1 Summary
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1.1 Introduction
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Taleb conveniently quotes one of his friend's summary of this book: "Everything gains or loses from volatility. Fragility is what loses from volatility and uncertainty."

I think the point is better expressed by rephrasing: "Antifragility is what gains from volatility and uncertainty, up to a point. And being antifragile is a good thing."

Well, that's pretty much summarizes this 500-pages-long book. The rest is an accumulation of more or less relevant topics, delivered in Taleb's trademarked seering, holier-than-thou, hero-or-moron style. Why, even in "Dynamic hedging", his first, $100-book on trading exotic options, he was already both immensely entertaining and almost unbearably infuriating.

1.2 A few of the more interesting points:
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1.2.1 Every phenomenon in the world belongs to one of the following categories:
Fragile: vulnerable to unforeseen shocks
Robust: indifferent to shocks
Antifragile: thrive on shocks, up to a point.
That's what Taleb calls the Triad.

1.2.2 Most modern structures are inherently fragile
Salaried employment: while it looks safe on the surface (predictable salary every month) it is subject to the catastrophic risk of losing one's job.
Debt-fueled economies: debt has no flexibility, so these economies can't stand even a slowdown without risking implosion (cf current situation)
Modern societies: efficiency demands are pushing the structures to the maximum, so a little sand in the cogs make the whole edifice totter.
Touristification: turning adventures (kids growing up, people visiting foreign countries) from exciting, dangerous activities into bland, Disneyfied and safe ones.

1.2.3 Ways to be antifragile include:
Stressors: it is healthy to be subject to some punctual stresses to awake the organism from complacency (e.g. irregular meal times, violent exercise or ingesting small amounts of poison)
Barbell strategy: put 90% of your eggs into something super-safe and be very risk-seeking with the other 10% (swing for the fences).
Optionality: get into situations where downside is limited but upside is unlimited (non-linearity)
Redundancy: have more than one way to have things done.
Less is more: don't add unnecessary things.
Tinkering: empiricism is better than top-down academic research
Small is beautiful: large organizations are inherently fragile, but small structures are well adapted to be nimble and profit from unexpected opportunities.

1.2.4 For small troubles, better trust nature and do nothing than bring untested methods that can have tragic unforeseen consequence
Beware of neomania: don't embrace novelty for the sake of it
Stick to time-tested methods: what has stood the test of time has proved to be robust
Don't sweat the small stuff if it can lead to tragedy: radiation used to cure acne leading to leukemia, thalidomide prescribed to reduce morning sickness leading to malformed babies.

1.2.5 An antidote to the lack of accountability seen in the powerfuls who rule us (government officials, corporate honchos, bankers)
Have them have skin in the game, i.e. to share in the downside of their decisions. Taleb quotes the 3000-year-old+ Hammurabi code, "eye for an eye, teeth for a teeth."

2 Review
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So, what's the score? As with his other books, I found myself reading every page the first 40-50 pages, then turning the pages faster and faster as the neat, amusing prose turns into Fidel Castro-style interminable ramblings, hyperboles and inaccuracies, annoying personal anecdotes, and worst of all, the silly little tales with his imaginary heroes Nero Tulip and Fat Tony (Tulip seems to be some kind of idealized version of Taleb himself). One or two hours for the first third, 40 minutes for the second and 15 minutes for the last.
And I'll spare (or maybe not) the "very technical" appendix 2 with its silly little formula he seems to be so proud of. Thanks for teaching us high-school math about convexity (Jensen inequality as if it were rocket science? Come on!)

The basic point is sound however: we sure all need a bit more antifragility in our lives.
If we only ditched what is unnecessary (going to the doctor for trivial stuff, seeking novelty for the sake of it, buying stuff we don't need), we'd have gone a long way toward being more robust.
But going beyond that is more problematic: Taleb waxed lyrical about the upside of antifragility, but he says nothing about its cost.
And seeing how he came to his idea from the world of options trading, it looks dishonest. In options trading, when you buy and option and get all the good stuff associated with it (unlimited upside, limited downside), the flipside is that it costs money everyday (time decay). Spending all your time buying options is quite a good way to the poorhouse.
As in the financial world, so in the real world, unless you're talking about "free optionality" (the people who don't have skin in the game that Taleb reviles). Maybe being a free agent beats being an office drone because one doesn't need to fear getting fired, but what about the daily stress of needing to go out and find work without any certainty to get it? That's a cost that's a bit too high for probably most people.

In conclusion, this is an imperfect, overlong and often eye-roll-inducing book (as is usual for Taleb), but it presents an intriguing and original argument for the reader to chew on.

Oh, Taleb. You make it so hard to not use vulgar language in my review.

This book, which introduces and describes the concept of antifragility, is pretty revolutionary. Few books have fundamentally changed the way I think about the world, and this is one of them. My understanding of risk and how to address it has shifted dramatically, and the application of the concepts discussed has yielded surprising results.

That being said, the author is as pretentious as they come. Expect a lot of fancy-pants language for no reason other than to show off, and off-topic stories to illustrate just how much better than the rest of mankind Taleb is.

For example, “We gave the appellation ‘antifragile’ to such a package; a neologism was necessary as there is no simple, noncompound word in the Oxford English Dictionary that expresses the point of reverse fragility.”

*facepalm*

It is a frustrating read to say the least. It took me a couple months to slog through this book because of how frequently I wanted to punch Taleb in the teeth, but the content is 100% worth it.

This is a difficult book to review and while I would have liked to give it a 5 star, there is so much in it that I consider opinion and so much that is new and as yet unchallenged that I prefer to wait and see. Taleb has now written 4 books on how he thinks the world works. The one that most know him by is "The Black Swan" which I read a few years back. Like most books that I have read regarding how and why events occur in life, business, science, personal affairs and medicine, I try to see how they agree or disagree with my own life experience. Initial skepticism is my first reaction and it has served me well. Taleb has an overabundance of ego but much of what he says is backed up by good arguments. Despite having MBA and PhD degrees, he classifies himself as an autodidact with most of his really useful information coming from his reading and his life experience. I fully agree with this point of view and consider most of my useful education has come the same way. This is a very long book and a difficult book, but it is well worth the effort to read it in its entirety even when you disagree. His literary style is aggressive and in your face and he doesn't waste much time on other points of view. There will be lots of discussion and argument at an intellectual level before the test of time sorts out the validity of all that he proposes. I will keep this on my reference shelf.