Summary: Self-managed shelters claim that participants who have been homeless are better able to run a shelter than regular providers. Little research has investigated self-managed shelters. In this article, we have described the experiences of participants and peer workers with empowerment processes in Je Eigen Stek (Your own place, JES), a self-managed shelter, based on an eight-year qualitative responsive evaluation. Findings: We distinguish three clusters of individual experiences: (1) enthusiastic, (2) moderate to critical, and (3) negative, respectively, associated with decreasing engagement with social life in and management of JES. Those not engaged can still benefit materially and from the freedom of choice JES offers, which is generally appreciated. Empowerment provides a useful framework and JES in turn offers new insights into the dialectical nature of empowerment. Empowerment consists of freedom of choice and capacity development and neither should be emphasized over the other. The emphasis in JES is on freedom of choice, which does not automatically lead to developing capacities. Social workers try to balance both aspects of empowerment. Applications: Our analysis shows how offering freedom of choice can contribute to empowerment, although social workers need to be aware that participants might opt not to work on capacity development.