Later On

Failure is hard to take, on the whole. But since failure is the doorway to learning, it’s good to learn how to open the door—how to use failure to glean lessons and improve learning—than simply to bounce off it and never realize that it opens. People who don’t learn how to use failure tend to avoid it whenever they can, and that strategy traps them in an ever-narrowing circle of things that are easy for them. Far better to discover how to exploit failure, how to make the most of it, squeeze every answer—as well as some better questions—from every single failure. This is the idea that we learn more from our failures than from our successes—though that might be because we tend to think about and analyze our failures more than our successes.

In this connection, let me just draw your attention to Martin Seligman’s fascinating book Learned Optimisim (inexpensive secondhand copies at the link—note condition before you buy: nothing less than “good,” I should say).

And also note this article by Paul Tough in the NY 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.”

Randolph has been pondering throughout his 23-year career as an educator the question of whether and how schools should impart good character. It has often felt like a lonely quest, but it has led him in some interesting directions. . .

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