The purpose of this study was to investigate the relationship between cognitive flexibility, academic skills, educational trajectories, and career goals of college students with and without Attention Deficit Hyperactivity Disorder (ADHD). Participants completed a demographic questionnaire, objective and subjective measures of cognitive flexibility, and tests of academic achievement. Cognitive Flexibility predicted academic achievement; reading skills increased as subjective cognitive flexibility increased and as the tendency to perseverate (i.e., to stick with an ineffective strategy) on the Wisconsin Card Sorting Test decreased. Objective cognitive flexibility also predicted mathematical and writing skills. Although students with different college majors did not vary significantly in their cognitive flexibility, the interaction between cognitive flexibility and ADHD shared a significant relationship with career confidence. Our results expand on the literature examining cognitive flexibility and have implications for both academic and career planning, particularly for students who may struggle with attention.