This weekend I filled mostly with pounding out the third end-to-end outline for Always Outnumbered, Never Outgunned. And this time around, I cheated.
(Voices off: "It isn't cheating if it works!")
When you find yourself in a hole, stop digging. When you're stuck in a mud puddle, on ice, or a pile of wet leaves, stop spinning your tires. After two and a half outline drafts, I was stuck'r than ev'r, like someone trying to solve a jigsaw puzzle by throwing the pieces into a blender.
This time around, I drafted the outline in as high-level and general a way as possible. If I already knew what a basic plot beat was supposed to be, I didn't get bogged down in copy-pasting or rewriting the existing description of it; I just made a note to the effect of what was supposed to happen, and moved on. The point was to look down on the whole thing from as far up above as possible, something I'd (deliberately?) neglected until then.
Why did I not do this sooner? Good question. I suspect it has to do with my sense that outlining a book serves two functions — to establish the storyline, and to figure out the significance of each point in the plot as it pertains to each of the people it's happening to. E.g., "Alice went to Bob and talked about Carol" is the first half of that, while "Bob realized that Alice was trying to prejudice him against him against Carol, because she's done this sort of thing before" is the second half.
I think I was also afraid to step too far back, a fear that is best explained as being a fear of losing sight of the plot. But I knew what the plot was; I'd been rehearsing some form of it over and over in my head for months on end. I had to trust myself to know that I could sit down and put together a high-level outline that wouldn't meander or leave behind key points.
For a long time, I never outlined my books. I had an idea of where things had to end up, and I followed whatever path seemed best to get there. Over time I had to abandon this strategy — not just because the books were getting longer (well, Flight of the Vajra was something of a singular event in that respect; three years of my life!), but because my ambitions and consciousness about the way I approached my work had expanded. I had to be more meticulous, and the only way to be more meticulous was to Write It All Down. A sign of growing up, I guess.