This chapter explores specific examples in architecture and art that provide opportunities where down becomes up while we negotiate the space between the two. The examples include the Narcissus character of Heinrich von Kleist’s marionette theater story, the floor of the Kogod courtyard at the National Portrait Gallery (Washington, DC), Ai Wei Wei’s Surveillance Zone and Richard Wilson’s 20:50 installation of oil and its reflections. These spaces are unexpectedly given to us while enriching our existence between floors and ceilings as places for dreams. It is here that the unexpected and awry occur as one’s perceptions appear at the edge of vision or is captured above, below, behind. An embodiment of being simultaneously unaware yet knowledgeable of our bodies and our surroundings, we experience the Umwelt with a form of Einfühlung through experiential empathy training. Part empathy, the sense of Umwelt might be key to our ability to imagine the edges of our designs with more intimate awareness. The edges may hijack or completely transform the work through disturbance and transformation.