In this paper, we aim to broaden and deepen the current debate on expatriation in business and management discourse, and especially self-initiated expatriation. Following Bauman's [Liquid Modernity (2000), Cambridge: Polity; Liquid Love, On the Frailty of Human Bonds (2003), Cambridge: Polity] critique of postmodern society and, employing an anthropological lens, we examine work-related expatriation as set within a wider life context. Whereas conventional expatriation research focus is on the workplace, the focus of this study is the wider community. We take a longitudinal approach demonstrating the essential fluid nature of expatriation in general, self-initiated expatriation in particular. We show the importance of multi-generational links as overall critical considerations in effecting decisions to move or stay; we also show how over time, changes in circumstances, career plans and demands of significant others, drive the expatriate agenda. We pay particular attention to nontraditional expatriates and issues of health and disability in the extended family. Finally, we document the importance of the wider family and of the community in the process of adjustment and in engendering a sense of belonging.