The aim of this study was to examine the complex interactions between college students' life experiences, personality characteristics, and subjective well-being. The first objective is to understand how two specific life events affect the student population, namely academic stress and financial problems. Additionally, this study examines the mediating effects of certain personality traits such as openness, conscientiousness, extraversion, agreeableness, and neuroticism. Using a quantitative cross-sectional research design, 396 college students participated in the study. A self-administered questionnaire was used to collect data on academic stress, financial problems, personality characteristics, and subjective well-being. Smart PLS was used to understand the interrelationship between these variables. Results showed that academic stress and financial challenges affected students' subjective well-being. Moreover, students handled financial and academic stress differently due to personality variations. The results highlight the need for comprehensive therapies that recognize the interconnectedness of life events and their potential impact on students' subjective well-being.