The purpose of the study was to explore the life adjustment of senior high school students who entered the high school directly from junior level of the same high school. The “Life Experiences Questionnaire” was developed and completed by 66 participants. Data were analyzed by the three steps proposed by grounded theory. Results indicated that: (1) barriers perceived by the participants included academic self-efficacy problems, interpersonal relationship, and college entrance problems; (2) the entrance system from junior level directly to senior level provided specific protective factors for their life adjustment; and (3) a systemic framework can be used to explain high school students’ life adjustment. Implications for counseling practice and suggestions for future research are discussed.