On Skillful Calibration (and Safely Pokin’ Gators!)

To improve, calibrate. To calibrate, employ expected value calculations (which is more fun than it sounds).

Two years ago, a friend passed on the opportunity to invest in Anthropic. He now regrets passing.

This friend prioritizes calibration. Yesterday I learned why he generally avoids risks. When viewing a risk, he considers only the magnitude, failing to also include the risk’s probability.

Expected value is one of game theory’s most powerful calculations: 

  • Probability × Magnitude = Expected Value. 

My friend is not unique: people often drop one of the two terms. Include both in your simple math; your outcomes will be better calibrated. (And it only takes a second!)

Magnitude-Only: Frozen From Fear

Considering only the downside magnitude over-biases against action. This heuristic will keep you alive but not enable you to thrive.

This example occurs whenever somebody says, “But what if it fails?” as a conversation ender. Slap a probability on that bad boy and you’ve got an EV.

Probability-Only: Missing the Magnitude

A friend once described why they don’t vote: “the likelihood I’ll have an impact is near-zero.” Ah, but tomes have been written about the enormous magnitude.

When someone says, “It probably won’t happen,” or “it’s a drop in a bucket,” check they’re also considering the size of the bucket. If the impact is large enough, the low likelihood that your single drop makes it overflow may be enough.

EV → More Fun

During my all-time favorite date, Partner and I hooted & hollered at an alligator.

Twenty minutes earlier, we strolled down a path through a Louisiana swamp. Partner meandered toward some tall grass. I said, “I wouldn’t do that.” Partner was surprised because her self-preservation instinct usually eclipses mine. I mentioned alligators, and said: in this circumstance, the magnitude is very bad (being eaten by a gator) and the probability much higher than usual (Louisiana swamps contain alligators, and Pokémon has taught me to beware tall grass).

Compare that moment to later: on a bridge 10 feet above an alligator. The magnitude is still very bad, but the likelihood de minimis. (Teehee, alligators can’t jump 10 feet!) 

Since we knew ourselves to be safe, we could poke the gator with our metaphorical stick.

When something seems scary, investigate the probability. E.g. “I can’t miss work to see my child’s school play: I could lose my job.” 

This concern is well-founded, but misses two elements: the likelihood of losing your job (probability) and the fact that you can influence that likelihood via other actions (malleable probability). (I’ll write more on malleable probability another time, especially as it relates to luck.)

Expanding your Vocabulary

Expected Value is a core step, but it is only the first step.

Error bars can make this topic tougher. The question “How likely is extra-terrestrial life to exist in our universe?” prompts wildly different outcomes whether you include the error bars.

So even if you do the EV calculation, you’ll still be wrong sometimes, you’ll still lose sometimes, and there’s still more calculation to do. (For a fun example, see Pascal’s Mugging.)

There’s a Fine, Fine Line Between Campy & Bad

Bad + heightened + self-aware = camp. Bad + heightened – self-aware = bad.

Can you discern between campy acting and bad acting?

On Thursday, I watched a play. Half the actors performed camp; the other half were unskilled. Camp is the mimicry and affectionate mockery of bad. There’s a fine, fine line between them: to the untrained observer, camp could appear as bad.

Thus, the performers must train the observers.

What’s in a Play?

A skilled actor who cannot entertain is not a skilled actor. However, in this situation, I do not think the actors are entirely to blame. An actor in an uncurated environment can only do so much.

The director is responsible for show cohesion, just as a coach is responsible for team cohesion. (A football player can reasonably say, “I played my role perfectly; today’s loss is not my fault.”)

Thursday’s show presented individuals but lacked a bigger picture. Every actor played according to their ability. Some of those abilities were poor. The director failed to account for this gap. Again, I think this is a coaching issue. Plenty of highschool sports teams have bench warmers and waterboys. Plenty of highschool plays contain “tree #1”. (And New York City theater likely has far more people auditioning than available roles.)

Just as a comedian must wink at the audience lest we think him a liar, this play needed a wink. The play was a small-theater (but professional) production of A Funny Thing Happened on the Way to the Forum, a musical containing archetypes — archetypes that, as over-the-top portrayals, may not be authentic. Inauthentic acting done well may be camp. Done poorly? Amateurish.

