Speaking from my perspective...

In a studio/live situation (and when your drum is in a bad place) it takes a lot of concentration to hear for the music.
This could be partially due to phase cancellation and excess bass build-up in the corners or areas close to the wall.
In such situation you gotta use your feel and draw upon your (hopefully) vast pool of experience.

So... it's equal amounts of practise (as mentioned by so many people above) and experience in not-so-optimal situations.

LOL whole topic went out-of-subject.