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.