When the actors first entered the stage, playing mock-audience members, one could have said, “This is going to be campy.” A director’s note in the printed programs could have said, “We lean into the camp.” Instead, the performances fell into the uncanny valley.

A Holistic Hole

A basketball coach must do more than ensure each teammate performs their role. They must ensure the team gets the ball into the basket. Otherwise, you end up with beautiful acrobatics but complete strategic failure.

Or, in this case, a play that audiences did not want to watch.

In Favor of Race-Ism

Not that kind; the playful kind. 

Two days ago, Partner asked, “Are most games races?” 

As a lover of games and bad puns, I present to you: 

RACE-IAL DYNAMICS: a taxonomy of games if we assume all games are races.

Why Touch Upon Race? 

Race is a touchy subject. Why perform this taxonomy at all? 

Story structures come from games. Flirting often mimics tag. Political jabs often mimic “I’m not touching you”. 

Separating the races allows us a clearer vocabulary about the different race mechanics found in a game. 

If you’re playing game A, which has race dynamic Alpha, would the game be better with race dynamic Beta? 

What’s in a Race? 

A “race” is approximately a competition involving time. Common words/constructions include: 

  • “First to X” 
  • “Most Y in [time]” 

RACE-ISM is the categorization of games by their races. (People who subscribe to 

this categorization are therefore RACE-IST.) 

Segregating the Races

Some races are pure: reach the victory condition before the opponent. Most games contain some amount of RACE MIXING (the incorporation of different race-like components, which tends to create stronger games, as we’ll get into later). Let us attempt for a moment to see the races in their purest forms. 

Who’s Racing, How & When? 

  • SIMULTANEOUS RACE
    • “I race while you race” 
  • SEQUENTIAL RACE
    • “I race, then you race” 
  • ASYMMETRIC RACES
    • “Can I X before you Y?”
  • ANTIPARALLEL RACE
    • “You want to go in one direction; I want to go in the other” (e.g. tug of war). 

Race Physiognomy 

  • RACE-RACE
    • “First to X”. 
  • SLOW RACE
    • “Who gets there last?”
  • SCORE RACE
    • “Most points wins” or, for golf “least points wins”
  • QUALITY RACE
    • “Best X within [time]”, where X is about quality traits, not numerical (e.g. the Great British Bake-off or gymnastics.) 
  • ENDURANCE RACE (or SURVIVAL RACE)
    • “Who quits last?”

Race Ends

The word “end” can mean either culmination (“the end of my work shift”) or goal (“you are working to what end?”). As this piece contains copious puns, I shall employ the word to mean both. 

  • RACE CULMINATIONS
    • TIME-ENDED RACES
      • A clock concludes the race 
    • PLAY-ENDED RACES
      • A player action concludes the race
  • RACE OBJECTIVES can be
    • the SAME
      • (“first to touch the tree”)
    • DIFFERENT INSTANCES OF THE SAME
      • (“first to checkmate the opponent’s king”)
    • DIFFERENT
      • (“can I tag this runner before they get to the base?”)
    • SUBJECTIVE
      • (“most satisfying to X person”)
    • OBJECTIVE
      • (“Highest measurable count of X”) 

Race Mixing

Most people only watch footraces at the Olympics once every four years, which implies we find them less interesting than other sports. Football, for example, contains:

  • An antiparallel asymmetric race
    • (offense vs defense) 
  • with mini asymmetric antiparallel races
    • (cornerbacks guarding wide receivers; offensive line protecting the quarterback while the defensive line attempts to pressure and/or tackle the quarterback), 
  • with multiple race ends and sub-ends
    • (the game itself concludes after the clock runs out of time (time-ended race), but the clock can pause due to various in-game mechanics)
    • (the number of downs is a play-ended race, influenceable by both teams) 

Football’s different races require different skills: speed, strength, and hand-eye coordination of course, but also time management, rapid-fire decisionmaking, and balance of risk-taking. Since games parallel the skills we use in the rest of our lives, the simple ones tend to be less generally valuable, just as the ability to perform one simple task (picking up a pencil) is less valuable than performing a more complex task (writing a biography). 

