This chapter explores the ways in which young planners' views of planning institutions and planning professions are influenced by their encounters with the contradictory contexts of real-world planning. It discusses based on the sources as listed, through the personal experiences of one young planner, Kaisa Yli-Jama. The chapter shows that her accounts are indicative of, and give voice to, the wider experience of young planners in the field. What is it like to be a young planner in Finland? Thirty-two-year-old Kaisa Yli-Jama provides one answer in a piece she wrote for the Finnish Journal of Urban Studies on her experiences working in a large municipal planning office. The chapter argues that while it is necessary to understand where the pathologies originate from at the system level, overcoming these pathologies takes more than just an understanding of the societal context of planning.