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Elaine de Kooning: Basketball #11, 1981, Acrylic on canvas

I played basketball growing up. I was the type of young player that shot the ball almost every time I touched it. This was in the 2000s - and at least in my little community, it wasn't extremely common to play that way. Mainly because everyone would hate you. The game we learned to love was one of collaboration - with iconic duos like Kobe and Shaq or underdogs like the Bad Boys 2.0 (2004 Pistons). But for some reason, I was playing a different game - one that was more popular in the future. Steph Curry style, except I was missing way more shots. But all that to say, I knew my skill, I was a shooter. Did I score all the time? Certainly not. But shooting was the part of the game that I was best at, and I enjoyed it the most. I knew my game.

Upon reflection, from a very young age I was stubborn and wouldn't compromise. I felt that it waste of time to do things I wasn't good at. There was period where I would learn something new, but felt I couldn't become the best, and I didn't enjoy it, so I'd decide to let it go. I wanted to focus on what I enjoyed and could become very good at. My parents put me in all sorts of lessons and I'd think: "What are we doing here? I'm going to be in the NBA.."

I'm 29 years old now. I'm definitely not in the NBA. I'm getting older, but I'm still 'young'...supposedly. I still play basketball (not professionally), but I play a few other games in a professional capacity: namely writing, investing, and working with startups. As i've spent majority of my time in my adult life playing these games, I've met some interesting characters or players along the way - All of whom have this defining characteristic:

They refuse to play other peoples games. They know their game.

Growing up, you will see people take paths that make sense. One step after the next: get a degree, a job, a promotion, a spouse, a house etc. These types of life stories have an imaginary thread that you can tug on, that feels linear, and demonstrates a logical progress. We all want a cemented position in the world understood by others. I've learned now, thats one type of game. A game I do not know how to play.

I recently started reading the autobiography of tennis legend Andre Agassi - named "Open" and amidst the first pages he touches on the nomenclature and structure of the sport:

"It’s no accident, I think, that tennis uses the language of life. Advantage, service, fault, break, love. The basic elements of tennis are those of everyday existence, because every match is a life in miniature. Even the structure of tennis, the way the pieces fit inside one another like Russian nesting dolls, mimics the structure of our days. Points become games become sets become tournaments, and it's all so tightly connected that any point can become the turning point. It reminds me of the way seconds become minutes become hours, and any hour can be our finest. Or darkest. It's our choice"

I can't help but feel he is right. Life is a collection of games, and you have to decide how you'd like to play it.

In my world of investing and company building, there isn't that much logic to how success plays out. The ways you get to that first round of funding, win your first customer, or find your team members - happen through experimentation and constant failure. There is an element of taking matters into your own hands, hacking away against curiosity, discovering people through ideas. Today - the internet helps make serendipity happen. I don't mean to romanticize the journey - its not easy. In fact, its brutal. For every successful outcome, there is an endless pit of stories about rejection and failure, my own included. And yet, we continue.

I attended a talk recently, where Patrick Collison touched on how normal people (those with lives that make sense) are: micro-content, but macro-unfulfilled. Whereas people who forge their own path, whether as entrepreneurs or otherwise are: micro-unhappy, but macro-fulfilled. This resonates with me as I see people feel stuck in their jobs and pursue happiness through a bonus or a nice vacation. While those who live life on their own terms are perpetually under pressure, seeking satisfaction through making shit work - small wins and big wins alike.

But the ultimate truth is that - these two types of people are playing different games.

It requires time to understand your game and perfect your craft. You have to figure out who you are in relation to other people, understand your superpower, and have the willingness to say no to breadth - in pursuit of depth. You have to have an undying dedication and a level of conviction even when there is no sense or evidence that your path will work. There has to be an attachment to optimism and a simultaneous awareness of the worst case scenario. And you've got to have ice in your veins, to keep moving forward without fear - and with faith. But this goes for anything - whether you are starting a cosmetics brand, or a cupcake company, building a venture firm or a software company. This even extends to writing a book or becoming a film maker. Your game is inherent to your style.

Refusing to play someone else's game isn't for everyone. It is polarizing and isolating. If you are truly original its hard to see results. But playing your own game puts you in a league of your own. When you do something your way, you reinvent who you are in relation to your competition. In fact, you might even realize your competition is no longer in the same arena. Your progress might be difficult to measure, but your skill will only compound over time.

A lot of people can play the same sport - investing, writing, company building. There are different ways players claim expertise, outline theses, tell stories, design products, be a "value add". The only way to truly thrive, is to lean into your style...and write about it.


As synchronicity would have it, a few days after I wrote this note to myself, I discovered this quote:

"Part of the game is to come into your own. You must find some way that perfectly fits your personality. It is a competitive game, so you’re going to run into a lot of hardworking fellows. The only way to gain an edge is through long and hard work. Do what you love to do, so you just naturally do it or think about it all the time, even if you’re relaxing. Over time, you can accumulate a huge advantage if it comes naturally to you. The ones who really figure out their own style and stick to it and let their natural temperament take over will have a big advantage. The game is a process of discovering: who you are, what you’re interested in, what you’re good at, what you love to do, then magnifying that until you gain a sizable edge over all the other people." - Li Lu (source)

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