Four diverse English-speaking Montreal public school students who self-identify as being disengaged with their schooling experience constructed photo essays telling the story of their disengagement in school. Analyzed in conjunction with photo-elicitation interviews and fieldnotes, we find that youth are involved in a struggle against systemic unfairness as they enact and embody their own life goals and identities, which are firmly grounded in future visions of well-being, while rooted in educational histories of failure and unfairness. Responding to calls by some engagement researchers for social-ecological frames (Lawson & Lawson, 2013), this article re-theorizes engagement as being less about the individual, and more about the nestedness of the individual and school within an ecology shaped by social unfairness, namely, income inequality.