The overall goal of this study was to gain insight into the experiences of urban Aboriginal youth who were participating in Aboriginal youth organizations in Vancouver, British Columbia. I begin by examining the literature on Aboriginal youth within the larger context of mainstream society and the urban environment in order to highlight the role that current and historical structural policies have played in their lives. I then trace and critique the positive youth development movement, and examine the various wholistic models of Aboriginal education that have been applied to mainstream and Aboriginal community- based settings. An Indigenous wholistic framework that incorporates an intergenerational methodology is used to examine the two research questions. A sharing circle workshop and open ended interviews with youth and an Elder from the urban Aboriginal community were chosen for the methods. I have also interwoven key teachings that I have learned from Raven (the trickster) who has traveled with me throughout this journey and has significantly shaped this research story.