The purpose of this study was to explore the career transition experiences of elite gymnasts who became professional circus artists. Eight (inter)national level gymnasts who worked as circus artists were interviewed. Using a constructionist approach to thematic data analysis, we identified a three-phase career transition process. High levels of psychological resilience characteristics were required in the first, “realizing” phase (i.e., motivation, hard work, social support, and optimism). The second, “adapting” phase involved balancing context-specific demands which included general stress, a loss of competence, social adjustment, taking calculated risks, and physical recovery. The third, “thriving” phase involved experiences of freedom, personal development, and social connectedness. During the career transition, changes from an athletic to circus artist identity were experienced. Practitioners are encouraged to support the psychological resilience and experiences of autonomy among circus artists during their career transitions. This is expected to facilitate circus artists’ wellbeing, safety, and career longevity.