In this chapter athletes’ creativity is considered in relation to their pursuit of career excellence as sustaining a healthy, successful, and long-lasting career in sport and life. Grounded in the holistic developmental and ecological approaches, career development is viewed as mutual accommodation between athletes and their environments/contexts in which athletes’ creativity is about making optimal choices, developing resources and adaptability, broadening opportunities, and overcoming barriers to fulfill meaningful lives. Using the nine career metaphors framework containing inheritance, cycle, journey, action, fit, relationship, role, resource, and story, the authors analyzed how these metaphors as career archetypes triggered various career/transition-related frameworks, research, and applied approaches illustrating athletes’ career creativity or lack thereof. The multifaceted view of career development illuminated several paradoxes in athletes’ creativity. For example, money doesn’t necessarily stimulate creativity, but a lack of money does; when athletes maintain their careers “status quo,” they often are unwilling to be creative, but it is contrary when their careers are disrupted by negative events stimulating creative search for solutions. As a conclusion, the authors promoted narrative, existential, culturally informed and co-created participatory approaches in career research, highlighted creativity as a sport and life value, and advocated for career-long psychological support services.