This chapter considers experiences of the move from planning education to planning practice in the context of England in the late 1990s and the 2000s. Specifically, it focuses on the transition from student to planner of a small group of young planners who graduated in the period from around 1997 to 2007. The respondents reported a diverse range of challenges face when transitioning from being a planning student to practicing planner. The respondents were also asked to comment on any changes in the status of planning and planners which they had witnessed occurring, or had felt, since commencing their careers as practicing planners. The chapter also focuses on in-depth interviews with a small number of planning graduates from Master's level student cohorts at a northern English university between 1997 and 2006 who commenced their professional planning careers during the first decade of the 21st century.