Stop Playing Chess with Life: Why You Need to Start Thinking in Bets

Ocean Blue
4 min readMay 16, 2024

We live in a world obsessed with being right. Social media rewards hot takes and definitive pronouncements, while uncertainty is often seen as a sign of weakness. But what if this relentless pursuit of certainty is actually holding us back? What if the key to making better decisions lies in embracing the unknown?

Annie Duke, a former professional poker player and author of “Thinking in Bets,” argues that life is less like a predictable chess match and more like a hand of poker, where skill, luck, and hidden information are constantly at play. Instead of trying to control every outcome, she encourages us to reframe our decisions as bets, acknowledging the role of chance and focusing on making the best possible choices with the information we have.

This shift in mindset, Duke argues, is crucial for navigating the complexities of modern life, from our personal relationships to our professional endeavors. It allows us to detach from the emotional burden of outcomes, learn from both successes and failures, and ultimately, make smarter bets in the future.

Intrigued? Let’s explore some of the key insights from “Thinking in Bets” and see how they can help us navigate our uncertain world with greater clarity and confidence.

Embracing “I’m Not Sure”: The Antidote to Dogmatism

How often do you hear phrases like “I knew it!” or “I told you so!” We crave certainty, clinging to our beliefs even when faced with contradictory evidence. But this stubborn refusal to acknowledge uncertainty can be detrimental to our growth and decision-making.

Duke proposes a radical shift: Embrace “I’m not sure.” Instead of viewing uncertainty as a weakness, recognize it as an inherent part of life. By acknowledging what we don’t know, we open ourselves to new possibilities, diverse perspectives, and valuable learning opportunities.

Consider the example Duke uses of a CEO who was convinced that firing his company president was a disastrous mistake. He fixated on the negative outcome, overlooking the thorough evaluation process that led to the decision. By framing the decision as a bet, and acknowledging the potential for unforeseen circumstances, he could have learned from the experience without the crippling weight of regret.

In a world where misinformation and polarization are rampant, cultivating this “I’m not sure” mentality is more important than ever. It encourages intellectual humility, promotes open-minded dialogue, and allows us to engage with complexity instead of retreating into comforting echo chambers.

The Learning Loop: Turning Outcomes into Insights

We are wired to take credit for good outcomes and blame bad outcomes on external factors. This self-serving bias, Duke explains, is a powerful obstacle to learning. When we win, we pat ourselves on the back, reinforcing potentially flawed strategies. When we lose, we write it off as bad luck, missing opportunities to examine our decision-making process.

Duke challenges us to break this cycle by treating every outcome as valuable feedback. Instead of seeking validation for our egos, she encourages us to become truthseekers, analyzing both successes and failures with an objective eye.

To illustrate this, Duke recounts the story of “Nick the Greek,” a poker player who consistently lost money by clinging to a flawed strategy. Despite mounting evidence, he refused to acknowledge his mistakes, blaming his losses on bad luck. This unwillingness to close the feedback loop prevented him from learning and ultimately led to his downfall.

By actively challenging our self-serving biases, and treating outcomes as data points in a continuous learning process, we can improve our decision-making over time. Even when a decision results in a negative outcome, we can extract valuable insights, identify areas for improvement, and make better bets in the future.

Building Your Decision Pod: Truthseeking Through Collaboration

While individual reflection is important, Duke argues that collaboration can supercharge our growth as decision-makers. She advocates for forming a “decision pod” — a small group of trusted individuals committed to truthseeking, accuracy, and intellectual honesty.

Within the decision pod, members agree to challenge each other’s assumptions, scrutinize decisions, and provide constructive criticism. They celebrate the willingness to admit mistakes, embrace diverse perspectives, and actively seek out disconfirming evidence.

This collaborative approach, Duke explains, helps us overcome our blind spots, uncover hidden biases, and calibrate our beliefs more accurately. She uses the example of her own poker strategy group, where members would rigorously analyze each other’s hands, identifying potential errors and exploring alternative strategies. This open and honest exchange, she argues, is essential for continuous improvement.

Forming a successful decision pod requires careful consideration. It involves finding individuals who are intellectually curious, open-minded, and genuinely committed to truthseeking. It also requires establishing clear ground rules for communication, ensuring that feedback is delivered constructively and received with humility.

By cultivating this culture of collaborative truthseeking, we can unlock the collective wisdom of the group, challenge our individual biases, and make better decisions together.

Beyond Right and Wrong: Embracing the Probabilistic World

“Thinking in Bets” invites us to shift our perspective from a binary world of right and wrong to a more nuanced understanding of probabilities and possibilities. By recognizing the inherent uncertainty of life, we can become more adaptable, more resilient, and ultimately, more successful in navigating our complex world.

So, ditch the chessboard, embrace the poker table, and start thinking in bets. You might be surprised by how much your life improves when you let go of the need to be right and embrace the power of “I’m not sure.”

Ready to start thinking in bets? Check out Annie Duke’s book and join the conversation in the comments below!

--

--