Hand drawing is arguably architecture's oldest 'technology'. As artificial intelligence permeates every aspect of practice, the profession finds itself again at a significant technology threshold. The ability to control intent in our work becomes increasingly difficult as technology becomes more expedient and autonomous. What does that mean to architectural illustration? What lessons from hand drawing can we take with us ‘across the threshold’ to assure that craft and intent survive as technology evolves? Using hand drawn works spanning the career of architect and illustrator Wesley L. Page FAIA, Strategic Drawing outlines an intentional, purpose-based approach to the initial thought processes and decisions involved in illustrating architecture–whether digitally or by hand–and how understanding the overlap of drawing, design, and storytelling can amplify the effectiveness of architectural illustration. This presentation offers a holistic way of both thinking about and executing architectural imagery—not just drawing to illustrate, but drawing to deliver a more targeted, layered, and story-driven outcome–timeless concepts for any technology.