This article argues for an approach to understanding new lifestyle flows that acknowledges the roles of postcoloniality and privilege in facilitating migration and framing cultural politics on the ground within destinations. Through the deconstruction of postcoloniality and privilege, this article demonstrates the pervasiveness and persistence of these structural and systemic conditions. It illustrates this argument by drawing on the ethnographic case of North Americans living in Panama, documenting their efforts to displace ambivalence about their position within the local community through philanthropic and charitable activities. Despite these efforts, it becomes clear that they cannot completely erase the systemic and structural inequalities that underwrite these lifestyle flows.