This 11-year longitudinal study investigates the effects of vocational interest congruence, personality, and alternative options on college-to-career trajectories over time. Theories of vocational interest suggests that these constructs will have an influence on choices and attitudes about major and job. However, sparse research has investigated the determinant factors of career trajectories over time - from academic outcomes experienced by graduating seniors to future job outcomes for workers up to seven years post-graduation. The study tracks a cohort of students (N = 158) from 2007 to 2018 examining their vocational interest, matriculation major interest, degree, first job after graduation, and current job data. The study results showed that an objective measure of fit was more predictive of academic outcomes and a perceived measure of fit was more predictive of job outcomes. Additionally, there was an increase in fit from people’s first job to their current job, and people with a greater number of career changes had a greater increase in fit over time. These findings illustrate that people’s perception of fit is still changeable and unstable early in college, but that it solidifies with time and experience, and that people tend to find jobs with better fit over time.