This article explores the idea of the worthwhile risk of education, as necessarily involving a transition from one of initiation and risk to that of co-belonging. We commence by considering a contention that while education is a human activity whereby an individual might be initiated into various encounters, the potential experience thereof is as yet un-encountered and strange, and only to be imagined. Following on the idea of education as the subject of imagination--that is, not knowing what to expect beforehand, and thereby being prepared to take some risk--we turn our attention to education as necessarily being accompanied by risk. In this sense, if an individual takes a risk to experience something new and strange, the possibility exists that she could disrupt what she is about to encounter, because engaging with the other, is an activity associated with taking a risk towards increasing imagination. In this way, initiation into something new and strange seems commensurate with the act of taking risks which could involve disruption. By building on ideas of education as a worthwhile risk that engages people deliberatively, we extend our argument to that of education as an initiation into a co-belonging, which recognises people's ability to both deliberate, and not to deliberate.