Print out the recipe cards for all your cookie recipes and read them through at least once before you go shopping. Plan out the order you need to make each batch of cookies so they have enough time to cool completely and for any decorations to set. Take inventory of what you have on hand both for ingredients and supplies, and separate them out. This includes any packaging for the actual boxes. Get an idea of what else you want in your box besides cookies. Things like candy, roasted nuts, fudge, and cute little holiday knickknacks or ornaments, etc.