This article adopts the perspective of Sen's capability approach to examine elite athletes' environment and their capability to plan and prepare a career transition out of sport. Interviews were conducted with 14 elite athletes in Canada and results from the thematic analysis reveal that discrepancies exist in the athletes' environment. Three types of environments emerged from the findings: enabling, restricting, or hindering athletes' capabilities to plan and prepare their transition out of sport to a career they value. The difficulties reside more specifically in the possibilities they have to prepare an education path of their choice while being part of the national team. The results highlight that even though support from family and teammates is essential, it is not sufficient, as the support of coaching staff was shown to be crucial. The role of Game Plan advisors varies according to athletes' type of environment and underline the importance of going beyond their role of individual counseling in certain types of environments.