The globalisation of organisations has resulted in increasing expatriation. While extant research on organisationally-assigned expatriates has highlighted that organisationally provided cross-cultural training can minimise expatriate failure and challenges associated with working and living internationally, little is known about how self-initiated expatriates (SIEs) who lack such support, prepare. The current research addresses this gap in the literature by exploring the perceptions that Australian SIEs have of cross-cultural self-preparation (CCSP) for careers in South Korea or the United Kingdom; providing greater insights into the issue in nations of growing commercial importance to Australia. Drawing upon 24 semi-structured interviews, the findings are significant in highlighting: the value of cross-cultural self-preparation and differences in preparation needs based on perceived cultural distance/(dis)similarity and motivation to expatriate.