The Pokémon Card That Taught My Son More Than School Ever Could

My son, Jake, is nine years old. He has a binder full of Pokémon cards that he guards like a small, overly serious bank manager. Last Saturday, he spread them all out on the kitchen table for a “trading session” with his friend. One card kept coming up — a holographic Machamp that, by every reasonable measure, had lost its shine. His friend offered him three decent cards for it. Jake refused.

“It’ll come back,” he said, with the confidence of someone who has never paid a bill in his life.

His friend shrugged and moved on. Jake sat there, Machamp still in hand, having gained nothing and traded nothing. And that’s when I sat down next to him and said, “Hey, can I tell you something weird about your brain?”

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Here’s the simple truth: your brain hates losing something more than it loves gaining something of equal value. Twice as much, actually. So losing five dollars feels worse than gaining five dollars feels good. This isn’t a personality flaw. This is how almost every human brain on the planet is wired.

Psychologists call it loss aversion. Two researchers named Daniel Kahneman and Amos Tversky figured this out after years of studying how people make decisions. What they found was both simple and a little embarrassing for all of us — we are not the rational, clear-headed decision-makers we think we are. We are emotional creatures who really, really hate the feeling of losing something we already have.

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“The pain of losing is psychologically about twice as powerful as the pleasure of gaining.” — Daniel Kahneman

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So when Jake refused to trade that Machamp card, his brain wasn’t thinking, “What is the best deal I can make today?” His brain was thinking, “I cannot let go of what I already have, even if holding onto it is the worse choice.”

That’s the trap. And it’s not just kids who fall into it.

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Think about the last time you held onto something longer than you should have. Maybe it was a job you knew wasn’t right for you. Maybe it was a phone you kept repairing instead of replacing. Maybe it was an idea you’d already invested months into, even after you knew it wasn’t working. The reason you stayed too long? Loss aversion.

There’s a concept attached to this called the sunk cost fallacy. It works like this: you’ve already spent time, money, or energy on something. That spending is gone — you can’t get it back. But instead of making the best decision for your future, you make decisions based on what you’ve already lost. You keep throwing good money after bad. You keep holding the Machamp card.

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“The most dangerous words in investing are: ‘I can’t sell now, I’ll just wait until I break even.’” — Anonymous Wall Street saying

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Here’s a question worth sitting with: How many decisions are you making right now based on what you’ve already put in, rather than what’s actually in front of you?

Jake’s Machamp card was worth less than his friend’s three-card offer. That was the reality on the table. But in Jake’s head, selling felt like admitting defeat. It felt like losing. And his brain was doing everything it could to avoid that feeling, even at the cost of a genuinely better deal.

I explained it to him this way: “Imagine you had those three cards right now, in your hand. Would you trade them for your Machamp?” He thought about it. “No,” he said. “So your brain is confused,” I told him. “It’s protecting the card you have way more than it would protect those cards if they were already yours.”

His eyes went a little wide. Good. That’s the moment.

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The reason loss aversion is so powerful is because it was actually useful once. Back when humans were living in caves and hunting for food, losing a resource — food, shelter, a tool — could mean death. Your brain learned to protect what you have with everything it’s got. That instinct kept our ancestors alive.

The problem is that your brain hasn’t fully updated its software. It still treats losing a Pokémon card, or a stock position, or a negotiation, with the same emotional intensity as it would treat losing your dinner to a predator. The stakes have changed dramatically. The brain’s reaction hasn’t.

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“We suffer more in imagination than in reality.” — Seneca

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This shows up in money decisions all the time, and it costs people a lot more than a few Pokémon cards. Investors hold onto stocks that are clearly losing value because selling feels like “locking in” the loss. But here’s the thing — the loss already happened. The stock went down. Whether you sell or not doesn’t change what you’ve already lost. What it does change is what happens next.

Selling a losing position and putting that money into something better is the rational move. But most people can’t do it, because their brain is screaming at them that selling equals losing. So they hold. And they wait. And the stock goes lower.

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Ask yourself this: If you didn’t already own this thing — the card, the stock, the idea, the relationship — would you choose to buy into it today, at its current state? If the answer is no, you might be holding on because of loss aversion, not because it’s actually the right choice.

This question is called the “Would I buy this today?” test, and it’s one of the most honest filters you can run your decisions through.

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The really interesting thing about loss aversion is how easily it can be manipulated by other people. Salespeople know this well. When a salesperson says “This offer expires at midnight” or “Only two left in stock,” they’re not just creating urgency. They’re triggering your loss aversion. They’re making you feel like you’re about to lose the opportunity, and your brain kicks into overdrive trying to prevent that loss.

Once you know this, you start seeing it everywhere. The countdown timers on shopping websites. The “limited edition” labels. The “don’t miss out” emails. All of it is designed to make you feel like you’re one second away from losing something — even something you didn’t want five minutes ago.

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“The enemy of a good plan is the dream of a perfect plan.” — Carl von Clausewitz

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Back to Jake and the kitchen table. After our conversation, he sat quietly for a minute. Then he asked, “So should I have taken the trade?” I told him that wasn’t really the point. The point was to understand why he didn’t. Was it because he genuinely believed Machamp was worth more? Or was it because handing it over felt bad, even if the math made sense?

That’s the question worth asking. Not always — sometimes holding on is the right call. Sometimes you do have good reason to believe something will recover. But you have to be honest with yourself about whether you’re making a clear-eyed decision or just trying to avoid the feeling of loss.

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There’s a practical way to train yourself out of this. When you’re about to hold onto something past its useful point, write down two things: what you stand to gain by letting go, and what you actually lose by letting go. Not what you fear you’ll lose — what you actually lose. Most of the time, you’ll find the real loss is much smaller than it feels.

Jake eventually reconsidered the trade a few days later. His friend was still interested. They made the deal. Jake got three cards he actually uses, and that holographic Machamp — still sitting in his friend’s binder somewhere — hasn’t “come back” yet.

The loss he was trying to avoid? It was already there. Letting go of it was just the first step toward something better.