This paper explores reskilling, appearing both as a practice and a signifier in social media. By investigating reskilling narratives, this paper describes origins, actors and relation to skill. It contributes by first suggesting that reskilling is a process rather than a specific training form or about specific skill content. Second, individuals and organisations are simultaneously and paradoxically sold reskilling, but their interests do not always align. On social media, reskilling stands as a corporate (and societal) signifier of action as well as an opportunity for advertising employer brands. Third, through a technology‐deterministic frame, reskilling can be understood as a signifier of optimism, that is, turning pessimism in the shape of possible displacement into optimism where society, organisations and people may ‘keep up’ with technological change. Thus, reskilling can be understood to materialise optimism, and that optimism is an attempt at the restoration of human agency on an inevitabilist path.