The aim of this chapter is to convey how educating through occupations works. This is supported by the connections Dewey sees between educative occupations and Kilpatrick’s sense of projects. Yet even though Kilpatrick was very successful with his project method, both Dewey and Kilpatrick experienced diffi culty communicating the more subtle aspects of their ideas to teachers who already held various positions on education aligned with one or more of the four curriculum ideologies. However, to comprehend educating through occupations a teacher must be aware of how to work with the occupations of others. This requires a phenomenological understanding of occupation as place of be-ing, as being-inthe-world, as care. In order to work positively with the occupations of others, Heidegger suggests that one needs to leap ahead of the others in a way that allows them to maintain their care, rather than leaping in for them and taking their care away. Teaching in this way (cognizant of occupation) involves understanding that occupations are constituted by both interest (phenomenological) and eff ort (pragmatic). Occupations are therefore phenomenological, as interest or care, as well as being pragmatic in the sense of the eff ort necessary to resolve problems impacting on the continuance of the occupation, via trial and error and regulated refl ection. In Dewey’s terms, teachers must therefore discover an occupation as the signifi cant interest or care (being-in-the-world) of those they are teaching, and they must arrange the occupational eff orts required as doing and knowing. In this way occupations are concerned with being, doing and knowing, a threefold refl ected in Dewey’s understanding of the trinity of the school as the life of the school, methods and subject matter.