i also do this - ive noticed i end up rereading my emails so many times looking for inappropriate comments that never exist that the sentences become meaningless jumble and at that point i ultimately end up inserting actual errors in the form of typos   something that has saved me is using boomerang to schedule my emails to send later whether it be 2 minutes or 2 hours it takes the weight off pressing send and i usually end up only looking at the outbox draft a couple times in the meantime before i move on   it has also kind of worked as mini-erp a bit since ive started doing this it seems like for lowest stakes emails ie with a person or situation with the lowest perceived consequences for a feared slip up now i can sometimes just press send on after a couple reads