While alternative educational settings in Australia have expanded over the past two decades, there has been little formal research conducted into teacher perceptions of what it means to teach outside the mainstream. This paper outlines part of a longitudinal study involving the School for Student Leadership (SSL), an alternate educational setting in Victoria, Australia, which offers residential programs for Year 9 students. The SSL began operating in 2000 as the Alpine School situated at Dinner Plain and since then two further campuses have been added. A research partnership between Monash University Gippsland and the SSL began in 2001, with this component commencing in 2009 involving a mixed methods study consisting of both surveys and interviews. The focus of this paper is the qualitative findings resulting from interviews with 33 teachers across the 3 campuses. While a small body of literature relating to environmental and experiential education (Brown, 2006, Schartner, 2000, Simmons, 1988, Smith-Cabasto & Cavern, 2006) from a teaching perspective does exist, none really captures the breadth of the type of program offered through the SSL, which does not sit in isolation from broader educational, social and global discourses. While there is an ongoing debate about how we should educate young people there are some points of general agreement. One is that we live in a world of rapid global, technological and social change and education should equip young people to deal with these changes. This particular research provided an opportunity to seek teachers' perceptions about whether this goal was easier to achieve in a non-traditional setting. A particular focus was on participants' current perceptions about their role as 'teacher' and whether it differed depending on the setting. The findings provided interesting insights about the focus of the teachers that choose to become involved, with most suggesting that they were searching for more meaningful ways to connect their pedagogy and practice. They also felt that mainstream settings rarely provided opportunities for the development of substantive relationships with students. There was an acknowledgement that the alternate setting of the SSL did provide a greater opportunity for equipping students to deal with change but this also required teachers to respond differently, shifting the emphasis from content to context and from being a teacher to being an educator, facilitator or mentor.