Inferior Races 

There are no inferior races. RACE-IAL PREFERENCE is a matter of taste. 

For example, my favorite type of race happens in cooking: One person speeds to finish the rice before another person can toast the marshmallow, all before the oven is pre-heated. As an added benefit, at the end we enjoy a tasty race krispie treat.

Rotational Monotasking

The Subconscious Collaborator

You can’t multitask. But your subconscious can.

The literature against multitasking is vast. The human brain, for example, only possesses one language processor.

But how many of us have received a brilliant idea while performing a completely unrelated activity?

Harness it. Treat your subconscious as a collaborator: pass it work, receive it back.

Conscious & Subconscious

One’s psychological resources do not extend over the horizon, infinitely in all directions. Sometimes you can’t concentrate enough to read a single additional email. But in these moments of email exhaustion, you could compose a slide deck. (Or at least cook dinner.) 

Take my writing process: 

  1. Spew
  2. Nugget
  3. Outline
  4. Polish

Spewing more than one topic back-to-back forces my eyes to cross and my mouth to fill with cotton. Spewing on a topic, then immediately nuggeting it, prompts an outsized interest in the activities outside my window. But I can spew topic A, then nugget topic B, outline C, and polish D, no sweat.

My calendar becomes a beautiful spiral, like strands of A, T, C, and G in double-helixed DNA.

The Spiral

Plenty of games contain this sort of interlocking loop. When the same shape shows up across domains, the underlying move tends to transfer. Weightlifting benefits from a rotation of muscle groups. A football play contains individual loops per player, each intersecting and overlapping. Recognizing the shape enables you to take the tactics from one game to the next. 

Why not relate to your mind in this way?

The Subconscious Collaborator

In college, I practiced the skill of passing information to my subconscious. “What is six times seven?” could be performed consciously (visually) or via telling oneself, “Come back to me when you know six times seven.”

I call this process rotational monotasking, since you’re not performing two tasks at once. Your single activity is passing and receiving. (I don’t think of these as two activities, just as I don’t think of listening and talking as different activities, but as sub-parts of “conversing.”)

Years later, friends would introduce me to the bomb defusal game Keep Talking and Nobody Explodes. In this game, the defuser must pass information about the bomb to specialized experts, who perform their mini-tasks, then pass information back to the defuser. By no coincidence, I performed naturally as a defuser, thanks to it mimicking the same process: pass and receive.

In play: I tell someone the colors of horizontal wires. They tell me they need the serial number. I say “one moment” and circle back. We pass information, ignoring the irrelevancies, and pulling the right answer when ready for it. The team works faster when everyone has a productive activity. Your job as defuser: ensure everyone else always has a task. 

In what other areas does one perform this pass and receive? 

  • As a leader/delegator. (“Tell them the end state and the why; let them invent the how.”)
  • With oneself, to improve one’s skill at a topic without dedicating conscious resources. (“Brainstorm fun ideas for my blog title” → you’ll start to notice them while grocery shopping.) 
  • When one has hit a wall. (“I don’t know what else to do here. Give me the next move when you know it.”)

Some people have developed impressive loops. Can you feel the difference between 41°F and 41.5°F? Many river guides can. Can you tell yourself to wake at 6 a.m. and do it? You can learn it.

Rotation buys you the ability to focus on the present without losing that other idea.

When you pass a topic and return to it: 

  1. You’re newly rested, so you see it with fresh eyes and enthusiasm
  2. You’re in a new circumstance, so may have new ideas based on the new context
  3. You can spend the intervening time on other activities (rather than banging your head against the wall)
  4. Your subconscious has time to work on it (ah, the glory of the shower thought!) 

When you have an idea, you needn’t tackle it immediately. With infinite seconds between now and a deadline, what are the odds that now is the right time to think on it? Process creates product. Improved process → improved product. 

This very post: spewed Wednesday, outlined Thursday, and polished Friday for your enjoyment.

Consistency, Consistency, Consstncy

“Every Day” means Every Day! means ¿Every Day? 

I have a motto: Seven days a week means seven days a week. (Except when it means five.) 

