The number of out-of-school youth in South Korea has been increasing recently, leading to a corresponding rise in school dropouts. Moreover, the importance of schools is also diminishing. However, schools are a national system designed to protect adolescents, and the collapse of this system is far from desirable. Despite this crisis, support policies for out-of-school youth remain overly simplistic. Current policies in South Korea regarding out-of-school youth are based on a fragmented understanding of these adolescents, focusing primarily on preventing dropouts. These policies fail to consider the various sociocultural backgrounds and contexts influencing adolescents’ decision to leave school. For example, “dropping out” and “academic discontinuation” are more problematic issues. The ultimate goal of this study is not only to prevent dropouts but also to assist adolescents in making the best decisions on the basis of a deep understanding of their identities. As a first step, a diary was designed to enhance self-understanding by fostering narrative identity formation. A user test was conducted to create a Q&A diary that can assist out-of-school youth, and a literature review was performed to design practical solutions for preventing dropouts. Ultimately, this paper proposes increasing the flexibility of the school system and strengthening self-understanding activities in career education as measures to prevent dropout.