I am trying to decide what I think of this. I've seen the phenomenon-- I saw it particularly plainly when I was on the editorial board of my college paper. We made all the incoming applicants write out essays about why they thought they should get their board of choice, and one of the questions asked them to identify their weaknesses. There was a pronounced variation by gender -- the women all wrote long, self-flagellating things like "Sometimes I think I am too passive-aggressive when criticized," and the men all wrote brief sentences to the effect of "I had too many proofreading errors in my early stuff, but I've basically fixed that by now."
The title "Will Wilkinson Wants People to Be More Like Will Wilkinson" is glib and kind of funny. But it's not really fair. Most people want others to be more like ourselves. Or, at least, to value what we value. It's not so much narcissistic as human.
Also, unlike PEG, I don't think Wilkinson and Shirky's suggestions are mutually exclusive. Extreme exemplars of either tendency probably should be tryin to meet each other in the middle.
This also reminds me of a conversation Pnin and I had about his experiences at a conference with many Asian academics. He noted that norms among them were quite different than in the States; people were much more respectful and deferential, less inclined to ask gotcha questions, etc. I had been perhaps influenced by too many of the multi-paragraph ads for Asia-based Biglaw recruiters that pop up on Above the Law, but I wondered aloud then if more women shouldn't make a point of trying to work in Asia instead of the U.S. After all, from Pnin's description (and from others, too) it sounds like Asian corporations might be more hospitable to stereotypically female personality types than American ones are. This is all a bit quixotic, I know, but perhaps not totally ridiculous.