Digital freelancing has emerged as an important avenue for employment generation, income diversification, and digital economic development in Bangladesh. However, limited empirical evidence exists regarding the factors that shape freelancing outcomes in the country’s growing digital labor market. This study aims to examine the influence of economic factors, flexibility factors, motivational factors, infrastructure and institutional support, and social factors on digital freelancing outcomes in Bangladesh. A quantitative, cross-sectional research design was employed using a structured questionnaire to collect data from 250 digital freelancers. The data were analyzed using SPSS through descriptive statistics, reliability analysis, exploratory factor analysis, correlation analysis, and multiple regression analysis. The findings reveal that all five factors have significant positive effects on digital freelancing outcomes, with infrastructure and institutional support emerging as the most influential predictor, followed by economic factors. The results further suggest that successful digital freelancing is driven by a combination of economic opportunities, flexible work arrangements, individual motivation, institutional and technological support, and social influences. This study contributes to existing literature by providing empirical evidence on the multidimensional determinants of digital freelancing outcomes in the context of a developing economy. The findings offer practical implications for policymakers, platform providers, educational institutions, and other stakeholders in designing policies and support mechanisms to strengthen Bangladesh’s digital freelancing ecosystem and promote sustainable participation in the digital workforce.