The cursor has been blinking over “send” for twenty minutes. The message won’t get better. Press it.

Past a certain point, rereading stops improving a message and starts eroding your nerve. You are not editing any more, you are looking for permission, and no number of passes will produce it, because the discomfort is about sending rather than about wording. The twentieth read finds exactly the message the third one found.

Give yourself two reads and a rule. If it is honest, clear and not cruel, it goes. Then close the app instead of sitting on the delivered receipt, because waiting is a separate skill and it starts once your part is done.