Minimal existing research reflects the experiences of homeless youth, the impact of those experiences on the physical and psychological health of this population, and their ability to achieve expected developmental milestones. Few public services are designed for homeless adolescents. The qualitative, phenomenological study examined the challenges that impact these youth and how these difficulties relate to their psychosocial development. Using non-random, purposive sampling, 15 participants, who were currently homeless or who had been homeless between the ages of 16 and 23, were selected. Recruitment was done through flyers placed in mental health and teen drop-in centers, the local Homeless Collaborative, as well as shelters, libraries, and public service agencies. Flyers were also distributed on the street. Participants were asked to complete a self-administered survey to obtain demographic information and to establish a homeless profile. Each person participated in an unstructured interview, using open-end questions. This allowed the participants to concentrate on their own experiences and tell them in their own words. Interviews took place in settings of the participants' choices. Data was analyzed using a simple Q-sort method. The results revealed that homeless adolescents have experienced trauma, leave home due to abuse, neglect, or sometimes because of their own behavior. Foster care or other out of home placements were risk factors for homelessness. Normal developmental milestones of adolescence were impeded. Homeless teens had disconnected from family and from society, but showed resiliency and determination to overcome barriers and to survive homelessness.