Win the Hand, Lose the Tournament

“You already want. Want at the right level.”

Somehow, moving 6,205 lbs in 45 minutes is easier than moving 0 lbs.

My life was forever changed when I encountered this idea in Aristotle’s Nicomachean Ethics

  • Virtue is formed through habitual, repeated actions.

In college, I focused on habit formation. Routine is simple – and for me, can be easy: “Every day” is often easier than five days per week. Habit is a valuable default. 

But sometimes, excellence requires non-habit. Sometimes, wanting to win can make you lose.

Know When to Fold ‘Em 

The hunger that makes you a cutthroat poker player can also lose you tournaments. 

In many poker tournament situations, the winning move is to fold. There are plenty of spots where one has the guaranteed best hand yet the proper move is folding! (E.g. pocket aces with a short stack on a tournament bubble when multiple other players are all-in.) 

The fastest way to lose a fortune at poker is over-bluffing. 

Give up on this hand. Find a better spot.

Know When to Walk Away

The strategy that makes you a skilled weightlifter also exacerbates your injuries. 

Ten years ago, I bulged a disc in my spine. 

Three weeks ago, I re-activated the same injury. I paused deadlifts and squats, only returning to them 3 days ago. My sciatica flared up again. I stopped.

In the long term, one day without lifting doesn’t matter. One week wouldn’t matter. A re-injury could bench me for life. 

Wanting to lift weights makes you a good weightlifter. But wanting to lift weights can also make you a permanently-bad weightlifter.

Know When to Run

For the next 6 weeks, any lifts involving my back would be “rolling the dice”. Contrary to popular opinion, I don’t like gambling: I like situations where gambling leads to an edge. 

This isn’t one. Today, I’m taking a rest day from the gym.

Count Your Money When the Dealin’s Done

The game isn’t one poker hand. The game is long-term winning. 

The game isn’t today’s weightlifting. The game is long-term health. 

These intellectual reframes – “it’s not about this hand” and “it’s not about lifting today” – can have cascading effects. They relax your mind. They create new patience. 

Today I will take a rest day. And each second when I’m not lifting weights, I will remind myself I’m getting stronger.

The Game Is Over Our Head

To win, position. To position, OODA: Observe → Orient → Decide → Act.

Despite what my enemies tell you, I am not the enemy.

Between 3:52 and 6:15 pm today, I played 2 games of Catan with friends I met a couple of weeks ago. One guy clearly saw me as a threat, so he tried to stifle me. He missed the importance of rallying others (i.e. an embargo against the leading player), so he failed.

He observed correctly, but he failed to orient. (To orient is to figure out what your observation actually means. He saw I was a threat: Observing. He missed that the answer was rallying others against me: poor Orienting.)

Almost all skillful game behavior is about positioning. Positioning means observe and orient, then repeat (and repeat…) before you decide and act.

Chess: Literally “Proving It”

Most high-level chess matches end in resignation, not checkmate. In these situations, chess is not played to win, but played to superior position.

At the highest levels, a player sometimes resigns before your average (ie 1500-rated) chess player even understands why. It’s not even “Player A is now ahead by a knight.” It’s “Player A would be ahead by either a knight or two pawns in 4 moves and they both know it.”

High-level positional chess games are almost incomprehensible to your average observer, just as a fighter pilot saying “Is the humidity 45% or 46%?” wouldn’t mean anything to me. I don’t even know if humidity is relevant to a fighter pilot! That’s the point.

Even better for me and my point and the puns in this post: in chess, they literally call the process of someone playing an advantage to its victorious end “proving it.” The positioning is the game; the proof is execution. 

OODA? Ooh! Duh!

Speaking of fighter pilots (“What a segue! This guy can really write!”), in the early 1970s, US Air Force Colonel John Boyd established the OODA loop as a decision-making framework for his pilots.

In an OODA loop, one Observes, Orients, Decides, then Acts.

Four moves. Three are about positioning.

