I used to be able to do this - take a double espresso, wait an hour, and sleep through the night. But as I've gone through my 40's, insomnia's been a problem.

Further, Pollan's interview suggested that even if I could sleep, caffeine was interfering with "deep wave sleep" - so I gave it a shot. I consider myself lucky that none of the headaches or [extra] irritability kicked in, so there's that.