John Dewey was inspired by what he termed "the miracle of shared experience and shared communication." His faith in the power of individuals working in democratic association also included warnings of a darker side, the "monstrosities" that individuals can become when they live and work in isolation from others. In this father-son letter exchange, two educators, one mid-career and the other with the perspective of several decades, consider the contemporary relevance of Dewey's teachings, as well as the failings of the progressive education story. At the heart of this critique is a challenge to teachers and students to create and embrace powerful identity narratives--individual and collective--to anchor our work in schools and enhance our maturation as a society.