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. 

The Frame Is the Game

You win the game by playing to win. You play to win by reframing the game.

I used to play competitive pickleball. I once won the silver medal at the Hoboken Open. While playing, I hated my opponents. Hated them. They were some of the most deplorable people I had ever met. Then, afterwards, we shook hands and they returned to the dentist and lawyer they had always been. 

Today, Partner and I are in Florida. We don’t want to be here; we’re here for the sort of getting-your-teeth-cleaned-style obligation that you do because it’s important but not desirable nor fun. But while we’re here we might as well make the most of it. So we lie to ourselves. We call it a vacation. We walk along the beach. We eat oysters and shrimp. 

The actions are identica. The flights, the hotel, the ubers, the appointment: none of it changes. What changes is whether we’re playing to win or playing not to lose. 

Big difference. 


Partner does a small version of this every day: I pack water because I know it’ll be nice when I drink it, as opposed to packing water because I’m afraid I won’t have it when I need it. Same bottle, same backpack, different relationship to carrying it. The first is light. The second is a lump of fear dragging you down every step. 

The NYC subway ads have the same problem. Subway surfing kills. Theoretically, nothing is worse than death, so this should be the most motivating message ever written. It isn’t. Teenagers ignore it, so they ride outside the train cars and die. Apparently coolness and thrill are more exciting to move toward than death is to move away from – even though the thing to move away from is LITERAL DEATH. 

This isn’t unique to messaging. It comes up everywhere. Are you eating healthy because you love yourself or because you hate yourself? Are you running a marathon to feel proud crossing the finish line or because you’re scared of being out of shape? 


Reframing is self-deception. Every sinking ship could be a swimming opportunity; every torture chamber could be an abusement park. There are people in genuinely bad situations who are surviving them by calling them vacations, and they’re going to wake up at some point and notice the ship is underwater. I’m not naive about this. (It’s the plot of one of my favorite movies.) It has its own dangers: overwork, misdirected effort, self-hoodwinking. 

But the alternative is paralysis. People who are motivated only by avoiding bad outcomes mostly end up doing less. They don’t send the email because it might be imperfect. They don’t take their pills because they don’t like being reminded they’re sick. They don’t go to Florida because going to Florida means admitting why we’re going to Florida. So they stay home, and they stay safe, and they stay smaller than they have to be.


Some days, you can’t choose what happens.

Some days, the frame is the only thing you can choose. 

Wouldn’t you rather choose a nice, kind, attractive, fun frame?
Every event; every observation; every activity is a fantasy.
Wouldn’t you rather choose yours?

Top-Secret Games: Trader Joe’s

The goal of the game is to win the games. The hard part is noticing they exist.

I was in the Trader Joe’s in Santa Cruz, California, standing between two checkout lines. Both stations had a cashier. Neither line had people waiting. I was deliberately ambiguous about which line I was in.

A shopper arrived behind me. She asked which line I’d chosen. I answered slowly: whichever one finishes first.

She found this unacceptable. She appealed to the Trader Joe’s gods — that is, the cashier. The cashier ruled against me. You have to pick a line. I hemmed and hawed to buy myself time and picked. 

About two years later, I was shopping with a friend at that same Trader Joe’s. My friend performed the exact same hedge. A person asked which line we were in. My friend answered the same as I had. Once again The Gods smote us. So I stood in one line and she in the other. Whichever line finished first: our group re-combined there. 

It’s like the old saying: “Everyone is playing a game that you know nothing about.” 


Here are my Trader Joe’s games: 

The dual-line straddle. If you stand at the right angle between two lines, you can commit to whichever one moves faster. This is optimal play — it’s an option you should always exercise when the structure permits it. It’s also widely considered rude, for reasons that truly make no sense to me. I’m there first; I deserve to be served first. This is a queueing theory problem: one line is more fair, BUT people also feel more annoyed that they’re in a longer line. (And here’s the thing: the person directly behind me isn’t actually the one harmed by my slowness. The person farther back is — the one whose checkout would have opened up if I’d committed earlier. We’re all glaring at the wrong people.)

The tag-team shop. Often, I stand in line while Partner grabs more items. The line moves; I advance; she rejoins. We’ve doubled our throughput. In the US, this is fine. In France, it’s a violation — my sister once spoke to me in a bakery line outside Paris and the woman behind us made it clear: this is a faux pas. Different country, different rules. (And yes, it’s perfectly reasonable to permit joining, or to restrict joining, or to permit joining but without an item, or to permit a direct substitution of equal numbers of people for equal numbers of people / equal items for equal items. If you can think of it, I can justify it.) 

