The available literature on self-initiated expatriates (SIEs) is generally based on the assumption that SIEs are protean in character and manage their careers independently. The current qualitative empirical study offers an alternative to this assumption, using 23 interviews with Western SIEs employed by local organizations in China to examine how and why SIEs target obtaining a labour market fit through career self-management behaviour, particularly in culturally distant career contexts. The assessment of the career self-management behaviour of Western SIEs was undertaken using King's framework (2004). Three approaches to self-management behaviour were identified based on the motivation and outcome expectations of SIEs: labour market entry, employability maintenance and career advancement. The research illustrates the flexible and dynamic nature of career self-management behaviour and reflects individuals' revised career expectations and the employment context of the host country. The findings contribute to the extant theory on SIEs by illustrating emerging means of realizing international careers in cross-cultural career contexts, and the significance of third-party initiatives supporting expatriation facilitated by the Internet and social media.