My pumpkin clown and his friends.
Step 1: Tools and Work Area
As you can see from the picture I use a lot of tools. Clay sculpting tools along with x-acto knife, steak knife and pumpkin carving kit. I also place the pumpkin in a box to hold it steady. The hardest part is knowing once you cut it off, there is no going back.
Step 2: Have Fun
The trick is not cutting too deep unless you want a whole like the eyes. some people cut open the top and insert a light so they can see how thin the wall is. I draw the face I want on the pumpkin so I get the placement of the features right.