The sentence I rewrote forty times
I counted once, out of morbid curiosity — forty-one versions of the opening sentence of an essay that eventually ran about grief. Not because I'm a perfectionist. Because the first forty versions were all, in some way, protecting me from saying the actual thing.
Version twelve was too clever. Version twenty-three hid behind a metaphor so nobody could tell what I meant. Version thirty-seven was almost honest but still had an escape hatch in it — a joke at the end to soften it.
The forty-first version had no escape hatch. It just said the thing. It's the only version that ever got a reader to write back and say "me too."
I don't think that's a coincidence. I think most of my bad drafts are just me looking for a place to hide.
Part of the deeper dive: The Complete Guide to Actually Finishing What You Write.
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