This chapter begins by illustrating the role of children in philosophy, and how childhood may impact philosophy, by turning to the work of Stanley Cavell. In particular this chapter focuses on his idea of philosophy as a confrontation with our culture’s criteria, but read in the light of Pierre Hadot’s understanding of philosophy as a way of life. It goes on to consider how the philosophy for children movement has developed through three generations of thought and practice. To illustrate how these generations have emerged, the chapter surveys differing views of the use of picture books in children’s philosophizing and philosophy. Going on from the third generation’s criticism of how the philosophy for children movement’s use of picture books has been insufficiently aware of its own assumptions, limits, and borders, the chapter concludes by showing that the critical moves from one generation to another in the field itself can be seen as a philosophical way of life, a way of life that involves philosophy for children confronting its own criteria, by emphasizing and questioning not only the boundaries of the content but also of the places where philosophy with children happens.