Right over here (in the comments to the Livejournal version of this blog), Obadiah and I got to talking about something I’d been meaning to riff on a little bit, so here’s an opportunity.

The question is about the value and importance of outlining (or at least advance planning) when writing fiction.

Those in favor of outlining feel it’s too easy (without an outline) to meander around aimlessly, and follow digressions that seem appealing to the writer in some way. One minute you’re writing a story about a character who was headed somewhere, and eventually you realize the guy has been pursuing something tangential for 1,200 words. Some of the words may have been fun to right, but in the best case you’ll cut them (thus wasting a lot of work) and in the worst case you’ll leave them in there because you love them (thus putting the reader to sleep for those 3-4 pages).

Those against, also known as “freestylers,” argue that the fun in the creative process derives from exploration, and if you’re following a pre-Mapquested route, it becomes boring and it’s hard to get motivated to keep going. Also, some argue their subconscious will come up with interesting new twists they might never have discovered had they remained bound to an outline.

I used to be a freestyler, and now I’m an outliner. As I’ve mentioned numerous times before in this blog, my early writing involved too much wank. That is, I spent too much of my writing time just doing what felt good — fun, banter-y dialogue, cool people, inventive locales. The problem is, the stories usually amounted to little more than mood pieces. They had no cumulative impact.

Writers who can sit down and freestyle, who intuitively spin compelling plots, and whose stories end up in a place that makes perfect sense once you look back at the setup and the character in the beginning, are lucky writers indeed. I don’t doubt such creatures exist, but I ain’t them.

In my opinion, the trick (which I’m still trying to perfect myself) is to outline and plan in advance just enough to keep the writer on track. I want to give myself just enough of a hint of a destination off on the horizon that I can make my way, not wander too far off course, and yet “freestyle” a bit en route. I love the little details of discovery a writer makes when they come to a “what next?” moment in the story, when the subconscious scrambles to fill in a blank and comes up with something much more compelling, on the fly, than anything that could’ve been outlined in advance of wading into the scene.

Another way of putting it would be, you should know some important things about your characters before you start, have a general idea of where the plot will end up, then let yourself freestyle from point to point until you get to that ending, and be as inventive and crazy as you can along the way. Pack in as many outside-the-lines details as you can, like a jazz improviser who can go wild even though he knows he has to join back up with the rest of the group after the solo.

Keep it fun, but don’t waste time and effort going too far down blind alleys. Remember the need to make sense of it all by the end.

These are the tricks I’m working toward.