I have this compulsion where I obsessively reread things I've written after sending them, but I didn't have any insight about why I do this until I read the essay about the illusion of transparency.
Immersing myself in my perspective via obsessive and uncareful rereading serves (I think, probably) to assuage my anxieties about any lack of coherence and clarity in my writing. By blinding myself to my writing's ambiguities I can feel more assured of its quality, and also feel better about my abilities as a writer. So I think this behavior is caused, at least partially, by an unintentionally acquired habit of leaning into this bias.
I hope to notice myself engaging in this behavior and treat it as a warning that what I've written is probably quite ambiguous.
A critical and focused rereading is my goal when I start; however my focus is not long lasting, and the process inevitably devolves into mindless retreading of whatever trail of thought I wish I was communicating, with little effort devoted to verifying that this is how I should realistically expect to be interpreted. It is repetition past this point which I suspect is motivated primarily by a desire to feel self-assured. I was wrong to believe that I could treat this behavior as evidence of ambiguity when its cause is likely unrelated to the specific content of my writing.
This is the one thing I've found which reliably helps.
By the way, thanks a lot for the work you've put into this group!