Beginning with social inequities in terms of access to quality, inclusive education for children from disadvantaged backgrounds, especially rural teenagers who leave school early, the Holtis Association, with the support of the UNICEF Representative in Romania, developed a number of interventions intended to facilitate the transition from lower to higher secondary education of students from vulnerable and disadvantaged groups. One of the interventions was the establishment of teenagers’ clubs for volunteer activities, leadership development, and participation in the community to encourage social and emotional learning. (1) Background: This study aims to investigate the extent to which participation in the Holtis club projects contributed to the development of transformative social and emotional learning (T-SEL), as observed from the perspective of the Collaborative for Academic, Social and Emotional Learning (CASEL) competencies among adolescents. (2) Methods: The study was qualitative and used focus groups for data collection. Out of the 65 active clubs, 18 were selected, and their representatives participated in the focus groups. (3) Results: Participating in the club activities, which were organized in the school, with the aim of organizing activities outside the school space stimulated and developed T-SEL competencies among adolescents. (4) Conclusions: The data, which were collected through the voices of teenagers, underlined the personal transformation from the perspective of the CASEL model competencies of SEL, and the study privileged their perspectives.