There is a moment at the beginning of “Maineland,” a quiet marvel of a documentary directed by Miao Wang, when a young high-school teacher in Shanghai holds forth on the concept of Chinese happiness. Her students, who have just completed their calisthenics exercises, are dressed in identical uniforms of blue and white. Heads bent in parallel forty-five-degree angles, they jot the teacher’s lesson in their notebooks with the kind of silence and discipline that has characterized Chinese learning for millennia. When the teacher finally asks what is meant by the mantra “happiness belongs to those who know the meaning of contentment,” it seems only natural that the bell should sound, forestalling any attempts to make sense of this vague and open-ended statement.

Ask any Chinese parents what it might mean for their progeny to achieve happiness, and they will likely cite not contentment but success. “Maineland” examines an experience that has become increasingly common for middle- and upper-class Chinese families seeking an express route to this goal: exporting their children to a high school abroad. The project began when Wang, a filmmaker who moved from Beijing to the States at the age of twelve, was invited to Fryeburg Academy, a boarding school in rural Maine that she’d never heard of, back in 2011, and was immediately struck by the on-campus presence of students from mainland China. “It took me almost two hours to get from the Portland airport to the school, and when I arrived I was fairly certain I was in the middle of nowhere,” Wang told me. “So I had to ask myself, how did these fifteen-year-olds get here from the other side of the world?”

Wang traced prospective Chinese students of Fryeburg Academy back to the beginning of their application process, in a corporate suite in Shanghai, where suit-wearing admissions officers offer an information session for the teen-agers and their parents. When the annual tuition for international students—fifty thousand dollars—pops up onscreen, no one bats an eye. For these parents—successful entrepreneurs who constitute the winners in China’s vertiginous economic growth—Fryeburg is a solid investment. When a middle-aged father named Mr. Zhu proudly observes, in a Shanghainese accent, that “In ten to twenty years, China and America will be the two dominant powers,” he has just finished showing us his factory, which manufactures humidifiers and other home electronics and has made him a fortune. Tellingly, one of the core principles Mr. Zhu has chosen for his company is “Never Let Yourself Be Content.” He drives a BMW, and the mansion he has built for his family wouldn’t look out of place in Newport or Beverly Hills. “They will be the future élite,” he says of his children, nodding approvingly at his daughter.

The man’s daughter, Stella—a pretty, effervescent fifteen-year-old who claims to have fallen love with America when watching the movie “High School Musical”—is one of the two principal protagonists whom Wang follows over the course of three years, from sophomore year to graduation. The other is Harry, a bespectacled, introspective boy whose alert, perceptive eyes suggest that his “very blurry impression of the U.S.” as a place “where people must all be so happy and fortunate” might be upended upon arrival in the country. Harry’s father informs him that, as the only male child born in the past three generations, he carries “the hopes of the entire family.” “What you saw of the outside world far exceeded what I saw going abroad in 1981, at eighteen,” the older man says. “Now you don’t have to worry about tuition, you’re pretty lucky. You must seize this opportunity.”

Witnessing this intergenerational drama unfold, I felt the familiar weight of this father’s words. A generation ago, my own Chinese mother admonished me to “seize the opportunity,” using the exact same terms as Harry’s dad, precisely because my tuition had largely been covered by scholarship funds. My luck in scoring a free ride, my mother warned, could not be squandered. At Deerfield Academy, the boarding school I attended, in rural Massachusetts, every student I knew who had come from the mainland received scholarships. The rich were predominantly white and hailed from Park Avenue or the suburbs of Connecticut. Fifteen years on, the roles have been reversed: Chinese students like Harry and Stella are the cash cows of Fryeburg Academy—never mind that their English is halting and their grasp of American culture tenuous. Not only are they entirely self-funded, their tuition is almost five times that of the local day-student population that makes up the majority of the school. Whereas Harry and Stella travel the world and take classes during summer vacation, their American counterparts, most of whom are white, work at hardware stores and ice-cream parlors.

This inversion reveals the dramatic transformation that urban China has undergone in the past decade and a half. Stella and Harry were born when I was a sophomore at Deerfield, and the economic distance between us feels to me like an unfathomable chasm. Yet in some ways the cushion of wealth has not spared these students a sense of alienation among their American peers, or the weight of expectation from their Chinese parents. The beauty of “Maineland” is in its depiction of the predictable arc of the foreign student’s experience—the way Stella anxiously monitors her grades, and how other kids ask the embarrassed Harry to say random things in Chinese—and in its burrowing underneath it. In one of the movie’s most touching scenes, which takes place in a documentary-making class, a group of Chinese students makes a short film about common perceptions of Asians. Huddled around a screen, the Chinese students intently watch the playback as they are described by fellow American students as hardworking, respectful, shy, and smart. “Is any of it true?” the teacher asks. The students look at one another, not speaking at first. Then a young woman says, “Most of it,” and another student corrects her: “All of it is true.” A third student, wearing square-framed glasses, adds, “Maybe they think Asians are kind of strange . . . When they talk to you, they don't look at your eyes.”

“Why is that?” the teacher asks.

“Because we are nervous,” the young woman says.

“We’re afraid,” the bespectacled student adds.

“Of what?” the teacher asks.

“Making mistake,” the young woman responds.

“Maineland” depicts other subdued conversations like these, where unresolved moments of vulnerability stand out as the clearest indication of what is gained through these students’ cross-cultural education. For the parents of Stella and Harry and others of their generation, Fryeburg signifies cultural capital of the sort they never had the chance to accrue. But for the two teen-agers Fryeburg is the defining experience through which they’ll measure their distance, in terms of values and cultural perspective, from their parents.

“There’s a big difference between how the Chinese and Americans understand happiness,” Stella says during her first year at Fryeburg. “Before I left China, my dream was to become very successful and make a lot of money.” She goes on to explain with a measure of cynicism: “For most Chinese, they feel happy only after achieving a level of financial security. But now I start to have my own opinions.” Security and contentment are not words that are defined in the film. As we watch Stella and Harry study, take exams, attend prom, and make their annual pilgrimage to China and back, we are left speculating as to the extent to which they might find satisfaction within their expanding worlds. At the end of her senior year, on the cusp of graduation, Stella gripes to a Chinese friend that ultimately her parents didn’t make enough to free her from money worries, and we wonder if, despite her immersion in the American education system, she will reprise her father’s striving after all and inherit the family factory. Most of all, we wonder what lessons she will have learned from her experience at Fryeburg, and what slippery notions of happiness she will pass on to her own children one day.