This chapter makes the case for transformative career education in schools and colleges by drawing on the links that can be made between career development theory and transformative learning theory. Transformative career education has the power to make profound and lasting differences to young people’s lives. It is not well researched, although there is considerable evidence that career education can have small to moderate impacts often for modest inputs. The scope and value of career education in the curriculum are often contested. This chapter explores the potential to achieve radical and progressive outcomes from more ambitious programmes of career education. It explores the potential benefits for individuals, the economy, and society in relation to how people live, learn, and work in rapidly changing and unpredictable times. It discusses how career education can be embedded in the curriculum and explores the supporting structures, systems, and technologies that schools and colleges can harness to facilitate transformative career education. Last, the chapter describes effective pedagogical approaches to teaching, learning, and assessment that can assist learners in transforming their self-understanding, their relation to others, their potential to act, and their worldview.