Over the past few years, academic scholars have shifted toward paying more attention to work-family balance, family social support, and subjective well-being, as these are critical issues for mature employees. Besides, Y-Gen managers are more concerned about their digital leadership skills, which is also crucial for subjective well-being. However, for this study, the researchers have constructed the main research variables (work-family balance, digital leadership skills, family social support, and subjective well-being) based on the assumptions of spillover theory and conservation of resources (COR) theory. The current study has three distinct objectives: (a) to determine the impact of work-family balance, digital leadership skills, and family social support on subjective well-being, (b) to test the mediation effects of family social support in the relationships between work-family balance, digital leadership skills and subjective well-being (c) to test the moderation effects of gender on the relationships between work-family balance, digital leadership skills and subjective well-being. Using the convenience sampling technique, data was taken from 314 Y-Gen mid and top-level managers working in the private sector in Bangladesh. The findings revealed that work-family balance, digital leadership skills, and family social support positively affect Y-Gen managers' subjective well-being. Besides, family social support partially mediates the relationships between work-family balance, digital leadership skills and subjective well-being. However, gender does not have any moderation effect on the relationship between work-family balance, digital leadership skills and subjective well-being. Therefore, the higher authority needs to focus more on Y-Gen managers regarding work-family balance and digital leadership skills.