Work in the 21st century is often talked about in terms of constant change, heightened consumption, and freedom of choice. As these discourses align in mutual support, organizational participants are often positioned in a cycle of continued anxiety, consumption, and pursuit of perceived self-interests. As self-subordination and self-alienation emerge, organizational participants become increasingly disengaged and unresponsive to others. As a result, unhappiness at work is framed as an individual problem and hope for meaningful change fades. Hope is redeemed, however, in responsiveness to others and a willingness to participate in conversations that reclaim alternative meanings and reveal a horizon of possibilities for happiness and fulfillment at work. Inspired by Gadamer’s notion of genuine conversation as play(ful) interaction with others, the author finds hope for meaningful organizational change residing in responsive dialogue about discontent with work that expands possibilities, shapes new identities, and carries contemporary work life beyond interregnum.