I explore a contemporary politics of social reproduction among middle-class youth in Silicon Valley during the economic downturn subsequent to the tech boom of the 1990s. Drawing on ethnographic data collected at a public high school serving middle-class and affluent youth, I examine the relationship of the school and community environment to students' styles of self-cultivation and aspiration. In particular, I explore values and notions of success - such as freedom of expression, the pursuit of authentic passions, and conventional markers of academic and social achievement - that shape students' forms of self-discipline, self-definition, and aspiration. While arguing that young people's styles of self-cultivation suggest an entitled orientation toward work and life that may promote class privilege, I suggest that they also reflect a neoliberal politics of citizenship-shaping processes of social reproduction through schooling for middle-class youth. This politics of citizenship obligates middle-class youth to 'package' or market authentic personal traits to showcase their exceptional qualities, welt-roundedness, and authentic originality, and to frame such acts in terms of personal choice. Linking such processes of subjectification to political-economic and social conditions, I ultimately argue that middle-class youth bear increasing responsibility for middle-class status. Moreover, I suggest that the pressures resulting from this burden and the ways in which young people negotiate them suggest a domestic politics of 'hyper-vigilance' that may transform young people's self-perceptions, attitudes towards schooling, and aspirations, while also potentially posing risks to youth.