The growing phenomenon of serial migrants – people who have moved at least three times and profess belongings to more than two places – challenges the dialogic relationship imagined in studies of transnationalism. This is particularly true in the case of the mobile middle class, which has attracted less attention than the multiple migrations of low-waged labour migrants and the global professional elite. Drawing on interviews with 35 Australian and Indonesian migrants in Singapore, this article proposes the idea of orientation in order to understand the serial migration biographies of middle-class migrants. Rather than focusing on the propulsion and direction of movement, the notion of orientation suspends a migrant between reflection, action and imagination as they forge provisional pathways that upend or cleave to more conventional social trajectories. Developing this concept helps us to understand how migrants with middling resources navigate post-national socio-political formations contoured by race, gender, and class.