I'm here today to say that the school-style outline and the writer's outline are often very different things.
I outline fanatically. I always have an outline of some sort, even for a long book. Outlines help me because I often write puzzle-like stories where the required outcome is known, but I don't know how to get there. Once I figure out intermediate events I have to make sure they all fit - relevantly and somewhat neatly - into the space between point A and point B. However, my outlines don't look like
I. Blah Blah
1. blah blah
Which is to say that I don't organize my thoughts into concepts and sub-concepts. That's a pretty natural organization for a persuasive paper, where you have to build and support a particular argument. For a story it's not necessarily of any help at all.
I've tried two main strategies for outlining and I believe most firmly in something I'd call "organic outlining." This is opposed in my mind to chronological outlining.
In chronological outlining, you take a look at the book's calendar of events and you write down what logistically has to happen at what time, and then use that as a scaffold for placing plot- and character-related events. Whenever I do chronological outlining, I find I end up with something that has lots of events in it, but is lacking in the larger dynamics the story needs. Things don't converge to form the big highs and lows that make a story exciting. I also end up with big gaps that say "something has to happen here," and I often can't figure out what to put in those gaps, which makes the story feel both long (too many words, yikes!) and diluted.
In sequence outlining, you start with events first and worry about calendar later. Often I start with a list of questions or suggestions that come directly from my sense of the demands of the story. Such as:
- Someone has to be the target of an assassination attempt.
- Sorn has to be part of some nefarious plan to influence the voting.
- Tagret has to learn that Selemei wants to expose his mother to the public eye.
- Tagret has to do something bad in order to save his girl from the candidate Innis.
I try to find as many required relative sequences as possible, and then I see how closely I can place them to one another. The other thing I do is I try to take related events, which happen to different characters, and pile them up into the same time period so that the story intensity will go way up. I'll think to myself, "This is basically Tagret's point of greatest despair. How can I make it so that his ally also experiences despair at this point, and his enemy elation, so that it all lines up and the dynamics are stronger?" Or, "What can I line up with this so it provides the climax?"
Once I have those relative chronologies in place, then I worry about schedules. Schedules provide the scaffold only after I have all of the relative pieces in place. Nobody will try to assassinate any candidates except between their initial nomination and the voting round where it gets down to two candidates, because if one of two gets killed they'll have to start over. Tagret won't do a bad thing unless he absolutely has to, which means it's going to happen after he's determined candidate Innis can't be ruled out any other way, and before Innis gets enough power to act on the girl directly. This chronologically confines the timing of that particular event.
What I end up with (as will you, if you try this) is clumps of densely packed event sequences (a bt like Cheerios in a bowl!). Gluing those sequences together in a logical way can be tricky, but if I can do it, that gets me to an initial sense of how the story flow has to work - with the added advantage that I don't feel like a slave to the calendar, and I don't feel like the story is either wordy or diluted.
In a story as complex as the one I'm working with, this technique is proving to be extremely helpful. Indeed, the more complex you want your story to be, the more outlining can make the difference between getting through it and petering out in the middle.
It's something to think about.