The current study explores the efforts of one summer youth employment program to provide students with meaningful work experiences and the participants' perceptions of the meaningfulness of their work and its effect on their future orientation. Most of the students in the study were under the age of 18. The Youth Enrichment Services (YES) Summer Learn and Earn program provides students with summer enrichment, their first work experience, and meaningful opportunities to engage with work. The purpose of this study was to better understand YES participants' perceptions of the meaningfulness of their summer work experiences. A secondary goal was to investigate how participants' work experiences related to their future orientations. YES is a community-based organization in Pittsburgh that gives socially and economically disadvantaged youth opportunities to achieve success through its academic enrichment, alternative to detention, peer mentor certification, life skills, cultural enrichment, diversity awareness, workforce readiness, and wellness-based programming.