So, I read a lot. I work in a library, I don’t own a TV, I’ve been in college/grad school for the past 8 years and I just like to read. I pretty much exclusively read non-fiction because I feel like I get a lot more out of a non-fiction book. Every now and then I’ll read something which will make me say: yes, yes, yes. An author will say the things I think about in a clear and concise way. Articulate the things I rage incoherently about and do so in such a way that I can just tell people, read this book. As you probably guessed I had one of those moments not that long ago when I stumbled across a book by Nassim Nicholas Taleb.
To quote Mr. Taleb directly: “‘My major hobby is teasing people who take themselves & the quality of their knowledge too seriously & those who don’t have the guts to sometimes say: I don’t know.…’ (You may not be able to change the world but can at least get some entertainment & make a living out of the epistemic arrogance of the human race).”
The first book I came across by Mr. Taleb was Fooled by Randomness. 
Nassim Taleb is both brilliant and arrogant. You can probably guess why I like him. He loves taking pretentious traders down a notch. His attacks on the inability of society to comprehend and properly use statistics are spot on. Fooled by Randomness uses countless examples from Mr. Taleb’s time on Wall Street to brilliantly illustrate points.
The followup book, The Black Swan: The Impact of the Highly Improbable 
is equally as insightful. I’ll take a passage from the book which tries to explain the basics of the Black Swan:
“What we call here a Black Swan (and capitalize it) is an event with the following three attributes.
First, it is an outlier, as it lies outside the realm of regular expectations, because nothing in the past can convincingly point to its possibility. Second, it carries an extreme impact. Third, in spite of its outlier status, human nature makes us concoct explanations for its occurrence after the fact, making it explainable and predictable.
I stop and summarize the triplet: rarity, extreme impact, and retrospective (though not prospective) predictability.* A small number of Black Swans explain almost everything in our world, from the success of ideas and religions, to the dynamics of historical events, to elements of our own personal lives. Ever since we left the Pleistocene, some ten millennia ago, the effect of these Black Swans has been increasing. It started accelerating during the industrial revolution, as the world started getting more complicated, while ordinary events, the ones we study and discuss and try to predict from reading the newspapers, have become increasingly inconsequential”
The author has a tendency to really pound home points. But his points are really worth driving home and understanding. The outliers, the unpredictability of events, our inability to really look at the long term and how we attempt to use past data to extrapolate future trends, fail, and then turn around and add the new data and believe now are models are perfect.
The role of luck in success, winner-takes-all payoffs and survivorship bias are also focused on in these books. Essentially, only the lucky keep playing a game. The unlucky drop out. So when you look at a successful stock trader it is really difficult to separate whether he is lucky or good. Over the short term really bad dumb people will still make it to the top because of pure chance while many really smart people will be forced out because of a string of bad luck. Because people so badly misunderstand the odds, they will take large risks and be wiped out by outliers in the long term. Eventually being dumb catches up to you. An example the author uses in Fooled by Randomness is playing Russian Roulette. If someone is offered a lot of money to play the game and they win they will look like they’re successful. However on a long enough time line, if they keep playing the game, they will lose badly. It is possible to have someone who’s played numerous times survive and tell you he’s blessed, but only the people who survive are around to talk about it.
Nassim Taleb also points out that what we don’t know is just as important as what we do. The politician who mandates locks on September 10, 2001 and prevents a terrorist attack is never known. Instead he is lambasted for spending money on useless programs. Human beings are much better at reacting after the fact to the threats of the past. The events that don’t happen are every bit as important as those that do, but they are harder for most people to grasp.
In any event, I’m just going stream of consciousness here talking about these books. I highly recommend them. Luck plays so much more of a role in success than anyone is ever willing to accept. In the short term it is impossible to separate the good from the lucky. Both of these books are must reads, 
(well those are asterisks but imagine stars).