I used to think my first draft had to be perfect before anyone saw it
I wrote a fantasy chapter six months ago and thought the dialogue was great. My writing buddy read it and said, 'This sounds like a history book, not people talking.' I rewrote it last week, just letting the characters argue like real people, and it's so much better now. How do you know when to stop polishing a rough draft yourself and just show it to someone?
Letting the characters argue like real people" is exactly it. I used to overthink it too, but you just have to send it out when you can't see the problems anymore.