Upper‐middle‐class Chinese families send children to the United States for high school to exit what some perceive as an ‘unhappy’ educational environment in China or in pursuit of a ‘better education’ in the United States. However, for some students, the American high school experience itself may be marked by ‘unhappiness’, endured in the pursuit of ‘success’. Based on ethnographic interviews with Chinese youth attending private American high schools, this study illustrates how narratives of unhappiness surrounding such transnational educational choices result in multiple success frames among students, categorized as ‘pragmatists’ and ‘rebels’. Those who downplay happiness or experience unhappiness in the US context tend to adopt the ‘pragmatic’ frame, while those emphasizing their exit from an ‘unhappy’ situation are more likely to align with the ‘rebel’ frame. Despite slight deviations from parental expectations, the relative economic security of these families enables Chinese youth to develop ambivalent success frames based on their familiarity with both US and Chinese contexts, questioning the dominance of a singular success narrative.