I have never understood why the children of the affluent — at least, some of them—are not allowed to chart their own course through life. Why are they not allowed free time? Their own choice of career? Why is every moment guarded? Many of them will have the freedom—and money—to choose, in theory, any path they want, but they are instead steered toward a limited roster of choices . In these kids’ lives, every moment is transactional, leading to money-making careers or, in the case of many of the women, to money- making careers that lead to marrying people who will have money-making careers. When Trevor takes the PSAT, he has to pick his intended college major so that colleges can potentially recruit him. He scans down the list of careers, looking for real estate, and I laugh, thinking he’s joking. Later, I realize that his parents have told him that he will enter real estate—not as a lowly broker as I had thought he was joking about— but as a major player in commercial real estate. His conception of college is so transactional that I have failed to understand it.

This transactional nature governs a great deal of what the affluent do, including having fun. Gatsby himself saw entertainment as a means to an end: his house was to attract parties, his parties were to at- tract Daisy, and even his shirts were to impress her. But all his transactions were aimed at earning love. At the end of his property, he could see across the bay to the green light at the end of Daisy’s pier. His parties were to find something like love, as he conceived of it with Daisy.

It’s not always clear what the 1 percent are looking for. It is clear that, from a young age, they have constructed a schedule for themselves like Gatsby did in the flyleaf of a Hopalong Cassidy book. Gatsby, then James Gatz, developed a self-improving schedule that involved fifteen minutes of barbells and wall-scaling each day, followed by an hour of studying electricity and two hours of studying “needed inventions .” He allotted only half an hour for baseball and sports, as if to contain his fun The reader is left wondering how much Gatsby adhered to these self-improving exercises, as he later made his fortune through connections to gangsters and a possible involvement in throwing the 1919 World Series . Gatsby’s route to riches was not eased by hard work and self-improvement as much as by graft, but he was raised in the American religion of adherence to strict times and to the ethic of self-betterment against all odds .

Trevor’s family, and others like his, worship also at these twin temples, though they are set up in direct opposition to each other . Like the young and impressionable James Gatz, he is held to a tight schedule and relentless self-improvement through rigorous schools, workouts, sports games, and tutoring . His parents also know, however, that they must at times resort to greasing the wheels of his future with donations—which is not graft but which runs counter in many ways to the ethos of self-betterment . Still, they are bireligious, observing at both places of worship.

Among the kids I tutor, Warren, son of the multigenerationally rich, seems to have the best sense of how to shape his free time . He is able to practice instruments and play music many days a week, and he decides to learn foreign languages just for fun. I often find his parents with an open copy of the New Yorker, and they continue to ask him about his writing . He rarely looks tired and stressed, and he often sings under his breath as he opens the door to me for our tutoring sessions. I love stepping into his house for an hour. He offers to make me tea, and he is so thoughtful about what he writes. Over the course of our work together, he develops strategies that help him emerge as a very gifted writer. He has the stuff—deep attention to detail, a knack for a pithy, witty phrase, the capacity for analysis—that makes his writing not just clear but beautiful. And best of all, it is not torture to him. He loves reading and writing and thinking, and he takes the time to do so.

Born into a family that was established even around the time of the Civil War, Warren is the closest figure to the Buchanans in The Great Gatsby (though, unlike Daisy and Tom Buchanan, he and his family are kind) . Some of the family relics hang on the walls of his house, such as portraits of bluestocking women. I am not from this class, myself; instead, like most of the students I work with, I am from the Gatsbys, the strivers, the creators of the new American dream. My people were turn-of-the-century Russian and Polish Jewish immigrants to Jamaica Plain, Massachusetts, where they worked in shoe factories, and to the Bronx, where they worked sewing shower curtains, and to the Lower East Side of Manhattan, where they made alcohol in the bathtub during Prohibition.

Does one have to be from Warren’s people to feel that the world is lovely, as he does? His parents aren’t obsessed with money, and they have passed this along to him. Every time I pass his brick loft building in SoHo, decked in a wreath for Christmas and f lower boxes in the spring, it seems to offer the promise that the light at the end of Daisy’s pier promised Gatsby—the ease, the comfort, the style of knowing that you’ve arrived. Unlike the Buchanans, Gatsby did not really know how to have fun. The Buchanans’ fun often ended in disaster and disruption, but they were avid about play- ing polo and golf and taking joyrides. For Gatsby, on the other hand, each moment was considered, each party dedicated to an end goal rather than a reckless abandonment of cares. Perhaps the American religion of capitalism as a whole forbids this type of hedonism. Whatever the case, it is foreign to most of the children I work with.

They, too, have gotten used to parceling out time for dedicated aims. When they are left to their own devices, they generally don’t know what to do with unmarked time unless it involves losing themselves to alcohol or drugs or video games. Even pursuits that seem hedonistic aren’t really. One of the students I work with becomes a professional racecar driver at the age of sixteen. He leaves New York to travel to races around the country. Racing involves training each day on simulators, thinking about turns, working out with a trainer, thinking about one’s next race. He has the burdens of a pro athlete even before he’s gotten his license. The only place where it’s legal for him to drive is on the track.

* * *

On one glorious May day, in order to free up classrooms for AP exams for juniors and seniors, Trevor’s class is allowed to go to Coney Island with some teachers. The students have never been. They approach the subway nervously, as most have not taken it as far as Brooklyn—far, far into Brooklyn, where they will decamp at the end of the line. Along the way, the subway emerges above ground at points, and they see parts of New York most of them have never been to. They spend the journey shooting spitballs at each other out of plastic straws.

Let loose on the raunchy, rundown boardwalks that were thronged in Gatsby’s time, they gaze at the ocean. “Is that a house of prostitution?” one student wonders aloud, looking at the ramshackle, boarded-up houses along the boardwalk. I wonder if he’s ever heard the word whorehouse. This possibility clearly interests him, and he is more animated than he is in class. The kids eat at Nathan’s for the first time, enjoying french fries as the sand whips around them. They try in vain to frighten seagulls away from swooping down on the fries that have landed on the ground. They get badly sunburned and almost get lost on the subway home. As soon as they return to the Upper East and Upper West Sides, they head to squash, running, and baseball practice. One day stolen out of time. The next day, they’ll be back at school.

Excerpted from I Left My Homework in the Hamptons: What I Learned Teaching the Children of the One Percent by Blythe Grossberg © 2021 by Blythe Grossberg, used with permission by Hanover Square Press.


  • Blythe Grossberg, Psy.D. is a learning specialist in New York City. She has worked with children and adults with learning differences, ADHD, and autism spectrum disorders to help them be more effective and comfortable in school and work. Dr. Grossberg's work and writing have emphasized the talents and insights of adults and children with learning and other types of differences. A graduate of Harvard College, she received her doctoral degree in psychology from Rutgers. She grew up in rural Massachusetts at a time when the talents of children with learning differences were not always recognized, and she is excited to be part of the revolution in the way the world looks at people who learn and think differently.