Knowing when to stop 
While she denies it, my wife is a very good writer. Before she put her writing career on hold to go back to school (and to do a bunch of other things) a few years ago, she was starting to crave out a decent career as a freelancer. Her work was solid, flowed well, and was always an interesting read. On top of that, she wrote both non fiction and fiction.
Her main problem was that she’d write something, be not quite happy with the results, and completely remold it. In some cases, what was a perfectly good (and often better than that) piece of writing would lose whatever charm and spark it had before the rewrite. This was especially true of her fiction.
It’s not only my wife who I’ve seen do this. Several other writers — and wannabe writers — have succumbed to the same thing. They just don’t know when to stop trying to improve a piece of work. And, in some cases, those improvements actually ruin what was solid writing.
Attacking the symptoms
So, what drives some writers to go an edit or a rewrite too far? The only answers that I can come up with are lack of faith in their own abilities or a unreasonable perfectionism.
Believe in yourself
It’s natural for a writer to have doubts about their ability — I know I still do. But those doubts can drive you to improve your skills. Feeling that nothing you write is any good doesn’t help, though. Sure, your first draft will be rough but if you keep cutting the heart (or at least one of the lungs) out of your work by rewriting then those doubts are only going to get worse.
It’s hard to build the perfect beast
We all want our writing to be the best that it can be. But due to any number of constraints — time, subject matter, ability, lack of experience, and more — it can’t be. Sometimes, not even close.
How to know when to stop
That’s a tough one. Here are a few bits of advice:
Try limiting the number of drafts that you write. My maximum for anything is four drafts; usually two. Anything more than four drafts and you start getting into diminishing returns.
Keep copies of the previous drafts and compare those to the current one. You might find that one of the earlier drafts is better than the edit.
Accept that a particular piece of writing is as good as it’s going to get, and that any tampering will just dilute it.
If all else fails, have someone else read an earlier draft and the latest one.
Do you have any suggestions? If so, leave a comment.
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