People are homeless due to a complex series of factors. Evidence points to the association between homelessness and individual factors, including lack of education, mental illness, addictions, and poverty, and community factors such high unemployment. Yet within the current context of rapid economic growth and low unemployment in Calgary, Canada, homelessness is increasing. The purpose of this qualitative study was to better understand inner city homeless shelter residents and their needs within a context of rapid economic growth. This study is part of an ongoing research initiative formed through a partnership between The Salvation Army (TSA) and the University of Calgary to build a foundation for co-learning among the residents of TSA, inter-professional clinical teams, as well as university students and faculty to improve the health and well-being of the community. In-depth semi-structured interviews were conducted with ten TSA residents. Three patterns of resident behaviors and needs emerged: Stepping Stone, Embedded in the System, and Teetering on the Brink. The service implications of these patterns are discussed.