i have been sucessful,just this week i did one, drilling ceramics. start with the smallest bit that you have and go through the top, increase the size gradually. it usually pops out a larger piece at the bottom so if the material is thin(less than a 1/4 inch) it may not work.
nice pot by the way,you may want to put bigger stones under one side to stop the roots from getting stuck in there cuz leatherback makes a good point