This qualitative study examines both the cognitive and emotional development of design students as they transition from high school to the first year of design school. The study investigates this through the lenses of multiple constituents, including design school undergraduates, educators, directors, scholars, and current program structures. This study also considers the future of design education and what kind of experience might best prepare students for their transition into design school. Through a literature review, interviews, focus groups, survey, and the evolving industry, the transitional experience is contextualized. This study aims to provide both pre-college and undergraduate programs, educators, and directors with information for how they can improve their students’ transition into undergraduate design programs.