The negative space of omitted details is where the reader is drawn into the work and individualizes it. Every detail omitted ceases to be dictated by the author, and an author trying to tell you a character's shoe size when it isn't in his book, is no less authoritative or correct than any random person telling you that detail. In fact, that would be intrusive upon the readers. When someone else reads your work, it's no longer yours.
In each stage -- outlining, first draft, revision, editing, and polishing -- the selection of details plays a different role.
The Outline Stage
In the outlining stage, I tried to tell the story as quickly as I could. I wrote down everything I considered a major event.
The First Draft Stage
I write each chapter in one sitting with very few exceptions, and sometimes it can be a nasty sitting. At this stage, the selection of detail is intuitive. I write what I want to write. This means I don't overthink it, under the assumption that those unconscious or less conscious decisions are a valuable part of the detail selection process.
Sometimes I hit all the major points I wanted to and sometimes I don't -- sometimes that works, and sometimes it doesn't. Usually it's a bit of each, and I'm always surprised. The surprises usually fall into one of these categories:
1) I forgot some important details I have to add in.
2) I forgot some details I realize I forgot because they were unimportant.
3) I added some nifty details that I could never have thought of until I was immersed in writing the chapter.
4) I added some unimportant crap that I thought was nifty at the time, or I had to write to get from one point to another.
The surprise aspect is one of the most valuable aspects of this stage of writing. I have an outline written, and a notebook full of ideas I had for the chapter when I was going about Real Life, but if I look at those too closely and sit down to write with anything too specific in mind, I get jammed up like a neurotic athlete (like the one Woody Allen said apologized for stealing second).
I was never a very good athlete because I overthought everything, didn't trust my reflexes or instincts. If you overthink what should be second nature in sports, you will mess up. In first draft writing, I trust my instincts. The irony is, K. Bookman is a much better athlete than me because he can trust the reflexes internalized by his practice, and yet, he doesn't write first drafts this way at all. So again, the process is wholly individual, and the important thing to remember is it's all about awareness.
The Rest of the Stages
I'm not there yet. Don't want to bore anyone with speculation.
What makes details worthy of selection?
Yikes. Tough question. Details included in a story should all add up to something. It's okay if you can't say what that something is. Writing is about the unsayable, and I don't believe in reducing a work down to its "point." The "point" is the experience of reading it. But there are important ideas that tie a work together, feelings which inform the work, preoccupations that should be reflected in every detail to make it a satisfying read. If you don't know why a detail is there, it probably doesn't need to be. Try taking it out. If it doesn't work without it, ask yourself why. The articulated answer will help you evaluate the worthiness of details in the future.
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