Working it out

Yes, but never for the twentieth time. If I can't get the story right in three or four drafts, I'll set it aside for a while and work on other stuff. Then after a few weeks, I'll go back with fresh eyes and renewed perspective and make one or two more passes; and if that doesn't help, then the story is no longer worth my time, and I'll can the damn thing for good.

One way I've learned that I'm working too hard on a piece is when I start memorizing the story, word for word. By that time, I can't tell if what I've written makes any sense, let alone whether it passes muster.

The story has to remain interesting for the writer and provide enough spark to keep him going. When you can no longer stand reading your own words, then it's well past time to give that piece, and yourself, a break and seek inspiration in other ideas for stories you might want to pursue.

I don't tend to bash on a story for more than three drafts if it's just not coming together. What's it sticking on? Plot or character? I tend to be very character-driven when I'm writing shorts, so if the character just isn't "hitting," I can't really drive a good plot. Sometimes the plot's just wrong for that character, and I'll rework it or do some tooling to get it right. Finally, you need to look at your supporting cast as well. I had one story that I was trying to tell third person from the protagonist's POV and it just wasn't working. Finally I ended up switching to a first person POV centered on a different character who was a helper for the protagonist and it all fell into place.