The purpose of the present study was to investigate how the difference between individually initiating a sojourn overseas and responding to one's organization's initiative to be sent overseas, affects the way Western sojourners adjust to living in Japan. The independent variable was the motivation to go to Japan with two levels--overseas experience (OE) based on individual initiative and expatriate assignment (EA) based on individual response to organization initiative. The six dependent variables were sociocultural adjustment, psychological adjustment, desire to go specifically to Japan, local language ability, time spent in social interaction with locals, and inquisitiveness. Questionnaires were sent out to 500 randomly selected members of the American Chamber of Commerce in Japan, and the Australian and New Zealand Chamber of Commerce in Japan--250 to each organization. A total of 166 useable surveys were returned for an effective response rate of 33.2%.Six null hypotheses corresponding to each of the dependent variables were tested using two-tailed independent samples t-tests. The results showed that those who initiate OEs were significantly more socioculturally adjusted than EAs (p = .001), had significantly more desire to go specifically to Japan than EAs (p < .05), and had a significantly better grasp of the local language than EAs (p < .001). No statistically significant difference was found between the groups in terms of psychological adjustment, time spent in social interaction with locals, or inquisitiveness. Additional exploratory t-test analyses revealed that OEs tended to be younger than EAs, but spent more time living in Japan than EAs. EAs on the other hand, were significantly more likely to have gone to Japan to support their organization than OEs. An exploratory correlational analysis revealed a number of relevant associations.For example, sociocultural adjustment was found to be significantly related to psychological adjustment (p < .001), Japanese language ability (p < .01), time spent living in Japan (p < .01), age (p < .05) and time spent in social interaction with host nationals (p < .01). The results of the present study suggest that for organizations engaged in selecting individuals for overseas postings, considering candidates' prior self-initiated sojourns could lead to greater adjustment during subsequent overseas postings than simply considering any sojourn at all.