This chapter examines two drawings by the architect-trained artist Saul Steinberg, arguing that they offer alternative modes of architectural representation. In a world of Building Information Modelling (BIM), with Computer Aided Design (CAD) and REVIT drawings and models that aspire to produce accurate and precise documents, Steinberg claims the imprecise territory of visual riddles through the even more imprecise tools of moods and atmospheres. Unlike modern notions of architectural drawings that assume the space of clarity and straightforward answers, Steinberg’s visual riddles take on the process of inversion where two apparently conflicting realities collapse into each other. Building upon ideas about boredom in the works of Xavier de Maistre, Siegfried Kracauer, Walter Benjamin and Gaston Bachelard, this chapter looks at Steinberg’s technique of folding boredom into daydreaming through the construction of boundaries, specific bodily postures and, deriving from the first two, a particular relationship of the self with the world.