As far as NaNo goes, I am also annoyed by it — but only in that people seem to think it makes them better novel writers. I think it’s good for camaraderie and community-building and getting in good habits and all that, but in my mind it’s just kind of nonsense for the skills you need to really organize and think about novels. But then again, it seems to work for some people. Just like outlining works for some people (and not me). And just like writing a short story a day (SHANE) in preparation for future novels works for others. Figuring out how to write a novel has been a whole new experience for me and is a learning process in trying to keep my interest, trying to plan, trying to write, trying to get a draft done without freaking out, and so on.

So yes, in a way, I think being a good short story writer will prep you for novel writing. But I also think if you have a Big Idea that you want to really sprawl out with over 100,000 words, then do it. I also think (and this, Kira, is where I might actually have some helpful advice instead of just rambling) that much of the work in novel writing comes in the editing phases. So in that sense, maybe writing short stories first *is* good advice… as long as you actually spend time editing them so they work as finished pieces.

Writing short forces you to see, over and over, how beginnings and endings tie together. I just do not buy into the idea that this comes easy, any more than hitting ten free throws means you don’t have to work on free throws anymore. The people who are really good at free throws shoot shitloads of freethrows. Once upon a time I could reliably (~70%) hit free throws with my eyes closed, and it’s because I shot a lot of them, so they it was automatic.

It’s this automaticity that matters, I think. There’s a large psychological literature on automaticity and expertise, with the idea being that experts in most domains, even ones considered highly cognitive, don’t think more. They’ve just internalized the rules. The idea is that when you’re at word 20k if you have to think and plan about how to manage your pacing, your characters, your conflicts, then the battle is lost. Beating it into your brain via executing these patterns a zillion times, in a zillion variations, is what gets you there.

So I am dead-set against everything NaNoWriMo stands for. I think it’s utter bunk. Maybe it’s a good idea for other reasons, for people who need to convince themselves that they can get into a routine, or need permission to put words down, or god knows what. But if you want to do good work, I haven’t seen one iota of evidence that the road to good long work doesn’t go through a shitload of good short work first.

Speaking personally, I got tired of making my own writing life hard, which is why I’m going back and trying to get the fundamentals in order, and I couldn’t be happier with how it’s going so far.

I don’t know that I’m the best person to be making recommendations but I think you need to try to just push through it — even if you feel icky and stuck — and try to get something resembling an ending. Then you have something to work with.

I like DAL’s suggestion.

I try to use what I have and find a few key events that lead toward an ending so I have points to write toward. I’m not suggesting that this makes it easy but at least I’m still moving forward.

For what it’s worth, I have the same issue. Here’s how it typically plays out these days with a short story. I write about 1/3 to 1/2 of it without outlining or organizing (because my subconscious can do a better job than I can), then I come to an abrupt halt. After a day or two of pacing around frustrated, I take a few big pieces of copy paper (11″ x 17″) and “organize” what I have: motifs, settings, what each character wants, &tc. For me, it’s important to do the “organizing” as fast as possible — freewriting, really. The big pieces of copy paper end up covered with a bunch of arrows, question marks, loops and scribbled text… you get the idea. I put all this “organizing” away, pace around some more — a day or two. Then a “solution” dawns on me, often while exercising. I use that solution to write to the end of the story, without organizing or outlining any further. Then I revise for a long, long time until I consider the story at least an “8″ on a 1-10 scale.

I don’t know if that helps you any, but maybe it will!