This is a study of cognitive/image mapping exercises with houseless individuals, based on principles set forth by Kevin Lynch. Specifically, this study asked people to draw cognitive maps of their “daily lives” and then geospatially captured important information using Esri's ArcGIS Survey 123. Our research found 13 recurring patterns, including that the houseless often travel in regular routes throughout their day and parks and alleys are important. This work can ultimately help improve the design and planning for shelters and services.