly ordered, to a level of high entropy, highly unordered. Take for example a 400-page book, where you have removed the binding, leaving you with 400 loose pages. If you were to throw all those pages in the air and let them fall to the ground, chances are your book would no longer be in numerical order. Of course some pages would still be, but you would most likely no longer have a book ordered from 1 to 400. Toss them in the air again and the pages would most likely be in even less order. If you were to keep doing so you could expect the pages to continue to be in less and less order, in other words going from low entropy (highly ordered), to high entropy (highly unordered). However, there is a non-zero chance that on your 102nd time throwing the pages in the air, they would land back in perfect order from 1 to 400. But the chances of this happening are so slim, that if it were to happen, you would not think that it happened by chance but would assume that someone tampered with your experiment and ordered the pages themselves. In fact the idea that it happened by chance, most likely, wouldn’t even enter your mind. You would assume that there was some human or intelligent interference that made it so. The reason why we would be so astounded and confused is because while there are a dizzying number of combinations that see those 400-pages in less than perfect order, there’s only one combination that sees them in numerical order.

Human interaction is what can actually reverse the process of low entropy to high entropy. Think of a beautiful painting. There is a non-zero chance that if you threw enough gobs of different colored paint at millions of blank canvases, that eventually one of those tosses would yield the Mona Lisa. But you could save a lot of time (and paint) by hiring a talented artist to organize the paint in a strategic way that would create a beautiful painting for you. This artist is taking disorder, and creating more order, also known as reversing the entropy theory and going from high entropy, to low.

In fact, if you are to look around, and consider for a moment all the things that we admire other humans for doing, you will find this is what we admire. Their ability to take chaos and make it something less chaotic, more ordered, and therefore quite beautiful. A quarterback that hits his receiver in perfect stride or a basketball player that’s able to sink three pointers time and time again. Musicians that string notes together in just the right way to create beautiful music, or a leader who is able to take a group of individuals with their own agendas, goals, and ambitions, and direct them toward impossible team efforts.

The reality is that building and leading high-performance teams is so difficult because you are doing just that. Taking something that has so many possibilities for disorder, and arranging them in the right way that it is ordered and productive. The end result of a beautiful painting, song, touchdown pass, or team effort may seem like low entropy at its finest, but I can assure you it was the fight against its natural inclination to become highly entropic that made the end result so amazing.

That is what leadership is all about. Discovering and implementing different ways to fight high entropy, and produce great teams.

Game of Thrones, as a show, may be one of the greatest equalizers of our generation. No matter who you talk to, everyone loves Game of Thrones. I once observed what I stereotypically assumed was a computer science geek working as a grocery store checker wax poetic to a muscle head customer about the intricacies of the latest Game of Thrones season. Ten years ago, this tank-top wearing lothario probably stuffed this pocket protecting future app inventor in a locker. But now these two couldn’t be more enthralled in their conversation. In fact, they were so enthusiastic about their newfound commonality, that in an effort to get out of Trader Joe’s before they started talking about next season, I began bagging my own groceries.

I’m serious when I say with the amount of common ground that seemingly polar opposites have found with this show, they should start making politicians watch it together before partaking in bi-partisan talks. They should make China watch it with the US before trade negotiations. They should make India watch it with Pakistan before they make decisions on the Kashmir, and they should make Putin watch it with, well anyone.

But full disclosure – I haven’t watched a single episode. All this observation is without any context for the greater plot of the show. How, do you ask, can a man who sees the obvious reaction to this show, not be in the least bit interested? It’s for that very reason that I abstain from even giving it a try.

I have no doubt that I’d love Game of Thrones, and would descend straight into binge-watching, should I allow myself a single taste of episode one. For a guy who grew up on movies like

Braveheart, Gladiator, Last of the Mohicans, and Rob Roy, I’m sure I’d be hooked. But here’s the reality of going down that rabbit hole. There are eight seasons of GOT, for a total of 73 episodes. At an hour each, that’s 73 hours of time spent to complete the series, and that’s if I do zero rewatching (which seems doubtful as apparently the complexity of the show is unparalleled). In the course of a lifetime three days of straight GOT viewing doesn’t seem substantial, but I think about what can be accomplished in 73 hours. At two hours a day of working out, that’s five weeks of hard-nosed training. A committed individual could be well on their way to learning a new language with that time. Maybe not fluent, but well on their way. 73 hours spent with your spouse or significant other could get you to know them on a deeper level. You get the picture.

