This multiple case study aimed to discover and understand the experiences of Senior High School graduates in job searching in Davao Region. The data were taken from the three (3) participants and three (3) informants whose responses were collected through in-depth interviews. Using the thematic analysis, essential themes were extracted from the participants’ responses. On the lived experiences related to job searching, the results revealed nine (9) major themes: preference for college graduates over SHS graduates, difficulty in job application process, stress and pressure in job searching, sense of unfulfilled career potentials despite K to 12 training, job instability and short-term opportunities, impediments to self-confidence and job security, importance of preparation before a job interview, economic insecurity, and deprivation of field experience during the work immersion. Furthermore, on how they overcome their struggles from job searching, six (6) themes emerged: preventing burnout from rejections through leisure activities, earning income through side hustles, intensifying self-reliance and independence, cultivating positive mindset, seeking advice and preparing for interviews, and applying for an industry that accept SHS graduates. Moreover, from the insights gained by the participants, six (6) major themes emerged: disregard the educational-based bias, nurture job resiliency, enhance the job readiness skills for practical experiences, call for work immersion opportunities for SHS students, meet the demands of the industry, and invest in career guidance programs. Cross-case analysis were also utilized to determine the similarities and differences of the themes that transpired. The results of this study were deemed significant to senior high school graduates, parents, teachers, school administrators, DepEd authorities, and future researchers.