The current study investigated links between students' level of perceived challenge (being over- or underchallenged) and students' career aspirations. We hypothesized indirect effects of over- and underchallenge on career aspirations via academic self-concept and academic trait boredom and tested our hypotheses in a sample of N = 662 Swiss eleventh grade students in the domains of German, French, and mathematics. Our results were consistent across all three domains and showed that being overchallenged had a negative impact on academic self-concept. Lower academic self-concept, in turn, was associated with decreased career aspirations. Being underchallenged enhanced academic self-concept, which was positively related to students' career aspirations. Further, both being over- and underchallenged enhanced students' domain-specific boredom experiences resulting in a decrease in their career aspirations. As such, the effect of being underchallenged was of particular importance as its influence on career aspirations via academic trait boredom was negative, whereas via academic self-concept there was a positive indirect effect.