Difficulty engenders innovation. Hard problems often bring out the best in us. How can we make drawing difficult? Computation brings some kind of difficulty to drawing. This difficulty is intertwined with form and its co-conspirator in the domain of drawing: depth. In architecture, we often assume that every drawing is the result of a projection of three-dimensional form onto a two-dimensional surface. In this chapter, we explore conceptions of depth that are just as rigorous, that allow more ambiguous relationships between objects in space and matter and machines. This approach to drawing uses projective representation as a way to speculate, interpret, analyze, and perceive, rather than a method to assert or communicate. Three exercises are dispersed throughout the chapter: automatic drawing, the depthy line, and the pursuit of flatness. The chapter concludes with attention to the form of ink and the drawn object.