The best books on realistic knowledge and decision making for the uncertain future

Nassim Nicholas Taleb published several bestselling books, including The Black Swan and Antifragile, after his Fooled by Randomness established randomness, luck, and uncertainty as concepts that nobody should ignore when analyzing the past and making decisions about the future. Some people dislike Taleb’s arrogance but I do recommend this book because I dislike the arrogance of the establishment, especially when they attribute all their successes to skill while blaming others for their failures. We all like order and certainty, so it’s easy to swallow the nice but misleading theories of experts and scientists who ignore the reality of randomness and uncertainty. I became more alert to this issue after reading Taleb’s hammering of ignorant experts. 

I was familiar with the theory of evolution when I read this book several decades ago, but it deepened my understanding, and I also liked Dawkins’s writing style. The most impactful insight was the role of spontaneous replication. As humans we replicate with a purpose, but that does not diminish the impact of purposeless replication of the simpler units that make us, such as our genes. The book explains how spontaneous replication of random mutations results in the dominance of new organisms that are better adapted to a changed environment. This insight and my familiarity with physics and math helped me understand that everything in nature evolves by trial and error—from the physical processes that create order out of quantum chaos, through evolution in biology, to how humans learn and think.   

I am not a fan of the history genre, but this book glued me to its pages. I like how this scholarly presentation of our evolutionary history became a publishing phenomenon that surprised publishers and booksellers. I like its in-depth but clear explanations and the distilled messages that can help us make better decisions for the future. The most impactful message for me was how the stronger and bigger-brained Neanderthals disappeared whereas we, the Sapiens, evolved rapidly because our predecessors were able to communicate and operate as teams of individuals with diverse skills.

I like how William James—the first educator to offer a psychology course in the United States—distinguished reasoning from mere knowledge by the following sentence: “Reasoning helps us out of unprecedented situations—situations for which all our common associative wisdom, all the ‘education’ which we share in common with the beasts, leaves us without resource.” With the authority of a Nobel laureate, Daniel Kahneman uses his terminology of fast and slow thinking to popularize the distinction between “associative wisdom” and “reasoning.”

I recommend Thinking, Fast and Slow because it is important to understand this distinction and Kahneman provides many examples that illustrate it. However, I disagree with the interpretation of examples such as people’s choices between the certainty of taking $400 and a 50 percent chance to win $1,000. The 50 percent chance is better if we could make this choice many times, but we usually have only one bite at a cherry. Therefore, it is wrong to brand people as irrational because they select the certainty of $400. 

Certainty is a black-or-white concept, either zero or hundred percent; uncertainty is something between zero and hundred percent, and this grayness is a difficult concept. In the context of dealing with uncertainty and making better decisions, I find Annie Duke’s use of poker in Thinking in Bets clever for two reasons: (1) People can engage with the concept that winning or losing in a poker game is neither exact science nor pure luck. (2) Given that poker games are so different from our everyday reality, there is no danger that people would expect decision recipes for dummies.