The purpose of this study was to identify: (a) the latent profiles of the difficulties associated with the school-to-work transition (decline in confidence, mood swings, family disagreements, the burdens of familial expectations, economic hardship, and a lack of support) made by university students, (b) predictors (gender, age, grade, university location, co-residence with parents on weekdays, monthly household income, and parental educational attainment) of these profiles, and (c) how the profiles were associated with mental well-being. The participants of this study were 311 senior or above students (164 males and 147 females) under the age of 29, who were unmarried and preparing for employment. The findings of this study were as follows. First, the latent profile analysis revealed three distinct profiles: the “low overall difficulties” type (25.4%), the “moderate overall difficulties” type (49.9%), and the “high overall difficulties” type (24.7%). Second, the factors that predicted each profile included gender, age, co-residence with parents on weekdays, monthly household income, and parental educational attainment. Third, the “low overall difficulties” type demonstrated the highest level of mental well-being (emotional, social, and psychological well-being). This study was significant for examining the latent profiles of the difficulties associated with the school-to-work transition made by university students preparing for employment, while also exploring their mental well-being. Based on the results of this study, practical implications, limitations, and suggestions for further study were discussed.