The Undoing Project: A Friendship That Changed Our Minds
By Michael Lewis
W. W. Norton & Company (2016)

A promised on its cover, The Undoing Project is the story of an important friendship: that between psychologists Amos Tversky and Daniel Kahneman. Tversky and Kahneman are key figures in the study of cognitive biases — e.g., risk aversion, representativeness, anchoring, etc. The upshot: humans are bad at calculating probabilities in our guts. As such, we’re not rational actors.

The book tells the story of Kahneman and Tversky’s collaboration as a straightforward linear narrative. Their biographies track the creation of the state of Israel: Tversky was born there, while Kahneman’s family immigrated after the Holocaust. Both became formative figures in Israel’s armed forces.

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The Alignment Problem: Machine Learning and Human Values
By Brian Christian
W. W. Norton & Company, 2020

The Alignment Problem covers one of the central technology issues we face today: building smart systems that reflect and respect our values. More specifically, it’s “about systems that learn from data without being explicitly programmed, and about how exactly — and what exactly — we are trying to teach them.”

It’s a central issue because we are in the process of putting important parts of the world “on autopilot.” As such, we ought to ensure that our smart systems don’t inadvertently cause harm. The book evokes the sorcerer’s apprentice, with humanity cast in the role of Mickey Mouse chopping down increasingly powerful and clever brooms:

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Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries
By Safi Bahcall
St. Martin’s Press, 2019

In a famous TV spot, Apple toasted cultural, social, and technical innovators:

Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world, are the ones who do.

True, true. But the crazy ones wouldn’t go far if not for others (the sane ones?) who integrate and scale innovations into broader systems. And conversely, the sane ones wouldn’t have much to go on if not for people in their midst who introduce disruptive ideas.

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Simple Rules: How to Thrive in a Complex World
By Donald Sull and Kathleen M. Eisenhardt
Mariner Books, 2015

Many people assume that complex situations call for complex solutions. The authors of Simple Rules argue that you can’t fight complexity with complexity. Instead, defining (and abiding by) simple rules can help us act skillfully in complex, fast-moving situations.

The authors offer many examples, but a memorable one is treating injured soldiers in a battlefield. In the past, injured soldiers were helped on a first come, first served basis. However, some need treatment more urgently than others. Prioritizing under pressure calls for triage based on a simple set of memorable rules.

The authors define simple rules as “shortcut strategies that save time and effort by focusing our attention and simplifying the way we process information.” Such shortcuts allow us to act skillfully in a bottom-up manner when dealing with dynamic situations where we lack information. (I.e., always.)

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Wanting: The Power of Mimetic Desire in Everyday Life
By Luke Burgis
St. Martin’s Press, 2021

In the Buddhist tradition, the source of suffering is desire — attachment to things, people, ways of being, etc. Understanding how attachment and wanting leads to suffering is the second of Four Noble Truths: axioms that lead toward liberation. The West is rediscovering what the East has long known: that most of us stumble through life unaware of the desires that drive us. Understanding our wants and attachments leads to a healthier relationship with reality.

Wanting is a new book about desire based on the work of French academic René Girard (1923-2015), who focused on how desires affect human relations. Girard came to my attention via Peter Thiel, who cites him as an important influence. Hearing Thiel discuss Girard in an interview made me want to read a primer on his work, which is what brought me to Wanting.

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Framers: Human Advantage in an Age of Technology and Turmoil
By Kenneth Cukier, Viktor Mayer-Schönberger, and Francis de Véricourt
Dutton, 2021

Isaac Asimov said, “The saddest aspect of life right now is that science gathers knowledge faster than society gathers wisdom.” We’ve created incredible technologies yet seem unable to coordinate their use towards the common good. Typical responses to this conundrum range from naïve tech utopianism to emotional anti-rationalism.

Framers argues for a third way, one that leverages a human capability unmatched by any algorithm: the ability to think differently about situations by reframing them. By changing how we understand ourselves and our situations, we can approach problems from different perspectives. Given the role of design in making new technologies accessible to humans, designers must understand framing.

The key to approaching the subject is a concept familiar to designers: mental models,

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All Things Shining: Reading the Western Classics to Find Meaning in a Secular Age
By Hubert L. Dreyfus and Sean Dorrance Kelly
Free Press, 2011

We’re beset with wicked problems. Ecological degradation. Political extremism. Social injustice. Wealth inequality. On top of all those, a pandemic. It’s easy to despair given so many complex challenges. Our response depends on how we frame our understanding of reality.

Dreyfus and Dorrance Kelly are philosophers, and All Things Shining is a book of philosophy in the practical sense: not a dry, academic tome about esoteric distinctions but a guide on how to lead a better life. At its core is one of the key questions of modern living: how do we keep nihilism at bay?

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The Scout Mindset: Why Some People See Things Clearly and Others Don’t
By Julia Galef
Portfolio 2021

We live in an increasingly polarized world. All spheres of life are becoming politicized. Tribalism and zero-sum thinking seem inescapable. In this context, Julia Galef’s The Scout Mindset is a refreshing (and much needed) call to lead more rational lives.

We’ve been sold self-deception as a way to get ahead. (E.g., by projecting unwarranted confidence.) The book makes a compelling case for making clear and realistic assessments instead. It’s a practical guide on how to stop deceiving yourself — “to see things as they are, not as you wish they were.” The goal: to know truth in service of better decisions, leading to more skillful actions.

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