You'll want to use a bigger bowl than the one shown here unless you're amazingly good at not making a mess (note: I am not). This does give you an idea of the amount of dough you're working with though. It's not a ton, but it will make a surprising number of cookies. And, on a related note, I would gladly trade ALL of the cookies this dough made for any sort of natural light in my sad little kitchen (please excuse our hand-me-down couch in the background...)
I find that this works best when you're using the press on a cool surface, so I rotated my 3 baking mats across 2 cookie pans so that I could always load up the cool one with dough. Don't sweat it if they aren't completely perfect (they will spread a tiny bit in the oven), but if they keep coming out lopsided you may want to check the dough in the barrel to make sure it isn't loaded unevenly with more dough on one side. The exact number of cookies you'll make depends on what shape you're using (the original recipe says 40-60), but the little heart shape made about 100 cookies for me, so you'll have lots of chances to practice.
These cookies are perfect for decorating. I brushed a light layer of glaze on mine and then my toddler went to town with the sprinkles. He may not have mastered the art of sprinkle distribution yet, but they're adorable little cookies either way. Or you can frost them or even pipe on icing if you're extra fancy. Have fun with it! Store leftovers in an airtight container.
Pressed Sugar Cookies
Source: Williams Sonoma Yield: ~5 dozen or more (depending on shape)
1 cup of unsalted butter (room temperature)
1 cup of white sugar
2-1/2 tsp of vanilla extract
1/2 tsp of salt (I used kosher salt)
2-1/2 cups of all purpose flour
Cream together butter and sugar until smooth and creamy looking (about 3 minutes). Add in the egg, vanilla, and salt and mix until well-incorporated. Stir in the flour until just combined.
Load your cookie press and use according to manufacturer instructions. Place the cookies about 1" apart on a cookie sheet lined with a baking mat or parchment paper. Bake at 375 ℉ for 7-10 minutes until golden around the edges. Cool completely on a cooling rack. Decorate if desired. Store leftovers in an airtight container.