As educational challenges evolve in the 21st century, there is an increasing focus on prioritizing educators' well-being. This study explored the challenges, coping strategies and insights of school leaders in managing work-life balance and well-being. The study employed a qualitative phenomenological approach, engaging seven school leaders from elementary, secondary, and higher education levels in Davao Region, Philippines through in-depth interview. The findings revealed that school leaders are challenged on the overlapped and extended time of administrative responsibilities, clashed human resource concerns, struggled with emotional and mental strain in leadership roles, interfered rest and personal time and neglected career development. To cope with these challenges, school leaders emphasized on strategies including cultivating awareness through self-care and reflection, strengthening family bonds, optimizing productivity through strategic scheduling, fostering positive relationships and delegation of work. School leaders highlighted valuable insights such as holistic well-being and sustainability, time management, work-life boundaries and career fulfillment. Notably, findings recommend for future research to address generational differences, enhance leadership effectiveness, promote holistic well-being, and harmonize responsibilities even in challenging tightropes.