This article will propose that the achievement of a sustainable practice of everyday urban life is directly linked to the creative potential of the awkward space that emerges and punctures the cities we circulate. To tune in a holistic design of the urban landscape the article considers the city as a living system, a complex assembly of flows, structures, connections and owners. Awkward space emerges amongst the organisation of these parts and as such speaks of the city's synergy. Focusing on a space squeezed into existence between two buildings can draw attention to the design of the structures surrounding that space and open up questions concerning how the city is self-regulating itself as a whole so as to work towards designing more holi...