First, I make a basic list of what I want to bake. Usually, it's about 20 different cookies, of as many different shapes (round, bar, tassies, crescents, etc.) and flavors (molasses, chocolate, mint, lemon, coconut, cinnamon, etc.) as I can muster.

I do not do rolled and cut cookies. I can't take it. Too much process. Then I start baking and freezing, but there's an order to it. The first to get done are the simplest, as they last longest in the freezer. Molasses crinkles, snickerdoodles, simple bars. Anything that's really just butter, sugar, and flavor. Next up are more complicated shapes, but still simple doughs. Macadamia crescents, rugalach, things like that.

The last to get done are usually the hardest, and anything that gets frosted, as the frostings usually don't do too well with the freezing and defrosting. Drop cookies get packed in large ziploc bags and dumped in the freezer unceremoniously. If there are a lot in the batch, I try to line them up and make rows, kind of like cylinders. That way, I can stack the bags more easily. More delicate bits and bar cookies get packaged in large rectangular plastic containers with waxed paper between the layers.

Everything, everything, gets labeled with masking tape and Sharpie, both of which have permanent homes in my top kitchen drawer. Finally, when the time comes, I take out whatever stack of plates I've bought that year, a large roll of mylar, some curling ribbon (although I may go to cloth ribbon this year), and my hand-scrawled calendar/list. I bring up the bags and boxes and assemble a few days' worth of platters at a time. It's best to be at the end of the list. I'm much more parsimonious in the beginng. And that's it.

Just start in October, and it's easy!  ~Digital Hausfrau