Here's something that'll either come as a shocker or Jack's Complete Lack Of Surprise: I've already started outlining my next novel. No title yet — I had a title, a leftover from a previous project with some distantly similar DNA, but it no longer fit the flavor of the new project, and so out it went. But I have an idea, a story, and a cast. And in the process of jiggering all that together to see how it could fit, I ran once again into an old issue: the way a story doesn't look remotely the same in the trenches as it does at the 30,000 foot level.
For the longest time I wasn't in the habit of outlining or planning my work. I got away with that sort of "pantsing" (as some folks call it) because the stories I created were small enough and straightforward enough that I could fit the whole thing in my head. Or so I believed, anyway.
Later, as my ambitions ramped up, I realized that even a relatively short work of, say, 125,000 words needed detailed planning to really achieve proper airspeed. A longer work — like the 210,000 of Always Outnumbered, Never Outgunned or the (gulp) 350,000 of Flight Of The Vajra — would be just so much flotsam on the page without a detailed top-down plan.
But even those plans had to yield in the writing process to the insight in the moment. When you plan a story at a high level, the scenes exist mainly to move everyone from one point to the next. When you actually write those scenes, and they come to exist in the form of people talking to each other, bouncing off each other, reacting to each other (and to themselves), they yield up insights into the story, both in the big details and the small, that you simply didn't have access to before.
Here's a metaphor I've pressed into the service of this discussion before: the road trip. You know that you and your friends and your car are gonna start in New York and eventually end up in Chicago. You know that you're gonna take Route 80 for starters and end up on Route 90; you know you're gonna stop at least once to sleep. But you don't know what the bed's going to be like in the motel; you don't know what you're going to end up talking about at the Waffle House when you stop for lunch.
Those lifeblood-of-the-moment details shape things as much as your high-level outline did. That Waffle House talk might well turn into an argument that drapes both you and your carmates in a sullen silence the rest of the way, turning a roadtrip adventure into an isolation-chamber bummer. Or it might instead flip an aimless drive where you were Just Gonna Go West into something riven with meaning and purpose.
The thing I keep running into with each of these outlines is how you have to leave room for how those in-the-thick-of-writing-the-scene insights can drive the story. Sometimes I think of an example of such a thing to address and I add it to the outline ahead of time, but the vaaast majority of those "Oh! This is going to come to her mind!" insights happen when I'm between one sentence and the next of the actual draft. Not at the outline or summary level.
Goading myself into trying to have more of those insights at the higher levels doesn't work. If they happen, fine; I note 'em down and make use of 'em. But what matters more is allowing the door between the outline and the actual draft to swing in both directions.
New York City
Other Lives Of The Mind