Shelby Steele's "The Content of Our Character" (subtitled "A New Vision of Race in America") was a Big Deal in 1990 when it came out, and it continues to be a Big Deal because of the picture of race and racism that it introduced and (to some extent) legitimized, and that has been taken up and become popular, and spawned variants, in all sorts of circles.
Steele's main claim is that while there is still significant residual racism in America, the main obstacle that prevents black people from advancing is a collective attitude of victimization, that leads people and leaders to focus on the wrong things: on past victimization and collective action rather than on present opportunity and individual success.
When our leaders put a spotlight on our victimization and seize upon our suffering to gain us ineffectual consesions, they inadvertantly turn themselves into enemies of the truth, not to mention enemies of their own people.
Strong stuff. The book's message is focused and strongly expressed, and put very convincingly. I have no idea how true it is; I haven't lived as a black person in America, I haven't had the deep and heart-to-heart conversations with a variety of black people, or spent the years living in the places, that it would take to have a good idea whether or not it's true. Are we in America, and in particular are black people in America, in the state that Steele claims? I dunno. But it's definitely well expressed.
Aside from the question of truth or falsehood, it looks to me like there are really two things bundled together within the main thesis. The first (and in some sense primary) one is that an emphasis on victimhood over opportunity is a bad thing. The second, hidden within the first as Steele expresses it, and never explicitly called out or explicated, is that victimhood is collective, whereas opportunity is individual.
So when Steele writes:
Collectively, we can resist oppression, but racial development will always be, as Ralph Ellison once put it, "the gift of its individuals."
he's not saying that as part of a worked-out claim that collectives can only resist, not develop; he's saying it as a statement of something assumed, something obvious.
Deep down I tend to agree; I picked up a strain of individualism somewhere, and when he says stuff like this I tend to be one of the folks that just nods. But I think it's important to note that the claim isn't self-evidently true. There's a powerful current in leftist (progressive, whatever) thought that stresses the importance of collective development and advancement. And even on the non-left it's quite common to think of development in terms of families or subcultures.
I recall a Michener novel (although I don't recall the name) that convincingly described the advancement of an Asian family in early America. It would be very hard to describe them strictly as individuals expoliting individual opportunities for individual gain; they were all about the current and future prosperity of the family, the long-term view down the generations. Each individual was content, even driven, to sacrifice their own short-term good for the ultimate prosperity of their descendants. It's by no means a self-contradictory picture; collective advancement, free of pathological victimhood, is by no means impossible to imagine.
So if Steele's book failed to connect with many people that he might have wanted to connect to (and it certainly did), I think it's partly because he didn't bring out into the open and address this assumption that victimization and collective identity are necessarily linked; that advancement and individualism go together. "Our collective identity shouldn't mire us forever in a culture of victimhood" is relatively uncontroversial (although one can argue about whether or not it's actually tending to do that); but "only by abandoning collective identity for individual identity can we advance" is something that you can't simply assume without alienating those readers who aren't already singing in the individualist choir.
Something like that, anyway.

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