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A wave of technological change in the first decades of the twenty-first century is prefiguring a fundamental restructuring of society. Key among the driving forces behind such change are powerful technologies with the potential to exert major transformations on a range of human activities and, crucially, to do so without direct human intervention. The technologies collectively referred to as Artificial Intelligence, or AI represent a productive lens through which to investigate two interrelated transformations: the emergence of self-driving cars and the coming shifts in education. This is in particular because AI’s versatility has led it to be directly applied (and increasingly valued) both in new automated driving technologies, and in the development of new forms of instruction. From the educational perspective, this means that the same technologies that are transforming workforce conditions are also reshaping – directly and indirectly – the approaches, objectives, and experiences of students and educational institutions. This chapter lays out how these twin transformations are likely to play out in the case of the automotive industry and the educational pathways of two occupations closely associated with it: automotive engineers and repair technicians. Two key arguments underpin this examination. First, educational programs for these two occupations, (and beyond) should be broadened to develop versatility and adaptability through tools and perspectives that allow people to move vertically within organizations and laterally across industries in the face of rapid technological change. Second, these educational programs must explicitly tackle AI and the coming technological revolution from a variety of dimensions that connect technical skills acquisition with the context on how these technologies are incorporated in society, how they are governed, and what are the various responses to them. This will allow students and professionals to navigate a rapidly changing labor landscape better while endowing them with the vocabulary to actively participate in the debates that shape its construction.