In a hypercompetitive academic culture propelled by acceptance into the nation's prestigious colleges and universities, there has been a growing number of secondary students who are fixated on pursuing advanced coursework. This phenomenon of students beginning a sequence of advanced mathematics courses at the middle school level so they can take more Advanced Placement (AP) courses in high school is called fast-tracking. However, there is an underlying problem affiliated with advanced courses in that it may manifest a hypercompetitive culture, which can result in undue stress and anxiety due to the pressures to succeed. In the focal school district, nearly 75% of 8th grade students fast-track in math. Utilizing Bronfenbrenner's (1979) "Bioecological Theory of Development" as a theoretical framework, this qualitative, ethnographic case study explored and identified the interlocking factors at the macro-, exo-, meso-, and micro- levels that influence students' choices to skip grade levels and self-track into advanced mathematics courses. Through the multi-dimensional analysis of individual and focus group interviews with 14 Asian and White students, two tenured teachers, three guidance counselors, and three administrators, the overarching finding for why students decided to fast-track in middle school math was for the objective of "looking good" for college, parents, and peers. Students fast-track for others and not necessarily for themselves, with some students feeling conflicted about their choices by admitting that they do not want to pursue Science, Technology, Engineering, Mathematics (STEM) fields and that they are sacrificing their well-being by filling their lunch period with an additional class or feeling stressed to fit in. In particular, Asian students felt pressure from parents to fast-track and do well in school, and for some, live up to the model minority stereotype. This research has important implications for students, parents, teachers, and guidance counselors regarding the positive and negative outcomes of the fast-tracking phenomenon. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]