On Writing: After Five Tries, Give Up
Also called the “Sisyphus 5” rule.
Every good writer is at least a little overconfident. Absent the conviction that you can always say just what you want with economy and style, you wouldn’t be in this racket. Now and then the over-estimation shows. You will find yourself trapped in a cycle of building and tearing down misshapen sandcastle-paragraphs on the way to an ingenious passage you’re sure is just ahead. It’s not ahead. You’re lost.
Satan will sometimes amuse himself by telling a writer after hours of flailing that he or she actually got the passage right the first time. Psst! Try that first thing again! If you catch yourself listening as the Evil One whispers such encouragement about a paragraph you rejected twice or three times already — “Hey, maybe that dogpile I threw away two hours ago wasn’t so bad” — quickly cross yourself and delete the whole page. I find if I can’t express myself in five tries, it usually means what I’m trying to say is so rancid in its stupidity that no amount of wordsmithing will hide the smell, and failure is my subconscious rebelling and screaming epithets to give up. Do so without shame.
Please pull all of these insights into a book - it would be the "strunk and white" of our times. You are quite seriously one of if not THE best stylist of your generation.
I’m not sure this applies to poetry. Actually, I’m afraid it probably does -- it it doesn’t start to chug down the rails on its own after five good tries, the engine pushing this train is probably conceit and not inspiration. Beauty is about craft, goodness is about your intention as a writer but truth is the real hardass. You can’t fake it and you can’t fool it, and well crafted falsehood is the worst kind of dangerous.