This study aims to help Filipino online freelancers increase their job and career satisfaction by understanding the effects of government programs, digital technologies support, and cultural and social norms on their work. Unlike corporate employees, online freelancers do not get the same benefits such as insurance, training, and social recognition. Not everyone working in the gig economy can also pay their own SSS, PAGIBIG, and PhilHealth, which are essential. Online freelancers are responsible for covering their own local security system and national health insurance through voluntary contributions since they work for themselves (Zoleta, 2022). Moreover, the academe is not yet very aware of the opportunities in the online freelancing industry. Educational institutions often encourage students to pursue a traditional full-time job (Mulachy, 2019). The respondents also believe that the academic sectors do not prioritize helping Filipinos learn the skills to thrive in the gig economy. Further, the study used descriptive and causal research designs to investigate job and career satisfaction factors. Results indicated that government programs did not significantly affect job and career satisfaction. Hence, the recommended intervention programs involve integrating online freelancing subjects into current college curriculums for aspiring Filipino online freelancers and providing the necessary safety nets for existing Filipino online freelancers.