Define the Game
Aug 23, 2023
I grew up playing tennis with my sister at the public courts near home. I made it onto the high school varsity team, but quit too soon. For a long time after, I just cherished the joy of playing and watching the careers of the "big 3" unfold. But recently I’ve started to appreciate something more about tennis: the clarity of the meta-game around the game.
It’s easy to tell when you’re good at tennis, and just how good you are.
Every professional tennis player’s dream is to win the most prestigious tournaments, the grand slams, and to be ranked #1 in the world. Tennis is largely an individual sport, making it easier to figure out exactly where you rank. Not only that, it feels meritocratic. If you win enough matches, you move up the ranks; the winners aren't chosen by some committee.
Sports do a great job of defining a game — both the micro and macro.
But in most fields, there isn't a clear set of rules at either level. This is freeing but also unfortunate. As much as we criticize playing "the game" in our field, we usually end up doing it. Too many people think that they’d rather play undefined games, or games with no rules. But I’ve started to think otherwise — that defined games are valuable far beyond sport.
I’ve started noticing defined games in other worlds I pay attention to. Many of them, tech and startups included, are arguably undefined arenas, but there are rare examples.
The Undisputed Best
In the world of music, there’s a long-standing game. Every artist wants to hit #1 on the Billboard Hot 100 singles chart (the most popular singles in the US). They dream of their album going gold, platinum, and diamond — an official certification for huge sales. Record deals and distribution has historically been gated, but the growth of on-demand streaming and discovery via the likes of TikTok makes rankings feel more meritocratic.
As someone deep in the world of consumer social, it's a stand out in tech: Everyone who builds social apps wants to chart on the Apple App Store. Hitting #1 in the Social Networking or even in Top Free Apps is the dream. Consumer social is arguably one of the most meritocratic sectors; no matter who you are, it’s hard to chart, and even harder to stay there.
The Chosen Ones
It’s rare to have such cleanly defined, seemingly-meritocratic games with objective rankings. Instead, a common system is experts bestowing awards to “top” performers in a field or category.
This exists in creative fields of course — Oscars, Grammys, Pulitzer, Booker, and more. Then of course there are the lists — the Midas List, Forbes 30 under 30, and the like. These types of games breed status chasing and create frustration in the process. Who was deserving? Who got snubbed? Who was responsible for the success? 
A related system is admitting or accepting people into an exclusive group. This isn’t spoken of as an achievement, but in practice it becomes a credential. This is the world of Ivy league college admissions. In tech, we see this around getting into Y Combinator or being backed by a “tier 1” VC fund. There are such earned “in-groups” in every field.
Some games have long been defined, but you can design new ones too. People who create and play them early tend to form a respected class.
Many games we play today were once new. In sporting, snowboarding and pickleball are good case studies. Both were conceptualized in the mid-1960s and were championed by their creators and early athletes-turned-advocates (watch HBO's "Dear Rider"). Endurance challenges like the Tough Mudder and Spartan Race are another niche category.
A non-sporting example of designing a new game is Dickie Bush's "Ship 30 for 30," a challenge for people to publish 1 atomic essay a day for 30 days. The ultimate goal is to get more comfortable and better at writing online. There are many ways to accomplish this, but one way is to gamify the challenge with a clear goal and compel collective action.
Bryan Johnson, the biotech multimillionaire obsessed with reducing his biological age, has popularized and further defined the longevity game. He's open-sourced his regimen called "Blueprint" and co-created the Rejuvenation Olympics, complete with an "epigenetic leaderboard" that tracks the top age reversals. The more extreme, the better to define it.
The point is that even as we criticize non-sporting games, we gravitate towards them. And I don’t think it’s a bad thing. When the game has no rules, it's not necessarily more fun because you don’t know how to play it. On the other hand, a defined game can help you set goals, work towards them, and appreciate the outcome. So, perhaps controversially, I’d argue that people should embrace playing more defined games. 
And if you haven't found a game that you want to play, make one up. Define the game, give it some rules, and invite others to join you.
I'll prescribe a tactical approach too. First design a single-player game and play it. This has inherent value even if nobody else is playing alongside you. (In fact, I think successful people in every field do this by nature). Once you've worked out the details, refine the game rules, and share it with others. If enough players join the game, it can graduate from having just pioneers to chosen ones and maybe even undisputed best.
If you do it right, you might even start a movement. I’ll always be partial to tennis, but I admit that pickleball has done exactly this, and quite well too.
If this working theory resonates, please consider sharing it with a friend (or on socials) & subscribe to my newsletter below. 🙏
And a perennial thank you to Bharat Kilaru for the nuanced conversations & writing feedback.
 Something like the New York Times Bestseller list seems like a mix between "undisputed" and "chosen" in that it can be gamed with category selection and preparation. In fact, anything where you can prepare can suffer from this, e.g. even App Store rankings can be gamed by building up demand for launch (though it's usually a short-lived advantage).
 That said, I do think there are “better” and “worse” kinds of games to play. The closer something is to being meritocratic, the better. This is one reason I believe sports have always been popular (and are growing in popularity among white collar professionals too). And there’s the obvious caveat that you should choose a game you enjoy playing, not just seek the prize, status, or whatever awaits at the finish line.