Multinational organisations continue to staff their international operations with expatriate employees and extant research has highlighted that organisationally provided cross-cultural preparation can contribute towards intercultural effectiveness and minimise expatriate failure and challenges associated with working and living internationally for these individuals. Yet, the cross-cultural preparation of self-initiated expatriates, especially those from regions outside of North America and Europe, has received considerably less attention in the literature even though they represent a growing and significant component of the global talent pool. This research addresses this gap in the literature by exploring the perceptions that self-initiated Australian expatriates have of cross-cultural self-preparation for careers in South Korea; providing greater insights into a cohort of expatriates living and working in a nation of growing commercial importance to Australia which has been accorded limited attention in the expatriation literature. The research draws on semi-structured interviews with 20 self-initiated Australian expatriates and repatriates working within diverse industries including construction, education, engineering, government, legal, manufacturing, and pharmaceuticals. The interviewees were primarily males aged between 20 and 30 years who had worked (on average) for 24.5 months in South Korea. The findings are significant in highlighting: the value of cross-cultural self-preparation; differences in preparation needs for those in urban and rural areas; prior work and non-work experience for preparedness; and the importance of adjustments in attitudes.