PurposeDrawing on a framework of sustainable career theory, this paper aims to understand the interplay of agentic and contextual factors for digital micro-entrepreneurs to lead sustainable careers.Design/methodology/approachEighteen YouTube content creators in India participated in semi-structured interviews, offering coverage of digital content creators across acting, cosmetics, finance, fitness, food, law, modelling, music, teaching, travel, and video games.FindingsThe findings showed three agentic and three contextual themes associated with the career sustainability of a digital micro-entrepreneur. Additionally, four paradoxes were identified, capturing the interplay between the agentic and contextual themes.Practical implicationsThe career of a digital micro-entrepreneur is a dichotomy of promising hope, stardom, and flexibility while concealing challenges like precarity, hate comments, and financial instability. Knowing this can help individuals make better-informed career decisions.Originality/valueThe study advances sustainable career theory by capturing insights from digital micro-entrepreneurs in India to understand the interplay of agentic and contextual factors that create a series of paradoxes for such individuals to navigate over time.