I don't think the "reward feeling" for losing at a video game is the same thing as what our "Inner Bruce" goes after. They may be related, I don't know. But losing as a video game can be fun, more than losing in real life. Fun in the same way the rest of the game is fun, it's not a special kind of fun.
I get that a lot in Spelunky, where you often make a small mistake and splat blood flies and you have to start over again. but it can be fun.
That's an important distinction between hardcore and casual games. Some players don't mind getting killed horribly and having to start over again - it's what they expect. But other players will be discouraged and feel bad if the game tells them that they suck. That's why most casual games are very nice to the player, and often you just can't lose at all. A decade or two ago, the game industry was mostly focused on hardcore players; recently they have found out you can make a lot of money with casual games (targetting "middle aged women"), but you have to make the games differently.
Maybe it's because hardcore players expect to die over and over in video games, and they know viscerally that it doesn't matter at all, so when they lose, they don't have any negative associations. On the other hand, new players haven't made that dissociation, and feel bad about losing.
I never thought much about the relationship between "self-sabotaging to lose in real life" and "enjoying losing in video games", it's interesting ...
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?