The expansion of digital technologies and social media has enabled Generation Z to transform personal interests into economic activities, although limited capital, inadequate skills, market competition, burnout, and unequal technological access may constrain this process. This study examines how Generation Z converts hobbies into business opportunities through digital technology and social media and identifies the factors that facilitate or hinder this transformation. A mixed-methods approach with a descriptive-analytical design was employed. Quantitative data were collected through questionnaires from 200 respondents aged 18–26 years, while qualitative data were obtained through interviews with 50 respondents. The data were analyzed using descriptive statistics, Pearson correlation analysis, and thematic analysis. The findings indicate that 70% of respondents had transformed their hobbies into business activities, 80% of which were initiated through TikTok and Instagram. Moreover, 60% developed relevant skills through self-directed learning, and 55% used free artificial intelligence tools to optimize content creation. Hobby-related content publication frequency was positively associated with monetization (r = .72, p < .01), while self-directed learning was positively associated with business success (r = .65, p < .05). Burnout, market competition, and limited technological access emerged as the principal barriers. These findings demonstrate that consistent content production, self-directed skill development, and accessible digital tools are important components of hobby-based entrepreneurship among Generation Z. The study contributes to digital entrepreneurship research by clarifying how personal interests, platform use, independent learning, and artificial intelligence tools interact within resource-constrained business development. Practically, entrepreneurship programs should strengthen digital competencies, technological access, and strategies for managing burnout and market competition.