Mainstream schooling, whether delivered by the government or the independent school sector, does not suit all young people. And yet most young people are effectively required to spend 12 years of their life in the formal education system. What happens when a more flexible alternative is offered to some secondary students – an alternative based on their interests, which supports the students to identify and consolidate their post-school plans, and fosters a more personal relationship with the teacher and a small group of students? In this paper we hear from an unusual group of students (and parents) – a cohort of secondary school students who moved from mainstream schooling into a Big Picture alternative. The Big Picture Academies/inspired schools are located at five government, independent and community based schools, in a low socio-economic, outer metropolitan region. Listening to the students talk about the reasons for their move out of the mainstream provides an important perspective on what students want from school. This in turn provides valuable information on student engagement and aspiration. Unique to this cohort is the diversity of reasons for turning to the Big Picture alternative. At one end of the spectrum are disaffected students who had disengaged and were expunged from mainstream education. At the other end of the spectrum are students who were still engaged and succeeding academically but wanting their education to be different. They identify structural, curricular and pedagogical aspects of traditional secondary schooling that make schooling unsatisfying for some students, and act as a major obstacle to learning for others. Educators can learn a lot from listening closely to what these students and their parents are fleeing from and turning towards. Informed by critical pedagogy this article engages the individualisation of responsibility for student disengagement and highlights the ways broader social, economic and cultural conditions meet the individual student to exclude some and privilege others.