Contemporary education has become increasingly complicit with neoliberal ideals; it is subjugated to economic criteria. Following meritocratic ideals it cements the privileges of socio-economic class structure. Yet, because of its utterly relevant position in the reproduction and naturalisation of ideology, pedagogy might offer the opportunity to prise open new horizons of possibility. In order to spark this counter-hegemonic endeavour and to re-direct pedagogical practice towards its immanently critical aim, this paper asks about the possibility of incorporating psychoanalytic approaches of Critical Theorist Erich Fromm into a contemporary analysis of (post-)modernity, as emblematically virulent in Zygmunt Bauman’s influential concept of liquid modernity. We particularly stress the importance of affective and vulnerable subjectivities and argue in favour of an education that seeks to incorporate them into its practice and theoretical reflection. Bildung, then, forms the bedrock upon which new forms of social life and solidarity can be erected and which strives for re-imagining social relations of acceptance, inclusion, and humanity. Consequently, this form of Bildung has to strive for autonomy and reflect upon its own potential enmeshment in complicit relations in order to be capable of establishing practices of freedom and transgression.