In Love and Investing, Whoever Plays the Fool First Wins

Prologue: Two People Who Refused to Lose

Jiho and Eunchae had been in the same study group for half a year. Anyone could see they liked each other. When it was time to buy coffee, each reached for the other's cup first; their conversations always ran a little longer than they needed to. At the subway station where they parted, both of them glanced back at least once.

And yet neither said it first. Jiho did the math: if he confessed and got turned down, the group would turn awkward, and even the ease they had now would vanish. Eunchae did the math too: the one who says "I like you" first somehow seemed to be the one who loses.

"If I reach out first, I lose."

Both of them were clever. They knew how to avoid getting hurt, and how to keep their feelings from leaking out. So nothing happened. Spring passed, the group ended. The two of them parted safely, having lost nothing.

And having gained nothing.

This is written for people like that — the ones who, hating to lose, never managed to begin anything at all.

Chapter One: Two Clever People Never Fall in Love

Love doesn't begin when two people are both safe at the same time. Opening your heart only after you've checked every one of the other person's cards isn't love — it's a transaction. And a transaction has one rule: if no one is willing to show their hand first, the game never begins.

To be clever is to know how to weigh gains and losses. Showing your feelings first feels like handing the other person your weak spot; saying "I like you" first feels like becoming the lesser party. So the clever person waits — for the other to move first, until certainty sets in. The problem is that the other person is just as clever.

In love and in investing alike, when both are clever, nothing happens. Someone has to decide to be foolish first for the game to open.

This essay is about that person — the one who chooses to be foolish first. About why we're so afraid of being the first to play the fool, and why, in the end, it's the one who plays the fool first who takes the whole game.

Chapter Two: An Age Where No One Wants to Lose First

Somewhere along the way, relationships got their own profit-and-loss statement. Is this relationship a gain or a loss for me? If I pour out feeling and don't get it back, that's a loss. So the one who likes first loses, and the one who gave less wins. We've grown comfortable calling this "cutting our losses."

Cutting losses was originally an investing term — selling at a loss to prevent a bigger one. But once the phrase crossed over into human relationships, we started treating relationships like assets. At the first sign of risk, we liquidate early. We put distance between us before we can get hurt. We were taught that this is the smart way to live.

And so everyone became safe. And everyone became lonely. When no one is willing to stand in the place where they might lose, the very space where deep connection could form disappears. As the price of perfectly avoiding emotional risk, we lost emotion itself. A room left with only safe people is, in the end, a room where no one can touch anyone else.

The moment our instinct to avoid loss works perfectly, we lose everything we could have gained along with it.

Chapter Three: The One Who Shows Weakness First Opens the Door

We believe that if we look perfect, we'll be loved. So we hide our weaknesses, cover our wounds, and pretend to be unshakable. Strangely, though, deep intimacy doesn't come from perfection. It begins the moment we show each other our lack and our wounds first.

There are people who do nothing but endlessly bend themselves to fit the other person. To avoid being disliked, to avoid conflict, they fold themselves to match the other's rhythm every time. But when you only ever adjust, the other person never actually meets the real you — they only see a smoothly polished surface. Connection happens not through the surface but through the cracks.

"What's the bravest thing you've ever said?" asked the boy. "Help," said the horse.

— Charlie Mackesy, The Boy, the Mole, the Fox and the Horse

Showing weakness isn't fragility — it's courage. "I'm actually scared." "I actually like you." "I actually don't know." These sentences leave me defenseless. And it's precisely that defenselessness that gives the other person room to lower their guard too. Only the one who opens up first can open the other's door.

Chapter Four: Weakness Defeats Strength

An old piece of Eastern wisdom puts it this way: water is the weakest thing in the world, yet it defeats the hardest. Rather than asserting yourself forcefully and flaunting your power, it's in standing in the low, seemingly weak place that greater strength actually comes. No one stays beside the person who drags them in by force, but people gather around the one who lowers themselves first.

This paradox works the same way in leadership. The person straining to prove their strength puts everyone on edge. The person who admits their weakness and shortcomings first, by contrast, moves people's hearts. The moment you set down the calculation of looking strong, something calculation could never win follows on its own.

