This article discusses a selection of works by filmmaker Mark Cousins, arguably an under-examined figure with regard to film studies. It is contended that Cousins has fashioned a distinctive approach to the essay film. Adopting a “psychogeographical” perspective, this article will analyse What is this Film Called Love? (2012), Here Be Dragons (2013), and Life May Be (co-directed by Mania Akbari, 2014), all of which feature Cousins as a central figure and active participant on screen. In essence, each film is a documented dérive, a practice pioneered and developed by the Situationist International that locates intersections between specific locations and their psychological impact on the “self”. It is posited that Cousins “Do-It-Yourself” practices rupture many conventions of filmmaking, producing a singular body of work in contemporary cinema.