The trick to converting your idea or picture into a jack-o-lantern is understanding the concept of positive and negative space. Think of the portions that are removed or cut-out as being the negative space and what is left behind on the pumpkin as the positive space. More advanced techniques will employ peeling of the orange skin deep enough to create the appearance of a middle value or grey tone somewhere between the bright yellow and dark pumpkin surface.
Simple jack-o-lanterns are usually made up of facial features such as eyes, nose, and mouth, often showing teeth. It's fun to change things up by carving outside of the traditional triangular box by creating other shapes such as stars, circles, ovals, almond shapes, spirals, and zigzags. You can cut out the whites of the eyes and leave an iris, then reuse the cut-out shapes as the ears later. I usually cut out a hole where the ear would be and insert the curved piece into the hole and stabilize using a toothpick. The hole will also highlight the shape of the ear.
When making my cuts I like to make the first cut as a diagonal line thru the shape I've drawn then whittle away a piece at a time until I get the desired shape. It works to cut out smaller triangles, letting them fall inside the pumpkin before carving away a more curvy edge.
There are two schools of thought when cleaning out the inside of a pumpkin. Some will go right to the carving while others will completely remove the innards before making a single cut. I prefer the latter, though I always plan ahead to decide what kind of a lid I want and where it is needing to be placed before scooping out the goop. The multi-face pumpkin (below) was a lot of fun to do and way more fun than the decorative 'Martha Stewart' hole patterns flanking it on either side (see below left lit up).
The minion (below) was carved by peeling the face and cutting away the whites of the eyes and the body leaving the uncarved portion to suggest overalls. Notice the vents that have been cut out of the lid. This is used to let air and heat escape thru the top. Always check on your pumpkins after lighting them to ensure that they aren't being cooked. Vent cutting, candle size, and placement are important design elements and final steps before displaying your creation.
My favorite part is the lighting of the candles. I like to finish carving just before dark and then light them inside first with the lights turned off.
Sometimes I will rotate the lid slightly to allow light to seep out underneath for an added effect. You may also decide to carve more than one side of the pumpkin, creating a lantern.
I like to arrange my pumpkins at different levels. Small tables or front porch steps work well for this. Notice the lid on the Husky pumpkin is the shape of the letter 'H'.
