In an effort to understand and improve interactions between homeless young adults and the nonprofit organizations that serve them, I engaged in a long-term, qualitative, participatory action project. My project involved input from homeless young adults, nonprofit organizations, volunteers/staff, and communication scholarship. While taking a community-engaged, participatory, and qualitative approach, I focused on the interactions between youth and the organizations. Particularly, I drew on homeless young adult experiences to inform services and illuminate compassion within the context of the nonprofit organizations. In the end, this project extends the individual model of compassion to include presence, identifies potential ruptures in the process of compassion, and models compassionate dynamics in organizations. It also articulates a method I call pragmatic fieldwork, a qualitative and pragmatic approach to participatory action research. Each of these outcomes speaks to varied community interests, from theoretically nuancing scholarly models of compassion to informing policy in the interest of more effectively and compassionately serving homeless youth.