One of the important roles of medical schools is to support medical students in deciding upon their future career path or choosing their specialty. The purpose of this study is to suggest a career advising model and strategies for medical students through a systematic approach. This study consists of three parts. The first part introduces some main career theories: super’s career development theory, career decision-making theory, social cognitive career theory, and ecosystem theory. The second part proposes a systematic career advising model using the results acquired from previous studies and theories. This model considers a medical school as a social system that consists of two domains (internal and external). This social system is considered as a complex where various factors interact with each other: students’ individual characteristics, institutional policies and culture, curriculum and learning experience, students’ perceived specialty characteristics, and aspects of the external environment such as healthcare systems. The third part suggests some career advising strategies based on a systematic approach that medical schools can apply. These research results can be used for designing career advising courses for medical students, integrating various career advising programs and resources of medical schools, and evaluating the outcomes of career advising programs at an institutional level.