This paper uncovers the system-level challenges confronting freelancers in emerging markets, framing freelancing as a form of digital entrepreneurship with significant social implications. Through a systematic literature review of 23 peer-reviewed studies (2020–2024) using the PRISMA protocol, we identified five critical challenge domains: opaque algorithmic management that limits freelancer autonomy, financial instability due to irregular income and weak social protection; regulatory ambiguity that erodes trust in digital platforms, technical barriers including limited infrastructure and digital literacy, and career development gaps marked by burnout and isolation. These challenges disproportionately affect freelancers in developing regions, highlighting structural inequalities within the global digital labor market. By synthesizing literature across geography and sector, this study positions freelancing not just as a labor trend, but as a pressing issue of digital inclusion and social sustainability. The findings inform policymakers, platform designers, and support institutions about intervention points to foster equitable, resilient freelance ecosystems. Future research must explore how technology, policy, and cross-sector partnerships can create inclusive innovation frameworks that sustain independent digital work.