Enjoyed the post Charles. It’s not just experts who have the problem you describe. When we learn something we almost invariably forget the early steps, particularly the fumbling mistakes, the blind alleys, the miss perceptions and so on. We forget what it was like not to know. Schools, universities full of well intentioned folk (aka teachers) who have forgotten what it was like not to know whatever it is they are trying to teach to newbies.
I have an interest in what I have dubbed public click pedagogy or learning in public. You see snippets of it here and there online as folk write about their struggles with problems, a new idea, a different way of thinking about some phenomenon etc. A wee scribble here if interested: http://www.lancaster.ac.uk/fss/organisations/netlc/past/nlc2014/abstracts/pdf/bigum.pdf