This phenomenological qualitative study investigated the lived experiences of school heads in handling administrative tasks and multiple ancillary functions within the context of the MATATAG Curriculum implementation in the Philippines. Ten school heads from the Divisions of Davao City and Davao Occidental participated in in-depth interviews. The study participants were chosen using a purposive sampling technique. The study revealed three major themes in their experiences: multifaceted leadership demands, time and resource management challenges, and stakeholder relationships and community engagement. School heads employed various coping mechanisms, including strategic workload management, seeking professional growth and support, and maintaining holistic well-being and communication. Key insights gained emphasized the importance of visionary and adaptive leadership, collaborative and efficient management, and data-driven decision-making. The findings highlight the complex nature of school leadership and the need for targeted support from educational authorities. Recommendations include streamlining administrative processes, providing specialized leadership training, and establishing work-life balance policies to enhance the effectiveness of school heads and improve overall educational outcomes.