I was somewhat disappointed to find a lack of Magic: the Gathering players on LessWrong when I asked about it in the off-topic thread. You see, competitive Magic is one of the best, most demanding rationality battlefields that I know about. Furthermore, Magic is discussed extensively on the Internet, and many articles in which people try to explain how to become a better Magic player are, essentially, describing how to become more rational: how to better learn from experience, make judgments from noisy data, and (yes) overcome biases that interfere with one's ability to make better decisions.
Because people here don't play Magic, I can't simply link to those articles and say, "Here. Go read." I have to put everything into context, because Magic jargon has become its own language, distinct from English. Think I'm kidding? I was able to follow match coverage written in French using nothing but my knowledge of Magic-ese and what I remembered from my high school Spanish classes. Instead of simply linking, in order to give you the full effect, I'd have to undertake a project equivalent to translating a work in a foreign language.
So it is with great trepidation that I give you, untranslated, one of the "classics" of Magic literature.
Stuck In The Middle With Bruce by John F. Rizzo.
Now, John "Friggin'" Rizzo isn't one of the great Magic players. Far from it. He is, however, one of the great Magic writers, to the extent that the adjective "great" can be applied to someone who writes about Magic. His bizarre stream-of-consciousness writing style, personal stories, and strongly held opinions have made him a legend in the Magic community. "Stuck in the Middle with Bruce" is his most famous work, as incomprehensible as it may be to those who don't speak our language (and even to those that do).
So, why am I choosing to direct you to this particular piece of writing? Well, although Rizzo doesn't know much about winning, he knows an awful lot about what causes people to lose, and that's the topic of this particular piece - people's need to lose.
Does Bruce whisper into your ear, too?
You made me think: Is there some possible evolutionary advantage of having a Bruce? Or more precisely, is there an instinct that would do something useful 100000 years ago, which makes us self-sabotage today?
Perhaps there is an instinct "not to appear much more successful than the rest of your tribe". Because there is a competition inside your tribe. Success is good, but it also brings enemies, any you may not be ready to face them. So unless you are ready to fight them all and become a leader of your tribe, it is better to sabotage yourself sometimes.
This instinct was fine-tuned to an ancient environment, and is not so necessary today (unless there is a Khmer Rouge revolution around the corner). But if you are smarter that the average, sometimes the instinct may kick in after an unconscious decision that you are already "dangerously successful".
More precisely, the instinct is somehow valid today too (success still brings you enemies), but it sometimes mistakenly assigns too much danger to relatively small success. Maybe it is related to the size and degree of specialization in our "tribe" -- in ancient world, when you were in top 1% at something, you were probably the best in your tribe; nowadays just studying something or doing some sport or game easily puts in top 1% of population with regard to that specific thing.