I explore some of the challenges I have faced as a public anthropologist who fulfills multiple roles as researcher, staff member, and volunteer at a prison reentry organization. I discuss the strategies I used to establish my research agenda with the reentry program, the ethical challenges I face working as an anthropologist and as a staff member, and the benefits of working with an organization. This article may prove useful for students who are in the planning stages of research projects, or for anthropologists considering the rewards and challenges of working with a nonprofit organization.