Why do we need expatriation? Who are expatriates? What are their experiences? Who benefits? What are the challenges of international work? For decades, the international mobility literature has concentrated on these and related issues. This special-issue introduction provides an overview of pertinent research insights, relevant current questions, and promising future areas of investigation on the micro (individual), meso (organizational), and macro (society/context) levels. In particular, it presents the contributions included in this special issue, highlighting the highly diverse contexts in which self-initiated expatriates’ careers are launched and unfold over time.