Career and Technical Student Organizations and Career and Technical Education programs in secondary education claim to prepare its students and members for post-secondary success. However, these claims are inherently difficult to study and quantify. By using a synthesis of the literature on emerging adulthood, self-directed learning, and self-leadership, this study explores the relationships between the presence of learner choice and readiness to engage in self-direction. Learners’ readiness to self-direct in learning was assessed using the SDLRS and analyzed using a comparative quantitative methods design based on involvement in a Career and Technical Student Organization or completion of a Career and Technical Education pathway. This study also explores the roles that student leadership and gender may play in self-directedness. The results of this study are intended to bring about a deeper understanding of the relationship between self-directed learning practices in CTE and CTSOs to aid advisors and leaders in optimizing the organization's operation and implementation of opportunities toward postsecondary success.