Pair the OODA loop with my favorite fighter pilot quote (“How many fighter pilots does this guy know?”): 

  • “A superior pilot uses his superior judgment to avoid situations which require the use of his superior skill.”

The process becomes:

  1. Get good enough at the skills, so
  2. you understand how the skills work, and therefore
  3. don’t have to use the skills anymore, because
  4. you’re dodging the danger.

(Can you imagine how much of a fighter pilot’s practice is Observing and Orienting? Reminds me of my brother-in-law!)

The Games Behind the Pokerface

In The Count of Monte Cristo (my current tome; spoilers incoming), our hero escapes from prison and is picked up by a nearby boat. The prison fires off a cannon shot. Immediately, the boat’s captain asks, “What does that cannon mean?”

Our Hero calmly states, “A prisoner has escaped from the Chateau d’If [prison], and they are firing the alarm gun.” 

Our Hero’s nonchalance convinces the captain that Our Hero isn’t the escapee. Your average person might feign ignorance. But Our Hero – by his claimed background – would know what the cannon means. This move may appear more dangerous, but it’s much safer.

Our Hero’s OODA loop is beautifully speedy: not only does he observe and orient quickly, but he also decides and acts speedily, all while not appearing to be doing so.

This approach is also true for game experts. Many poker players win games in ways you don’t even realize they’re playing:

  • Getting invited to the softest games
  • Table selection
  • Position at a table relative to both good and bad players
  • Talking with fellow players before any cards are dealt to learn their psychology and therefore their leaks.

Stop Acting

(Note to self: find some subtle way to mention to the reader that this section title has a double meaning.)

I am quite skilled at a particular tactic my mother describes as “Baffle them with bullshit.” It’s all Acting, and no OOD. I recognize the pattern → Act. It lacks… a certain elegance.

Relaxing and contemplating (Observe and Orient) have historically been my weaknesses.

To be fair, it’s live Observe and Orient that’s my weakness. I’ve stored plenty through years of preparation, which is why those around me say I’m skilled at games. But Pattern-Match → Act is just stored OO at hyperspeed. In known scenarios, this works. Live execution in novel territory is a different animal.

My poker game has won thousands of dollars despite my complete lack of poker face.

I wish I could install an old turntable in my brain. It would Observe, then Orient, then Observe again… until sufficiently positioned, then Decide and Act. The beauty of the turntable: it’s stuck in the OO grooves (“Ooooooooooo”). I’d have to thunk it on the side to shake it into DA.

As my new Catan group improves at the game, each player will develop our own approach. My Catan-enemy will either improve at his orientation or continue being shot down.

It’s like that key rule everyone knows in the game of real estate: Position, Position, Position.

A Hole in One Case

There is no Platonic ideal of any game.

When I was 8 years old, my father told me the Supreme Court had ruled that walking the course is not fundamental to golf. My father was, at the time, interested in golf. I, now, read Supreme Court cases for fun. Let’s intersect these.

In 2001, in PGA Tour v. Martin, the Supreme Court ruled that walking the course was not integral to golf. Casey Martin, a professional golfer with a circulatory condition that made walking dangerous, sued the PGA under the Americans with Disabilities Act for the right to use a cart in tournaments. He won, 7–2. The majority held that walking wasn’t essential to golf, so accommodating Martin didn’t fundamentally alter the game.

Whether Martin should’ve gotten the cart is a question outside the scope of this post. Commentary on it would require considering What Golf Is, What Role Golf Plays in Society, What Role Golf Should Play in Society, and a host of other deep, philosophical questions. This post will be long enough: hard pass.

What I want to argue is narrower and weirder. The 7-2 ruling rested on something I think is wrong: the idea that golf has an essence, and that judges can determine what is and isn’t part of it.


Here’s how the majority framed the question:

“a modification of the tournaments might constitute a fundamental alteration in these ways: (1) It might alter such an essential aspect of golf, e.g., the diameter of the hole, that it would be unacceptable even if it affected all competitors equally…”

“An essential aspect of golf”. They genuinely deliberated whether changing the diameter of a hole would alter the essence of the game. Prior to 1891, different courses used different hole sizes. And to think those players – on holes with 6-inch diameters – thought they were playing golf!  

