National Lampoon’s Outlining Vacation

I’ve got myself a pretty healthy self-esteem streak, but I’ve never been much for giving advice. I prefer to share stories about what’s worked for me, share stories about cool things I’ve seen other people do, and let the reader take it from there. So in that context, let’s talk about story preparation. Some of you might call it outlining but I think that’s way to official a term for what we’re dealing in and loses some of the spirit of what it’s true purpose is.

I’ve read some interesting posts in the last couple weeks from Laura Lippman and Stephen Blackmoore who both have some interesting ways of doing things. Laura is the most like me in that she outlines after the fact. I’ve been attempting novels since I was in high school and I’ve tried various versions of outlining before the fact and never had any success mostly because my imagination is very “in the moment” and only provides me with cool stuff when it has to.

I’ve heard people describe outlining and plotting in terms of road trips before and in this case I think it matches my own preferences. I can’t plan a trip out in detail before hand because I won’t really know all of the options until I get to where I’m going. All of the best experiences I’ve had on road trips have been little side trips that I could have never planned. So what happens is I pick a general direction, drive for a while, and when I’ve driven long enough to have options I start looking around to see what’s cool and where I should go next. This is how I outline my books.

I think about the book quite a bit before I start and usually have some sketchy idea of where I’m going and usually a solid idea for how I’m going to start. Once I write 200 pages or so and see what kinds of characters and situations I have to work with, then I’ll start doing some planning to get me to the end. With the book I’m working on right now that’s exactly what has happened. I was stuck about 20k words in, made a New Year’s Resolution to get off my ass and write like the pulp writer I want to be and churned out 40k more in a little over a month. Then it was time to start thinking about the ending.

This is a caper-esque story so the ending involves a bit of choreography and I want to make sure it has the biggest bang for it’s buck because I hate reading and writing those huge set-piece climaxes so if it’s going to be small scale it has to be executed perfectly with a good emotional core. So for the first time in five novels, I slowed down and stopped generating new pages so I could think about what I wanted to do.

I chipped away at it and tried a few things until I figured out what I wanted to do. By this time I also knew there were things in the first part of the book that were going to need to be cleaned up and smoothed out to make sense with where I was going and instead of waiting until I finished the book to go back and do that work, I’ve started doing it now. This way I can make sure the foundation is nice and solid before I push it to the end. The side benefit has been finding little character clues and plot points I’d unwittingly planted earlier in the book that make perfect pieces to spin the last chunk of the book toward a satisfying conclusion.

Man, now I want to go on a road trip.