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Facing increased employment precarity and transformations in occupational structure, young people use social media to navigate uncertainties in their career aspirations. Moving beyond the static approach of prior studies, this research adopts a pragmatic and symbolic interactionism perspective, examining how youths’ aspirations unfold in response to changing structural situations, and how online and offline interactional contexts mediate youths’ perceived situations. Based on interviews with Chinese-educated youths transitioning to IT—a sector characterized by both potential growth and uncertainty due to layoffs—this study underscores the varying ways individuals engage with online contexts. In stable times, youths evaluate career choices based on personal values; during uncertain times, they seek to perceive themselves as conforming to societal norms. However, perceived conformity is actively constructed rather than passively received to reinforce aspirations. This paper expands theoretical understanding of youths career aspirations, illuminating their non-linear evolution and the role of social media in managing career uncertainties.