As automation increases and single-skill set jobs become non-existent, employees can no longer only possess the technical knowledge of their industry but must also be well versed in a variety of essential skills that artificial intelligence cannot acquire. It is evident from the research that the United States’ traditional approach to teaching and learning has not kept up with the demands of the changing labor market because young adults are graduating from high school lacking the 21st-century skills needed for contemporary careers. High school educators can develop these skills within students by implementing community-based learning (CBL) activities into the curriculum. CBL, a form of experiential learning, provides students with opportunities to simultaneously develop academic skills, 21st-century skills, and communities. To transition from traditional learning to CBL, it is critical to understand the barriers to implementation. In this qualitative phenomenological study, semi-structured interviews were conducted with 10 New York City public high school teachers to answer the question, what barriers prevent New York City public high school teachers from implementing community-based learning into the curriculum? This study yielded 88 unique responses, leading to 99 primary, secondary, and tertiary sets of themes. From the collected data, themes of lacking and needing support and knowledge emerged for teachers, administrators, students, community partners, and other stakeholders. Strategic planning was recommended to provide all stakeholders with the support and knowledge needed to effectively implement CBL into the curriculum.