Based on three-annual-wave data from 3,196 Chinese adolescents across the high school years (Mage = 15.55 years old, SD =.44; 52.8% girls at Wave 1, 10th grade), this study examined the curvilinear associations between adolescents’ perceived parental career expectation and their career adaptability and ambivalence and also tested the potential mediating role of adolescents’ internalizing problems in such associations. Results showed that, after controlling for a set of critical covariates and the baseline levels of outcome variables, there was an inverted U-shaped curvilinear association between adolescents’ perceived parental career expectation at Wave 1 and their career adaptability at Wave 3 via adolescent internalizing problems at Wave 2. Similarly, a U-shaped curvilinear association also was identified between adolescents’ perceived parental career expectation at Wave 1 and their career ambivalence at Wave 3 via their internalizing problems at Wave 2. These findings suggest that adolescents’ perceived parental career expectation may have “too-much-of-a-good-thing” effects on their career development. Implications for future research and practice were discussed.