Chuck Wendig, who must be wise because he gets to write Star Wars books, agrees with me in that October is for outlining. From his meaty post, which you definitely should read if you intend to write a book, be it for NaNoWriMo or not:

Outlining fucking sucks. I fucking hate it. Every time I do it I have to grit my teeth and swig whiskey and engage in a movie montage where I ragefully punch frozen beef and run through snow. And it takes me like, a day or two — three, tops — and then it’s done and suddenly I don’t fucking hate it anymore. It’s probably like building a house and starting with the basement. Building the basement has to be super shit-ass boring. It’s a basement. It’s just a cinderblock prison. It’s a horizontal dirt cave. The house itself above it — oh, that’s fancy. You get to think about where doorways are and which room will be the living room and the dining room and the SEX TARP room. You get to place windows and floors. But the basement: Ugh, fuck the basement. And yet, you need the basement. You need the foundation.