What to do when you are a chronic re-writer?

I am afraid I don’t have an exact answer for this question. It is one of those things that I am musing over. See, I am one of those people who have a hard time getting something truly done because they keep going back to re-write. It is almost to the point where this is not a good thing. In fact, much like workaholism or money addiction, it is seen as a healthy obsession to have. Take, for instance, these often-quoted cheers for rewriting.

“You write to discover what you want to say. You rewrite to discover what you have said and then rewrite to make it clear to other people.” Donald Murray
Get used to rewrites,” advises Dr. John Yeoman. “Make [your stories] as good as you can, and then drop them in your sock drawer for a month. They’ll develop errors, dull interludes, and patches of downright ugliness all by themselves. That’s the time to fix them. Then drop them back in the drawer for another month and do it all over again.” (Five Winning Habits of Successful Writers)
But how much is too much? At what point are you no longer clarifying a piece but imposing a new plan onto an old structure? Know when the piece is done. Before the seventh grade, I was incapable of drawing a decent looking stick figure. Then I got this wonderful, amazing art teacher named Mrs. Barrigar (I may have her name misspelled) and after only a year of pencil sketches, she dropped me straight onto oil painting. There were two things she said to me, and they seem ironic when paired together. “You move too fast.” and “Don’t overwork it, or you’ll ruin it.”
I can only remember ruining one or two things. Some were better than others. But know what? Nothing in this world would have made those lesser-works as good or better than the ones which stood out. There sometimes was no rhyme or reason to why one piece would be gripping while another faded into the background. The brilliant pieces had flaws. The lesser pieces had less noticeable troubles. Sometimes they had better colors, or a more dynamic structure. But in the great works which stood out, there was just something alive about them. I don’t know why, and no amount of revision would being the lesser works alive. And if I were to touch the great pieces to fix the flaws, I might kill them. It only took the death of one painting for me to understand when something was done, and it needed to be left alone. I can still see where the paint was spread too thinly with linseed oil. I can still see where I left blank spots in the canvas. But I won’t touch the painting. It’s finished. Not perfect, but there was something about it.
One of my favorites I painted while watching the art booth at a small art fair. It was a close-up of two draft horses, both gray, one calm and old, the other young and impatient. The only color was a red scarf tied to the bridle. The face of one was too small. The scarf on the other was muddy, without the neat folds needed to really make it pop. But it was perfect, somehow, and I left it to start drying. Oil paintings can take weeks or months to dry, but are usually able to be gently handled after a few days.
There was this lady who was admiring the various drawings and paintings of the students, and her whole face transformed when she saw those horses. She wasn’t thinking. She stroked the cheek of the older horse, the one with the scarf. Naturally she was embarrassed and apologetic since she had smudged it, but I didn’t mind. The smudge worked. I found her a napkin so she wouldn’t ruin her clothes. Oil paint can be hard to get out. You see, I wasn’t alarmed by her desire to touch the horse, because I understood. She felt a connection with the painting. It was pigment and oil smeared over cotton, done by a teenager who had only wielded a brush for a few years. It wasn’t technically accurate. It wasn’t rendered with amazing finesse.  But it was alive. You could feel that these two horses were waiting for the cue. And their spirit somehow came through. I think it was in their eyes. I was always good with eyes. More than one person tried to touch the older, gentler horse. He was very popular, and there were at least three or four gray-fingered people attending the show that weekend.
Something about those eyes seemed to be telling his impatient companion, You move too fast. Don’t overwork it. You’ll ruin it.
That horse wasn’t perfect. But he was right.

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