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This paper investigates how Japanese SIE’s labor markets in Asian societies provide career opportunities for young Japanese workers. The number of locally employed Japanese workers in Asia has increased since the 1990s. Previous studies, which have relied on the Lifestyle Migration view, pointed that the primary reason for expatriation is self-seeking and that Japanese expatriates feel finding something worthwhile for their lives by expatriation at the expense of status attainment. However, these studies paid little attention to the demand-side aspects of Japanese SIE's career, which directly determines their opportunities. This study aims to provide some empirical findings based on the structural and institutional accounts that are different from the previous studies. The authors analyze the interview data of staffing agencies and the salary data in Singapore, Hong Kong, Thailand, Indonesia, and China, which the Japanese expatriate workers are likely to choose as destinations. From the qualitative analyses of the interview data, the authors find four dimensions relating to Japanese expatriate’s labor market chances; market growth in the local society, the existence of Japanese community, legal restriction of issuing work permits, and the degree of localization of Japanese firms. According to these factors, it is possible to classify the five societies into two groups: one has a premium of Japanese self-initiated expatriate workers, and the other does not. The quantitative analyses using the salary data from a staffing agency also confirm the cross-society difference of economic remuneration. In China, Indonesia, and Thailand which are included in the former group, the salary of native Japanese workers is significantly higher than those of other worker types, but it is not in Singapore and Hong Kong. The authors discuss the differences between the present study and previous literature and the future research prospects in the concluding remarks