This autoethnographic study examines the conception, development and evolution of the Voices of Singapore Festival (VOSF) and the Voices of Singapore (VOS) organisation that evolved from it. The principal question of how the festival and organisation have been shaped by my multifaceted artistic practice as a musician, artistic director, composer, conductor and arts leader is examined through personal writing and reflection, informed by relevant literature. Beyond autoethnography, this study also employs the principles of action research informed by focus groups discussions comprised of festival participants. Throughout this research, VOSF grew and evolved from a festival to a nationwide singing organisation known as VOS—a journey that this thesis also details.