Education, in its many forms, is an institution that mirrors the society around it, including its patterns of privilege and marginalization (Marx, et al., 2017). The purpose of this article is to provide a reflection of my experiences while working alongside four interns from an alternative school hired to work for an agricultural internship. I highlight my shifting perspectives through an autoethnography. Autoethnographic projects use selfhood, subjectivity, and personal experience ("auto") to describe, interpret, and represent ("graphy") beliefs, practices, and identities of a group or culture ("ethno"). (Adams and Herrmann 2020). After working with four interns, I was confronted with various privileges. Most notably, I learned to appreciate more on systemic factors that influenced these individuals. I also became more aware of my language use, which perpetuated a deficit model. Finally, I was challenged with my notion of delinquency behavior and community engagement.