Decision-Making Tips Painfully Taught by 1,000 Lost Chess Games

Every move is a decision, and it can be improved — lessons from two years of playing chess and how they apply to real life.

Mar 14, 2025

It’s 2022, and my friend asks me to play chess. I know the rules, so I agree.

How bad could it be? Well… it was terrible. I lost in just a few moves. I tried to convince myself I wasn’t stupid, but the more I played, the worse I became

Wandering outside of your circle of competence can be painful for your self-esteem.

As with anything new, you must expect to lose — a lot. In chess, even after improving, you still lose about half your games when playing against people at your level.

In two years, I went from barely knowing the rules to reaching an average level on a popular online platform. My rank is in the middle, so half of the players are below me, and half are above. It has been a humbling experience, full of mistakes and failures.

Chess has taught me a lot about decision-making, and these lessons are useful in real life. In this article, I’ll share what I’ve learned.

Why Chess?

I've chosen chess because:

Every move is your decision. There’s no randomness — just you and your opponent.
You can learn from your mistakes. A chess engine shows what you did wrong after every game.
You learn how you perform best. You can test if you play better at different times of the day, after different meals, or with more sleep.
It’s humbling. You will make lots of mistakes.
It’s fun. It helps me focus, and I have friends who play.

3 Decision-Making Lessons

1. Use a Decision Checklist

I got much better when I started using a mental checklist before making a move:

Are my pieces safe?
Why did my opponent move like this? What is their plan?
Does my opponent have any weaknesses now?
What are my options for the next move?

I wrote this down and reviewed it after each move. Now, I try to run it in my head when I play. I’m not yet able to follow it strictly and patiently every time, but when I do, it helps a lot.

Outside the Game:

We make hundreds of small decisions every day. A checklist for important ones can help us avoid relying only on gut feelings. Figuring out your own checklist for the decisions you make helps you improve over time.

With tools like ChatGPT, you can even ask for potential checklists for different situations — such as for hiring, investing, or making major life choices.

2. Don’t Trust Your First Instinct — Pause

I made countless blunders (bad moves that immediately put me in a losing position) — because I moved too quickly.

It’s tempting to trust your gut and play fast. Sometimes, I was so sure that my first move was the best and I didn’t even consider other options. But when I forced myself to pause and find at least one alternative move, I played better.

Outside the Game:

People often trust their first instinct too quickly. They make decisions based on emotions, biases, or habits. But taking a moment to pause before reacting is a superpower — Pause – Decision-Making Superpower

3. Focus on Avoiding Mistakes Over Seeking Perfection

At the level I play, I feel that winning isn’t about playing brilliantly — it’s all about making fewer mistakes than my opponent.

Chess analysis shows that in most games, the player who makes more blunders loses. Instead of trying to make genius moves, I focused on "playing it safe" and my results improved.

Outside the Game:

In many areas of life, avoiding huge mistakes is more important than trying to be perfect.

This applies to career decisions, business strategies, and personal growth. Playing it safe and steady often beats occasional brilliance. Think of all the big mistakes that reset your progress, or derail your life, like going bankrupt.

Bonus: Remove Bias From Your Thinking

When I played against stronger opponents, I focused more because I knew it would be tough and I played better. But against weaker opponents, I was too relaxed and made more mistakes. It was interesting how much it influenced my game. Thankfully, the platform allows me to hide player ratings. I did it, and that bias disappeared.

Outside the Game:

True skill is what matters — not labels, ratings, fancy CV or their status. Make sure not to label people just by their appearance, but actions.

I did my best to remove bias while recruiting people, I found myself judging people based on their degrees, previous big companies in their resume, and years of experience. At some point, I started checking listed experiences after I had meetings with them, not before.

Summary

I won’t lie — after two years, losing is still unpleasant. But playing chess has helped me handle losses much better than before.

Takeaways for your decision-making process, drawn from chess:

Consider different options before acting
Use a checklist for better decisions
Focus on avoiding errors instead of trying to be perfect

Chess is full of lessons. It's a great playground for improving your decision-making skills. In return, you get satisfaction from seeing your improvement over time.

Think for a while: What’s a decision-making lesson you’ve learned from a hobby?

Thanks for reading!

— Michał

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P.S. For over 30 years, I avoided chess because I was afraid of looking bad — I wrote about that in my article On Scary Chess.

P.P.S. To be precise about the stats: I’ve played around 2,100 games with a 49% win rate, 47% losses, and 4% draws. It really feels like losing a lot.