In this study, I examine the pilot year of an alternative learning environment in which I, as a practitioner, explored the possibilities for transforming learning for a small class of Grade 11 and 12 students. Drawing on a pedagogy of care, a constructivist model of learning and a student-centered approach to learning, the students and I negotiated new curriculum, combining regular classroom courses with courses constructed by their own learning interests. In this case study, a rhizomatic analysis of student and practitioner data, collected both during and after students’ graduation from high school, showed that students were highly engaged with learning when guided by their personal interests. In the study, I also found, however, that students struggled to fully embrace the potential of their own interests, held back by the ambiguity of self study and the clear metrics of the regular school system to which they were accustomed. As practitioner, I struggled to meet the demands of the prescribed curriculum and those of the curriculum that constantly evolved and changed according to students’ interests. The study also speaks to the tensions in defining the role of a teacher in this alternative learning environment. In conclusion, I suggest we seek to make possible an alternative high school learning environment that more closely resembles free schooling (i.e., learn what you want, where and when you want) within a public school that would, combined with a traditional course of study, meet the provincial criteria for graduation accreditation.