And it doesn’t stop with GOT. Think of anything you spend time viewing. Sports, other shows, random Youtube videos, pick your poison. And it’s not just screen time. Books, for the sake of this lesson, can be a dangerous game too if we allow ourselves to be consumed by them too often. The point is, we watch these shows and sports, or read these stories, to feel good, to live vicariously through the characters we like the most. But at what cost? I’ll tell you, at the cost of being those people ourselves. We constantly use lack of time as an excuse for not being the people we want to be, so instead we choose to watch the people we want to be. Eventually, however, our time becomes nothing but watching others live the life we thought we were destined for.

Now, before diehard GOT fans pen nasty responses to this little thought, I’m not actually suggesting you deny yourself the thrill and entertainment of shows like GOT, or cancel NFL Redzone. I’ve obviously oversimplified this analogy to bring to the forefront a much more interesting way to look at how you spend your time. If we want to accomplish things, conquer our fears, or experience this world, we have to put down the remote or the book, at some point, and pick up the sword. Let’s see if maybe the next show made is inspired by your life. Is that really so crazy?

“Many people read books, few people write books, but fewer still have books written about them.”

I have a friend named Peter. He’s the youngest of three, comes from an extremely athletic family, and is by far the most gifted athlete in the group. Growing up, he was the kid on the playground constantly frustrating the other kids with his obvious athletic superiority. But maybe the most frustrating quality Peter had on the playground was his laissez-fair attitude toward the outcome. Even today, while playing with or against Peter, he never lets the outcome dictate his day, or even his life.

It has taken some keen observation, but watching my friend over the years, I’ve noticed what Peter chooses to spend his energy on. He’ll get month-long inspirations to achieve the seemingly most tedious, mundane, and irrelevant skills. One summer he became obsessed with trying to get better throwing balls with his opposite hand (he was in his 20’s when this happened). One winter had him focusing on slight-of-hand card tricks. A lover of music, for two years straight, he spent almost every free day going to concerts.

But that’s not all. Peter has also focused on a wide-range of long-term goals. Inspired by his older brother, Pete wanted to learn to row, and ended up making the varsity boat of his collegiate team. He wanted to write and perform songs with his guitar, and managed to release an album while in college. Then he started playing at coffee shops and restaurants to further himself. Pete got a degree in finance and started working in that industry, but realized he was interested in the sales-side of business, and two years later, made President’s Club at his firm in San Francisco.

Whether throwing with his left hand, performing in front of a small group at a wine bar, or lining up to race in a collegiate rowing regatta, Pete puts all his effort and energy into the task at hand. Because he’s been so easily inspired by such a wide range of activities, he never became as good a rower as his brother, or a professional singer/song-writer, or even a magician. He just never had the time. Pete could probably be famous for something by now, but he’s not. Instead, he chose to let himself be defined not by one thing, but by many – a true “Jack of all Trades”.

The result? Today Pete is one of the most interesting, talented, well-balanced, modest, and well-liked men you’ve never heard of. He’s well-liked not just because of his temperament, but because of his ability to seamlessly slip from one conversation to the next, always having a way to relate to the person he’s talking with. He’s modest because he’s secure in the accomplishments he’s achieved up to this point in his life, and doesn’t feel the need to constantly reiterate them to others. Pete’s well balanced life comes from not resting his entire happiness in the achievement of one particular goal or possession. He wins and loses, like us all, but unlike many of us, properly proportions his celebrations and lamentations.

This unique approach to life makes Pete an interesting guy. Pete’s complicated and hard to nail down. He’s original and certainly not one who naturally goes with the flow. Pete thinks in ways that we should all be thinking – and that is, in many ways. There is no recipe for happiness, as we’ve been told so many times before. But whenever I’m with Pete, and see him with his broad grin and lovable demeanor, I am reminded of a Peter Pan whimsy, and think maybe he’s got something. Maybe he’s got the closest recipe so far.

The richer person is one who’s known for many things, rather than the person who’s known by many for one.