Generational relations and entrepreneurialism in organizations are attracting increasing attention from organizational scholars. This article bridges these areas of interest, by examining how entrepreneurial identity is shaped by generational encounters within a small organization context. In so doing, it contributes to ongoing challenges to the scientistic orthodoxy regarding the formation of entrepreneurial persons. Evidence from an ethnographic study of two joint ownermanagers in the port fendering industry is presented. Wenger’s ‘community of practice’ framework is used to show that generational encounters, through their influence on self-identity, are an important social context of the decision to embark on an entrepreneurial career. By emphasizing micro-socially situated aspects of identity formation, this article provides an interactionist complement to recent accounts of entrepreneurs and identities as being (re)produced by discourses that have hegemonic effects.