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loqi comments on Coffee: When it helps, when it hurts - Less Wrong
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My parents drink coffee before going to bed. I've always assumed that it was because withdrawal during the night would be worse than the "stay awake" effect, but maybe there's another explanation.
I've found that caffeinated sleep tends to be fairly satisfying and invigorating. The trick (for me, anyway) is to fall asleep before full onset. 100mg caffeine pills do the job nicely, assuming I'm sleepy enough to nod off in time. The penalty for failure is pretty stiff though - I've lost half a night's sleep that way.