Abstract Bethesda Project (BP), a nonprofit organization located in Philadelphia, PA, provides shelter, housing, and programs to 2,000 chronically homeless men and women. Many of BP’s clients struggle with addiction and mental health issues that prohibit them from living self-sufficient lives. Challenges originating from fighting an under resourced battle with chronic homelessness make employees vulnerable to unrecovered stress and concurrent pessimistic thinking habits. In response to this, we recommend that BP adopt resilience training to support staff well-being. As a first initiative, we propose introducing the optimistic explanatory style and the ABC model of cognitive thinking to allow employees to develop flexible, accurate thinking about their work, the clients they serve, and the environment within which they work. When introduced in a systematic way on a site-by-site basis, BP can build a research-informed program tailored to its needs that enhances employee well-being.