This is a creative work of psychogeography, theory and autoethnography, which offers a unique insight into the personal world of music-meaning-making, working-class heritage, and the transformation of identity through a life-long obsession with aeroplanes and flight. Combined, these aspects articulate a progressive journey of transformation through informal learning and higher education, exploring personal progression through the narrative techniques of life-writing and innovative theory work. The book provides readers with a sequence of intimate and informative provocations through memory and imagination. Shaped around the experience of a car journey (as part of a commute to work), the book invites readers to explore a chaos of memories – provoked by a range of songs encountered as part of a playlist, which emerge as part of a compelling analysis of music, the symbolism of flight, and educative hope. Through a combination of storytelling and scholarly analysis, the book utilises cultural theory, process philosophy, and biography and invites readers to adapt and incorporate the concepts and psychogeographic techniques for creative student engagements as part of curricular and assessment practices.