There is a growing body of literature supporting the importance of dual careers in assisting athletes to prepare for their athletic retirement. Indeed, many countries have developed dual career programmes to help athletes combine their sport and academic aspirations. However, the commitment to fulfilling a dual career for an athlete can lead to added anxieties and tensions caused by the likely entrenchment in two environments that are subject to high evaluation. This chapter explores some of the challenges of maintaining a dual career and the adverse effect that this can have on athlete wellbeing.