Ayinde is quiet and studious. As he answered my questions, he sounded like he was in the final rounds of a high-stakes game show, taking a little pause and saying “Uh-huh,” before offering his measured answer. He’s always loved to push himself. As an eighth-grader, he applied to intensive high schools that would drive him, as he put it, “to be the best version of me possible.” When he was accepted to an elite prep school, his advisor at a diversity-access program he attended pressed him to go. The advisor told him it would be challenging—perhaps even in ways Ayinde wouldn’t be able to handle at first.

Ayinde discovered what his advisor meant in his first days at the school. He was surrounded by mostly white faces. Soon he would learn that many of those faces belonged to bodies that lived in penthouses and were ferried around by private drivers. As students do in the first days of school, they talked about how they spent their summer vacations. The other kids mentioned jaunts to Europe. Computer camp, at the very least. Ayinde’s family, meanwhile, had never taken a vacation. When his turn came, he confessed that he didn’t go anywhere.

“Don’t your parents ever get tired of working?” he remembers the kids asking.

At first, Ayinde didn’t feel frustrated, just isolated. His classmates’ everyday occurrences were his distant dreams. The frustration would come later, when he began to feel that many of his classmates weren’t even trying to empathize with him. Some kids complained when Ayinde received a scholarship to cover the cost of the school’s $275 prom ticket, which he wouldn’t have been able to afford otherwise. They would rather have seen him stay home.

Ayinde eventually found a group of fellow outcasts who welcomed him. But during his freshman and sophomore years, he found he couldn’t infiltrate most cliques because he couldn’t afford to take part in their shared activities—going to the Hamptons on weekends, or even buying fast food every day. He was confounded by questions like, “Where are you going to summer camp?” Like so many other outsiders, Ayinde needed a way to respond “Nowhere,” without further singling himself out as the One Poor Kid.

In their book, Extreme,304 Emma Barrett and Paul Martin examined people who push the limits of human endurance—polar explorers, K2 climbers, and so forth—to figure out what bound them together. (The book’s cover was blurbed by Man vs. Wild’s Bear Grylls, if that gives you a sense.) Here’s one charming anecdote in the book from Sir Ranulph “Ran” Fiennes, who trekked across the Antarctic: