Maybe I misunderstand what you mean, but I don't think transcending privilege has anything to do with it. I am also from a middle/upper middle class background. I can't and won't pretend that isn't true. Although I have proven to be relatively downwardly mobile in my adult life, I still benefit from the privileges of my background, my family, and my current circumstances, to say nothing of being a white dude.
I think, at least form myself, it is more important to be honest, to leverage what benefits I can from my privilege, both for myself and those I love, and towards the greater project of destroying everything that gives me those privileges.