I have three categories of “Every day”: 

1. Religious Commitments 

If lightning struck me and I awoke in the emergency room, I would still write every day. 

The commitment is inflexible. The details are wishy-washy. Sometimes “day” stretches into the early morning hours of the next day. Sometimes “writing” means a scribbled sentence onto a post-it note reading “I don’t want to write today.” When I was writing two pages per day for my first book, many days started with writing “I don’t want to write today… I don’t want to write today…” until I got in the groove and shifted to the topic. Most days, I pen and publish a brief essay. 

When I injured my back, I performed a prenatal core workout as my daily 5 minute abs. 

This “every day” works because the requirement is rigid but the goal very easy

2. When 7 = 6 

    I lift weights every day. 

    (Except for ~2 days per week.) 

    I tell myself I lift weights every day. Sometimes this approach is honest: Over the last two months, some weeks, I lifted 7/7 days. 

    The issue: Weightlifting relies on unpredictable activities. How well will I sleep? How recovered will I be? Sometimes, I need a rest day to prevent injury. 

    7 days per week therefore becomes 6. But if I aimed for 6, 6 becomes 5… and 5 becomes 4…  and very soon I’m watching cartoons with Dorito dust on my chest

    This “every day” works because the requirement is flexible but the goal very intense. 

    3. The Failure of Flossing 

    Jeff Foxworthy’s dentist asks, “Have you been flossing every day?” 

    “Not every day…” Jeff admits. “The last time I flossed… You did it!” 

    Most people don’t floss. I don’t brush my teeth in the morning. (I only brush at night.) 

    Turns out I brush in the morning every day the way most people floss every day. 

    Default to Yes

    I experience a large mental cost oscillating about action. 

    Writing 5 days per week is somehow more difficult than 7. If I give myself an out, I consider and negotiate. Instead, I commit and know my category. 

    Seven days a week means seven days a week.

    (Except for the contexts where it should mean five.)

    (Or zero.)

    (Or negative one.) 

    Four Umpires

    Games require fairness. Fairness requires… Umpires?

    Bottom of the ninth, tie game, runners on first and third, the coach signals for a new pitcher.

    The Away team choruses from the first-base dugout: “You got this, Julian!” “Go get ’em, Julian!” (No relation.)

    The new pitcher takes the mound. He has the wispy, windswept hair of an early-2000s teenage heartthrob, and just enough muscle to suggest he started working out when puberty hit a couple years ago. 

    Julian throws his first warmup pitch.

    A player walks from the third-base dugout to behind home plate. Maybe 15 years old. He accuses a woman old enough to be his mother: “Are you taking videos?” 

    “No,” she replies. “You guys were [doing something she found objectionable].”

    Julian throws his second warmup pitch. The boy continues the accusation: “Were you taking videos?” 

    “No, just pictures.” She continues her explanation. 

    “I don’t care.” The boy stomps back to third base. 

    A third warmup pitch. The umpire calls the game back in play.

    Julian straddles the mound. His neck swivels, unable to see the opposing players on first and third at the same time. The previous cheers have gone silent. Julian twitches his knee. Something catches his eye near first. He looks over at it.

    “Bawk!” yells someone from the third base dugout. 

    “Bawk!” the umpire agrees like a chorus of chickens. “He lifted his knee and put it back. That’s a bawk.”

    “What’s a bawk?” Partner asks me. I start laughing. 

    “What’s a bawk?” she repeats. 

    “It’s…” I begin.

    Suddenly, everything is happening at once. The umpire clears the path between third base and home, like he’s making way for prince Ali. The player touches home. His friends cheer. A tall man says “Excuse me” to someone beside us; he removes a sun-shaded phone from the fence, where it was probably recording or livestreaming the game. The umpire walks over to the Away team to explain the rule violation. A younger looking boy has both palms against his cheeks and mouth agape like a real life Scream. Someone says, “At least we gave them a hard fight.”

    I turn to Partner and explain. “Basically, the pitcher isn’t allowed to trick the base runners. So there are a lot of very precise rules about what he can and can’t do. I think I’ve heard my father say ‘breaking the plane of the knee’ at some point, meaning you have to pitch immediately when you do that. If you break the rule, as punishment for your shenanigans, the players are awarded a free base.”

