In the last decade, Colorado has increased its efforts and requirements around postsecondary and workforce readiness through the implementation of Individual Career and Academic Plans (ICAP) in high schools (CDE, 2009; CDE, 2014; CDE, 2020). Although based on career development research, no studies have inquired as to the meaning students make through ICAP. Eight Colorado high school graduates were interviewed to examine the meaning students ascribe to their high school career development. The qualitative study identified four categories in which students assign meaning: Experiential Activities, Professional Skills, Significant Relationships, and Relevance. The article provides application recommendations for school counselors.