The Games We Don’t Realize We’re Playing
Poker, love, wine, Silicon Valley—and the scoreboards we mistake for reality.
8 min read
The hardest game to leave is the one we mistake for reality.
Silicon Valley is full of rooms people spend years trying to enter.
The dangerous part is what happens after they get in.
Boardrooms, conference rooms, living rooms where someone casually mentions selling a company for $300 million before asking whether anyone wants more pizza.
The right founders are there. The right investors. The introduction behind the introduction. And occasionally someone in a custom T-shirt whose company could buy ten Grand Cru vineyards and still have money left for dinner.
Getting in feels like winning.
And maybe it is.
But every room comes with an invisible scoreboard. It tells you which companies matter, which numbers deserve admiration, which ambitions sound serious, which people are worth knowing.
Stay long enough and something subtle happens.
You stop noticing the scoreboard.
You start calling it reality.
That is the game I’m interested in.
Not poker. Not Silicon Valley.
The games we become very good at before asking whether we ever chose to play them.
Fold, All In, and Other Adult Decisions
Poker has one enormous advantage over life: everybody knows it’s a game.
The cards don’t care whether you are a good person. Luck has never read your résumé. Positive thinking remains stubbornly ineffective at producing pocket aces.
But the cards are only the most visible part of the information.
A decision depends on position, stack size, betting patterns, previous hands, the person across from you, what they think about you, what you think they think about you—and occasionally the fact that someone has developed a sudden and suspicious emotional attachment to their water glass.
Then there is you.
Are you tired? Angry? Overconfident? Did someone bluff you twenty minutes ago and are you now privately starring in a revenge movie?
Congratulations.
You are part of the data.
We like to imagine decisions come from facts. They rarely do. They come from facts inside a system: context, history, incentives, incomplete information, other people and our own emotional state.
Poker also gives us two wonderfully dramatic options: fold and all in.
Silicon Valley particularly enjoys the second one.
All in sounds courageous. Founders risk everything. Lovers cross oceans. Entrepreneurs mortgage houses.
Nobody makes a movie called She Reviewed the Available Information and Decided the Risk-Adjusted Return Was Unattractive.
Sometimes all in is courage.
Sometimes it is stubbornness with excellent PR.
The interesting skill is knowing the difference.
Life makes this harder because the past keeps demanding voting rights.
We stay in careers because we invested ten years. Keep businesses alive because we invested millions. Defend opinions because we defended them rather confidently over dinner last Thursday. Finish expensive bottles we don’t enjoy because admitting it would somehow make the invoice hurt more.
Economists call this sunk cost.
Grandmothers call it stubbornness.
Both have a point.
The past has a remarkable talent for pretending it deserves the future.
Poker asks a colder question:
Given everything you know now, what makes sense now?
Not romantic.
Extremely useful.
And this may be poker’s greatest advantage:
Poker has the decency to tell you that you’re playing a game. Life usually skips that part.
Give Humans a Scoreboard
Outside the casino, we invent games constantly.
Someone gets promoted and suddenly our perfectly respectable job looks like an administrative error.
A friend buys a beautiful house and, for reasons unclear to economics, our own kitchen immediately loses value.
Someone gets invited to a dinner we didn’t even want to attend.
Naturally, this is devastating.
Someone is younger. Richer. Thinner. More successful. Happier on Instagram—which may be the least reliable data point in the entire model.
Nobody necessarily took anything from us.
But give humans a scoreboard and we will find a competition.
Preferably one we were already winning.
The problem becomes stranger because people standing next to each other may be playing entirely different games.
One optimizes for money. Another for freedom. Another for mastery, reputation, power, meaning or time.
Then we compare scores.
Someone choosing autonomy looks unsuccessful to someone optimizing prestige. Someone choosing meaning looks naive to someone optimizing compensation.
And someone walking out of the most impressive room in Silicon Valley may lose the game everybody can see while winning one nobody is measuring.
We spend enormous energy climbing.
Much less asking who chose the mountain.
Stable Does Not Mean Good
Game theory has an elegant name for another trap: the Nash equilibrium.
In simple terms, everyone can be making a perfectly rational move in response to everyone else and still produce a situation nobody particularly wants.
The word equilibrium sounds reassuring.
Balanced. Peaceful. Almost healthy.
Unfortunately, game theory has terrible bedside manners.
An equilibrium doesn’t have to be happy.
It only has to be stable.
A manager doesn’t trust the team, so every decision requires approval. The team stops taking initiative because nothing survives the approval process anyway. The manager sees the lack of initiative and concludes:
“I knew they couldn’t be trusted.”
