After the introduction of research on the high school credit system and leading schools, the curriculum has been quantitatively expanded, while controversy is heating up centered on possibilities and limitations of whether students' right to choose can be properly guaranteed in the school field. Hence, while a qualitative improvement of career and academic planning guidance is emphasized, previous studies have limitations in that they list problems or alternatives by segmentally analyzing the experiences of teachers and students. Accordingly, there is a need to understand the career and academic planning guidance according to totality, context, and specificity of the school field. Therefore, this study sought to specifically explore the experiences in the career and academic planning guidance of the teachers and students through a qualitative case study method. As a result of the study, it was possible to discover factors and implications which hindered or promoted realization of their career and academic planning guidance as intended. Based on the study results, it was discovered that provisional career and academic planning guidance centered on understanding of the curriculum and life vision, the career and academic planning guidance for everyone centered on growth of the students, and daily guidance centered on a relationship based on cooperative culture and learning were needed. In order to put this into practice in the school field, it is suggested that along with practice of reflective education by the teachers in their organization and community support for the teachers’ role as a relationship expert, differentiation of their training methods centered on the students’ cases and institutional and environmental changes should be made together.