Across the globe, many countries are at a nexus of multiple crises. The COVID-19 pandemic, structural racism, the climate crisis, and a severe economic downturn have all converged. These crises have wreaked havoc on minoritized communities in particular. This moment requires imagination to write a different future -- to not return to the status quo. Imagination becomes crucial for fathoming a different world. Musicking -- the different ways of making music that include listening, performing, creating, and beyond -- may allow us to engage in such imagining. Musicking offers a vehicle for dreaming and provides a vision for the future. In this paper, I explore movements in education that inform this political moment including critical reconstructionism, abolitionism, and critical pedagogy from the perspectives of people who theorise these movements. Subsequently I consider the role the arts might play in imagining. I engage in particular the work of Bettina Love and Maxine Greene. Ultimately, I examine potential ways that different facets of musicking, including listening, performing, and creating may enable children and youth to engage in what I call the dual roles of imagination.