This is the type of book which truly requires some introspection and reflection on your part. You cannot take this at face value and read it truly as a work of nonfiction. While you are reading, you must imagine how antifragility and all its domains work in your particular life and lifestyle. As Taleb relates at the end of his book, look around you – what is fragile and antifragile? What likes volatility; what dislikes uncertainty? And do you yourself like variation and disorder? That means you are truly alive.

I haven't read many reviews for this book. However, I am sure that there will be a few who will complain about the grammar and syntax Taleb uses when writing the book. While disconcerting at times, you have to look past it. I wouldn't say this about most any author. In a weird sort of way, the variation in grammar and syntax truly makes you more of an antifragile reader! You are more inclined to go back and re-read many of the passages; you are encouraged to take notes. And, like most any book which is worth it's salt, it deserves a second and a third reading to truly grasp the full meaning of what the author is trying to convey.

1 Summary
----------
1.1 Introduction
==========
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:
=========================

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
---------
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.

A true gem that reflects the flaws of modern thinking, forcing the reader to view instead the ancient vision of wisdom that comes from via negativa, a method of reducing uncertainty by removing that which is fake, flawed or fluff.

Breathtaking in its delivery, this book cannot be digested in a single session and must be re-read time and again to assimilate all its valuable nuggets of truth.

First of all, read the book. Whether you agree with Taleb or not, he has here a serious critique of serious things.
Be prepared for a bit of a slog - the 5 stars is for the significance of his ideas, not his literary talent. Imagine striking up a conversation at an airport bar with a very smart, slightly drunk aristocrat who grew up in a war-torn Lebanon, returning from a conference full of people he considers spoiled and irresponsible Westerners. Press record. That's how the book reads.
And that image in my head helped me enjoy the book. Taleb is utterly pissed off by an economic and political ruling class that he sees as oblivious to the fragility of the systems they are creating, and so to the catastrophes they are setting us all up for. The book is less a reasoned arguments than an impassioned rallying cry for people to stop drinking the cool-aid of economic and social quick fixes, attempts to overly-isolate people from the natural vicissitudes of life as well as from the consequences of their own actions. We learn and grow from the stressors of life ( up to a point), and this is how we become " antifragile".
What I find especially refreshing is that this thesis really doesn't come across as being either liberal or conservative - Taleb isn't operating along that axis. He is arguing for us to re-value simplicity in systems, learning from and trusting our experience, taking responsibility for our actions, and being "heroic" in the classical sense of working for (and perhaps sacrificing oneself for) the good of others. It is a deeply traditional view, balancing the individual with society and with nature.
Now be warned, this all comes at you in a somewhat inebriated tirade that bounces all over the map, from the mouths of Brooklyn bankers and (occasionally untranslated) classical writers, and illuminated by episodes from Taleb's globe-trotting life that can sometimes get a bit stale. But that's exactly how you have to hear it - the style is intentionally over-the-top and excessive, the "I'm mad as hell and I'm not going to take it anymore" of a former economic insider. But he has the saving graces of a sense of humor and a deep historical sense, that commands your respect more fully than just another pissed-off Fox New pr CNBC commentator with an axe to grind.