This chapter delves into the complexities of institutionalized education and its impact on society, as viewed through the lens of Ivan Illich’s theories. The chapter begins by discussing how our overreliance on formal education systems has led to a diminished capacity for independent thought and learning. Illich’s concept of “vulgar learning” serves as a cautionary tale, warning that the absence of educational structures could lead to new forms of social control. The chapter explores Illich’s proposals for new political frameworks that focus on individual freedoms in learning, such as anti-discrimination measures based on competence rather than certification. It also discusses the need for a resource-rich environment to facilitate independent learning. The chapter then transitions into the realm of artificial intelligence, examining its potential to transform education and society. It discusses the ethical and societal implications of AI, including the risks of exacerbating existing inequities and the potential for widespread unemployment and social displacement. The chapter concludes by emphasizing the need for a balanced approach to AI development, incorporating both regulation and integration, to harness its benefits for the betterment of humanity.