In Australia and the US, many young people exist in debilitating lives. For a range of reasons, they have experienced broken relationships with their schooling, challenging relationships with the law, and often brutal relationships within their family environments. These young people are typically identified as problematic and ‘deficit’ through the theory and practice drawn on by many of the people and institutions they are forced to engage with. Given that over 40 years of theories, practices, programs and strategies have had little impact on reducing the numbers of these young people, there seems to be a vital need to ‘respeak’ young people in vastly different ways. This chapter offers a way to reframe the current thinking and understandings of these young people. It draws on 40 semi-structured interviews with young people living in the extremes of disadvantage and the staff who worked with them, in Australia and the US. These interviews were conducted during an 18-month ethnographic study with Youth Off The Streets (YOTS) in Australia and two US Charter Schools. I argue that these young people’s actions are often simply a way of ‘speaking back’ to the dominating power that is embedded in their lives. By exploring this data through Lyng’s, extension of Goffman’s notion of “action”, concerning risk taking in extreme sports, I propose that a theorisation of edgeworking, is a more applicable way of theorising young people’s responses to difficult lives.