Matt_Simpson comments on "Stuck In The Middle With Bruce" - Less Wrong
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Slightly off topic, but I doubt Magic is especially good for teaching rationality compared to other board games. There are a lot of games besides Magic and Poker that are about decision-making under uncertainty, although most aren't nearly as popular. One way to measure ones progress in rationality might be to play a wide variety of these games and keep track of one's win/loss record.
Magic is the Hardest Game Ever, which on the one hand suggests that it contains a lot of angles for one to apply rationality and gain an advantage, but on the other hand suggests that the advantages of rationality may be drowned out by the effect of raw brains and the ability to systematize.
The thing about magic which sets it apart in terms of rationality training is that you can't go at it with theory alone. It takes hours of experimentation to get your deck built right, testing a variety of maindeck* and sideboard* permutations until you find one which is optimal against the current metagame**. As soon as the metagame changes, it's back to testing. Since magic is never "solved," at least not permanently, it forces you to become good at coming up with guesses and testing them, at least within this specific domain.
terms for the bewildered:
*maindeck and sideboard: your deck consists of at least 60 cards in the maindeck and exactly 15 in the sideboard. During a match (at least 3 games, sometimes 5) after the first and second games, you can trade cards from your maindeck for cards in your sideboard.
**metagame: the game outside the game, in other words, the different decks you are likely to face. In any given format, there are usually a handful of strong decks which dominate the field in some variation or another. As such, you end up playing against them more often then other decks.