Job-related international mobility shapes life-courses and impacts self-initiated expatriates’ (SIEs’) careers abroad and upon return to the home country and thereafter. This chapter examines the evidence for the effect of expatriate experience on their careers and explores some of the factors that impact that. It discusses some of the similarities and differences in the motivations to work abroad, the types of career, and the outcomes for assigned expatriates (AEs) and SIEs. The chapter explains how those differences are relevant for understanding the influence of long-term international experience on careers. It approaches the diverse accounts of the effect of assignments on careers. Empirical studies of expatriates define career success as the accomplishment of desirable, positive psychological or work-related outcomes as a result of international experiences accumulated over time. While the expatriation literature has mostly concentrated on the micro level, as described previously, the organisational context into which self-initiated repatriates are embedded is crucial to grasping their career experiences.