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Keep it charging until you need to take it with you in the morning; the Droid's meter is also less than accurate half the time, so unless it's actually dead before it should, I wouldn't put much faith in the levels.
That doesn't sound right/normal to me at all. I know some people have talked about losing some power while the phone is off, but 40%? I don't think that should be happening.... assuming you aren't sleeping/leaving it off for several days...