The Court debated this topic despite the Court itself not having achieved its own Platonic form: 50 justices, one from each state, with each justice’s height varying in one-inch increments from 7’6″ down to 3’4″. You hear how insane that sounds? It’s not just the height thing. It’s the very notion of a Platonic Court. Let’s drop the heights: is the Platonic form of the court one Justice per state? If so, the Platonic form of the Court would sometimes have an odd number and sometimes even. If not, how do you ensure fair state representation on such an important body?

There is no Platonic Court. There is no Platonic golf. 

Chess is a wildly different game whether it’s played untimed, with a long timer (“classical”), a short timer (“blitz”), a timer with an added increment per move (a “Fischer clock”), or by a computer. Which of these is the Platonic Ideal of chess? Four hundred years ago, the technology didn’t even exist for timed chess. If the Supreme Court had existed, should they have solidified any traits of it as integral to the game?

Games evolve. They evolve through edge experimentation. Edge experimentation requires edges. 

The location of basketball’s 3-point line varies between the NBA and NCAA. Professional baseball has two leagues with two different rules: Is the designated hitter part of the Platonic ideal of baseball?  

Is golf about getting a ball in a hole? Is it about selling polo shirts? Is it about ad revenue on TV? In all cases, you cannot distill a game down to its Platonic ideal. Just as chess has evolved technologically, so has golf. So has the Supreme Court itself (and modes of interacting with it). 

Evolutions in games are often derided, then adopted, then universalized.

Personally, I preferred Pickleball before the USA Pickleball Association banned wearing clothes the same color as the ball starting in the 2023 season. I was a player when that change happened. I understand why they did it. I preferred the previous game. And even that preference isn’t a comment on Pickleball itself — it’s a comment on Pickleball-as-the-USAPA-defines-it. Personally, I define Pickleball as a game where it’s legal to dress as a pickle (even though the ball is generally a yellow color two notches away from brine). 


Scalia’s dissent saw all this clearly. The line that wins all the points:

“It is as irrelevant to the PGA TOUR’s compliance with the statute whether walking is essential to the game of golf as it is to the shoe store’s compliance whether ‘pairness’ is essential to the nature of shoes.”

I recently bought two shoes of different sizes. Please don’t assume same-sizeness is essential to the nature of shoes!

Then Scalia’s sharpest paragraph, dripping in glorious sarcasm: 

“It has been rendered the solemn duty of the Supreme Court of the United States, laid upon it by Congress in pursuance of the Federal Government’s power ‘to regulate Commerce …,’ to decide What Is Golf. I am sure that the Framers of the Constitution, aware of the 1457 edict of King James II of Scotland prohibiting golf because it interfered with the practice of archery, fully expected that sooner or later the paths of golf and government, the law and the links, would once again cross, and that the judges of this august Court would some day have to wrestle with that age-old jurisprudential question, for which their years of study in the law have so well prepared them: Is someone riding around a golf course from shot to shot really a golfer? The answer, we learn [from the majority decision], is yes.”

And then, the philosophical conclusion:

“It is quite impossible to say that any of a game’s arbitrary rules is ‘essential.’ Eighteen-hole golf courses, 10-foot-high basketball hoops, 90-foot baselines, 100-yard football fields — all are arbitrary and none is essential.”

Just because rules are arbitrary – just because they are non-essential – does not mean they are unimportant. In fact, it is their arbitrariness which contributes to these games being low-stakes and light and playful, which are generally key to them being fun. Why is the basket 10 feet high? Because at that measurement, the game is fun. Move the basket to 8 feet and slam dunks become trivial. The arbitrary numbers are what make the games fun. And over time, as people excel at these arbitrary numbers, we change the numbers but keep the name. 


Here’s the meta-point: the Supreme Court is also playing a game. Their game has rules. One of those rules is that process matters. Another is that the Court should answer questions it can answer, and decline to answer questions it can’t.

