http://www.xkcd.com/1432/ XCKD kind of weighs in on the "devil's advocate" thing.
On the one hand, I get that (especially white dudes) injecting a "let me play devil's advocate here" can be destructive and hurtful of non-dominant voice and views. On the other hand, for me "devils advocate" thinking is also an exercise in empathy, a way to try to take on alternate viewpoints and understand the feelings people who disagree with me have, to see what's influencing people, whether or not we agree.
http://www.beagleton.com/flash/whatmessage_postswiff.html Posted this over ten years ago. I like people who also think most URLs should be permanent.
Sometimes I really long for a technically-minded career coach, or mentor of some kind. Even though I'm reaching the midpoint of my career, I think I need some guidance, feedback, and cheering up in general.