More and more Taiwanese workers voluntarily accept and/or apply for expatriation assignments. This type of self-initiated expatriates is very different from the traditional expatriates. In response to the scarcity of empirical research, especially non-Western studies, and the discovery of our qualitative research, we propose a quantitative research to explore the relations of expatriate career commitment and re-expatriate willingness among self-initiated Taiwanese expatriates. Besides, family affective support may enhance the relationship between expatriate career commitment and re-expatriate willingness. The purposive sampling method was used to conduct surveys with structured questionnaires among self-initiated Taiwanese expatriates. A total of 135 participants returned valid responses for further analysis. The results revealed that expatriate career commitment were positively associated with re-expatriate willingness. However, there was no evidence proving the moderating effect of family affective support. According to our findings, we propose that it is important for enterprises to select the workers with the higher expatriate career commitment in order to manage overseas assignments effectively and efficiently.