The end-of-line dash. Partner’s specialty. As we approach the register, Partner likes to make a mad dash for one final item. Discussing this game, she was the most beamingly radiant I’ve seen her in a while. It has all the traits of a good game: clearly-defined, time-pressured, skill-based, some luck to keep you on your toes, low-stakes if you lose. Sometimes she meets me after the checkout emptyhanded. Sometimes she brings the stracciatella we don’t actually need but ends up being delicious with a little honey and salt. That’s not the point. The point was the game.


Here’s the secret: Trader Joe’s is also playing a game.

Their queueing system isn’t optimized for throughput. There isn’t always a central queue, no take-a-number system, no signal from the register that they’re almost ready for the next customer (so the next customer can start walking). When I asked where the bathroom was, the employee walked me halfway across the store rather than pointing. They’ve decided their game is warm experience, not minutes per customer.

Which means the friction I keep running into at Trader Joe’s isn’t accidental. It’s the residue of a different optimization. They’re playing for one thing; I’m playing for another; the shopper behind me is playing for a third (presumably their personal, egotistical perception of fairness powered by a deontological backing of the inefficient rules of Trader Joe’s (because it sure as hell ain’t actual fairness; actual fairness means the first arrival gets to checkout first)). All three of us are right, given our games. We’re just not playing the same one.

Most disagreements about etiquette aren’t moral disagreements. They’re disagreements about which game everyone thinks they’re playing. 

In serious situations, I’ve heard people say, “I’m not here to play games.” 

Perhaps it’s no coincidence that they always say that angrily. 

Return of the Sandwich Shop

The goal of the game is to make money. You make money by selling sandwiches for more than they cost. 

(Part 2 of the sandwich series. Part 1 is here.)

The previous customer had ordered and left without entering his phone number for loyalty rewards. So I entered mine.

Today’s cashier had panache. Flair. Real excitement about which side was heads and which was tails. When I asked if they were still doing the 50%-off coin flip, he said “of course!” like his job was attitude, not mere cash-register-button-pushing.

The cashier showed us the coin: this side is heads, this side is tails. Partner called it: “sandwich logo.” 

It landed sandwich side down.

She lost.

The cashier rang up 50% off anyway.

I hadn’t considered this until today: when I win the flip, I get 50% off 100% of the time. When I lose, I get… 50% off some percent of the time? The expected value just got better.

Since a sandwich is bread, meat, and veggies, the shop probably still exceeds its cost of goods even at half off. So they’re not exactly losing on the flip. But they could have netted more revenue by simply charging me the appropriate amount. 

In any case, the promotion is working: they pay a small acquisition cost to attract me back. Which they have. I’m here, eating my second sandwich in three days, and they also have my phone number. 

They played me. I played them. And the dinky coin flip is what made it work.

Partner says my odds will increase even further if I’m cuter. I think she says this so I keep bringing her places.

Well played.

What If It Were Easy?

The goal of the game is to do. You do by removing friction. 

A few years ago, a shaman watched me explain something I was struggling with. Then he asked, “What if it were easy?”

The friend with me said, before I could answer: “Julian associates difficulty with value.” 

He wasn’t wrong. I think most people do. We assume that if something is hard, it must matter; if it’s easy, it can’t be the real thing. Cultures everywhere reinforce this: no pain, no gain; if it burns, it’s working. 

But sometimes a thing is hard because it’s valuable, and sometimes it’s hard because of friction. Both feel difficult. They’re worlds apart. 

I notice the difference most clearly with games.

When I’m playing a game I love, three things happen: 

  1. I pay attention without effort. 
  2. I want to improve. 
  3. When it ends, I want more. 

This feeling – total absorption, no friction between me and the activity – is rare and precious. Most activities require me to push myself to do them. Games don’t. They grab me by my noggin and suddenly I’m along for the ride. 

A movie buff once told me he loves movies for the immersion. I experience immersion with movies sometimes. With books and theater, sometimes. With games, almost always. That’s information about me, not about games. Games are my art form.

This week I made a list of things in my day I find unenjoyable. Except for the entries about physical pain, every entry was a type of friction: either current or future. Some friction is necessary as a means to an end (waiting on hold with a doctor’s office). But some of it is inherited assumptions about how a life is supposed to feel.

If the shaman asked me again today, I’d answer: I think more of it is supposed to be easy. Not all of it. But more than I’ve been letting it be.

I’m game. 

The $10.125 Sandwich

The goal of the game is selling sandwiches. You sell sandwiches by making it fun. You make it fun by taking fun seriously. 

