Books like 21 Lessons for the 21st Century — picked by fans

This is an interesting collection of essays on the history of the CIA.

A spy agency thrives on deceit and uncertainty, making plans and taking actions when the adversary also thrives on those same elements.

Arranged in chronological order, the essays cover nearly 20 different incidents, describing the challenges, uncertainties, goals, and decisions made by both high-level political decision-makers and practitioners in the field.

Topics covered include early stages in the development of the CIA (founded in 1947), including covert action against the Soviet Union in the 1950s, the Bay of Pigs (1961), the Iran-Contra affair (mid-1980s), up to more recent events with bin Laden, fake news, and more.

War is the realm of uncertainty. Clausewitz sums this up by referring to the "fog of war".

Military commanders must confront this uncertainty, making far-reaching decisions when the fog of war obscures their understanding of the situation and the implications of their actions.

The book contains concise professional and historical biographies of 6 generals of the IDF, serving from early 1973 (prior to the Yom Kippur War) to 2013. The studies focus on decisions made – or not made – by these generals, the uncertainties that they confronted, and the military, political and social constraints they faced.

An interesting aspect is the personal and individualistic nature of the decision-making process. While military activity has a long history and much theory, it is more of an art than a science. The art of war, and of preventing war, is very personal, and it differs from one general to another. Some generals… show more.

This is a very readable account of Hannibal and his exploits, though it’s perhaps a somewhat idealized, romantic, and heroic portrayal of the man. Nonetheless it’s a great read.

The book follows Hannibal’s many military exploits in Carthage, Sicily, Spain, and many more, up to Cannae, Rome, and his ultimate fall from power and exile.

One sees the continual tension between three factors: Hannibal’s military genius in making military decisions despite deep uncertainty about his own capabilities and about the adversary's intentions, the military genius of his opponents, and the ruthless hand of uncertainty in human history. Hannibal’s life illustrates all three factors.

The author presents a reasoned rational explanation of historical events: Agents act rationally from self-interest. History makes sense.

As I read the book, I was challenged to ask: how rational is human behavior? What does rationality mean in a world that we hardly understand because it is fraught with uncertainty?

Uncertainty and surprise are important in history: What will be the next revolutionary invention? Who will be the next charismatic leader? What new ideology will sweep away conventions? Does history really make sense? Can we really make rational decisions when we face deep uncertainty about the world?

This is a popular science book, so a little different from the others on this list. It is a beautifully written book that is accessible to people who don’t know much about AI but is simultaneously thought-provoking for experts.

It contains probably the best discussion of "intelligence" that I've read, interesting insights into how Google and other tech giants came to develop their machine learning strategy, and a fascinating chapter that views recommendation engines and their users as parts of a single intelligent organism. It's concise and easy to read.

I've read many popular AI books, which are highly variable in quality, and this criminally underappreciated work is the best by miles. 

The famous British philosopher A.C. Grayling tells the story of a hard-fought struggle over the past five centuries for the rights and freedoms now enjoyed in Western democracies. He emphasizes that our rights and freedoms are both precious and precarious: they could easily be lost if governments and citizens don’t adequately appreciate them or don’t understand how difficult they are to win.

For Grayling, our rights and freedoms began to contract around the beginning of this century. He points, for example, to the rise of state surveillance, particularly in response to terrorism but often just for the convenience of policing.

The great fact of economic history is that we all used to be poor, and now most of us are not. 200 years ago, almost 90 percent of the world’s population lived in extreme poverty, today around 9 percent does. This is the story of that remarkable transformation and what made it possible. Of course, there are many good books on this, and I have greatly enjoyed for example Joel Mokyr, Deirdre McCloskey, and David Landes, but this is a powerful, short book by a great historian, that manages to weave together economic, political, technological and intellectual factors into a very compelling narrative of progress and its preconditions over the past one thousand years.

In this book, Pankaj Mishraj describes how the failures of secular modernity led to the rise of revanchist movements seeking to provide those left behind with a common sense of purpose.

I greatly appreciated the international scope of Mishraj’s analysis, with which he reveals how the growth of reactionary, theocratic, and xenophobic populist politics across the globe are manifestations of the same sense of malaise.

He convincingly argues that these tensions are as old as modernity itself. Rather than engaging strictly with the same old historical and sociological sources to make his case, the author refreshingly engages the poets and novelists of the era he describes.

I like to look at the big picture. This book’s picture is huge: it explains three waves of human civilization, from agriculture and land ownership, to centralization and mass manufacturing, to distributed and custom everything—the wave we are in now. It was originally published in 1980 and predicted our current culture and technology with astonishing accuracy. I, and many entrepreneurs of the time, tried to use those predictions to guide our businesses, and many, like Amazon, succeeded as a result. Are there still more third wave things to invent? Yes—think of how streaming video channels are just now taking over from cable and broadcast, not to mention movie theatres. Will this help you invent the next big thing? Maybe. And what will the fourth wave be?

I find Sam’s book imperative: love it or hate it, praise it or criticize it; Sam gets us to think seriously about culture and identity as he opens an important debate for our complex democracies to engage with. I taught with Sam at Harvard and never ceased to be amazed by his profound understanding of the world. We may disagree with him, but he certainly gets us talking.