In June 1997, when I graduated from Horace Mann, one of New York’s most prestigious private schools, the New York Times published a story about our class that began as follows: “They were, by some accounts, the class of mediocrity.”

A reporter had tagged along with our valedictorian, Loren Easton, and found the freckled 17-year-old wrestling with disappointment, a sense that we hadn’t lived up to the school’s expectations. “All we cared about was getting into good colleges and we didn’t even do that well,” Easton told the reporter. The truth was that 44 percent of us had gotten into an Ivy League school. But for Easton, who spoke for at least some portion of our class — and who’d chosen the University of Pennsylvania after being rejected by his first choice, Dartmouth — it was less about the data and more about the feeling that we weren’t a particularly impressive bunch. “We’re not like last year’s senior class, which had so many geniuses, so many stars,” he lamented.

This obsession with achievement is familiar to anyone who has been in the orbit of an elite private school. Since time immemorial, or at least since the mid–20th century, affluent parents with soaring ambitions for their children have jockeyed for precious slots at schools prized for vaulting grads to the Ivy League and into illustrious careers. When the president of the class above mine got into Harvard, the only person visibly prouder than him was his mother, who immediately traipsed through the halls wearing a crimson sweatshirt emblazoned with the university’s crest.

My father, a corporate lawyer who often reminded his sons that “a man can never be too thin, too rich, or too well dressed,” worked his way up and out of the middle class without the benefit of brand-name schools. When he wrote the first of a handful of $15,000 tuition checks to Horace Mann (which now costs $68,700 annually, more than a Harvard undergraduate degree), I think my dad imagined I’d develop excellent posture while readying myself for a career as a Supreme Court justice, literary titan, or captain of industry.

Instead, after graduating from Pomona, a small liberal-arts school in California, I spent my early 20s playing in a series of ill-fated bands whose achievements — performing at Central Park’s SummerStage and various Verizon Wireless amphitheaters, signing a publishing deal — were thrilling but fleeting. I also spent a few years writing screenplays no one wanted. I did manage to wrangle $1,000 from William Shatner to rewrite a comedy he’d dreamed up, but he didn’t like my take and the movie never got made.

Meanwhile, after working as a reporter at a small newspaper for a couple of years, I bounced between jobs that felt embarrassing for someone with my privileged background: copyediting a yoga magazine, tutoring distracted teenagers, headhunting hospice nurses (which was every bit as ethically uncomfortable as it sounds). To me, these didn’t feel like the customary day jobs that most creative types take to pay the bills; they felt like daily reminders of my inability to make good on the advantages that had been handed to me.

By my mid-40s, I’d built a modest career doing communications for nonprofits whose missions mattered to me but whose dysfunction drove me bananas. My daily responsibilities hardly seemed to require a first-rate education. I wasn’t sure if I’d failed Horace Mann or if Horace Mann had failed me. In any case, whatever advantages my elite schooling had conferred, I was pretty sure I’d squandered them.

One day a few years ago, during a break from yet another funereal procession of Zoom meetings, I was complaining to Marc Bush, a friend from Horace Mann who’d been a model student: managing editor of the school newspaper, ardent water-polo player. In his yearbook photo, he stands proudly in a blue blazer, tie, and khakis, surrounded on the page by quotes from Plato and Shakespeare. Marc went to Yale and, when he was only 22, founded a nonprofit that packaged cross-country cycling trips as affordable-housing fundraisers. Now, in his mid-40s, after a stretch of unemployment, he was a demoralized part-time consultant for an educational-strategy company. Professionally, he seemed and felt lost.As we commiserated, Marc suggested I revisit the Times story about our underperforming class, whose shadow seemed to be looming over the two of us. I needed to know if other classmates were similarly afflicted. Did the residue of unrealized potential linger in any of them the way it did me? I was less interested in what they’d accomplished than in how they felt about their work and the lives they’d built, especially when measured against the exalted aspirations of our youth. I decided to go searching for the class of mediocrity.

Easton, our valedictorian, now works in private equity. I reached out, but he didn’t want to talk. In........

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