Spirituality continues to exert a strong influence in people’s lives both in work and beyond. However, given that spirituality is often non-formalized and personal, we continue to know little about how moral reasoning is strategized. In this paper, we examine how Buddhist leader-practitioners interpret and operationalize a process of self-decentralization based upon Buddhist emptiness theory as a form of moral reasoning. We find that Buddhist leader-practitioners share a common understanding of a self-decentralized identity and operationalize self-decentralization through two practices in Buddhist philosophy—skillful means and the middle way—to foreground social outcomes. However, we also find that practitioners face tensions and challenges in moral reasoning relates to agency—the ‘re-centering’ of the self as an enlightened self and the use of karmic reasoning to justify (un)ethical behavior—and contextual constraints that lead to feelings of vulnerability and exclusion. We present a model that elaborates these processes and invite further research that examines novel approaches and dynamic interpretations of the self in moral reasoning.