This introspective and reflective idea brief explores the nature of the gap between what leadership educators hope to accomplish in the lives of students and what actually happens. The author draws upon 30 years of leadership education and a wealth of interactions with leadership educators and student leaders across North America. Five latent barriers to successful leadership education are presented for further discussion, debate, and application. These include hidden narratives, limitations of past leadership styles, student leader collapse, the attached umbilical cord, and the price of being a student leader. The reader is encouraged to engage in supportive dialogue with colleagues to address difficult questions and cultural obstacles to our work.