Drawing upon the thought of Eric Fromm, this paper argues that efforts to understand and counter behaviour that causes difficulties in education should begin in a critical and reflective engagement with both the conditions of human freedom and the character of educational institutions and society as a whole. Fromm’s critique of dominating ideas about good mental health within capitalistic societies is examined in relation to disablement and attention-deficient hyperactivity disorder. A study of a sixth-form college in the south of England elucidates connections between Fromm’s insights into social psychology and disablement as a process of oppression.