This is a problem, of course, for all parents, not just affluent ones. It is a central paradox of contemporary parenting, in fact: we have an acute, almost biological impulse to provide for our children, to give them everything they want and need, to protect them from dangers and discomforts both large and small. And yet we all know — on some level, at least — that what kids need more than anything is a little hardship: some challenge, some deprivation that they can overcome, even if just to prove to themselves that they can. As a parent, you struggle with these thorny questions every day, and if you make the right call even half the time, you’re lucky. But it’s one thing to acknowledge this dilemma in the privacy of your own home; it’s quite another to have it addressed in public, at a school where you send your kids at great expense.
And it’s that problem that Randolph is up against as he tries to push forward this new kind of conversation about character at Riverdale. When you work at a public school, whether it’s a charter or a traditional public school, you’re paid by the state, responsible, on some level, to your fellow citizens for the job you do preparing your students to join the adult world. When you work at a private school like Riverdale, though, even one with a long waiting list, you are always conscious that you’re working for the parents who pay the tuition fees. Which makes a campaign like the one that Randolph is trying to embark on all the more complicated. If your premise is that your students are lacking in deep traits like grit and gratitude and self-control, you’re implicitly criticizing the parenting they’ve received — which means you’re implicitly criticizing your employers.
When I asked Randolph to explain just what he thought Riverdale students were missing out on, he told me the story of his own scholastic career. He did well in boarding school and was admitted to Harvard, but when he got to college, he felt lost, out of step with the power-tie careerism of the Reagan ’80s. After two years at Harvard, Randolph left for a year to work in a low-paying manual job, as a carpenter’s helper, trying to find himself. After college, he moved for a couple of years to Italy, where he worked odd jobs and studied opera. It was an uncertain and unsettled time in his life, filled with plenty of failed experiments and setbacks and struggles. Looking back on his life, though, Randolph says that the character strengths that enabled him to achieve the success that he has were not built in his years at Harvard or at the boarding schools he attended; they came out of those years of trial and error, of taking chances and living without a safety net. And it is precisely those kinds of experiences that he worries that his students aren’t having.