School heads in remote areas face several challenges on their journey of providing quality education. This qualitative phenomenological research study investigated the lived experiences, coping mechanism, and insights gained by 12 public school heads assigned in remote schools of Division of Davao del Sur. Research participants were not a resident of the school they were assigned. The researcher used a validated semi – structured interview guide for individual in-depth interview and focused-group discussion. Colaizzi’s method was used to analyze the data gathered. The result shows that school heads in remote areas faced physical discomforts, emotional discomforts, teaching and community adjustments, and work consolations. Their coping mechanisms include physical enduring practices, emotional surviving technique, teaching and community coping technique, and positive work atmosphere They developed personal realization, social realization, and professional realization. It was concluded that despite the challenges encountered, they established their sense of commitment toward their vocation and willingness to continue their journey. The findings of this study may help the Local Government Unit officials to create an ordinance to cover safety and security of the teachers. The officials of the Division Office may provide an additional payment or insurance to the teachers and a wellness program may be organized to destress the teachers in remote area. The school heads may improve their ways on managing the school by partnering with non – government parties.