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CronoDAS comments on Ask and Guess - Less Wrong
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Umeshism: "If nobody ever says no to you, you're not asking for enough."
Converse Umeshism: "If you never miss an opportunity to get something by asking, you're asking too much."
Second-order Umeshism: "If nobody ever says no to you and you never miss an opportunity to get something by asking, you're worrying too much about when to ask for things."
Possible more colorful version: "If you've never missed out on something you needed because you didn't ask, people find you too greedy."
Overlapping Umeshisms: If you don't ask for enough, people will still think you're greedy. If you ask for too much, you'll still neglect to ask for things you could've gotten.