I read it as being optimistic that people can shoulder their burdens and work to improve their lot, without dismissing the fact that people do have outsized burdens compared to others. I mean, he talks about his familial issues with chronic depression and his daughter's horrifying medical problems, I can't think of anything more emblematic of "actual struggles".
Maybe not "doesn't understand", it could just be disregard.
Very simply the book seems uphold a philosophy that ignores that other people might have actual struggles and histories.
I have a couple specific examples I can put up when I'm out of the office.