Formal education has arguably never been more important to young people’s life chances and, on a global scale, more young people than ever receive formal education. Yet, despite this, formal education competes with opportunities to learn through informal means (amplified by the use of digital communication technologies), and, for individuals, the ways in which educational knowledge and qualifications are useful in gaining secure employment are obscure. As formal educational provision expands to meet the ever-increasing demand for educational qualifications globally, education is also an increasingly ‘autonomous’ domain, with tenuous links to other domains, including work. These developments form the backdrop to this discussion of the challenges of educating for late modernity. In late modernity, young people bear the brunt of the changing relationship between education and work. They are required to navigate their way in a context where institutional pathways and structures are not able to provide certainty or predictability. This poses significant challenges for the design of a new generation of educational systems by governments. Many of the basic assumptions and structures on which the mass education (secondary education) is based have become increasingly less relevant in a post-industrial era in which tertiary education is the new mass education sector. In this chapter I argue that new realities that include the emergence of new economies in which high and long-term unemployment for young people are the norm create challenges for the design of the expanding new mass education systems. The pace of change and the increasingly precarious nature of labour markets inevitably places the onus on individual young people to navigate the increasing chasm between education and work. This chapter argues that this makes identity work more central to formal education, because of the kinds of ongoing decision-making and reflexive biographical work that young people need to do to survive. It also places pressure on compulsory educational institutions to break with traditions that use age as an organisational principle, and that see young people as decision-makers in the future, not in the present. But the real challenge faced by educational institutions in educating for modernity is the wider question of how societies value and reward education by creating sustaining, meaningful work that values and rewards young people’s knowledge and skills.