I linked to this in my last post, but I feel like I need to highlight it particularly because it remains one of the best essays on privilege that I’ve ever read: “The Distress of the Privileged”.
I think it’s worthwhile to spend a minute or two looking at the world from George Parker’s point of view: He’s a good 1950s TV father. He never set out to be the bad guy. He never meant to stifle his wife’s humanity or enforce a dull conformity on his kids. Nobody ever asked him whether the world should be black-and-white; it just was.
George never demanded a privileged role, he just uncritically accepted the role society assigned him and played it to the best of his ability. And now suddenly that society isn’t working for the people he loves, and they’re blaming him.
It seems so unfair. He doesn’t want anybody to be unhappy. He just wants dinner.
But even as we accept the reality of George’s privileged-white-male distress, we need to hold on to the understanding that the less privileged citizens of Pleasantville are distressed in an entirely different way. (Margaret Atwood is supposed to have summed up the gender power-differential like this: “Men are afraid women will laugh at them. Women are afraid men will kill them.”)
George deserves compassion, but his until-recently-ideal housewife Betty Parker (and the other characters assigned subservient roles) deserves justice. George and Betty’s claims are not equivalent, and if we treat them the same way, we do Betty an injustice.
A Trick of Light 
I want to distinguish 3 kinds of privilege.
There’s government privilege — the government gives you special rights. Banks have this kind of privilege — if you do what a bank does you are “kiting checks” or otherwise committing fraud and you can go to jail for it. But banks have a license.
Then there’s private economic privilege. If you have money or special rights about buying or selling, you can use that to get what you want or influence the world.
Then there’s social privilege. You can be in a position to influence public opinion and do intellectual hatchet jobs without necessarily getting paid for it.
Look at SF fandom. The government mostly ignores the whole thing, but enforces copyright and contracts.
Publishers have private privilege — they get to decide who to publish. Authors try not to aggravate them because even if you have a publisher you never know when you’ll need another one. Editors have similar privileges — they make actual money decisions.
Authors and Big Name Fans have some social privilege.
Ideally we would arrange for everybody to be equal wrt government. We can’t begin to do that, but we ought to. We can’t make felons equal, and we can make anything a felony we want to, so it’s torn right there. But at least homosexuality is no longer a felony. We aren’t like Scotland where it used to be illegal to be a McGregor.
For economic privilege, I want great big businesses to be illegal. Like, Walmart has 2.2 million employees. Make them split in half, and again, and again, and again, we’re better off with 16 competing Walmarts than 1. Make the 19 companies with more than 250,000 employees split up. Then set the limit at 125,000. The more the power is diluted, the better. Let’s set the maximum corporation size as low as we can manage.
Socially, privilege can change fast. About the time somebody is complaining that they’re losing out socially, it’s because somebody else is winning and taking away their privileges. I don’t know what to do about that. Chances are the new people on top are no better than the old ones. They’ll condescend, they’ll bully, they’ll demand that their inferiors do what they want. The people who were on top before will probably be on the bottom now. Does it serve them right? I dunno. Not my problem. I don’t get to choose unless I’m on top, and even then the other guys on top will probably overrule me.
If you’re on top socially and the former social topsiders beg for mercy, you get to do whatever you want. That’s what it means to be on top. The Bolsheviks were once on top in the name of the proletariat, socially and also governmentally and they tried to stop out private stuff. Your friends can be on top socially in the name of women. You can say “Never mind the former topsiders are begging for social mercy, women have been kept from money and women have been raped, they’re responsible!”. If you actually have the power to make them pay socially, then it’s your choice.
Just remember, the time will come when it’s your turn in the barrel. Again.