Serbia is said to have one of the highest rates of brain drain in the world. For the generation glossed as the “children of the 1990s,” stances toward mobility and migration have shifted along with geopolitics. Following nearly two decades of wartime entrapment, in 2009 the conditions of possibility for mobility fundamentally changed for Serbian citizens. Of both symbolic and material consequence, the country’s return to respectable geopolitical standing also marked a shift toward more nuanced stancetaking in relation to mobility and migration. Namely, by the time of my research, the expectations of youth—not only of “normal mobility” but of “normalcy” more generally—had become more and more often calibrated against personal experiences of real-life travel. Based on fifteen months of ethnographic fieldwork in Belgrade, Serbia from October 2014–December 2015, this dissertation tracks some of the consequences of this shift for young potential migrants in Serbia. I explore how the problem of skilled migration is constituted, the discourses produced, and the practices prompted. I analyze the mobility narratives of young potential migrants as proxies for commentary on a host of other socioeconomic issues. My focus is on the real and symbolic geographies invoked in talk of leaving and staying in Serbia; on how young potential migrants narrate their everyday navigations in the “here and now” and give moral weight to migratory aspirations for, and experiences of, lives lived in the “then and there.” I argue that the foundational motif of these varied imaginaries is a deep investment in meritocracy--a value-laden register called upon to articulate aspiration as well as critique. Engaging the politics of mobility holistically, I also excavate what it means to stay in a context so many others leave. I explore the growth of social entrepreneurship and the digital economy as recent efforts to coax dignified work from an inhospitable climate of precarity (and as key to governmental “solutions” to brain drain). I untangle how entrepreneurialism is promoted as a project of reforming values while also serving as a realm of authenticity and “apolitical activism” for some. Training attention on work in the digital economy I illuminate how economic subjectivities are cultivated in complex relation to place and belonging in ways that muddy the dichotomy between staying and leaving. Finally, I show how both promoters of entrepreneurship and Serbia’s digital transformation harness the dominant discourse on brain drain to cast themselves as certain social types and legitimize their agendas. This dissertation demonstrates how contemporary stances toward mobility and migration articulate aspirations to dignify the conditions of life and work, are implicated in a reconfiguration of middle-classness, and reveal how postsocialist subjects understand themselves and construct life projects in the context of ongoing political and socioeconomic change.