Occupational sex segregation persists in part due to cultural beliefs in the existence of gender differences in skills. This article explores potential resistance to the gender-typical aspirations and outcomes that re-create occupational sex segregation: cognitive skills in gender-atypical areas (i.e., math skills for women and verbal skills for men) and beliefs about women’s prioritization of family over paid work. Using the National Longitudinal Survey of Youth, 1979 cohort, I find that individuals with skills in areas considered gender atypical have less traditional occupational aspirations and outcomes than their otherwise-similar counterparts. This process varies by gender, however. The results reflect the differential valuation of math and verbal skills. I conclude that programs designed to encourage women to pursue gender-atypical occupations that align with their gender-atypical skills are focusing on the least resistant group.