This paper explores how a group of freelance musicians worked to create an interactive school concert aimed at fostering inclusive musical participation in a suburban community in Oslo, Norway. The concert was part of a broader outreach project initiated to strengthen community through joint singing and live music. Each year, this group of musicians invites local primary schools to participate in their concerts. In 2024, the project founders and the presenting researcher initiated a collaboration to explore possibilities for a research-based development project involving community stakeholders. A preliminary action research study was designed with the dual aim of understanding and improving practice (Bradbury, 2015). The researcher joined the group to facilitate critical reflection and to explore how the musicians understood and worked toward participation in their creative process. The researcher observed rehearsals and concerts and initiated individual interviews and group reflections. The study thus employed a critical action research approach, characterized by participants who are «willing to be participants in public spheres in which they explore whether and how their practices have irrational, unsustainable, or unjust consequences» (Kemmis, McTaggart & Nixon, 2015, p. 453). The paper discusses themes that emerged during the creation and evaluation of the concerts. Strategies included careful repertoire selection in terms of musical feasibility and representation, balancing of functional and aesthetic goals, and encouraging active engagement that differed from students’ everyday school experiences. The group drew on various narratives and ideas to frame their work, concerning the local community as challenged, yet resourceful, personal experiences of musical awakening moments and previous school concerts, conceptions of music as a tool for personal and communal wellbeing, and schools’ shortcomings regarding music education. Reflections were critically nurtured by thoughts on gender, class, ethnicity, and neurodiversity, as the group deliberated how to engage all students. The musicians expressed concerns about their capacity to represent and include a diverse population and wrestled with the meanings and implications of musical participation and its connections to recognition, wellbeing, and community. While they envisioned possible changes to address these challenges, they pointed to barriers to radical reinventions that was due to their situation as freelance musicians, which also stopped them from fully partaking as co-researchers in the study. This suggests that although a more extensive participatory systemic inquiry (Burns, 2015) across stakeholders may be desirable to create responsive communal and music educational practices, systemic interventions cannot rest on the shoulders of freelance musicians alone.