The question What Is Golf is not a question SCOTUS can answer. Even the PGA can only define What Is Golf As Regulated By The PGA. Players can influence What Is Golf by playing the game. Tradition can inform What Is Golf Today. None of those is the Supreme Court of the United States. And none are really clear answers of What Is Golf. Personally, I prefer golf with windmills and tiny gnome figurines. I prefer golf where each player gets two tee-tosses per 18 holes. I prefer golf where one deducts a half-stroke for bonking an opponent’s ball with one’s own ball. (This is a real game with real rules that I have really played. It is entitled Julian Wise Presents: a Julian Wise Production: Wise Minigolf, brought to you by Julian Wise.)

By answering What Is Golf?, the Court broke its own rules. They played their game badly. They claimed jurisdiction over a domain they couldn’t competently rule on, using a standard (“essence of golf“) they invented for the occasion.


One more thing the Court got wrong, while we’re here.

Games are unavoidably unfair in their outcomes. They have to be — that’s what makes them games. Scalia, sharper than I could put it: “The very nature of competitive sport is the measurement, by uniform rules, of unevenly distributed excellence. This unequal distribution is precisely what determines the winners and losers.”

The ADA, on Scalia’s reading, guarantees Casey Martin equal access to the competition, not an equal chance to win it. The latter is impossible by the nature of competition. Some people are taller. Some people see colors better. Some people have circulatory conditions. The unevenness is the game.

Due to visual processing changes, I see colors with less contrast than I did three years ago. I’m therefore a worse player at speed-jigsaw-puzzling, for reasons that have nothing to do with skill or effort. The unevenness isn’t a bug. It’s the thing being measured.


My insight here is not legal nor moral. It’s that games lack a single, definable essence. Every game is the version currently being played, by the people currently playing it, under the rules they’ve currently agreed to. Golf, chess, the Supreme Court, marriage, work, the publication you’re reading. You can never step in the same game twice. There is no Platonic version sitting elsewhere, waiting to be discovered.

Games evolve. The evolution becomes the new game. We use the same name because it’s easy.


Further fun facts:

  • The “Rules of Golf” are (or at least were as of 2001) jointly written by the United States Golf Association (USGA) and the Royal and Ancient Golf Club of Scotland. The latter, to my disappointment, is not formally abbreviated RAGS.
  • Reading this case has increased my desire to be a religious organization. In the US, religious organizations have their own rules. From the case: “The provisions of this subchapter shall not apply to private clubs or establishments exempted from coverage under Title II of the Civil Rights Act of 1964 … or to religious organizations or entities controlled by religious organizations, including places of worship.”
  • The district court judge “found” that the purpose of the walking rule was to inject fatigue into the skill of shotmaking, but that the fatigue from walking was insignificant. This isn’t a finding. It’s an opinion. You can tell because I found that the purpose of the walking rule is to increase the number of rules that start with W.

Playing with “Play” 

You win the game by playing appropriately. You play appropriately by recognizing and mastering different kinds of “play”. 

We interact with games through play. If you are a participant in a game, we say you “play”. This is true regardless of the intensity of investment. What about a mandatory game (all students of Ms. Jones’ 3rd grade class will now play tag) during which you participate minimally — sit in the corner of the yard, picking grass? Are you still playing? Does it matter whether anyone ever tags you, or is the mere fact that you could be tagged enough to call you a player? Do you even need to react within the constraints of the rules (make an effort to tag another player once you’ve been tagged)?

We generally relate to games through play. When we are unsure of the verb, if the noun is a game, we use the verb play. Fencers fight, but they also play (“playfight”). Politicians manipulate, but they also play (“play politics”).

One can interact with a game without playing it. One can voyeur, heckle, or kibitz. All of these participate, more or less. A well-timed heckle may even throw off the pitcher, changing the outcome of the game. Still, none are “playing”.

Play has two meanings. One is the childlike lightness of being amid interaction. The other is interaction with a game. Some games are serious: politics, finance, war. Yet still we call participation in them play.

