Despite a rapidly changing labor market, little is known about how youth’s career goals correspond to projections about the future of work. This research examined the career aspirations of 3,367 adolescents (age 13–18 years) from 42 U.S. states. We conducted a large-scale coding effort using the Occupational Information Network (O*NET) to compile the vocational interests, educational requirements, and automation risk levels of career aspirations. Results revealed that most adolescents aspired to careers with low potential for automation. However, there were large discrepancies between the sample’s aspirations and the types of jobs available when the sample entered the workforce. Almost 50% of adolescents aspired to either an investigative or artistic career, which together account for only 8% of the U.S. labor market. There were also notable trends across age and gender, such that aspirations were more gendered among younger adolescents, whereas older adolescents appeared less influenced by gender stereotypes. Overall, findings indicate important discrepancies between young people’s dream jobs and employment realities. We discuss how lofty career aspirations can have both positive and negative effects, and we present implications for career theories and workforce development initiatives aimed at promoting a more dynamic future workforce.