I have yet to be able to write an outline, as I understand the concept.
The first hurdle I always trip and faceplant over are the changes. I try and try to make outlines, but by the time I’ve written a few dozen pages, it’s occurred to me that the best friend character will betray the hero. Oh, and I’ve decided it should be winter instead of summer for added complications, but that requires I plunge deeper into the hero’s biography to decide when and if he’s ever experienced snow and ice…and, when I come up for air, the outline doesn’t work any more.
Essentially, my attempts at outlining a novel match that old adage that “the battle plan never survives contact with the enemy.”
The other aspect that makes outlining a great and convoluted activity is digression. I try to keep “arm’s length” as I outline, just tapping the major points to guide my route. Inevitably, I reach a moment, say, this is where the hero escapes imprisonment. And…suddenly, I get a cool flash of a scene on how he busts loose, with some snappy dialogue or description. Before I know it, an hour has gone by, I’ve all but written two complete pages of the book and, oh look, my original outline doesn't work any more.
The complicated digression can’t be ignored. I can’t take a chance that’ll I remember some sparkling line or character notion for when I’m done writing the outline. Very often, in an early attempt an outline, I have so many detailed sparkling ideas that it becomes far too similar to juggling torches. I'm sweating not to lose track of any of them.
The best I can do with an outline is to pick a direction. I start hiking West without any guides, drawing a map of the roads and towns as I encounter them. Dithering at forks, wondering which is the better choice. The essential thing is not being afraid to backtrack. “That was the wrong fork. Back to the original choice. Everything I’ve written down is tossed, maybe to use another day for another trip.” Just keep heading West.
But outlines sound so useful!
How are they for you?