In this chapter, the authors examined expatriates that self-initiate their international work for personal reasons and the factors that affect their departure from an organization. The authors conducted a systematic review of self-initiated expatriation (SIE) and its definitions in order to propose an integrated definition of SIE and model its nomological network. In addition, the authors construct a roadmap for future research directions in the SIE domain. Finally, using a qualitative research design, the authors studied the organizational practices designed to reduce SIE turnover in an exemplary multinational organization. Overall, our contributions are enhanced clarity of the SIE construct and the theorized practice of SIE retention.