Dan McCarthy’s Writers Who Change How You Read presents a great way to grapple with questions, conclusions, arguments, etc. that don’t seem to make any sense. Especially for political/ideologically toxic subjects, what he presents can be helpful for working through an issue:
In late 2008 I put myself through a crash course in the works of Willmoore Kendall, the “wild Yale don,” as Dwight Macdonald called him… Kendall himself had told of how R.G. Collingwood had taught him at Cambridge to read a book by asking what question the author was trying to answer. I didn’t find that approach too insightful, but I picked up something else from Kendall’s own methods—the habit of asking “What conditions would have to be true in order for this author’s arguments to make sense?”
That’s a more productive thing to ask of a serious work than simply, “Do this author’s arguments make sense?” The latter invites the reader to supply a misleading context: the author’s arguments may not match up with reality, but they must match up at least with his own view of reality, and that’s something worth figuring out and contrasting against whatever the reader thinks he already knows.
I think of this as having empathy as a reader, rather than reading to be entertained. Empathy means you’ll be interested in trying to think like the author.
“What conditions would have to be true in order for this author’s arguments to make sense?”