This article stems from my doctoral research, which considers moral contestation relating to education in the Eastern Cape Province of South Africa. Overall, I outline a case for working with young people: addressing asymmetrical institutional and generational relations of power in order to enrich the knowledge generated by research. My focus is a project entitled My Future, which involved approximately forty learners drawing diagrams and using disposable cameras to produce representations of their moral judgements. Notable distinctions between data gathered during two stages of fieldwork, of differing durations, are analysed with reference to my relations with interlocutors and related institutionalised and public discourses of morality. Using the concept of trust, which is established during exchanges of mutually beneficial sociality, I argue that how we understand others depends upon what they expect from us and what we expect of them.