This chapter explores the ways in which contemporary conditions as colonial aftermath are inextricably linked to the urgency in reimagining, creatively noting and performing for a future. Here the author explores Caribbean artworks created as commentary with intended agency, as contributions to the development of a complex practice and understanding of decolonialization. I propose that it is significantly through knowledge of artmaking by practitioners living, working and with lived experiences and histories of the Global South, that we are better able to engage with and adopt the practice that 'speaks' back to European centres of capital and empire. Texts including those by Françoise Vergès, Sylvia Wynter, Denise Ferreira da Silva and artworks by Christopher Cozier, Shannon Alonzo, Rodell Warner and Nicole Awai, Kei Miller amongst others are perceived as a relentless platform of critical engagement, creativity and intervention. The author explores the embeddedness of slow violence, contiguity, collective approaches and sustainability in the artmaking, to expose the precarity of the present political climate and cultural moments, creating the space of imagining differently configured living.