This article is taken from the author’s presidential address at the annual meeting of the Pacific Coast Branch of the American Historical Association, delivered on August 3, 2018. It explores the structural and personal sources of Japan’s surprisingly successful transition, in the decades around 1600, to an urban-centered market economy. Particular attention is devoted to artistic innovation as one indicator of the “climate of change” that enabled radical new choices in a society loosed from the authority of old regimes.