Quote Originally Posted by the image reaper
flip it over, give it a sharp smack on the bottom
Sounds good to me!

As was previously stated... many problems are fixable with enough lubricant and a firm smack.

Seriously though, I actually let my plants get overly DRY before transplanting.
I think your medium has a bit to do with it too. You will figure it out for yourself once you get to the point where you are dealing with nearly-potbound plants.