It took me a while to finish carving this thing..
but one side is, obviously, Bec’s head, like the one our dear Wayward Vagabond carried around…
and the other side is the Candy Corn Vampire from Problem Sleuth.

Since I draw the left side of things better than the right, I eyed the image I was going after for each side
Then drew the left half in pencil on a piece of paper folded in half.
Like this

And from there (this is after I finished the whole thing, but you get the gist) I folded the piece of paper on the same fold, but where the pencil met the other side of the paper, and I scratched over it, transferring a shadow of the lead on the other side to create the rest of my stencil.

From there, we proceeded with the usual messy gutting of the pumpkin, and I taped the stencils to the outside, using the tools of a basic pumpkin carving kit to transfer the outline of each design to either side of the pumpkin. 

For the Candy Corn Vampire, it was easy enough to pop out the shapes and such, the Bec head was a bit more time consuming. 

For that, I used an exacto knife to trace the outline, and from there, I guesstimated a constant distance outward from the stencil to make the line. I was able to, with the help of the drilling hole from the carving kit (to get the bit of pumpkin out of the way so you could see the outline, but not puncture through to the inside) to clear the way for the shape. 
and once that was done, you add the customary lit candle and enjoy!