#22: Game of One ☝️

the origin story

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Two weeks ago, I was crashing with my friend Daniel in San Diego and we spent the weekend surfing in Encinitas. A few days later, I flew back to San Francisco to be home for Thanksgiving. I got home at night and the next day, I was originally planning to drive into the city to get dinner with friends, but ended up making the right call to stay at home and use the day to rest up. Recently, ‘resting’ for me has felt less like laying on the couch watching TV and more like unpacking my wetsuit and getting my ski gear ready in the same afternoon. The day before Thanksgiving, I made the three hour drive (and back) to Kirkwood Mountain Resort for my first ski day of the season. Last year, I felt rusty with my skis going in different directions and those infrequently used leg muscles in between the quads and hamstrings firing off. This time around, things felt a lot more intuitive - a sign of progress. The slog of driving six hours just to ski for four is worth it to me because it meant I could still spend Thanksgiving at home with family. The pace of physically traveling from NYC to San Francisco to San Diego back to San Francisco back to NYC in the span of less than two weeks is a reflection of how my inner mind has felt lately. The number of Chrome tabs, to-do items, calendar events, books to read, and newsletter subscriptions is ever-growing and they appear to keep expanding like the Greek monster, the Hydra.

For every newsletter I read, I end up with two more to subscribe to. Every time I listen to a podcast, I feel compelled to add the mentioned books to my reading list. The overwhelming majority of this content is stuff I actually want to consume. But “overwhelming” is precisely the right word to describe this moment in time. The hard part is that these are all pursuits that I would characterize as genuine interests rather than external, pressure-driven, fake goals. I’m trying to do it all and I’m being pulled in different directions.

There is a progression to figuring out what you want in life and it’s comforting to know that I have a wide variety of genuine interests rather than not knowing what I care about. Now it’s a matter of shepherding these seemingly disparate ideas towards a common goal. Like a shepherd guides sheep in a specific direction, I have to focus, because otherwise all of these intriguing pursuits will get build up in agitation and then stampede.

There is a certain amount of wrangling, pruning, and prioritization that can be done, but ultimately everything comes down to tradeoffs. I would love to spend more time surfing AND skiing, living in New York City AND living in Hawaii, cooking homemade meals AND eating at restaurants, reading AND writing, spending time with old friends AND making new friends, but to do it all would be impossible.

You can do anything, but not everything.

- Paul Allen

While We Can, We Should

He might not even remember it, but my friend Parker (who I went to high school with and ski with every year) was telling me this story about his neighbor back in Virginia where we grew up. This middle-aged neighbor who’s maybe in their 50s, has had a successful career and finally has the time and money to get into mountain biking, a sport they’ve always found to be so thrilling. They had never actually mountain biked before, but the allure of it from magazines, YouTube, and second-hand stoke from friends got them interested. They’re aware of their lack of experience and since they can afford it, buy one of the nicest mountain bikes available. They assume that by spending more money they can learn faster, stay safe, and maximize their performance. But as the decades passed and their bank account grew, so did their body’s stiffness. By the time they finally carved out the time to dedicate towards the sport, their body could no longer push through the steep inclines and going full speed downhill would be too risky at that age.

I’ve reminded myself of this story countless times. It was part of my thought process in choosing to live in Hawaii and learn how to surf rather than remain in San Francisco or New York where I could keep investing in my professional network and career. It’s part of my plan to spend January to March skiing in Jackson Hole, Salt Lake City, Colorado, but mostly Tahoe, where I can be close to friends and family. These two examples suggest that I always end up choosing the more adventurous and less career-oriented path, but my plan to spend the majority of the next few years living in New York City is also based on the realization that right now is the best time to immerse myself in a city with so many other young, creative, ambitious individuals. It’s two sides of the same coin.

For every one person that’s like Parker’s neighbor who worked too much and waited too long to pick up a hobby, there’s a ski or surf bum living out of their car without a long-term plan. They’re having surface-level fun on the mountain or in the ocean, but have deep anxiety about what to do with their life later on. It sounds harsh, and I’m sure there are exceptions, but I’ve met people who fit this stereotype. For example, after I graduated in 2018, I found myself in a $4/night hostel in Ubud, Bali and met a girl who would work as a waitress in Colorado until she saved up enough money to travel again. Rinse and repeat. After a couple days of splitting a bunk bed, she opened up that she has no idea what to do with her life.

It’s easy to point to the corporate ladder climber and say they waited too long to pursue what they truly wanted in life. It’s just as easy to criticize the free-spirited wanderer for not studying harder in school or getting a “real job”. In reality, figuring out where you lie on this spectrum and then actually living that life that you envision is the only actual item on the To-Do List of Life which is really damn hard.

Do You Know the Game You’re Playing?

Life frequently is characterized as a game (or a beach, if you’re Lil Wayne). There’s the literal board game LIFE where you have to traverse an overly simplistic path and occasionally decide between option A or option B. There’s the concept of The Infinite Game, a game where there are no winners or losers. Rather than reaching a defined end state, the primary objective is to keep playing. Then there’s The Great Online Game by Packy McCormick, which is a blueprint for how operating in the online economy is like playing one massive video game. With all the doctrine, scripts, guidelines, and unwarranted advice filled with “You should”, it’s no wonder we can sometimes feel like we’re in a video game, but not actually given the agency of possessing the controller.

The way I see it, modern American society is a lot like a massive multilevel video game designed by our parents, managers, and government — all without any pre-planning, principles, or plot coordination between parties.

It’s no wonder the game’s plot feels weak and unsatisfactory. Where’s the hero arc? The ultimate salvation? The clear metrics in the corner that tell us if we’re winning the game or not? Instead, all we get is second-hand backstory and form-filled talk tracks. “Meaningless” is how some people put it. It’s just too easy to peek under the hood and realize there’s no master plan or final destination.
- Molly Mielke

I used to have a plan. I was going to live in San Francisco and work at my first job for three to four years to learn the ropes and then get a new job at a fast-growing startup where I could continue to work hard in exchange for hopefully an eventual big payday. None of that actually happened. The plan never came to fruition, but things not going as planned doesn’t entail that a suboptimal path was taken. I used to think that we were all gathered around the same table, playing the same game, by the same rules. Now I know that we’re all playing our own game with different rules, players, and goals. I’d like to think that I’m playing my own infinite game, one where the only goal is to keep playing and enjoy the process. I suspect that from the outsider’s perspective, this game will be confusing, have illegible rules, and maybe even seem not that fun, but it’s the one I’m choosing to play.

But beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living WITHIN that way of life.
- Hunter S. Thompson

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