I've always been a really big fan of outlining and structured writing, particularly for long form stuff. I suspect anyone who has ever argued with me about writing, or written in collaboration with me is probably nodding in understanding (or yelling "that's an understatement" and flipping the bird to the monitor). This probably explains my interest in things like LaTeX and Markdown, and the reason that wiki's have been frustrating for me, and the reason that I can pull my distractable attention span together enough to be able write long form projects. I mean, I even managed that as a teenager, which continues to impress me at least.

I like outlining because it allows me the opportunity to separate conceptual activity from implementation activity to a great extent. I can write an outline, figure out what's going to happen, what I need to tell, where I'm headed in an argument/plot, and then when I go to write, I don't have to figure out really core/low-level aspects of the story/essay as I'm trying to figure out how to move the characters around. Writing diologue and "people," in their world is a very different task from, figuring out the fate of that world, and a character's thoroughly. Or an illustrative motif in an essay. Outlining helps me to isolate and deal with these problems in different contexts, as well as provide continuity between writing sessions for particularly long work.

One of the biggest challenges (and successes) of the project that I'm working on at the moment was "making enough happen" in the story. I got an outline, that told a story that was too big for a short story, and yet didn't provide the "body," and rich environment that makes novels so enjoyable. So I wrote this draft of an outline, and then I spent the better part of a week thinking about "ok, now what can I add?" and "If I add this B-plot how will it triangulate and complicate the lives of the other characters." And I kept adding scenes, details, and turns that would make life hell for the characters.

In previous attempts (to varying degree's) I've said something like "I need to tell a story about "Telepaths who immigrating to Mars," and then I write the outline, and as I wrote the stories there was never enough there, characters distraught-ness was out of phase with what was happening (my criticism, other people don't seem to have this response, as much). So this time--so far--I've been really pleased with the way that the "tighter, more packed" outline has really helped the way that the writing of the story has progressed. You'll be able to judge for yourself in time, but it's sort of cool. What follows are a collection of the lesson's learned from this outlining process:

  • Write a full outline, before you go back and add stuff. The initial concept, and layout of the story is valuable, even if you should probably be resistant to just "going with it."
  • Even if you feel the "burring impulse of creation," outline anyway. For novels and long works, sustaining that impulse over many months is difficult. There are lots of different ways to outline (free writing, various levels of structured lists, note cards, etc.) something is bound to suit your style.
  • While conventional wisdom holds that you shouldn't edit works in process (as this breaks flow and rhythm), once you have an outline completed. Edit a lot. Not for polish, but imagine the story, and play around with the order of chapters/key scenes. Push as much of the action into the shortest amount of space you can. See what you can do to pump up the action in other parts of the book.
  • Add stuff. Add a lot of stuff. You'll be able cut later, tighten things up later, having material of "things that could happen," and having gone through the experience of playing with your story will help you, even if you say "nah, I don't want to write that scene," when you're writing, or you feel that a scene you had in your outline won't really work anymore. Cutting is easier later than adding more material
  • Three is a really great number for stories. We're all used to "good guy" versus "bad guy" plot dynamics, and the "bi-polar" approach to story telling, while familiar becomes boring really quick. Adding "thirds" to stories makes things much more complex, and much more dynamic. Third plotlines, third characters, third-major settings, and so forth. Or at least play with the idea.

Onward and Upward!