Athletes frequently describe the JST as the most difficult within-career transition, and many of them have acknowledged that they failed to cope well with it (e.g., Stambulova, 2009). Athletes’ development in the junior-to-senior transition (JST) is influenced by narratives existing within relevant contexts and settings. This study served as a follow-up to the quantitative longitudinal study to gain a deeper understanding of individual JST paths through a qualitative narrative approach. The aim was to explore two team sport athletes’ (John, the football player, and Anna, the basketball player) JST pathways, emphasizing psychosocial factors that were perceived as facilitating and debilitating the process. Narrative type interviews were conducted, and the holistic-form structural analysis (Smith, 2016) was used. Through their narratives, John and Anna reconstructed their JST paths, attaching meanings to certain events, recounting the people involved, and making personal reflections. John had a performance and family narrative and Anna, an enjoyment and relationship narrative. They perceived their key facilitating persons to be their family members and teammates. The debilitating factors were some coaches’ behaviors. At the time of this study, John and Anna had already terminated their athletic careers and had refocused on getting an education. Although they did not reach elite senior levels in their sports, they found their athletic career meaningful life experiences.