Over the last decades, sport federations have been confronted with new variants of sports, such as parkour. Parkour is considered a lifestyle sports which embraces a specific culture that often conflicts with the culture of federation-organized sport (Sterchele and Ferrero Camoletto 2017). Participation in lifestyle sports is increasing rapidly, which may pose a threat to the market position of federations regarding leisure sports (Gilchrist and Wheaton 2011). Despite the studies emphasizing the dichotomous relation between sport federations and lifestyle sports, our study explores why and how both can reconcile. In particular, our study examined how and why readiness for change was achieved in the gymnastic federation as well as in the parkour community for integrating parkour into the federation. Applying a single-case study design, drawing on Oakland and Tanner (2007) change framework, our study revealed several key mechanisms to develop a lifestyle sport in a federation context. Organizational learning proved to be an essential determinant to overcome the cultural differences. Furthermore, our results emphasized the importance of leveraging behavioural and technical leadership in the change process. This study enhances sport managers’ knowledge on how they should approach lifestyle sport communities, while delivering insights to lifestyle sport communities on the intentions of federations regarding their sport.