This article by a Princeton freshman has gone viral on social media lately. Some people love it, some hate it, but it does get people to talk about what we actually mean by "privilege".
The boy in question, as I said, is a freshman. He has just arrived on campus from a relatively homogeneous, suburban upbringing, and he feels as though he is called upon to apologize for having it good. He feels defensive, quite naturally, and makes a good case that everybody has baggage, and that using the meme "check your privilege" as a weapon is not a good way to further dialog.
I just spent all morning looking for a post I saw a few months ago, which explained "privilege checking" in a proper context. I can't find it, but it explained that we all have areas of privilege and areas of non-privilege. In any given conversation, "checking privilege" means (approximately) checking our cultural assumptions which devalue someone else's oppression. In those areas where we have privilege, we should be more circumspect about interjecting our opinions vs. listening to those who lack it.
For example, if Tal Fortgang was attending a symposium for grandchildren of Holocaust survivors, he would probably resent being approached by a Holocaust denier. Or a Palestinian activist who draws a moral equivalence between Nazi genocide and Israeli occupation. Or even a Rwandan refugee who tries to redirect the conversation to his own national tragedy. Because all of these, while they may or may not be appropriate conversations in other contexts, devalue the Jewish experience of the Holocaust.
I was thinking about this this morning while praying the Shacharit. Part of the morning blessings is:
.יְהִי רָצון מִלְּפָנֶיךָ ה' אֱלהַי וֵאלהֵי אֲבותַי שֶׁתַּצִּילֵנִי הַיּום וּבְכָל יום מֵעַזֵּי פָנִים וּמֵעַזּוּת פָּנִים
My translation (Google translate did a lousy job with it): "May it be Your will, YHVH my G*d and the G*d of my ancestors, that You will save me today and every day from oppressors and from oppressiveness."
This seemed to me to connect with the debate about privilege. Today and every day, we do not wish to be oppressed, but we must be introspective about ways in which we benefit from a system which oppresses others, as well. At the same time, we must remember that this is a process of introspection: using "check your privilege" as a bludgeon against others, to silence rather than promote dialog, is counterproductive.