The increasingly interconnected global economy demands more workplace flexibility and global mobility, leading to a rise in individuals seeking international careers, especially through self-initiated expatriation. Self-Initiated Expatriates (SIEs), engaged on a contractual basis without organizational relocation, are now more common than Organizational Expatriates (OEs). The purposes of this study were to explore cultural obstacles faced by Malaysian SIEs in Taiwan, their coping strategies to address cultural obstacles, and their cultural intelligence level. 20 Malaysian participants with over two years of work experience in Taiwan were selected through purposive sampling and in-depth interviews, and an interpretive approach was used to gain insights into their cultural adaptation experiences, aligning with the four dimensions of the cultural intelligence model that was proposed by Earley and Ang in 2003. Through content analysis, the findings show that the cultural obstacles of Malaysian SIEs in Taiwan can be categorized into social and legal aspects. The coping strategies Malaysian SIEs use to address cultural obstacles can be divided into problem-focused and emotional-focused strategies. Lastly, the findings also show the participants involved in this study possess a high level of culture intelligence. Practical implications derived from the findings of this study were discussed.

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