For the majority of action sport travellers and migrants, the transnational lifestyle is short-lived, a working holiday after university or between ‘real’ jobs. But for some, it becomes a career they pursue for many years. In so doing, committed action sport migrants develop meaningful connections within multiple contexts and networks across countries that contribute to their transnational sense of identity and belonging. Sustained mobilities in the action sport industry are often the result of many years of hard work, compromises, creativity and negotiations. This chapter consists of two parts, both of which draw upon interviews with long-time action sport migrants conducted either during their travels or upon adopting a less mobile lifestyle. To make meaning of their reflections, I adopt an interdisciplinary approach that engages selectively with literature and key concepts from the fields of sociology, cultural geography, and transnational and migration studies. In the first part I examine the opportunities, constraints and negotiations of career action sport migrants, focusing particularly on the experiences of those working in the ski industry. Here I also draw upon Foucault’s notion of circulation to examine the role of governments and the nation-state in enabling and constraining action sport mobilities via visa regulations. In the second part of this chapter I draw upon Conradson & McKay’s (2007) notion of ‘translocal subjectivities’ to examine the ‘dynamics of mobile subjectivities’ and describe the ‘multiply-located senses of self’ amongst action sport migrants who inhabit transnational social fields (p. 168).