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When doing a full carving don't try cutting through the walls of the pumpkin right away. You can carve the design first with a more precise hobby knife (X-Acto) before removing the skin and then finally using a larger serrated knife to cut out the pieces. This helps keep your design looking cleaner because the rough knife never has to cut through the skin, only the flesh.
Pumpkin carving tip?
If you think your carving is going to take a while (more than one day) don't cut the pumpkin open and clean it out right away. You can do a lot of the major carving before you'll need to test it with a light and the pumpkin will last longer. The downside is that the pumpkin will be heavier and the stem might get in the way (which you do not want to damage).
Carving
Out of context, talking about pumpkin carving can sound rather disturbing.
Cover work area in plastic. Remove the guts. Cutting will make it "bleed". Cut, dig, remove pieces of skin. Scrape the flesh down. Don't worry about getting messy. Then later on when it starts to smell just throw it in the woods.
Pumpkin carving tip #7
Don't worry about getting bits of pumpkin gunk on your light bulb, burning pumpkin smells delicious.
Pumpkin carving tip #6
The curvature of the pumpkin can make it difficult to apply a flat stencil so try to cut away as much of the unused area as possible. This includes cutting out the center of areas that won't be carved, not just around the edges. Cut the stencil into different pieces and apply them separately if you still can't get the stencil to lay flat. However this may change the look of the design a bit. Pieces may be closer than they look on the original stencil or may even overlap each other. You can also warp the stencil itself. Something like the "Inflate" (negative percent) effect in Illustrator or the "Pinch" effect in Photoshop can help reduce the
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This is actually a tip I could use haha 
I do this when shaving so that my tools have less chance of running over the edge of the area I need to shave. (I can't match your eerily good shaving techniques, however!)
I do this when shaving so that my tools have less chance of running over the edge of the area I need to shave. (I can't match your eerily good shaving techniques, however!)