    “And that’s called a bawk?”

    “Yep. Spelled B-A-L-K.”

    “Ballk.”

    “Yeah, but pronounced like what a chicken says. Rhymes with ‘walk’.”

    “Bawk.”

    Fifteen minutes earlier, Partner and I arrived to the baseball fields. Four fields, spread out in this grassy oasis one third of the way from the top of Central Park.

    Over the next hour, we will watch four ball games. The most notable play in every game will be by the umpire.

    More Like Guidelines

    The first players are either middleschool or highschool kids. Brown jerseys for the pitching team. No one on base. 

    The pitcher throws a warm-up pitch. The ball bounces three feet before home plate; the catcher tosses it back.

    The batter approaches the plate. The pitcher throws. This ball bounces too. “Ball,” says the umpire.

    Partner and I watch eleven subsequent pitches. Some fly high, into the chainlink fence behind the catcher. Most bounce, like the first two. None cross home plate between the batter’s knees and shoulders. 

    Dutifully, on each pitch, the umpire says “Ball” and the corresponding number.

    One at a time, players populate the bases. After all twelve pitches are thrown, the bases are full.

    The pitcher begins his windup. The batter steps out of the box. The pitcher stops. 

    “That’s a balk!” the umpire shouts at the pitcher. “You can’t [I stop paying attention].”

    “Let’s go to that game,” I say, gesturing across the field.

    “Walk around or through?” Partner asks.

    The umpire is walking back his previous position, calling it a “No pitch.” 

    “We can walk through. He’s not going to throw anything hittable.”

    Partner and I walk behind the third-base fence, then skirt into the outfield in foul territory. As we pass the left fielder, I notice the players on each base slowly advancing one base.

    When a child has thrown twelve balls in a row, are you really going to call him out for a balk? Sometimes the spirit of the game calls for bending the rules. If a child pitcher can’t throw a single strike, that sounds like a rule problem. I’m reminded of the problems I experienced playing pony baseball: Stealing is legalized before any catcher has the arm to throw out the runners. A runner on first is effectively a runner on third. 

    We walked to the baseball field where Julian would soon bawk, then continued toward the softball games.

    The Competent Umpire of Slow-Pitch Softball

    The softball game on our left looks competitive. The game on our right, less so. We go left.

    The cocky third baseman nabs a line-drive one-handed. “Out.”

    Partner and I walk behind home plate, where the umpire is chatting with an off-duty ump.

    This umpire wears no mask nor padding. No padding for the catcher. Nor helmet for the batter. I learn something new about slow-pitch softball.

    The next batter hits a ground ball toward third base. The third baseman fields the ball mid-stride and throws off-balance, clearly showing off.

    The umpire calls “out,” then turns three-quarters of the way toward the fence behind him.

    “I coulda played at Arizona,” the umpire continues. “A-S-U. Got a full ride. Said no. What did I know? I didn’t want to go to Arizona.”

    He turns back to the game: “Ball.” 

    He turns back to his friend: “I played everywhere. Puerto Rico, Dominican Republic…” Returning to the game: “Strike.” Returning to his friend: “Hawaii.”

    I’m impressed by how he can both continue the conversation and accurately referee the game.

    A batter waits just outside the batting box.

    “Can we go?” asks the pitcher.

    “I’m waiting for you,” the ump responds.

    “I’m waiting for you,” says the batter.

    “No you ain’t,” the ump responds.

    As an unbiased observer at this game, I can confidently say: they were not, in fact, waiting for the umpire.

    That Ain’t the Rules

    Partner and I approach our final softball game of the day.

    Ten kids in ragtag outfits and red pinnies, aged between 22 and 25, versus ten older guys, between 30 and 40, in matching jerseys.

    The pinnies are having a blast — yelling and hollering, cheering among themselves.

    The pitcher throws. Ball. Strike. The inning ends.

    The pinnies take the field. I count ten players and seven gloves. 

    “Don’t you have gloves?” the umpire says.

    Someone shouts back, “No.”

    Someone else says, “But it’s okay. We don’t need ’em.”

    “You need gloves,” says the umpire.

