Why losing $100 hurts twice as much as winning $100 feels good


Hello Reader,

Someone offers you a coin flip. Heads, you win $100. Tails, you lose $100. Fair odds.

You decline immediately.

They adjust: Heads, you win $200. Tails, you lose $100—positive expected value, mathematically advantageous.

You still decline.

That's Loss Aversion. Losing $100 hurts approximately twice as much as winning $100 feels good. Your brain weighs potential losses roughly two to one against equivalent gains. You're not evaluating decisions on math. You're evaluating them on emotional asymmetry.

This mental model is part of Re:Mind, my toolkit for clearer thinking in a world where others exploit your cognitive architecture. Understanding how your brain processes gains and losses differently is the first step to making decisions based on evidence rather than inherited risk aversion.

Why Use It

Your brain doesn't process gains and losses symmetrically. A $50 loss registers as approximately twice as painful as a $50 gain feels pleasurable. This asymmetry shapes nearly every decision involving risk.

You hold losing stocks longer than winning ones. Selling a loss feels like admitting defeat—locking in pain that's currently "on paper." The pain of realizing a loss is so intense that you'll hold bad positions hoping they recover, even when the rational move is to cut losses and redeploy capital.

You reject opportunities with positive expected value. A job offer with higher upside but more uncertainty feels riskier than staying put, even when staying guarantees stagnation. The potential loss (security, familiarity) looms larger than the potential gain (growth, learning).

Loss Aversion explains why penalty frames motivate behavior more effectively than reward frames. "Avoid losing $50" drives action more reliably than "Gain $50." Your brain prioritizes avoiding pain over pursuing pleasure.

When to Use It

Use this model when you notice yourself avoiding decisions rather than making them.

You're staying in a situation that's not working. The job isn't right, the relationship isn't healthy, the strategy isn't effective—but leaving feels like losing what you've invested. Your brain defaults to minimizing loss over pursuing gain.

You hold losing positions hoping they'll recover. The stock keeps dropping. The failing project keeps consuming resources. Cutting losses would mean admitting the loss is real, so you hold on. Loss aversion convinces you that unrealized losses don't count.

You demand more to sell than you'd pay to buy. You wouldn't pay $50 for that item, but you'd want $100 to part with it now that you own it. That valuation gap is a result of loss aversion distorting your assessment.

How to Use It

In Breaking Bad, Walter White refuses financial help from his former partners at Gray Matter, even though accepting would solve his medical debt and eliminate the need for illegal activity. He refuses because accepting feels like admitting he lost—that he made a mistake, that he needs rescue, that his pride was wrong. The pain of that perceived loss (dignity, independence) outweighs the enormous gain (financial security, safety for his family). Loss aversion drives him to choose meth production over a clean solution.

Here's how to recognize when loss aversion is controlling your decisions:

Make the implicit loss explicit. Write down what you're afraid of losing. Is it real or imagined? Would giving it up actually harm you, or does it just feel painful because your brain treats any loss as a threat?

Reframe loss as opportunity cost. Holding the losing stock isn't avoiding a loss—it's choosing to keep capital in an underperforming asset. Staying in the wrong job isn't preserving security—it's trading years of potential growth for a sense of comfort.

Test the endowment effect. Ask: If I didn't already have this, would I choose it now? If the answer is no, loss aversion is distorting your valuation.

Next Steps

Pick one decision you've been avoiding. Write down what you'd lose and what you'd gain. Then multiply the perceived loss by 0.5—your brain is likely overweighting it by approximately 2:1. Does the decision change?

Where It Came From

Daniel Kahneman and Amos Tversky introduced Loss Aversion in their 1979 paper on Prospect Theory. They demonstrated that people reject symmetric 50-50 bets even though the expected value is zero, and require roughly 2:1 upside to accept mixed gambles. Their work showed that losses aren't just negative gains—they're psychologically distinct, processed differently by the brain, and weighted more heavily in decision-making. Kahneman won the Nobel Prize in Economics in 2002 for this research.

Your brain's architecture isn't your enemy. But it is designed for survival, not optimization. Recognizing the asymmetry gives you a choice.

Until next time, keep questioning. Your mind is the last territory you truly control.

Think Independently, JC

Share or Join 👉

Re:Mind with Juan Carlos

Re:Mind is a weekly newsletter exploring mental models and frameworks that help you think clearly and make better decisions. Each week, I share practical insights and tools that transform complex ideas into wisdom you can apply immediately. Join me in making better decisions, together.

Read more from Re:Mind with Juan Carlos

Hello Reader, Here's the pattern: you set a target. You hit it for a week, maybe two. Then a bad day arrives (low energy, fractured schedule, unexpected chaos) and you miss. Not by much. But by the goal's own logic, a miss is a miss. So you log the failure. Then you miss again. Then the goal quietly dies, buried under a pile of "not todays." The goal didn't fail because you lacked discipline. It failed because it only had two states: perfect or pointless. And that binary is a trap. The ABC...

Hello Reader, My wife Taylor hosts a podcast called Doomed to Fail with her co-host Farz. The premise: take history’s most notorious disasters and epic failures, analyze the red flags, and ask the uncomfortable questions: How did things go so wrong? Could this have been avoided? They invited me to talk about a mental model that answers both questions. It’s called second-order thinking. And I wanted to share the core ideas with you here, because this pattern is everywhere. The Scene That...

Hello Reader, Austria and Germany share a border, similar cultures, and comparable healthcare systems. Ask citizens of both countries whether they support organ donation, and roughly 85% say yes. Yet Austria has a 99% organ donor registration rate, and Germany sits at 12%. Same values. Same medical infrastructure. Opposite outcomes. The difference? Austria uses opt-out registration. Germany uses opt-in. In Austria, you are considered a donor unless you actively decline. In Germany, you're not...