This paper explored the effectiveness of ensemble performance on the development of adolescent’s life skills. An explorative qualitative study investigated young musicians’ self-perception about the benefits and challenges of learning and playing music together. A convenience sampling technique was adopted for interviewing 15 adolescents (12–18 years old) who participated in a long-term music education programme led by a charity in the North-West of England. The data were analysed using NVivo, employing a thematic analysis approach. Two main themes emerged from the analyses: (1) the main benefits of playing and learning in an ensemble: the development of music and life skills; (2) the challenges experienced by the musicians learning in the ensemble. The findings suggest that participants were conscious of the positive effects of playing in an ensemble on their lives. This extended beyond merely learning a musical instrument, i.e. acquiring music skills. In particular, young musicians recognised they had developed greater self-confidence and cognitive skills such as critical thinking and self-awareness. Primarily, they developed effective communication and interpersonal skills. At the same time, these young musicians recognised they had to face challenges related to the process of learning music in an ensemble, such as managing emotions of frustration and adapting to different music learning styles and techniques. Finally, suggestions are made for the implementation and evaluation of future projects to explore the impact and effectiveness of classical music programmes, with a particular emphasis on ensemble-based initiatives and their influence on life skills.