100 Books Like 21 Lessons for the 21st Century

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. 

It’s a little weird that this book should find a place on my list. It’s a book about how society has become resistant to anything that is difficult and painful and the kinds of people that we have become as a result. But mathematics is difficult! To understand mathematics you have to think hard, sometimes for a long time. Moreover understanding something hard is discontinuous, it requires a leap to a new way of thinking. You have to start with a problem and this problem might be an ambiguity or a contradiction. A is true and B is true but A and B seem to contradict one another. When you sort out this problem you will have learned something.

The moral here is to embrace things that are difficult if you want to learn significant new things. “No pain, no gain.” You don’t have to worry about some super AI… show more.

If you want to learn about the history of the concept of authenticity and how it is understood in the western world, this is probably the best book to read (after my book, of course!). Charles Taylor is one of the most prominent living philosophers of selfhood, and this book (topping out at only a little over 100 pages) is an easy-to-read digestion of the ideas that he elaborated in his much-longer book Sources of the Self. Taylor is ambivalent about whether personal authenticity is a good or a bad thing in our era. He recognizes the harms imposed by some of the debased forms that it takes in modern society, but Taylor also tries to articulate an ethics that could rehabilitate authenticity in a way that affirms the dignity of and respect for each individual. I don’t like the fence-sitting, but this remains required reading.

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 British edition of this provocative book has the modest title The Scottish Enlightenment with the subheading The Scots’ Invention of the Modern World. I have the original in-your-face American edition though, which rejoices in a title that no Scot would have the brass neck to come up with: How the Scots Invented the Modern World with the subheading The True Story of How Western Europe’s Poorest Nation Created Our World & Everything in It. It was given to me by a Philipino-Californian surfing lawyer, Jesse Quinsaat, who studied with me at Edinburgh University in the early 1970s and continues his interest in Scottish culture when surf’s not up or the cases are not too demanding! He had bought the book in San Diego, loved it, and passed it on to me during a visit to Edinburgh.

I remember first reading Future Shock after buying a battered, orange-coloured paperback edition at a bargain price from one of the second-hand bookshops that once saturated London’s Charing Cross Road.

It hadn’t really occurred to me before how much the increasingly rapid technological changes around us might create a sense of shock—‘future shock’— for some people. It changed my thinking about the influence of technology on our world and the impact it has on people, society, economics, and politics.

Even after all these years, many of Alvin Toffler’s insights and ideas remain just as topical today.