I bought a sandwich today. The sandwich shop offers a cute promotion: from 3 to 6 pm, if you call a coin flip correctly, you pay half price. 

It’s fun, it’s attractive, and they net 75% of the normal retail price. 

But the experience is broken. 

First, you don’t pay until after the flip. So I, who sees loopholes without trying, am instantly aware that I could order the sandwich, flip the coin, and walk if it lands the wrong way. How would they even develop a process to stop me? I pay full price and then the flip determines my refund?

Second, the coin. It’s some B.S. commemorative coin — one side is the restaurant name, the other the logo — where neither side is obviously heads or tails. So the cashier has to tell me, and presumably every patron between 3 and 6pm, “this side is heads.”

Third, the flip. Less a flip than a half-spin. He calls it whichever way it lands in his hand. Not even the catches-it-and-slaps-it-onto-the-back-of-his-other-hand move that’s standard on any schoolyard.

What happened to the good ol’ quarter?
Why are we making this more complicated than it needs to be?
Why can’t the customer flip the coin onto the counter, where it would be easily visible?
Why not call the sides “name” and “logo” instead of heads and tails? 

The sandwich was good. It satisfied my basic need – fuel after the gym so I’m not grumpy. It wasn’t $13.50 good. It’s definitely $6.75 good. It’s probably also $10.125 good (the expected cost). 

Here’s what bugs me. The promotion could have been theater. A customer walks in, gets drawn into a small moment of drama, calls it in the air, wins or loses, laughs either way, tells their friends. Instead it’s a transaction with a dice roll bolted on. The cashier is phoning it in. The coin is wrong. The flip is wrong. The ritual isn’t a ritual.

The fun version costs them nothing. Same margin, same coin-flip odds, same sandwich. Just a real coin, a real flip, and a cashier who understands he’s running a tiny game show for thirty seconds a day. 

And sure, if there are people in line behind me, by all means do the quick version. But the main reason they’re doing this promotion at all is because they don’t have many patrons between 3 and 6pm. 

If they fixed it, I’d come back. If they fixed it, I’d bring people. The half-time half-price is nice; the experience could also have value. 

Also, I called heads and it landed tails. 

Content is what you know. Method is how you think. 

To play well, you must find the method. To find the method… well, that’s part of the method. 

Today I met a cabinet rep who knew, off the top of his head, that the tambour door came in 24, 28, 32, and 36 inches. That’s the content, and, as one data point, it’s not yet impressive. But the fact he can rattle off seemingly every dimensional trait for multiple different cabinet styles and product lines across multiple brands? That’s beautiful. It’s like showing a chess master the opening few moves of a historical game and seeing him place it precisely. 

But content you can find in a book. Trivia is by its nature trivial. What you can’t find in a book: method. 

Repeatedly, he heard our proposals and improved them. He looked at a 79-inch space, listened to what I’d planned (two 36-inch cabinets, side by side), and proposed: a 30 and two 24s. Total: 78 inches. Gives you 6 more inches of cabinets. 

After he did this a few times, I isolated his method: 1) Map the dimensions of the space. 2) Subtract standard sizes from total length. 3) Find the combination that leaves the minimum remainder.

The content — knowing the sizes — is the raw material. The methods — including “subtract to find the minimum remainder” — is what makes him good at it.


A chess-master friend of mine thrives in certainty but buckles when he arrives at probabilities. Since I grew up playing poker, I rarely see certainty but am comfortable making positive-expected value bets. These games teach different skills. For him, it’s the detailed, factual, calculation-heavy process of walking a specific position to its end. (It’s no coincidence he’s now in law). For me, it’s staying afloat until I see a spot with an edge; then pouncing on it. 

Having spent many years ghostwriting for top Silicon Valley founders, executives, and investors. I’ve enjoyed living in brilliant minds. One thing I’ve noticed: 

Experts can usually describe their content in detail, but most can’t articulate their method. A surgeon could tell you every action in her procedure. But she might not know that she’s left-handed and therefore angles every screw slightly off from where a right-handed surgeon would. That left-leaning screw is just something she does, and she might even recognize it as hers. But ultimately she knows more than she can say. 


Most people hire for content. What do you know? What’s on your resume?
Some hire for good method, assuming you’ll acquire content fast.

The worst are the ones who confuse content for method. They’ve memorized the right answers for the common cases. But they can’t handle a new scenario. 

Yesterday’s post in fewer words: 

  • Pattern-matchers have content without method.
  • Scientists have method that generates content. 
  • When I’m hiring a doctor, I want a scientist. 

