Doing systems work brings us to the limits of language as few human activities do. It uniquely joins the empathetic reading of human motivations, desires, and needs with a creative envisioning of new socio-technical arrangements in hopes of transforming the world. It is at once humble and audacious, finely detailed and grandly epic. Fundamental notions of goodness, truth, and beauty are relied upon in ways that forever challenge our ability to justify.This paper sets five voices in dialogue to explore the limits of language in doing system work. The five voices, C. West Churchman, Sir Geoffrey Vickers, Richard Rorty, Bruno Latour, and Pierre Bourdieu, represent a wide range of 20^th century traditions in system thinking, philosophy, sociology of technology, and social theory. Their dialogue is animated, conflictual, melodic, and unnerving, much like system work itself. Instead of a consensus on language, limits, or systems, they provide us a landscape and some paths for future exploration in our own dialogues.