Mindset Stories - The Day I Lost to a Con and What That Taught Me

In a quiet Spanish town, a small crowd gathered each day around a makeshift table in the street. At its centre stood a stern-looking Russian man, placing three smooth black discs on the surface. Only one of them had a white spot hidden underneath.

Curious, I watched as a tourist stepped forward, handed over some money, and followed the movements intently. He chose a disc...and won. They played again, stakes a little higher. Once again, he won.

The Russian began to look irritated. Then he turned to me and offered a friendly game. I stepped up. The crowd had grown. With each round, they were backing me, pointing out which disc they thought was right. I picked, I won. Their cheers got louder. It felt too easy.

So I played for money.

The Russian shuffled the discs smoothly. I focused, confident. I placed my bet, encouraged by the crowd, almost chanting for my choice. He flipped the disc.

I lost.

I was stunned. I’d practised the card version of this game - Find the Lady - for hours in my school days. I could even fool my classmates and win tuck shop food off them. But I’d never been on the receiving end of the game.

More than shocked, I was confused. The crowd had been on my side, hadn’t they?

Later, I found out from a local that the entire crowd was part of the scam. I had been the only outsider. And if I had won a larger amount, things might not have ended well for me.

That day, I learned firsthand how our brains can trick us. I fell victim to the overconfidence heuristic. I overestimated my ability and mis-calibrated what I thought I knew. Once my mental model of the situation was built, it was too late. I couldn’t see clearly through it, even with all the practice in the world.

I share this now because that same kind of overconfidence shows up in leadership.

Before I ever held a leadership position, I watched others and thought I knew exactly how I would handle things. The less I knew, the more confident I felt.

Once I stepped into leadership myself, I made poor decisions. I turned over the wrong discs, metaphorically speaking. And just like that crowd, groupthink often led me astray.

Since then, I’ve made it a habit to challenge my thinking. I actively look for blind spots. I play devil’s advocate. I seek feedback, reflect on outcomes, and try to stay humble. I’ve also become more empathetic, more aware of the people around me, and better at reading what’s real.

Now, the more I know, the more I realise how much I still have to learn. And while I still miss a white disc now and then, I get it right far more often than I used to.

What about you?

When was the last time overconfidence got in your way?

How will you know when it’s happening next?