David Graeber made a really good argument for why misunderstanding others is exactly a symptom of privilege. The whole article is worth reading (as is the whole book I originally read it in, "The Utopia of Rules"), but here's the argument in a nutshell:

"Those born to working-class families invariably score far better at tests of gauging others' feelings than scions of the rich, or professional classes. In a way it's hardly surprising. After all, this is what being "powerful" is largely about: not having to pay a lot of attention to what those around one are thinking and feeling. The powerful employ others to do that for them." https://www.theguardian.com/commentisfree/2014/mar/26/caring...