This Qualitative Research highlights meaningful insights drawn from the leadership journey and experiences of twelve (12) former presidents of a national association of human resource management professionals in the Philippines. Key points culled out through the in-depth interviews were analyzed, categorized into common themes and synthesized, resulting into the identification of three (3) major leadership journey stages namely: Leadership Awakening, Leadership Metamorphosis, and Leadership Transcendence. Each stage was characterized by insights that will be useful to anyone aiming to personally journey as a leader. The study participants were purposively selected considering the following criteria: He or She must be a former president of the Peoples Management Association of the Philippines (PMAP), still active in the association, willing to participate in the study, and practitioners in the fields of leadership and human resource management. The study reveals that a person’s leadership potential is awakened by an inner need for personal development and the external influences of their leadership mentors. They metamorphose into seasoned and competent leaders through the various challenges and problems they have gone through, and as they grow in wisdom and tacit knowledge, they start to transcend from self-centeredness to others-centeredness.