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

I have used this book almost daily since 2016, not to manipulate anyone, but to get my perspective across so it actually lands. 

It reshaped my advisory practice. I build liking by being personable and honest, reciprocity by giving real advice that sits outside the sale, and I notice scarcity everywhere now. The deflating part is watching someone's cognitive biases hold so firm that no amount of care moves them.

I would keep it away from anyone who persuades for manipulative ends, because in the wrong hands it is a manual. In mine, it is a way of thinking more carefully about my own thinking.

I have caused at least two of these five myself.

Early on, it was inattention to results, because my ego was convinced I ran the best digital agency going. Later, and more damaging, it was a fear of conflict: not dealing with problems until they turned personal. In any team above four or five people, these show up, and the hard part is that the founder usually cannot fix them, because they are one of them.

I have sat in a board meeting doing 85% of the work for half the value, watching one partner chase results and another dodge all accountability. It is a fable, and that is exactly why it sticks.

The rule I actually applied was the one about competing with who you were rather than the people around you.

I had been watching colleagues as comparison rather than research, and it dragged me down without helping any of the businesses. Reading it felt like having a teacher in semi-real time: each rule mapped onto something I was dealing with that week. 

It falls apart in small edge cases, and people love to use edge cases to dismiss a whole book. The one I disagree with most is finding and living your personal truth, because those truths shift as your life does. I doubt there is a single one you hold forever.

I read this in 2021, just after I launched my advisory, when I started noticing power dynamics in rooms I had never been in before and wanted to understand them.

I read Greene as describing the world, not recommending it. Most people never consciously learn any of this; they have copied behaviours that seem to work, a bit like a cargo cult.

Law ten, avoid the unhappy and the unlucky, still makes me deeply uncomfortable, and I think it only holds if you are a zealot. I recommend it not so anyone can run these plays, but so they can recognise the world around them when someone else does.

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. 

When I first read this book as a graduate student, Kathleen Davis’s ability to draw unexpected connections—between political power and temporality, feudalism and imperialism, medieval and postcolonial studies—melted my brain (in a good way). It’s not easy to do justice to her complex argument in a few sentences, but basically she shows how early modern jurists deliberately relegated certain ideas (servility, absolutism, religiosity) both to Europe’s medieval past and the present of the nonwestern world in order to justify imperial expansion, colonial domination, and even chattel slavery. A dense critique of both medieval historiography and postcolonial theory, Periodization and Sovereignty isn’t a breezy read but it’s well worth the effort.