Academics generate circles of thought. Their preferred modes of conceptualization—the intellectual constructions in circulation within academic discourse at a given moment—readily pass across disciplinary boundaries. During the past two centuries, philosophical critique and the criticism of art have a history of informing each other (Robert Pippin's After the Beautiful is a current example of the syndrome). Although the concepts of societal “modernism” and “modernist” art exhibit variation, both are hybrids of philosophical (linguistic) and aesthetic (sensory) indeterminacies. Rather than fretting over interpretive instability, we are inured to conceptual change and indeterminacy in every domain. But our world becomes circular—ironically, quite stable—when we direct logical reasoning to illuminate its aesthetic double (as Hegel did) or direct art to illuminate its philosophical double (as Heidegger did). Inattentive to anything outside the circle, we imagine our intellectual progress, for circularity is self-confirming. Our illusory progress accompanies a spotty record of predicting actual change. With respect to where our philosophical concepts of change have led us, chance is a better guide to our immediate intellectual and aesthetic preferences, even though it presumes no explanation of our comprehensive cultural formation. Although never right, chance has the advantage of never being wrong.