Regarding the chess analogies: Yeah, this is exactly why I suck at chess. I can do a decent job of not losing by making clever play after clever play, but I lack the ability to see the game in such a way that I am able to create a plan for winning. So I end up turtling because I don't know what else to do.
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To continue the thought, if a good chess players is losing, he will often lash out at his opponent's king and sacrifice additional pieces in order to complicate matters. Doing so may offer him a small chance of getting back into the game. This is potentally better than simply defending, which gives him almost no chance to win or draw if the winning technique is clear. Most of the time, this just means a quicker loss, but it's the difference between a 10% chance of avoiding loss and a 1% chance.
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This is going a bit into a related concept of all games: the favorite prefers "usual" circumstances and low-variance, while the underdog prefers "unusual" circumstances and high-variance.
Interesting Magic example:
Who's the Beatdown? That article probably doesn't make sense to people who don't play that particular game, but suffice it to say that the article can be summed up as saying, "Figure out whether your deck favors the long game, then from that decide whether to try to make the game go long (i.e. You're the favorite so reduce variance by giving your deck time to press its inherent advantages) or make the game go short (i.e. you're the underdog in the long run so make higher-volatility plays in hopes of cutting your opponent off before he is able to press the strength of his deck)."
Street Fighter example:
"Low Strong" - David Sirlin doesn't know how to outplay his opponent, so he adopts a tactic so weird that just maybe his opponent won't figure out how to counter it.
EDIT: Of course the poker example would be David Sklansky's "The System," designed to give the "underdog" (i.e. clueless player) as much variance as possible against good players.