Here’s why this matters: 

  • We diminish what we call play, which is why we mis-strategize in serious games we’ve labeled as play.
  • The two meanings of play allow people to dismiss game-thinking as childish, when in fact game-thinking is the most rigorous frame for serious activity.
  • People who seemingly aren’t playing — voyeurs, hecklers, kibitzers — affect the game without taking responsibility for it. 

We hear political games and our guard goes down because games are for children. We hear “playing the market” and we forget the player who loses actual ability to purchase food. We hear war games and sleep better at night because games are contained things, voluntary, with rules everyone agreed to.

We’re making serious games sound trivial. You know: wordplay. 

The fix isn’t to stop calling it play. The fix is to remember which meaning is in use. When you’re “playing the political game,” you’re interacting within a structured competition with real stakes. You’re not doing what kindergarteners do. Except for the name-calling. 

Forced Play

You can lead a human to a game, and you can make them play. 

In his seminal work Finite and Infinite Games, James P Carse posits that mandated play is not play: 

  • “There is no finite game unless the players freely choose to play it. No one can play who is forced to play. It is an invariable principle of all play, finite and infinite, that whoever plays, plays freely. Whoever must play, cannot play.” (End of his section 2) 
  • In other words: Play is only play when it is voluntary. 

I think this position is wrong. 

Carse is using “game” to mean something more specific than a structural definition. He mandates a specific quality (voluntary play). I think he’s wrong to exclude from the category of “game” things that share the structure but lack the voluntariness. In short: Carse’s definition is too narrow because games are structural, not single-trait-necessitating. 

Okay, so what about some concepts that are unquestionably games? 

  • Commerce is a game. It contains points, players, and rules regulating play, semi-arbitrarily defined
    • It is also *real* in that you cannot avoid playing it regardless of your culture. (I suppose the archetypical “mountain man” could avoid playing it by homesteading all his resources, alone. We could say he has shifted to playing commerce with nature, but I think that’s a step too far.)

Either Carse is correct and this is not a game, or there is a slice of “game” uncovered by his articulation. 

Carse has a light, airy definition of game. Like many writers, he intuits that a game feels like child’s play. Carse would claim wargames are games while war is a not-game. 

I don’t buy this. 

Imagine someone playing chess against an opponent. These two are unquestionably playing a game. Now, imagine that the pieces represent actual movers on the field of battle: each time player one moves his rook, an actual cannon shifts its position on a real-life battlefield. (Perhaps the pieces contain some sort of location-sensing technology that walkie-talkies directly to the pieces.) Are these two no longer playing a game? If the stakes of the game involve only one of them living (as, when one is surrounded, he surrenders and yields his kingdom), is that activity no less of a game? 

War is a game. To the people playing it, its practice is essentially indistinguishable from chess. Yet war is also, unquestionably, profoundly real and with the highest stakes imaginable. 

Why does this distinction matter? 

Well, sometimes people disparage games. A teacher will tell a student to “stop playing games in the classroom”. A CEO will say to their underlings, “We’re not here to play games”. A general could yell to his troops, “War is not a game!”

What they mean is take this seriously. And seriousness can be important. But it is not at odds with playing games. The teacher who demands focus is using that comment as a move in the authority-and-attention game they spend most of their day playing. The CEO is fanning the flames of the motivation game. The general is moving a piece in the morale-and-culture game. And then he returns to his nice, safe bunker where he pretends that those peons are chess pieces. 

Abstracting a game into its constituent pieces – players, goals, win conditions, rules – does not diminish the significance of the game itself any more than defining the goal of a war diminishes the significance of the war. Quite the opposite: by abstracting, we can often remove some of the demotivating emotion that prevents us (the players) from ideal movement. 

While you may naturally freeze when faced with a knife-wielding attacker, I would instead recommend avoiding that knife. Have you considered moving somewhere they cannot attack you? Perhaps one step to the side, because pawns can only attack diagonally.