What if the Secret to Success Is Failure?

This from the New York Times:

Dominic Randolph can seem a little out of place at Riverdale Country School - which is odd, because he's the headmaster. Riverdale is one of New York City's most prestigious private schools, with a 104-year-old campus that looks down grandly on Van Cortlandt Park from the top of a steep hill in the richest part of the Bronx. On the discussion boards of UrbanBaby.com, worked-up moms from the Upper East Side argue over whether Riverdale sends enough seniors to Harvard, Yale and Princeton to be considered truly "TT" (top-tier, in UrbanBabyese), or whether it is more accurately labeled "2T" (second-tier), but it is, certainly, part of the city's private-school elite, a place members of the establishment send their kids to learn to be members of the establishment. Tuition starts at $38,500 a year, and that's for prekindergarten.

Randolph, by contrast, comes across as an iconoclast, a disrupter, even a bit of an eccentric. He dresses for work every day in a black suit with a narrow tie, and the outfit, plus his cool demeanor and sweep of graying hair, makes you wonder, when you first meet him, if he might have played sax in a ska band in the '80s. (The English accent helps.) He is a big thinker, always chasing new ideas, and a conversation with him can feel like a one-man TED conference, dotted with references to the latest work by behavioral psychologists and management gurus and design theorists. When he became headmaster in 2007, he swapped offices with his secretary, giving her the reclusive inner sanctum where previous headmasters sat and remodeling the small outer reception area into his own open-concept work space, its walls covered with whiteboard paint on which he sketches ideas and slogans. One day when I visited, one wall was bare except for a white sheet of paper. On it was printed a single black question mark.

For the headmaster of an intensely competitive school, Randolph, who is 49, is surprisingly skeptical about many of the basic elements of a contemporary high-stakes American education. He did away with Advanced Placement classes in the high school soon after he arrived at Riverdale; he encourages his teachers to limit the homework they assign; and he says that the standardized tests that Riverdale and other private schools require for admission to kindergarten and to middle school are "a patently unfair system" because they evaluate students almost entirely by I.Q. "This push on tests," he told me, "is missing out on some serious parts of what it means to be a successful human."

The most critical missing piece, Randolph explained as we sat in his office last fall, is character - those essential traits of mind and habit that were drilled into him at boarding school in England and that also have deep roots in American history. "Whether it's the pioneer in the Conestoga wagon or someone coming here in the 1920s from southern Italy, there was this idea in America that if you worked hard and you showed real grit, that you could be successful," he said. "Strangely, we've now forgotten that. People who have an easy time of things, who get 800s on their SAT's, I worry that those people get feedback that everything they're doing is great. And I think as a result, we are actually setting them up for long-term failure. When that person suddenly has to face up to a difficult moment, then I think they're screwed, to be honest. I don't think they've grown the capacities to be able to handle that."