Think twice. Then thrice.
In his glorious book On Writing, Stephen King shares how he once received a note from an editor with this formula:
You may be thinking, "10%?? I can't possibly cut that much!" Oh, dearheart. Yes, you can, if not more than 10%. Not even Shakespeare moved forward with his first draft. Slash that story to bits. Delete lazy words like very, unique and gestured. Remove the boring scenes and puffy over-explanations that we all write when caught up in that ever-alluring inspiration.
"I'm all for the scissors. I believe more in the scissors than I do in the pencil," said Truman Capote in Lawrence Grobel's Conversations With Capote. Editing is the key part of the writing process. I know, I know, you're a genius who has conjured a creative idea the likes of which we've never seen. (Aren't we all that genius at some point?) Yet if it isn't presented clearly and coherently, then pffft. Your message wimps out.
I lost count of how many times I edited my first short story collection (due out this fall with Vine Leaves Press), but guess what? The 50 or so times I combed over my own work still wasn't enough. I didn't expect it to be. I'm working with an editor who's combing through the collection right now to help the work improve so it's ready to be published. It's nothing to be ashamed of. Writers need editors. They go hand in hand, especially if they're friendly or crossing a busy street.
Interviewer: "How much rewriting do you do?"
Hemingway: "It depends. I rewrote the ending of Farewell to Arms, the last page of it, 39 times before I was satisfied."
Interviewer: "Was there some technical problem there? What was it that had stumped you?"
Hemingway: "Getting the words right."
-- Ernest Hemingway, The Paris Review, 1956
Remember the theme Ralphie writes in "A Christmas Story"? As he rereads to himself his essay about the Red Ryder Carbine Action bb gun, he's nodding along, impressed by the words he's strung together. That's what we initially do: We impress ourselves. When the work rests for awhile, you read others' writing, carry on with your life and then revisit that work, you're returning to it all the wiser. It's much easier at that point to find plot holes, stereotypes and opaque characters. You're able to better see the writing instead of the story.
As Elmore Leonard told Newsweek back in 1985: "If it sounds like writing, I rewrite it."
So how do you know once you've edited enough? When is it time to submit?
It's tough to speak in absolutes, because we each have our own respected process and creative design and -- DO NOT SUBMIT A FIRST DRAFT EVER NEVER FOR ANY REASON. Ahem. I'd like to urge you not to submit a piece to a literary magazine or contest too soon. You have one chance at a first impression, and you want that to be with a slam-dunk piece in which an editor will have to struggle to find a word to change. Submitting is exciting, just like buying a lottery ticket. You think, "Maybe this one's the big one. Maybe this time, I'll win, and everything will change."
It's really exciting to publish. It is! Even though we don't write because we want to publish (we write because we must write, remember. Read Anne Lamott's Bird by Bird if you're responding with, "but?"), it's a thrill to be recognized. But a sloppy piece of writing will not win you publication or awards. A first/second/third draft is really unlikely to be accepted.
Don't let that be daunting! Take the time to perfect your story before shopping it around. Polish your writing until it gleams. Even if it's a gritty, zoot-suits-under-a-streetlamp kind of story, it should shine in plot, pacing, structure and word choice. Every word should have a job, with superfluous words getting the pink slip.
You are your work's first editor, for as many times as you can stand to revise it. Then revise it twice more. Find a writing group to workshop it. Search for an editor (I'm one!) to collaborate with -- and I put a huge emphasis on collaboration. As a writer myself, I know how precarious the writer-editor relationship can be, and how easily feelings are hurt in even the toughest of torsos. So it's important to work with an editor whom you trust, someone whose ability you admire (even if you don't particularly like their work: I'm not a big Kurt Vonnegut fan, but I'd trust his eyes on my prose).
It's so easy to pass off this editing stage as unnecessary, but when you're paying submission fees and trying to make a real go of it in publication, it's vital that you're submitting your best work. Invest in your work. If you believe your work is worth publication, then it's worth taking the time and perhaps a financial investment to get it to its best. You'll be a better writer in the end because of it.