The purpose of this study was to evaluate the links between grades, psychological disengagement mechanisms (discounting evaluative feedback and devaluing school), and motivation among female students in traditional and non-traditional career paths. We predicted that the association between grades and discounting is affected by the importance of the academic subject (mathematics or language arts) in one's chosen career path. For example, we expected that poor grades in mathematics are more strongly connected with discounting among students in non-traditional career paths as compared to those in traditional ones. Moreover, we postulated that the relation between psychological disengagement mechanisms and motivation is modulated by the type of motivation (autonomous/non-autonomous) and one's career path. As such, a stronger connection between discounting and non-autonomous motivation was hypothesized among students engaged in non-traditional fields as compared to those in traditional ones. This study was conducted among 236 female high school students projecting a career in either traditional or non-traditional domains. Results of multi-sample path analysis provide evidence that the assessment of the indirect course from grades to motivation via psychological disengagement must consider grades in specific academic subjects, one's chosen career path and the source of motivation.