Abstract Based on the theoretical frameworks of the career enactment and the stress perspectives, this study develops and tests a model in which career boundarylessness affects subjective career success through its effect on three career competencies—knowing-why, knowing-how, and knowing-whom—and career autonomy and career insecurity. The results provided empirical support for the importance of career autonomy, career insecurity, and the development of knowing-why and knowing-how competencies in the successful pursuit of a boundaryless career. The implications of these findings are discussed.