This paper utilises the first-person narrative to outline the development of my diasporic art practice across two racialised terrains. In so doing, this “thread” of lived experience situates the author as the principal actor in a story that weaves together, painting, aesthetics, art history, social movements, political figures and the construction and performance of cultural identity. Significantly, the narrative employs critical and selfreflexive methodologies in order to articulate the complexities of the creative process. This interrogative journey benefits the artist since she/he gains new awareness or metacognition concerning their own practice, which is both revealing and empowering. In addition, this new way of understanding aesthetics through research, reflection and writing in this instance the relationship between diasporic art and politics, allows for its wider dissemination as new knowledge.