This study examines the multifaceted barriers that hinder tech-enabled personal branding among Gen Z and Millennial gig workers who rely on digital platforms for professional visibility and credibility. Grounded in Social Cognitive Theory (SCT) and the Technology Acceptance Model (TAM), the research explores how individual self-efficacy, perceived usefulness, and platform trust interact to influence digital self-leadership. Ten interrelated barriers—including digital skill deficits, algorithmic opacity, platform trust issues, financial literacy gaps, and digital fatigue—were identified through literature synthesis and expert validation. Using Interpretive Structural Modelling (ISM) and MICMAC analysis, data from 154 gig professionals were analysed to uncover hierarchical relationships among these constraints. Results reveal that foundational drivers such as digital skill deficit, algorithmic opacity, and lack of platform trust cascade into dependent barriers like mentorship deficit and digital fatigue. The study offers an integrated socio-technological model illustrating how psychological, behavioural, and structural factors jointly affect sustainable online self-presentation. It highlights the need for algorithmic transparency, digital literacy, and mentorship-based interventions to promote equity, resilience, and authentic self-branding within evolving gig ecosystems.