    I turn to Partner. “You definitely don’t need gloves. Gloves were only an early 1900s thing. I’m pretty sure they’re not required.”

    Partner: “Might be a beer league thing.” (According to Partner, beer league is a type of casual softball where players drink beer in their dugouts between fielding.)

    The older team lends three gloves to the pinnies.

    Partner and I watch an inning or two. It’s riotous, raucous fun — all hijinks, everybody trying their best, but no pressure on winning.

    One pitcher throws a ball that arcs around 13 feet high. The ump calls “strike three.” The batter taps the top of his head.

    “That’s too high,” I say to Partner. “If it’s above 12 feet, it’s a ball.”

    The ump says, “It bounced before the line. That’s a strike.”

    The batter is out.

    The game rapidly evolves into “Who can throw the highest pitch that still lands short of the line?” Some are clearly over 15 feet, landing at the front of the plate, and still being called as strikes.

    I pull out my phone. In under ten seconds, I read aloud to Partner: “Four-to-ten-foot arc. Any pitch too high or too flat is a ball, unless the batter swings.”

    The players are now chopping at pitches coming down above their heads. The game looks less like softball and more like swatting flies.

    Yet, somehow, no one seems to mind.

    Partner is getting cold. We’ll watch this final inning.

    The pinnies are batting. Runners on every base.

    The umpire yells something to one of the baserunners. Another pitch. “Ball.” Then the umpire yells, “He’s out! Three outs!”

    I walk over to the third-base dugout. I ask one of the kids in pinnies: “How did that inning end?”

    He tells me: “The ump said no leading off.” He gestures toward second base. “He wasn’t on the base, so he called him out.”

    “And what about the pitches. Don’t they have to be under ten feet?” I ask.

    “I don’t know. I don’t know the rules,” he tells me.

    “How did you guys get to be here?”

    “We went to college together. Seemed like a fun thing to do.”

    I wonder what it would be like to play a game without knowing such fundamental information as What counts as a strike? and I should bring a glove.

    Walking home, I give Partner my shirt to stay warm, and I’m struck by how much more fun the pinnie team was having than any other team we watched that day.

    They don’t know that the ump ruined their game. So maybe… he didn’t.

    The Hand of My Dreams

    If the logic doesn’t follow, keep going. Don’t go back.

    This actually happened earlier today: 

    The Setup

    Two guys had run out of money in the poker game. One of them – the host – had lost angrily. He was displeased with two other people at the table, and responsible for the other broke-guy’s buyin. The host said, “And if we’re down by $54 and we send $50, what will you do…” 

    Then he told us, “You’ll take it and be grateful and not hound us for the other $4.” 

    A while later – minutes or hours, I don’t know – the final three of us were playing double-handed omaha. 8 cards per person, split into two hands. The board was A99Q. I had AAxx in one hand for the over-full: the second-best possible hand. Even better: my two aces were both spades. 

    The Opponents

    The woman on my left – an Asian girl from my highschool – had KKxx for the kings-over full house. (The board now contained A99QK, with still the final card to be dealt.) In her other hand, she had 99xx for quads, but also definitely did not have quads. 

    The woman on my right – a different Asian girl from my highschool – had 8cTcJc spread across her 8 cards, which went with the 9c, Qc, and Kc on the board to make a straight flush. Fortunately for me, the cards were separated across her hands so she didn’t actually have a straight-flush despite having the cards. 

    The Accounting

    We were already all in. I performed the accounting. The hundred-dollar chips were exhausted, so we used the silver bracelets each valued at $200. 

    The pot totalled around $1500. We hadn’t all contributed equally. I wasn’t concerned since I had so much equity. 

    The Broken Protocol

    We agreed to run the river three times. 

    We clicked my computer mouse to run the first river. It dealt an entire new board. We tried again. Same issue. I suggested we should use the same physical deck we were already playing with to run the river (duh!). 

    The Showdown

    I awoke.

    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 Game You Can’t Decline

    The goal of the game is to play well. You play well by knowing you’re playing.

    Last night, friends came over. They’d baked cookies. They brought the cookies in a Tupperware container. As they were leaving, Partner went to retrieve the Tupperware and hand it back at the door.

