We teach that the Enneagram symbol likely has Greek origins, given the Greeks’ development of mathematics and geometry, specifically the philosophy of Pythagoras and Plato’s use of geometric forms to describe and understand the Universe. But is the Enneagram symbol we know the same one transmitted by the Greeks? Might there be an earlier Greek version of Gurdjieff’s symbol, a proto-Enneagram? A geometric puzzle with third-century BCE Greek roots, known as the Stomachion of Archimedes, shares some intriguing similarities with the Enneagram, inviting investigation of the connections between them. In this highly visual presentation, we’ll become acquainted with the Stomachion and its complex history; see how the two symbols of wholeness map to each other using the Laws of One, Three, and Seven; and explore the provocative possibility that the Stomachion may be one in a line of geometric predecessors of Gurdjieff’s Enneagram, symbols of transformation, themselves transforming.