Superforecasting
This book is about making good predictions, and argues that this is a skill that can be developed.
Most of it revolves around Tetlock's Good Judgement Project, a contest on predicting geopolitical events, with the surprising outcome that the top forecasters consistently did better than government officials with access to classified information.
I would recommend this book if you want to learn about forecasting and happen to be interested in geopolitics; the useful advice in this book is hidden in the myriad anecdotes around US politics.
Takeaways
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Forecasting is a skill. You can improve it with practise and good technique.
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Think in terms of distributions, not absolutes. This allows for nuanced predictions and forces you to think about the uncertainty of your guesses.
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Update your beliefs frequently. The best performers in the study made small frequent updates to their predictions.
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Answer the question. You may subconsciously substitute a difficult question with a similar but easier one. Break the given question down into smaller manageable chunks to answer the question that was actually asked.
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Making granular predictions (eg 81.5% instead of a round 80%) can lead to better accuracy.
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Be actively open minded. The best performers actively seek information to challenge their assumptions.