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This paper documents within-class variation in high-SES students’ aspirations and achievement-orientation at the point of transition to higher education. Previous research suggests that high-SES students are socialized in a family- and class-environment that leads them to pursue admissions to high-status post-secondary institutions and develop an entrepreneurial and strategic attitude toward school in an effort to build a “competitive” resume for college. In this paper, I report evidence from a qualitative study of college-bound upper-middle-class high school students that complicates this dominant conception. Drawing on data collected across three high-performing suburban high schools in the American Northeast, I find that even though many upper-middle-class adolescents do in fact hold ambitious post-secondary aspirations and compete for admissions to high-status colleges and universities, some students display a much more reserved attitude toward college. These students maintain more moderate post-secondary aspirations than their peers and deliberately curtail, rather than maximize, their efforts to compete for admissions to top-tier colleges and universities. My analysis indicates that these within-class differences in students’ attitudes toward selective college admissions are the product of a combination of factors, including students’ academic high school environment or contingent events affecting members of their family or friends. These findings contribute to existing scholarship by shedding light on intra-class differences in high-SES students’ attitudes toward educational institutions and proposing several possible mechanisms that may cause such within-class variation.