This article examines the moral deliberations and value-creation strategies of Cuban and Ecuadorian return migrants who question hegemonic views of migration and strive to re-imagine life in their homeland accordingly. The alternative paths they take challenge the analytical emphasis on economic progress and social and existential mobility in studies of migration. By reassessing notions of virtuous economic practice and activating moral repertoires outside the field of migration, returnees strive to carve out a ‘simple life’ that contests taken-for-granted assumptions about the goal of their movements and the features of a ‘good life’. The precariousness of such endeavors highlights the high stakes of returnees’ responses to migration-related expectations and pressures, namely the possibility to maintain meaningful relationships and cultivate a valuable social life.