This quantitative study examined the perceived challenges associated with academic leadership roles in higher education, including positions like dean, associate dean, assistant dean, department chair/head, program chair/ head, co-chair, and academic vice president. Utilizing the One-Way ANOVA and multiple regression analysis, the research evaluated how leadership positions and perceived challenges affected the psychological well-being of academic leaders in various roles. The findings indicated significant differences in well-being based on leadership position, with program chairs and deans reporting higher levels of well-being. In comparison, department chairs and academic vice presidents experienced lower levels of well-being. Additionally, stress levels negatively impacted well-being, whereas the frequency of challenges was positively correlated with psychological health. This suggests that adaptive coping strategies may mitigate the adverse effects of stress. The study emphasizes the importance of institutional support and stress management training for academic leaders, particularly those in mid-level positions. Moreover, it highlights the need for resilience-building initiatives and comprehensive mental health support to enhance well-being and leadership effectiveness. Limitations include the use of a non-random sampling method and the absence of qualitative data, which may restrict the generalizability of findings. Future research should investigate these dynamics over time and across different leadership styles to provide a more comprehensive understanding of the factors influencing the psychological well-being of academic leaders.