Research on family homelessness is advancing and often focuses on homeless mothers; yet we know little about their life experiences from their unique perspectives. This gap is addressed in the present study, which involved weekly group meetings during a 3-month period with seven single mothers who were homeless and living in transitional housing. Each week, participants shared stories from their past, current experiences, and future goals, which were recorded using researcher field notes. Phenomenological analysis was used to understand the essence of their shared experiences, and resulting themes indicate participants' past family relationships, particularly with a maternal figure, systemically affected their current family situations and adult relationships. Family-of-origin adversities and related adult relational difficulties also influenced each woman's sense of identity, ability to create and maintain healthy boundaries, as well as parenting perspectives and behaviors. Implications of these findings for researchers, practitioners, and policymakers are discussed. Results suggest that residential transitional programs focusing on development of self might be key resources for permanent transitions out of homelessness, but additional research is needed to empirically verify the long-term impact of such programs.