Do you have any advise for highly analytical folks that get hung up on not knowing how people read things? My biggest frustration with writing is that I don't h

Do you have any advise for highly analytical folks that get hung up on not knowing how people read things? My biggest frustration with writing is that I don't have an interpreter I can run over my work to test that it "works" and I have a voice of anxiety in the back of my head that someone is going to misinterpret what I write I horrible[1] ways. Less dramatically, when I sit down to write documentation, I don't really know how to verify that it is understandable and get hung up on trying to figure out how to do so. [1] Like http://www.rawstory.com/rs/2014/12/mit-professor-explains-the-real-oppression-is-having-to-learn-to-talk-to-women/ http://www.rawstory.com/rs/2014/12/mit-professor-explains-th..., but I've long decided to avoid writing anything public about anything that could relate to social justicey or gender-related topics.