In this paper, I argue that current arrangements for school-to-work transitions support in England, now school-based, are designed to contribute towards ensuring the consent of the population for what I refer to as the 'state of insecurity' (Lorey, 2015): the neoliberal relationship between the individual and the state in which insecurity is promoted as freedom. Based on an analysis of policy, the paper argues that the government careers strategy for young people aims to contribute to shaping the precarious subjects which inhabit the state of insecurity, by encouraging them to internalise neoliberal values around freedom and individualism which accompany governmental precarisation. Drawing also on the work of Judith Butler (2011), I suggest that throughout the careers strategy, neoliberalism functions as performative or hegemonic norm which is cited to constitute notions of 'good' or 'normal' labour market arrangements, aspirations and selves. I suggest that this strategy is an example of Berlant's (2011) 'cruel optimism', which constitutes a fantasy of a 'good life' which is in fact likely to be unattainable to many young people, especially the more disadvantaged.