In this chapter we use the Swedish example of entrepreneurial learning as a springboard to discuss the curious alliance between student-centered progressive education and the economization of education. In doing so we wish to highlight the effects of this alliance on the relationship between teaching and learning and, consequently, on the teacher-student relation. In order to do this, we will first examine the conditions for the economization of contemporary education, and its impact on the teacher-student relation. Having done so, we will turn to progressive education, examining the link between the ideal of student-centeredness and the economization of the role of the student, as well as looking closer at the contradictory figure of the entrepreneurial teacher. The chapter concludes with a discussion on some inherent tensions visible in entrepreneurial learning, being at once an effect of the economization of education and a pedagogical project firmly rooted in progressive ideals.