There are people we remember, for a long time, by the nickname "fool." When everyone else was calculating and backing away, they threw themselves bare-handed into a fight they were sure to lose. To clever eyes it was a foolish choice. And yet that foolishness set people's hearts on fire. In a place where no one would step forward first, that one person who chose to play the fool first ended up changing the whole game.

Only someone prepared to be foolish first can move a game that no one else could budge.

Chapter Five: The Resolved Fool and the Plain Fool

Here a misunderstanding arises. "Be the fool first" does not mean throwing yourself recklessly at anything. Pouring out your heart without calculation and hurling yourself in blindly are two different things. Miss that line, and courage instantly becomes recklessness.

One insight from an old ethics defines courage like this: courage is the mean between fear and boldness. Being so crushed by fear that you can do nothing is cowardice; charging in while ignoring fear entirely is recklessness. Courage lies between the two — in the place where you look fear straight in the eye and still walk in.

Playing the fool first isn't about having nothing to lose. It's the resolve to pay the price, knowing exactly what you stand to lose.

So the "resolved fool" isn't really a fool at all. He hasn't dropped the possibility of loss out of his calculations — he's someone who, even after finishing all the math, still chooses to stand in that place. To onlookers it looks reckless, but inside there's the weight of someone who has prepared for a long time. Recklessness fails to see fear; resolve sees fear and stays anyway.

Chapter Six: In Investing Too, the One Who Bets First Takes It

What happens in love happens the same way in investing. When everyone is certain it's safe, there's already no share left in that place. The moment certainty fully sets in is usually the moment it's already too late. Buy when everyone says it's right, and you buy expensive; buy when everyone says it's foolish, and you buy cheap.

So the one who bets first — before certainty sets in, in the place that looks foolish — is the one who ends up taking the share. Of course, this has to be paired with the resolve I described earlier. Betting with no basis is recklessness; betting after long study of what others failed to see is resolve. From the outside both look like "foolish choices," but inside, something completely different is happening.

The same holds at work. The person who hides their failures and clumsiness to look perfect gets less support than the person who raises their hand while still lacking and says, "I want to try this — I'm not good at it yet." Showing your less-than-perfect self first looks like a loss, but people's hearts lean toward the striving process, not the flawless finished product.

The person who waits until they're perfect never begins. Only the one who decides to be less than perfect first opens the first game.

Story — Relationships: The Day Minjae Lost First

Minjae was a quick calculator. He was no different in front of Sowon, whom he met past thirty. He'd learned that showing you like someone makes you the lesser party, and saying it first hands the game to the other person. So for two months he only measured — exactly as much as she measured back.

One night, on the way home after saying goodbye, Minjae suddenly felt tired. What would he even gain by winning this game? Rather than safely gaining nothing, he decided he'd rather be the one to lose.

"I like you. I'm not trying to put pressure on you — it's just that hiding and measuring feels worse to me."

Sowon didn't answer right away. A few awkward seconds passed, and Minjae felt he had just lost, badly. For days he chewed over that silence and even regretted it.

But the next week, Sowon reached out first. And only later did she say it: she, too, had been measuring the whole two months. She'd only been waiting to see who would crumble first. It was on the day Minjae lowered his guard first that she could finally set the calculator down too.

The one who lost first was, in fact, the one who let both of them win.

What It Means to Play the Fool First

Playing the fool first isn't losing. It's opening a door no one else could open. If two people stay clever to the end, both stay safe and gain nothing. The more perfect the calculation, the more precisely empty the heart becomes.

The one who measures doesn't lose. That's true. But not losing is just another way of saying not gaining, either. In love, in investing, in work — the one who opens the game was always the one who lowered their guard first. The one who showed weakness first, staked their heart first, stood first in the place that looks foolish.

Still, that foolishness is different from the recklessness of jumping in anywhere. It's the resolve to bet even after knowing everything you'll lose and pricing it in. The resolved fool is actually the one who saw the furthest.

It takes courage to lower your guard first. But only the one who never staked anything ends up with truly nothing.

So the next time you find yourself hesitating in front of someone, or in front of some chance, tapping at the calculator, it might be worth asking yourself once: Am I trying not to lose, or am I afraid I won't win? The one resolved to play the fool first is the one who, in the end, takes the game.

— End —

This is my original post, first published on hian.page.