Thinking in Bets

Life rarely unfolds in neat, predictable patterns. Even the best-laid plans can lead to surprising ups and downs, and it often feels mysterious which choices will truly turn out for the best. If you've ever wondered why some decisions yield unexpected results while others go exactly how you hoped, you're not alone.

In a world driven by incomplete information and chance, adopting a “thinking in bets” approach helps us see that every choice is a wager on a future we can’t fully control. Rather than labeling choices as simply “right” or “wrong,” we focus on the quality of the decision process, recognizing that luck plays a role in any outcome. This shift lets us learn from both successes and failures without dwelling on regret or illusion.

One significant advantage of this mindset is that it invites curiosity and humility. By acknowledging “I’m not sure,” we open the door to better questions, more perspectives, and healthier discussions about possible outcomes. When we let go of perfectionism and accept that uncertainty is normal, our decision-making becomes more adaptive and forward-looking.

In these pages, you’ll discover how to parse luck from skill, recognize hidden biases, and collaborate with others for smarter, more compassionate choices. Whether you’re trying to navigate a career move, a tough conversation at home, or even an everyday dilemma, thinking in bets helps you do it all with more confidence and clarity.

Have you ever made a choice that felt valid at the time, only to be haunted by a poor result? In reality, a flawed outcome doesn’t necessarily mean the decision itself was bad. This phenomenon, known as “resulting,” occurs when we equate the quality of our decisions with their final outcomes. The truth is, even a well-thought-out plan can lead to an unfavorable result—simply because luck had other ideas.

A famous example comes from a Super Bowl game where a coach called a surprising pass play instead of a run. When the pass was intercepted, the media labeled it the “worst call ever.” Yet a deeper look revealed perfectly logical clock-management reasons behind it, along with low historical odds of an interception in that scenario. In hindsight, critics ignored the genuine deliberation that went into the play simply because it didn’t work.

Resulting blindsides us in everyday life too. You might choose a well-researched investment that still tanks because of factors no one predicted. Or you could skip diligently studying one night and still ace an exam by pure chance. Judging ourselves or others solely on outcomes creates a distorted view of decision quality and can discourage us from taking calculated, worthwhile risks.

To overcome this, focus on whether your process was rigorous, your information was sound, and your approach aligned with your goals. Evaluate the thinking behind your actions, not just the numbers on the scoreboard. That’s how you keep learning without fear of honest mistakes.