Today's western culture is characterized by high technology, time compression and a disconnection from the natural world (Dyment, O'Connell & Boyle, 2011; Louv, 2008; McQueen, 2010). What happens when a group of young adult, Generation Y students who are firmly embedded within this world, embark on a 6-day unassisted wilderness experience? This study begins by addressing generational theory to illuminate the differences between Generation Y and past generations, in order to identify the significance of Generation Y's experience of wilderness. The goal was to conceptualise a profile of the Generation Y student, subsequently developing a phenomenological research design investigating the essence of student transformation, as a result of a wilderness experience during a tertiary outdoor education subject in Australia. This study explores the response from Generation Y students, after being placed in a physically and mentally challenging, remote wilderness setting, devoid of the technology, networking and comforts of modern life as they know it. When divorced from the structural support of the everyday, and placed in an emotionally and physically taxing environment, one would imagine students would retreat to the security of the known world upon return. However, this qualitative study sheds new light on this phenomenon by revealing its antithesis. These students manifest a strong desire for a simpler life. What is the nature of the simpler life they envisage? What is its innate appeal? And what are the implications for those involved in outdoor/environmental education? Even if such a desire for a more primal existence were expressed, is it possible or probable, that this notion can be executed? Our research proposes that a necessary precursor for sustainable living and a deep attachment to the environment is for educators to provide experiences that strip back the superfluity of everyday life and introduce bare subsistence. This facilitates the transition into a heightened and more sensitive environmental ethic.