Convincing the masses

I had an interesting conversation the other night with Julien of In Over Your Head. The conversation touched on a lot of topics, so I may wind up making this a multi-parter to avoid writing another monolithic post. We were talking about racism at first, then sexism and other forms of oppression as well. Mainly the conversation was about entitlement and privilege. He didn't realize at first that was what we were discussing, but eventually I think I managed to get some points across. And boy is that hard, even with people who genuinely want to learn to improve themselves. I consider conversations like this one of my most important duties, but (as feminists have known forever) it sure is difficult to break through that privilege wall!

What sparked the conversation was an experience Julien had had at a conference he was attending. He went to a panel on racism, and eventually realized he was the only white person attending. This didn't cause any problems; someone asked the room if anyone objected to Julien's presence and nobody said they did. But when this happened he started thinking: what if someone had said yes? From the IM logs (edited for brevity, continuity and coherency; please excuse the candidness of the language used):

Julien: but like they actually asked everyone if it was ok if I was in the room. I was the only white person there
Dave: okay...
Julien: I thought "do you not want me to hear what you have to say?"
Dave: No, it's a valid concern
Julien: well sure. but otherwise i feel kind of like it's a circle jerk
Dave: If there are a bunch of people talking about how they've been oppressed their entire lives by white people, it's not necessarily very comfortable with a white person around
Julien: well ok. i see that point. however, if they can't be comfortable talking with white people who want to listen about how they feel oppressed, then nothing's going to change

So I spent much of the next three hours trying to explain the point of X-only spaces, where X is any given oppressed group. I explained that as noble as it was, his own desire to better himself and to reduce the negative impact he has on oppressed groups is less important than the need for those oppressed groups to have spaces where they can be away from members of their oppressing groups.

So why was this point so difficult to get across? Julien is an intelligent person, and has a real desire to see inequality and oppression end. He has taken modest steps to improve his own outlook and behaviour, and could be generally seen as anti-racism and pro-feminism. Still, there was a block somewhere that kept him from putting the needs of oppressed groups first.

Eventually I came to see this block as one of the more subtle incarnations of privilege. Julien seemed to be putting his own desire to be (and to be seen as) a good, moral, egalitarian person above the desires of the people who are the subjects of the oppression in the first place. This is a cousin to the inability to see, when one does not act in an oppressing way, how one still benefits from ones privilege.

So it is important, when discussing feminism with a man whose intentions are more or less in the right place, to help him see that despite all the effort he might put into being a good person the fact that he is male and benefits from male privilege means that he is still one of the oppressors. I've seen this concept met with fierce opposition.

Dave: So what we're talking about is not the effect that your racism or the lack of it has on people, but your status as a member of an oppressing class.
Julien: sure
Dave: Actually, about six or seven oppressing classes
[...]
Dave: So it is imperative that you recognize that you are an oppressor to just about everyone who is oppressed.
Julien: but david, i am not an oppressor. i am part of an oppressing class

Again, difficulty. I try to explain that we are more than our own actions, that we have to accept and come to terms with our membership in a group, that most kinds of privilege -- and the oppressor status that goes with it -- are impossible or extremely difficult to completely purge.

I'm convinced this is not a completely hopeless cause. After all, there are male feminists/allies out here who come from an embrace-the-patriarchy background. So what difficulties have you encountered with this sort of discussion? What have you been able to do to counter them? How the hell do you manage to break through that wall of privilege?