In an era that sees sports clubs facing a crisis, a few still grow and attract new members. They use technology for their benefit and provide a place where the members have fun, become aware of their competence, set goals for improvement and experience empowerment. The present qualitative study, conducted with a road cycling club in Germany, investigates how membership is negotiated and confirmed. By exploring the factors that influence the degree of belonging, this research aims to provide some answers on how active members of a cycling hobby club experience becoming part of such a community, what it takes to substantiate membership, and how individual and collective identities are formed and constantly negotiated. The situated learning perspective and Etienne Wenger's Communities of Practice concept have been adopted, and semi-structured interviews with ten participants were conducted. Moreover, observations and conclusions from a stimulated focus group discussion were used. The analysis shows that cycling in a group is a complex, multifaceted learning experience. Power, speed, or cycling skills do not suffice without the will and active efforts to harmonise with a group. Belonging grows parallel to competence, and the degree of competence gets constantly evaluated by the community in their practice, as a combination of contribution to the common goal and ability to be a trusted partner. Competence is thus a “becoming”, reflecting the members’ engagement with the sport and on an interpersonal level.