This article draws on the past and present work of the Society of Philosophers in America, Inc. (sophia) to consider eight challenges for growing communities of philosophical conversation in ways that pragmatism encourages and calls for, in terms of engaged public philosophy. The essay then proposes ways of addressing the eight challenges with solutions or outlooks for overcoming or diminishing obstacles to engaged, public philosophical and conversational community-building. The author argues that it is vital especially for pragmatists, but also for philosophers in general, not only to appreciate and work to address these challenges, but also to affirmatively support and recognize the publicly conversational and community-building philosophy that is an implication of pragmatist philosophy and scholars’ supreme intellectual obligation.