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.

I admit I was a little wary of this title when I picked it up. It seemed to me to be an over-stretched term, a term that no one deserved to use. However, Taleb argues really empirically, and really well, that his topics are worth defending, and this book is no exception.

I get the feeling that Taleb is a distracted economist, not a philosopher. But, all - in -all, he is way more philosophical than most economists.

So, the book has redeeming virtues. However, it must be appreciated from a highly contemporary, literary, standpoint, which Taleb branded himself. In some ways, it is what Salman Rushdie should be. It's like a non-fiction from Salman Rushdie.

The five stars are for the novelty and aptness of the insights in the book and the clarity with which they were presented. It truly culminates Taleb's three prior (fantastic) books, showing the ineluctable consequences of the truths of each and adding new perspectives. The historical references in support of his thesis are fascinating.

His critique of members of intelligentsia is blistering and accurate. It's not only that they have no clothes, it's that they are doing harm, and most are ethically blind. He mentions many of them by name.

Taleb's blistering will be hard for some to stomach. All should admit, however, that if anyone has the right to be blistering, it is Taleb. No one came close to his prediction of the last financial crisis (well before it came) and the reasons it was coming. And the scathing he took from lesser lights (including highly respected dim bulbs), was as wrong as it was merciless. The blisterings are well deserved (and Taleb makes a good case that not calling out people for serious fraud is unethical). However, be warned: They are harsh and vitriolic.

My concern about what would happen if the policy implications of Taleb's insights (e.g., consultants, professors of most social scientists - especially economists - are misguided charlatans, and large corporation and limited limited liability companies are bad) were to be implemented, the economy would crash deeper and longer than it did last time.

As accurate and insightful as it is, ultimately, the policy implications of the message that the current way economies operate (the far removed relative of the free market system Adam Smith had in mind - and fundamentally unethical and terrible) which has brought humans to an unparalleled level of prosperity should be ditched is a bad answer. [Taleb did not say it should be ditched, but if his criticisms where acted upon, not much of the current way of doing business would not survive.] There is no question a system based on Taleb's principles would be much more rational and less evil. Ultimately, however, Taleb offers little to persuade that such a system would lead to better outcomes. So now what?

I like to think that "Antifragile" is a universal theory of everything ... and it works pretty damn well. Yes, Taleb's got a knack for coming off a little (or a lot) self-absorbed and vengeful, but that makes the tone. As a voracious reader, he also loves to get bogged down in mythology (Greek mythology and Greek names are not my strength) and then just tag this Greek victim to some abstract definition. A little annoying, but doesn't detract from the meat of the book.

The crux of the book is, as you may guess, the "antifragile." Things that become stronger with small amounts of stress. Think the airline industry -- the lost Malaysian flight will only make the whole industry stronger. Fragile things -- glass, the current finance industry, pretty much everything that can't evolve -- Taleb sure has fun ripping into those. It's a bit sarcastic at points but in the best way, and a great read throughout. Makes you think a little more after each new chapter; by the end, you'll see the world a little differently.

Definitely 5 stars, it's a must read.