The study aims to determine factors affecting the job performance relating to cross-cultural adjustment as it affects work stress and work adaptation. For this study, the research framework was based on cross-cultural flexibility associated with work adaptation and work stress on job performance among expatriates. The research was conducted on a sample of 396 expatriates working in the hospitality industry in Taiwan. Structural equation modeling was utilized in this study. The obtained results confirmed the impact of cross-cultural adjustment on work stress, the negative impact of work stress on job performance; and also, the positive impact of cross-cultural adjustment on work adaptation, and work adaptation on job performance. The results show that the challenges faced by expatriates are derived from work adaption, work stress, and cultural differences. Expatriates who can adapt to the different cultures of foreign countries have higher work participation. It has also been found that a significant correlation exists between cross-cultural adjustments on work pressure. Higher work stress translates into relatively lower job performance.