["Human Resource Development Quarterly, EarlyView. ", "\nABSTRACT\nNumerous empirical studies have examined the work‐ and career‐related outcomes of self‐initiated expatriates (SIEs) in cross‐cultural work settings, thereby contributing to an emerging research stream in the HR literature. Building on self‐determination theory, this study examined whether the protean career attitude is positively associated with subjective career success. We further explored the mediating role of overseas work adjustment and the three‐way moderation of cultural intelligence and learning‐goal orientation to strengthen this indirect relationship. The data from two studies, encompassing non‐Asian (n = 289) and Asian (n = 192) participants, provide convergent support. The results showed an indirect influence of protean career attitude on subjective career success via overseas work adjustment. Moreover, this indirect influence is strengthened when SIEs possess either higher cultural intelligence or a stronger learning‐goal orientation. This study contributes to the literature by identifying key factors influencing SIEs' career success and highlighting the central role of learning in their workplace adjustment. It advances HRD by showing how learning and adaptability drive cross‐border career development.\n"]