This chapter invites reflections on how organising adjacent to everyday work can support the emergence of transformative ideas and sow seeds of organisational and societal change. It does so by connecting with the spatial aspects of prefigurative politics that manifest as the organising of processes, networks, and spaces in the present. This organising enables individuals to support one another in radical ways while embracing improvisation. Drawing on empirical material from a transdisciplinary research project, the chapter introduces a type of interstitial space termed as extra-work events that are organised adjacent to regular work activities. These spaces foster interaction among organisational actors and integrate visions of the future with organisational processes in less hierarchical settings allowing for the collective imagination to emerge as an active conceptual process. The imaginings are traced as a response to pressure or unsustainability in current conditions and are conceptualised as prefigurative impulses in organisational contexts.