The article examines the transnational mobility experienced by two language teachers of Mexican origin, one who migrated to the United States and the other to the UK. Drawing on autobiographies and in-depth interview data, the analysis shows the complex relationship of different factors in shaping how the participants experienced their transnational mobility processes. These factors include differences in their sense of agency, the link between their bilingualism and their professional identities, and the emergence of different positionings regarding their previous and current work contexts. The article concludes by outlining the implications that the findings have for policy and practice.