But isn't it true that the potential rewards outweigh the risks?
No. Revising/rewriting a story once, sure. If you need to, do so. But doing it over and over? No. There are very few, if any, potential rewards, and you're already experiencing the risk, which is not constantly writing new stories.
It's uncanny how many new shorty story writers fall into some version of this trap. They spend months rewriting the same story, and/or they rewrite a story after every rejection, even though the editor didn't ask for a rewrite because if the story was rejected, something MUST be wrong with it. After three or four or five rejections, they shelve the story, but a year or two down the line they pull it out and start the rewriting process all over again. This is the surest way to delay becoming a selling writer, or to prevent it altogether.
When you write a draft, it's usually a good thing to go through it again, making any changes you think it needs, and to give it a final polish. But then you need to submit it, and leave it the heck alone until and unless an editor specifically asks for changes.
The way to learn how to write well in not constantly rewriting the same story, it's not to rewrite a story with each rejection, it's not to shelve it, only to pull it off the shelf somewhere down the road and star the delay process all over again, and it's not to spend months and months working on the same story. It just doesn't work.
The way to sell short stories is to write a lot of short stores. It's new stories, each with a new idea, and each written in a reasonable amount of time, that turns a new writer into a selling writer. As Ray Bradbury, and a big bunch of others writers, puts it, quantity breeds quality. This is just how it works. Rewrite/revise/edit, yes. Once. Then leave it alone until someone asks for a new rewrite.
Here's something else many new writers don't understand. When you;re receiving personalized rejections, but the stories aren't selling, it's very unlikely your writing is the problem. It is, in fact, extremely unlikely that your writing is the problem. Editors don't send personalize, praising rejection when they dislike the writing.
They do send them when they like the writing, but dislike the story. You can't really change story by rewriting. It's still teh same story, and even if you could, unless the editor tells you how to change it, you're just guessing. Worse, the story probably doesn't need changed, it just needs to arrive at a place where the editor is looking for that kind of story, or will tell you what changes to make.
Learning to write well is the easy part of selling short stories. If you have any talent at all, you'll learn how to write well, or at least well enough, very quickly. For the most part, writers either learn how to write well quickly, or not at all. Unfortunately this is not what sells stories.
The hard part of selling short stories is not writing well, it's learning
which stories to tell, and what those stories should say.. It's learning how to tell the kind of stories editors want. This is crucial.
Look at it this way. MFA programs across the country are filled with writers who write extremely well. You have to write very, very well just to get into most of these programs. Yet only a small percentage of those writers ever sell a short story. They write very, very well, often breathtakingly well, but they still can't sell short stories because they never learn
which story to tell, and
what that story should say.
The way to do this is not to rework the same story over and over, and it's not to spend months painstaking writing a single story. The way to learn which story to tell, and what that story should say, is to write story after story after story until an editor says, "Yes! This is exactly what we're looking for!"
Or, at the very least, says, "This is extremely close to what we're looking for. It would be great, if you rewrite and revise it in this way."
This something just about every selling writer I've read about practiced, and preaches, be it Robert Heinlein, or Ray Bradbury, or William Saroyan, or Erskine Caldwell, or you name the writer.
Too many new writers can spend years on a tiny few stories. They do so, I think, because they think that story would sell if only they could polish it a little more, if only they thought, and worried, and pondered, and rewrote it again, and then again and again, and then again when it gets rejected, and then again after it's been shelved for five years.
Or they just shelve it after a dozen rejections, even though it might be the thirtieth editor who wants exactly that kind of story for his particular magazine.
Anyway, you learn to write the right kind of stories, and you learn what those stories should say, by writing story after story after story, by submitting each story, and by continuing to submit it until there is no place left to submit it. The wrong story is still the worng story, even if you rewrite it a thousand times.
Heinlein's Rule For Writing are not writing rules at all, they're solid, hardcore business rules, and they
work. They work because Heinlein knew what all these other writers learned. Writing well, or well enough, is easy, if you have any talent at all. Writing the right story is, for most, the hardest thing they'll ever do.
http://www.sfwriter.com/ow05.htm