This chapter engages with Michael’s work on ’specialisation’ and different ‘futures’ of education by applying perspectives, not from within sociology but from without through the theoretical legacies of the Italian Marxist, Antonio Gramsci. Dimensions of his political theory – hegemony, common sense/good sense and the role of intellectuals – are reworked in the conditions of the 21st century to create the concept of the ‘organic intellect’. This multi-dimensional framework, comprising ‘connective specialisation’ and ‘ethico-political consciousness’, is used to reflect on Michael’s approach to the ‘curriculum of the future’ – known in his later work as Future 3. From the perspective of the Organic Intellect, the latter part of the chapter outlines six challenges to encourage Michael to move beyond some of the constraints of his later work. In particular, I argue that Michael’s current focus on the role of subject specialization could be enriched by revisiting his earlier concept of connective specialization that has new meaning due to the tensions between the ‘verticalities’ of neoliberal economic and political life and the ‘horizonalities’ of emergent radical civil society. The chapter concludes by suggesting that the six challenges constitute an invitation to Michael to move from deep within sociology towards its boundaries and to engage with the world of modern political economy – a shift that could open up his fourth intellectual period.