Drawing on the aggregated story of 15 early-career urban planners who work in various settings, this chapter reveals their search for a place in the planning practice and also their views on the role of urban planning in shaping the built environment. It attempts to shed some light on the challenges encountered and insights gained by young planners as they work to climb the career ladder. The urban planning profession in America and all over the world, however, faces challenges that can change the requirements of planning practice and the potential areas of planning activity. These challenges include political pressures, inequities, environmental challenges, fiscal troubles, and harnessing emerging technologies. The scope and breadth of planning education has been restructured since the 1960s with strong foundation in the social sciences, especially geography, sociology, and economics. The biggest appeal of planning was its domain – the city and its contribution to the quality of life of residents.