The Prince

I don't understand why so many people start with this book. The Prince is short, and maybe that's what fools them. The idea is hard to put in context, because Machiavelli is writing for a fragmented Italy, full of principalities, mercenaries and popes with armies. Without that backdrop, the reader lifts a sentence out of place and turns it into LinkedIn philosophy.

I'm a big fan of Machiavelli, and what grips me is the honesty. He describes how power works, not how it should work. The discussion of virtù and fortuna is among the best things I've read about control: the part of the outcome that depends on you, the part that doesn't, and how a good ruler prepares for the second. That spoke a lot to what I later read in Taleb.

The chapter on being loved or feared is the most quoted and the most misread. He doesn't say it's better to be feared, full stop. He says that if you can't have both, fear is safer, as long as it never turns into hatred. That caveat changes everything.

My reservation lies precisely in bridging his time and ours. A lot of it needs translating, and the translation isn't always obvious. The historical examples also wear out anyone who doesn't know the period.

It's a hell of a book. I just wouldn't recommend it as a first read on the subject: I'd start with Sun Tzu and get here later.