This paper analyses the narratives of five professional musicians, involved in popular music, aiming for an exploratory overview of their individual formative routes, events, opportunities and influences. Through retrospective accounts, these musicians reflect on the influences and opportunities that have contributed to their professional choice, and, thereby, providing some insights relevant to music education and culture in these digital age, in Portugal. As participant’s routes are alike, but share an involvement in popular music as teenagers, a special focus is placed on issues concerning the characteristics of their musical environment. Also, the role of school music within those lives, the relative influence of school experiences, and the significant peer influences and models that seem sustaining and fostering their musical involvement and identities, are analyzed. Issues on music education, in its varied contexts and ways, are debated and draw upon writings on informal learning in music and the implications are of concern to student, educators, and policy makers.