This chapter examines some important ambiguities and tensions within James Hillman's ideas about the built environment and the psychological value of architecture both in and of itself, and to the organic forms of the natural world. Archetypal psychology is a school of thought that is derived in part from the analytical psychology of C. G. Jung, which in turn found influence in the psychoanalytic approach of Sigmund Freud. A close reading of Hillman's writings suggests that buildings are not problematic in their own right, but can be veritable sites for psyche. The problem is that they have ignored aesthetic considerations within their architectural design, and prioritise instead rationalised constraints, which seek to impress the ego's desire for order, with their emphasis on functionality, cost-efficiency, shallow prettiness, vast heights, and so on. Hillman's dislike for towers and tower blocks falls readily within this category.