The cabinet rep impressed me with his content. But we also shouldn’t ignore some of the other points of his method. “You sure you don’t want a panel on the side of the fridge? You’re gonna want to look at the wires and the side of fridge every time you enter your kitchen for the rest of your life?” 

The honest answer? Yeah, I’m game.

Money is Not Victory Points

You win the game by maximizing eudaemonia.

Money is a unit. It measures a specific thing — perceived value, mostly — but it’s often treated as the score for the whole game. Stop confusing it for eudaemonia (a vibes-based measurement of how much one is living a satisfying life, derived from Aristotle’s Nicomachean Ethics). Money is only one input, and it’s less weighty than friendship, work, impact, hobbies, and legacy. (Individual weights vary.)

Here are units that I or loved ones have applied to life in the last week.

Joy per calorie. A method of choosing what food to consume. One slice of candied orange brings me more joy than an entire non-dried orange. One slice of sun-dried orange may bring even more.

Attention-efforts. Measuring time not in minutes but in effort required to keep your attention on the task. This is like golf: low score is good. The lower the attention-effort, the more you’ll naturally do it (and, generally, the more you’ll enjoy it). I create the grocery list because it’s low attention-effort for me. Partner buys the groceries because it’s low for her. Both of us hate the other’s activity. Dividing the task into more precise chunks enables better isolating and optimizing. 

Keystrokes. How many discrete small movements it takes to achieve a task. (I presume it comes from a CS context where the number of operations mattered to a program.) My father uses this one — he texts “Y” for yes and “Ack” for “acknowledged.” With practice, by both minimizing and bunching together keystrokes into “chunks”, you’ll need fewer attention-efforts to execute the same program.

BTUs (British Thermal Units). The manner through which to keep Partner happy despite last week’s sweltering early summer here in New York City. A happy partner-hour is worth more BTUs than I’d otherwise run. (I installed an AC last week.)

Team alignment. A Partner addition. A vector with directionality (“for the team vs for the individual”) and magnitude. Use cases: “Are the other person and I aligned?” and “Is this person doing a selfish thing?” Also applicable in situations where your thoughts diverge from your feelings. When the Euclidean distance is too high, investigate. 

Money. Perceived value. Not to be confused with actual value.

A unit I used at 17 and now realize was terrible: Facebook friends. The game rewarded me for playing it. Turns out it wasn’t “social media” — it was an ad platform.

A unit I still use and probably shouldn’t: hourly rate. Old habit from the ghostwriting years, when optimizing it was most of the game. A better version: (joy-per-hour + dollars-per-hour) / attention-efforts-per-hour. More-precise denominator, richer numerator, honest about what I’m actually trying to maximize. 

As you age, you develop more precise units. You improve your own vision and you learn from friends. 

Thanks, Partner.

Wise to the Game

A relaunch.

I’m most alive when I’m playing games.

A few months ago, my sister asked me about an unspoken rule in her business culture – an implicit game. I told her about games where explicit acknowledgment of the rule breaks the rule, and pointing that out is also against the rule. She thanked me and said I should write about the philosophy of games.

I’ve been thinking about that ever since.

Near the end of my senior year of college, I ushered my father into a room above the library and drew three circles on a whiteboard: writing, philosophy, and befriending eccentric people. In the middle I wrote the question that would pick my profession: “in what areas am I in the top 5% of my classmates?” 

The answer that fell out: befriend eccentric people, then write their philosophy.

Not wanting to be a starving writer, I asked one follow-up: who in that circle has money? Growing up in Silicon Valley, the answer was tech founders. I spent the next six years building that business and rose to the top of the technology ghostwriting industry. It was fun while I was growing. It’s not fun anymore. The game is too easy. 

So today I ran the exercise again, with the ikigai framework:

  • What do I love? Games. Learning new things. Befriending eccentric people.
  • What am I paid for? Writing.
  • What does the world need? Play. Whimsy. Fun.
  • What am I good at? Making complex things clear.

The answer that fell out is games, which makes sense: games are a bounded, examinable instance of the thing the world needs more of. If the world needs more play, games are where play can be examined. I learned this at clown school: the first course isn’t about humor or fun or jokes; it’s about games. 

The three pillars of this publication, going forward:

  1. Games.
  2. Eccentric people.
  3. Practical philosophy.

Writing is the medium. Speaking, eventually.

The new name is Wise to the Game. (My last name is Wise. It’s a pun. A double-pun? No: a triple-pun. Try to keep up.) 

More tomorrow.