This dissertation presents an exploration of the career motivations, actions and experiences of thirty-eight skilled migrants, from Poland, Lithuania, Latvia and Estonia, who currently live and work in Ireland. Specifically, the analysis considers how career transitions and contexts, in conjunction with time and timing, influence the career actions and career outcomes of skilled migrants. These internationally mobile workers were interviewed over a two-year period. This study espouses a constructivist philosophical paradigm, with the study’s analysis based on the elucidations of the respondents themselves, in their recounts of their career actions and experiences in Ireland, the country context for the study. Adopting a holistic definition of career, the study embraces a whole life perspective (Litano and Major, 2016) on the interviewees’ careers. This perspective develops and extends the skilled migrants’ career development from an occupational and organisational perspective to a much broader, all-inclusive perspective, where profession and work have place and meaning; such as work being a means to an end (e.g. good quality of life) for the interviewees with an instrumentalist career script. This study draws on literature in the HRM, skilled migrant, careers, business, management and organisational studies domains. The research unpacks the contemporary conceptualisations of skilled migrant careers and relates these to the detailed empirical study. In doing so, the study provides a deeper comprehension of how the skilled migrant constructs and interprets his/her career experiences in the ever-changing personal, professional and social frameworks of both their home and host country careers. These findings and interpretations contribute to the existing knowledge on a number of key areas, such as skilled migrant and expatriate careers, underemployment, perceived career success, international careers and the effects of career transitions and structure and agency on career actions and outcomes. The research captures the individual migrant’s subjective perceptions of his/her career and world, and adopts an more inclusive view of career, examining the under-explored importance of the influence of family, context and time on the career actions and outcomes of skilled migrants in their home and host countries.