This phenomenological study explored the job-seeking experiences of Hospitality Management graduates from the Palompon Institute of Technology (PIT), Eastern Visayas, Philippines. Using Braun and Clarke’s (2006) thematic analysis, data from 11 graduates were analyzed, yielding four key themes: (1) Mixed Emotions in the Transition Period, (2) Taking Action Amidst Uncertainty, (3) Expectations Shattered by Reality, and (4) PIT as a Source of Preparation and Identity. Findings revealed that graduates navigated the post-graduation stage with a blend of pride and anxiety, shaped by the pressures of employment uncertainty. While pragmatic strategies such as processing documents, interim work, and skills training supported adaptation, participants encountered systemic barriers including employer preference for experienced hires, stiff competition, and financial burdens in job applications. Importantly, PIT’s academic preparation, OJT programs, and TESDA certifications were perceived as crucial in developing applied skills, professional identity, and confidence. Graduates also highlighted the importance of soft skills, discipline, and adaptability in sustaining employability. The study concludes that employability outcomes are influenced not only by technical expertise but also by transferable skills and institutional support. Recommendations are directed toward enhancing curriculum–industry linkages, addressing the “experience paradox,” and expanding policy interventions to ease graduate transitions.