The other day I was trying to explain to someone how I deal with endings — that it isn't about the exact plot or sequence of events in the ending of a story, but the feeling of the ending, the sentiment it produces in the reader and the philosophy or outlook that said feeling is a reflection of. I don't always know what will happen by the end of the story, but I do know how I want you to feel about it, and I can always derive the former from the latter.
Slippery statements like this drive some writers crazy, in particular the Syd Field types who need that three-act structure and that beat-sheet rhythm to feel at home. But to me, knowing what emotional response you want to provide for the audience seems like the whole point. Yes, I go off a great deal about philosophy and point of view, but I also know none of that matters if it doesn't reach the reader in the first place, and in order to reach the reader you got to move them a little. You have to give them an ending that they feel grateful for having made the effort to reach.
Another thing I've found useful about thinking of endings in emotional rather than mechanical terms is the way it frees you up from having to fulfill any particular plotline. If you get married too early and too thoroughly to how things ought to unfold, you end up contorting yourself into all sorts of idiotic positions to justify a particular plot. The what is always an expression of the who and the why and the how (as in, how it feels), and so the first of those should always be driven by the rest.
The trick is not to have contempt or indifference for plotting, but rather to understand its true function, and for a long time I had a feeling about plotting that was a sort of contempt or indifference. When I was in my teens and early twenties, I had this image of myself as the sort of writer who gets published in New Directions and written up in the Paris Review — an avant-gardist, someone who cared more about form and pushing boundaries and experimenting with the typography. In time I found was that this sort of rarefied experimentalism, much as I enjoyed appreciating it, I didn't enjoy creating it nearly as much. It felt clever and amusing, but never really very rewarding or thrilling, like card tricks at a party. At the end of the party, all you're left with is a card trick.
Over time I realized I'd missed out. Storytelling was not only more important to me, but more interesting, more challenging, and rather underrated. I may love me some John Cage and Stockhausen, but as Professor Bullough said to me in college, there's still a great deal of music to be written in the key of C. Now that I think about it, it's music, not literature, that seems like the real guiding principle here: what did you feel? Yes, it's important to make sure the feelings you evoke don't run contrary to anything else you're trying to do, but it helps to have those feelings firmly in mind from the git-go, the better to give you something to aim at headlong.