This chapter reports the search by a rural, professional theater company, never numbering more than a dozen members, for a cultural development paradigm that utilizes the inherent intellectual, emotional, spiritual, and material traditions and features of a community to encourage individual agency in support of community well-being. Based on its theatrical experiments, Roadside Theater eventually would claim that by sharing (performing) and examining one’s personal story in public settings marked by manifold perspectives, not only can one learn to speak for oneself from the depth of one’s own experience but one can learn to act in concert with others to achieve what is fair and just for the whole in which one resides. This assertion would be decades in gestation as the theater company’s artists and producers learned from hundreds of communities in its home region of Appalachia and across the United States.