    I winced internally. I should have said something. 

    Here’s the game I saw and Partner didn’t: you don’t return the Tupperware at the door. You keep the Tupperware. Eventually, you need to return it – which means you’ll see them again, which means there’s an open thread between you. The Tupperware is a mild promissory note. Yes, we’ll have you over, or you’ll invite us, or we’ll see you at the thing – because also, here’s your Tupperware.

    Returning the container at the door closes the loop transactionally. Everyone walks away even. But the loop is what builds the relationship. Even is not what you want when starting a relationship if the other person would find you returning the tupperware weird.

    When I mentioned it to Partner afterward, she got it instantly. She’d just never thought of it that way. We also agreed that it isn’t logical. Of course they want their Tupperware back. The whole thing is illogical. Most social dynamics games are.

    I’m reminded of a buddy of mine this past summer. A woman had stayed over at his apartment. Now, she wanted her ring back. He told her to retrieve it from his roommate. No, buddy! She left it so you have to see her again! 


    I once had a 9 AM appointment with a doctor. Due to a series of errors made by his office and lab, my appointment ran until 2:30 PM. Around noon, I mentioned wanting to grab a sandwich. He gave me cash and offered to pay for mine as well.

    Something felt wrong. I bought both sandwiches and gave him the cash back.

    I suspect he didn’t even register the move. But Partner had the same instinct I did when I told her: pay for his sandwich, refuse the cash. The discomfort was real and shared, even if neither of us could immediately articulate why.

    Here’s why: the cash created an obligation flow that didn’t match the relationship. He had spent five and a half hours of my day on his office’s mistakes. The appropriate flow was him owing me. His offer to buy me lunch was a way to pay down his debt of guilt. But not an appropriately-sized one.

    Buying the sandwich, refusing the cash, was the right move. It accepted the kindness implicit in offering food while refusing the implicit power-move. Imperfect, but instinct steered correctly. 

    And as we left his office, he apologized at least 8 times for the delay. By the end, he said, “I’m done apologizing. If I apologize again, hit me.” That’s the appropriate obligation for someone who’s wasted 5 hours of your day. 


    Recently, I made a friend who pocket-vetos any activities that are emotionally intense for him. He only plays the games he wants to play, in the ways he wants to play them.

    It’s no surprise this correlates with power and resources. As friends have gotten more powerful, more of them have developed this stance. No explanation, no apology, no negotiation. Generally no answer, not even a “No”. 

    If you’re young and broke and unattractive and awkward, you can’t pull this off. People stop inviting you. Every social interaction has to be navigated, every gift has to be reciprocated, every obligation has to be honored. The poverty of optionality forces you to play every game offered. 

    As you accumulate power and resources, you can decline games without consequence. People still invite you. People still want you around. They accept this trait because you’re still worth it. Like the celebrity who’s notorious for being prickly in interviews, the rudeness becomes a feature: a filter mechanism.


    Three observations: 

    1. Refusing to play is itself a move. 

    • A recurring claim of this blog. It holds here.

    2. Not-playing a game requires winning sufficiently in other games, or people will stop playing games with you entirely. 

    • The friend’s pocket-vetos work because the rest of his social game is in order. He’s not refusing because he doesn’t understand the games; he’s refusing because losing this game doesn’t matter for him anymore. If Warren Buffett never set a schedule, only meeting with people willing to show up at his offices in Omaha, people would still gladly sit in his office for hours, waiting for the possibility to talk with him. 

    3. Winning generally comes from choosing which game is being played and at what level. 

    • Most of us learn how to act in specific spots in specific games. That’s a fine level one, but it misses out on level two (shifting the odds in your favor) and level three (dictating the battlefield). 

    One more thing: the move I should have made about the Tupperware was overruling Partner in real time. I saw the game. I knew the right move. I let her make the suboptimal one because I didn’t want to interrupt.

    That’s a habit of mine – letting people make moves I see as wrong, then discussing afterward if it matters. The discussion-afterward version doesn’t recover the move. It just generates retrospective alignment for next time.

    Sometimes the right move is to interrupt. Saying wait, I’m gonna eat all those in the moment would have been weird. It also would have been the right move. Weirdness is sometimes the price of playing well.

