This paper explores the boundaries between art, drawing, and architecture, viewing them as parts of an interconnected system rather than isolated disciplines. It examines how the authors’ practices in exhibition-making and speculative drawing reveal an undisciplined approach, described as a transdisciplinary method that problematises issues that professional architects encounter, broadening their ecology of practice. Here, drawings and buildings are part of a dynamic ontology that challenges linear progress from drawing to building and questions the static nature of both. The author’s full-scale inhabitable drawings are investigated as an example of undisciplining where drawings are in space, rather than of spaces. The paper examines an afterlife of speculative drawing through Encountering Drawing and how these drawings transition into Pac Studio’s professional architectural projects. The research demonstrates the significance of interpretive translation and the amplified design loop between drawings and buildings, showing that the journey from drawing to building is not linear. The conclusion posits that speculative drawings and undisciplined practices allow for the constant pushing of practice boundaries.