Thinking in Bets: Why Your Bad Outcomes Aren't Always Bad Decisions

Thinking in Bets: Why Your Bad Outcomes Aren't Always Bad Decisions

You just blew a massive deal. Maybe you got fired, or perhaps that "sure thing" stock you bought just cratered. Your first instinct is to beat yourself up, right? You tell yourself you were stupid. You should've seen it coming. Everyone else seems to think so too. But honestly, you might be totally wrong about why you failed.

Annie Duke, a former World Series of Poker champion turned cognitive psychology expert, argues that we are fundamentally broken when it comes to judging our own lives. In her book Thinking in Bets, she highlights a toxic habit called "resulting." It's a simple, nasty mental shortcut where we look at a bad result and decide the decision must have been bad too.

The Pete Carroll Problem

Let's look at the most famous example Duke uses to illustrate this: the 2015 Super Bowl. The Seattle Seahawks are on the one-yard line. They have Marshawn Lynch—a human wrecking ball—ready to run. Instead, coach Pete Carroll calls a pass play.

Interception. Game over.

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The media shredded him. They called it the "worst call in Super Bowl history." But here’s the thing: according to the actual math of the game, a pass in that situation is statistically safe. Interceptions on that specific play happen about 2% of the time. If the pass is caught, they win. If it's incomplete, the clock stops and they still have chances to run the ball.

Carroll made a high-percentage bet. He just happened to hit the 2% "unlucky" outcome.

Does the interception make him a bad coach? Most people say yes. Duke says no. We confuse the quality of the result with the quality of the process. If we want to get better at life and business, we have to stop acting like the universe is a game of chess where the best player always wins.

Life is poker.

Life Isn't Chess (And That's the Point)

In chess, there is no hidden information. All the pieces are on the board. If you lose, it's almost certainly because you played worse than your opponent. Luck doesn't really live there.

But poker? You can play a hand perfectly—mathematically, psychologically, strategically—and still lose your shirt because the dealer flips a card you couldn't see coming.

Thinking in Bets is about realizing that your life is full of hidden information and "luck" (or variance). You can be a great CEO and still go bankrupt because a global pandemic hits. You can be a reckless driver and make it home safe every night.

The reckless driver isn't a "good" driver just because he hasn't crashed yet. He's just a lucky gambler whose luck hasn't run out.

Embracing the "I’m Not Sure" Mindset

Most of us are terrified of sounding uncertain. In a boardroom, "I don't know" sounds like a death knell for your career. We’re taught that leaders have to be 100% sure.

Duke thinks that’s total nonsense.

When you say you’re 100% sure, you stop looking for new information. You've closed the door. But if you say, "I’m 70% sure this project will succeed," you’ve suddenly done something brilliant. You’ve acknowledged there’s a 30% chance you’re wrong. That 30% gap makes you "information hungry." You start looking for the risks you might have missed.

How to Build Your Own "Truth-Seeking Pod"

You can’t do this alone. Your brain is a masterpiece of self-deception. We all have "motivated reasoning," where we only see the evidence that proves we’re already right.

To fix this, Duke suggests forming a group of people who are allowed—and encouraged—to tell you that you're full of it. She calls this a "truth-seeking pod." It's not a support group where everyone hugs and agrees with you. It’s more like a laboratory.

There are four rules for a pod, borrowed from sociologist Robert Merton:

  1. Transparency: You have to share all the data, even the embarrassing stuff.
  2. Universalism: The truth is the truth, no matter who says it. Your intern might have the right answer while the VP is guessing.
  3. Disinterestedness: You have to try to keep your personal stake out of the analysis.
  4. Organized Skepticism: You should actively try to find why a belief might be wrong.

Basically, you need friends who care more about being accurate than being "nice."

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The Art of the Pre-Mortem

One of the most practical tools in the book is the pre-mortem.

Usually, we do a post-mortem after a project fails. We sit around a table and talk about what went wrong. It's depressing and reactive.

A pre-mortem is mental time travel. Imagine it’s six months from now and your new business venture has failed miserably. Now, ask yourself: Why did it fail?

By imagining the failure has already happened, you bypass your own optimism bias. You start seeing the "potholes" in the road before you actually hit them. It’s not about being a pessimist; it’s about being prepared. You might realize the marketing plan was too thin or the budget was too tight. Now you can fix it before the "bet" actually starts.

Stop Betting Against Yourself

Every choice you make is a bet against all the other versions of "you" that could have existed. If you stay in a job you hate, you’re betting that the safety of a paycheck is worth more than the potential happiness of a new career.

When you frame decisions this way, you realize that doing nothing is also a bet. We often think that staying the course is the "safe" option. It feels like we aren't gambling. But in a fast-moving world, standing still is often the riskiest bet of all. You're betting that the world won't change around you.

Actionable Steps for Better Decisions

Stop judging your day by whether it felt "good" or "bad." Start judging it by whether you made smart bets based on what you knew at the time.

  • Track your confidence levels. Next time you make a prediction or a big decision, write down your confidence as a percentage. Don't just say "I think so." Say "I'm 65% confident."
  • Audit your "resulting." Look back at a big win from last year. Honestly, how much of it was your skill, and how much was just a lucky bounce? Do the same for a loss.
  • Ask "Wanna bet?" When you find yourself arguing a point, ask yourself if you’d put $50 on it. It’s amazing how quickly we realize we don't actually have the facts when our own money is on the line.
  • Run a pre-mortem. Before your next big move, spend ten minutes writing down exactly how it could go south.

Making better decisions isn't about being right all the time. It's about being less wrong over a long enough period. If you can get comfortable with "I'm not sure," you're already ahead of 90% of the people around you.