WHAT IF THE SECRET TO SUCCESS IS FAILURE?

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.”

Yes, I can think of at least one famous example of that phenomenon off the top of my head.