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If learning is to be understood as a process of enskilment which is multidimensional, social and embodied (Ingold 2002: 37), it also includes the affective dimensions of experience. I would like to argue that becoming enskiled in the kind of learning done in the context of higher education, particularly anthropology, requires a certain familiarization with a sensation of frustration or challenge. In this article I explore how the process of enskilment in discomfort can be taught in a supportive relationship with a ‘good enough teacher’. I draw on Donald Winicott’s idea of a ‘good enough mother’ who supports child’s development through secure attachment and permitting the child to experience well dosed episodes of frustration, rather than doing everything for them.