This chapter focuses on the extent to which students are prepared in planning school to deal with the potential mismatches that arise between the substance of planning and the contemporary context of urban development, and furthermore, the coping strategies to which they are exposed. It also focuses on the planning profession from the perspective of students rather than from that of educators or employers. The chapter discuses more about how the planners of the future are shaped during their education by focusing on three themes: storytelling, the role of the planner, and critical thinking. In the Swedish context, planning education can be more or less design-oriented, and is taught in social science departments as well as in engineering departments or schools of architecture. The confusion among students about who they are and what they know may consequently emanate from the clash between a strong image of 'the professed role' and a more diverse professional reality.