Every program in architectural education begins with some kind of overt or tacit philosophical position that students are exposed to through the work. This chapter explores a beginning via creativity in harnessing the real; design pedagogy and assignments that foster a critical questioning inspired by phenomenology and speculative realism. Interrogating the real 2 in this way accomplishes a full cycle of method, with ideas passing from an assessment of operational grounds and media, moving through realm of speculation into modes of representation from sketch, to scaled, to prototypes, and full-scale, built real-izations beginning with hand-scale and moving to the body/proto-building scale. This dual transformational process of student as designer and iterative, increasingly complex work is initiated in the initial twenty-week term. This model assumes all students have a significant creative capacity that requires nurture and development. The iterative project sequence is an embodied, transcendental transaction from idea-as-thing, to representation-as-thing, to thing itself in relation to self and world—a vibrant ecological world. The foundational concept of embodied means work beyond thought and representation is requisite—the feel and sense that tacitly adds knowledge and seeds verification through engagement with the work and reflection on the work. The concept of interrogating the real rejects a tabula rasa and builds from an assumption of accessible, inductive, phenomenological inquiry based on revealing and unconcealing. While building from a rich givenness, the speculative aspect places all things, assemblages, relations, and boundaries as open for new findings. Speculative realism is a newer philosophic construct, where a flattened ontology considers ideas, formal organizing principles, representations, materials, and associated phenomena as nonhierarchical equals, all open to speculative alchemy. The text moves sequentially across twenty-two 185weeks, from fall to spring, describing grounding of student work and a pedagogical framework that produced the outcomes described and concluding with the philosophic background that informed the pedagogy. It is important to note that while philosophy has informed the pedagogy, the philosophy does not rationalize the work but rather begins an iterative set of reflections of the faculty upon the work over years of iterations and with multiple cohorts of students moved through the program.