The study mainly focused on the challenges beginning teachers face when they enter the field of education. It utilized the qualitative research with hermeneutic phenomenology as an approach. Using reflective journal and focus group discussion, beginning teachers? personal reflections of experience were recorded and analyzed to distinguish the most challenging experiences among beginning teachers. Participants of this study were the 21 purposively chosen teachers from the City Schools Divisions of Calamba, Cabuyao, Binan and Sta. Rosa. In this study, the experiences of chosen participants in their first 3 years of teaching were analyzed. Results of the study revealed that the participants are all Education course graduate but most of them does not prefer this course. Meanwhile, the most challenging experiences of beginning teachers include student?s diversity, stupefied with works, dissension with colleagues and competencies mismatch. It is recommended that there must be a localized and school-based comprehensive training program aside from the Teachers Induction Program offered for the beginning teachers.