Earlier quoted context omitted.
Maybe rather than expanding your assumptions one checked privilege at a time, just drop your assumptions altogether? You simply can't know the experiences of others; even direct communication only transfers a very loose approximation of experience, and that's if both sides are both communicating earnestly and are skilled communicators. So if you can't know the experience of just one person then you certainly can't gr…
The entire point is that people are inherently unaware of many of assumptions or personal "theories of the world" they are applying to their evaluations of people, places, and things. Asking people to "drop their assumptions altogether" is like asking people "just don't behavior with any cognitive biases." You may as well punch the ocean for all the good it will do. People, like the OP, just will not be self-aware en…
The end goal is replaced with the process of gradually increasing mindful self-awareness of your biases and generalisations.
> And I do not degree, nor do I really understand (which is likely the issue) the idea that trying to become aware of your own privileges that you take for granted others don't have is somehow tied to a moral judgment of others.
My apologies, I'm still trying to formulate my thinking in this area. I think it's because considering people from the dichotomy of privilege/underprivilege leads to empathy with the less privileged but not the more privileged, which implies that people who are more privileged are less deserving of empathy. Saying that one person is more deserving of empathy than another is what I mean by a moral judgement. And while people who are less fortunate are in need of more support (inherently), failure to empathise with the privileged (key here being empathise, NOT sympathise) can lead to the bad things associated with dehumanisation - scapegoating, us vs them narratives, that sort of thing. I think this is a major failing of the progressive movement that is so very close to being a powerhouse for positive change. It's inches away from being both postmodern and system-oriented, so I'm liable to focus on its failings as a critic who wants it to improve.