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We develop a theory of career mobility based on the premise that turnover between positions in different organizations is influenced by whether these positions reflect social role identities or not. We contend that some organizational positions are embedded in broader social identities that shape cultural beliefs about the contribution and value delivered by those occupying the positions. Organizational roles and external identities imprint in individual identities which in turn influence turnover. Focusing on the role identity of the entrepreneur, we develop predictions about how occupying the position of a representative affects transitions to organizational founding and to conventional employment. We also re-evaluate, through the lens of social identity, how founder experience and charismatic authority are implicated in entrepreneurial transitions. Event history analyses of designers’ careers in the global fashion industry from 1945 to 2010 support our conjectures and the merits of a careers approach to studying turnover and entrepreneurship.