    [It’s late. I’ve read this one too many times to like it. The daily-publishing game is hard tonight. I hope I like this post in the morning. Sigh.]

    Do Fewer

    You win by making the right move. You make the right move by waiting for it.

    Before my jaw surgery in 2018, I made too many moves.

    I underwent a sleep study at a facility that allowed me to sleep on my stomach. Obstructive sleep apnea is positional. Bad medical care.

    A dentist prescribed an oral appliance and lied to me about its potential side effects. I wore it. The side effects were bad. 

    A surgeon told me I’d need to fix my deviated septum, so I might as well do it now. Unnecessary surgery. I’d later have maxillomandibular advancement, which would necessitate a septum fix at that point anyway. I had mis-sequenced, again due to bad advice from doctors.

    Six doctors mis-diagnosed or mis-treated me before I found the world’s expert in obstructive sleep apnea. Not himself a surgeon, he sent me to the only surgeon he liked. I had the surgery. It went wonderfully. 

    One quality move would have saved me ten years and six bad doctors, one bad surgery, and one damaging oral appliance.

    I had an insufficient respect for quality.


    A friend has spent the last decade on a large legal case about a contract violation. Ten years, about ten moves. He says most of his days are spent staring at a wall thinking. The hardest part hasn’t been any single move. It’s been the waiting between them — the part where you’re not doing anything visible. 

    It’s easy to get antsy. But the right move at the wrong time is the wrong move. And the wrong move, just to do something is even worse. 

    That’s not laziness. That’s respect for quality.


    Recently, two optometrists told me I should get corneal crosslinking. The pattern-matching said I needed it. Something didn’t smell right. 

    So I went to the actual experts — the ones who’ve seen thousands of patients who look like me over the past thirty years and done seven hundred-plus surgeries on people with my eyes. 

    At the end of this month, I’m flying to France to install permanent contacts. The pattern-matchers were wrong. The real experts were right. The move they suggested would have been unnecessary.

    Refusing a move is also a move. Sometimes it’s the best move.


    When I started freelancing, I asked everyone for client referrals. I had to. I didn’t know who would say yes, what worked, what my rate was, or who my buyer was. This was the explore phase. More information was better.

    By my third set of clients, the machine started carrying itself. My hourly rate was higher than many lawyers’. Inbound exceeded what I wanted.

    The shift on calls was exponential. I had good pre-call materials. I had good post-call follow-ups. The call itself was mostly listening and repeating back what the client had said.

    One call, I was sitting at a kitchen table on mute, pulling funny faces while my then-partner pointed at the phone whisper-yelling, “Pay attention! Focus!” The client stopped talking. I unmuted. I said five words. I re-muted. The client said, “Wow, you really get it!” Then-partner was floored.

    I would tell early-Julian to keep investing in the process. And not to abandon it when he got tired of it — to keep investing, just in a new way. The work shifts from doing more to doing fewer, better. Respect the elegance. 


    Flailing is not testing.

    When I hired my contractor, I went for volume — got fifteen quotes, narrowed them down. The cost of each one coming by was low — just some of my time — so I figured why not. But I wasn’t systematic. A bit more research upfront — learning how the process works, what the categories of contractor are, what the right questions to ask are — would have produced a faster result with fewer visits. 

    Getting a lot of information systematically is a research strategy. Getting a lot of information randomly is flailing. The two feel similar from inside. They aren’t.


    Closing on this apartment took eight months. The required topics ranged from negotiation to financing to weird legal processes to printing documents at 11 PM in rural France. About ten major moves in total.

    Once the incentives were aligned — me, my broker, the seller’s broker — the rest clicked pretty smoothly. The eight months were spent making the right moves slowly, not many moves quickly. And about half of the key moves were me saying no to other people’s requests. At least two of those would have ruined the deal. 


    It’s not about doing less. It’s about doing fewer, where each one is more elegant. Build the system that reduces the steps. Invest in infrastructure. Make the right move when the right move presents itself.

    If “fewer” ever becomes zero, that’s a different problem. This approach won’t fix that one. But it does need fixing.

    Life is full of games. Games require moves. Don’t do less. Do fewer.