A growing body of literature has demonstrated that the college preparation and admissions process is a powerful force in the lives of some high school students. However, mounting evidence illuminates unintended consequences of the college admission pressures on students. This study endeavored to gain an understanding of the lived experiences of adolescents as they navigate the competitive and achievement-oriented college-going culture. The participants' narratives described the ways these students accepted, struggled with, challenged, and resisted dominant cultural messages as they prepared for college. The insights gained from the participants' portraits have implications for school counseling practice and future research.