Everybody is behaving logically in response to everybody else.
Nobody enjoys Monday.
Relationships are exceptionally talented at the same trick.
One criticizes. The other withdraws. Withdrawal creates more criticism. Criticism creates more withdrawal.
Neither likes the dance.
Both know the choreography.
Changing first requires vulnerability.
So nobody does.
Stable.
Not good.
And suddenly we have moved from poker tables to boardrooms to bedrooms without changing the game nearly as much as we imagined.
Love Is Not Poker. Until We Make It Poker.
Love is supposedly where we stop calculating.
This theory survives approximately until somebody sends a message and notices it has been read.
Then suddenly we have strategy.
Who texts first? Who apologizes? Who cares more? Who waited eleven minutes to answer and therefore—obviously—deserves a minimum response delay of fourteen?
Somewhere, John Nash is smiling.
Love becomes zero-sum when vulnerability starts feeling like leverage.
Then affection gets a scoreboard. Who compromised last? Who initiated? Who won the argument?
Winning an argument can be surprisingly expensive.
Especially when the prize is a quieter dinner.
But two people don’t need identical scoreboards to be happy.
One may value adventure; the other stability. One may optimize for achievement; the other for time. One creates movement; the other creates somewhere worth returning to.
Different games don’t automatically create opponents.
The problem begins when one person decides the other is keeping score incorrectly.
You don’t need identical games.
You need to remember that you are not opponents.
Sometimes neither person wins.
The relationship does.
Wine Has One Small Problem
Human beings keep getting involved.
Left alone, wine behaves beautifully. Grapes ferment. Time passes. The bottle waits.
Add people and suddenly we have scores, classifications, allocation lists, cult producers, auctions, Instagram and someone explaining limestone while your dinner gets cold.
I say this with affection.
I spent years studying wine.
Two people can drink exactly the same bottle while pursuing entirely different rewards.
One wants pleasure. Another knowledge. Another belonging. Another access. Another desperately wants to identify the vintage before everyone else.
Same bottle.
Different game.
There is a dangerous moment when the palate stops asking:
Do I like this?
and starts asking:
Am I liking it correctly?
That is usually when wine stops being wine and quietly becomes LinkedIn.
Someone identifies the village. Someone else names the vintage. A third casually mentions visiting the producer before anyone had heard of him.
There is always a third.
The bottle sits patiently in the middle of the table wondering why everyone has stopped drinking it.
The bottle never joined the competition. We did.
And yet a great bottle can become better when shared. Your pleasure doesn’t reduce mine. Your knowledge may increase mine. The conversation creates something neither of us possessed before opening it.
Nobody has to lose for somebody else to gain.
Unless there is one glass left.
Then we are back to game theory.
The Games We Win Are the Dangerous Ones
We tell many stories about people who go all in.
We tell fewer about people who quietly stand up from the table.
Persistence deserves its reputation. Relationships, businesses, craft, learning—and definitely Barolo—often improve because somebody stayed longer than comfort recommended.
But endurance and wisdom are not synonyms.
Some games deserve mastery.
Others deserve to be left.
The difficult part is that the games most likely to trap us are not always the ones we’re losing.
Sometimes they’re the ones we’re very good at.
Every game trains its player.
A system that rewards aggression teaches aggression. One that rewards visibility teaches you to fear disappearing. A culture that rewards certainty makes I don’t know feel strangely dangerous. A job that rewards permanent availability eventually makes a free afternoon feel vaguely criminal.
It happens one successful move at a time.
Every victory rehearses a version of you.
Which makes How do I win? a less interesting question than it first appears.
A better one might be:
What must I practice becoming in order to keep winning this game?
Sometimes the answer is discipline, courage, patience or generosity.
Excellent.
Sometimes the answer should make you push your chair back.
Because nobody sends a notification when a game stops serving you.
There is no pop-up:
Congratulations. You have successfully outgrown this ambition.
You have to notice.
And success is particularly unhelpful here.
Pain makes us question a game.
Success gives us very little reason to.
You get the promotion. The invitation. The valuation. The title. The table at the restaurant that mysteriously had no tables when you called yourself.
The scoreboard lights up.
Everyone congratulates you.
Eventually, you may stop asking whether you still want the prize.
You simply know how to get it.
Perhaps that is why successful games are the hardest to leave.
Losing gives you information.
Winning mostly gives you champagne.
And champagne, historically, has not been famous for encouraging strategic reassessment.
There is nothing wrong with wanting to win.
I still do.
But before asking How do I win?, I increasingly want to know:
Who chose the game?
Because the hardest game to leave is the one we mistake for reality.