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JGWeissman comments on Misleading the witness - Less Wrong
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I got 3/3 and I would take the chance. My rational is that $60 is almost nothing. I can make that very quickly, and it won't buy much. I won't notice it in my monthly finances. $5000, on the other hand, is actually worth considering. That could change my month significantly (and impact the rest of my year as well). Would you rather have a 100% chance of getting a nickel, or a 0.01% chance of getting a small diamond?
What if we transform the problem, so that you have the opportunity to pay $60 for a 1% chance to gain $5000?
Exactly! This is gambling, isn't it? A small expected loss, with a tiny chance of some huge gain.
If your utility for money really is so disproportionate to the actual dollar value, then you probably ought to take a trip to Las Vegas and lay down a few long-odds bets. You'll almost certainly lose your betting money (but you wouldn't "notice it in [your] monthly finances"), while there's some (small) chance that you get lucky and "change [your] month considerably".
It's not hypothetical! You can do this in the real world! Go to Vegas right now.
(If the plane flight is bothering you, I'm sure we could locate some similar online betting opportunities.)