Reflecting on recent trends in the international labor force, this study investigates and compares organizational expatriates (OEs), who are dispatched by their companies to international posts, with self-initiated expatriates (SIEs), who by their own volition move and work abroad. Findings from a survey of 57 OEs and 124 SIEs in Tokyo show several differences in individual- and job-related factors, cross-cultural adjustment and job satisfaction between OEs and SIEs. More specifically, mediation analyses show SIEs to have higher interaction adjustment because of their longer stay in the host country and higher host-country language proficiency. However, SIEs have lower job satisfaction because they work more often under host-country national supervisors.