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Few new studies plus theoretical stagnation mark the inattention of educators to self-directed informal learning during career development in technology. Therefore this study explored the relationship between self-directed informal learning and the career development process among everyday technology users. Supporting questions addressed how self-directedness related categorically and holistically to informal learning during career development. This qualitative study used multiple narrative case studies to collect, analyze, and describe the results of life-story data recovered from 13 technology users purposefully selected using a sampling strategy grounded in the literature. Individual lifestory narratives surfaced tacitly held perceptions and social identities associated with career-related learning. The data were analyzed categorically and holistically leading to a rich description of common themes and patterns as well as triangulating content validity methodologically and thematically. Findings culminated in a conceptualization of self-directed informal learning as entrepreneurial in nature, which without appropriate strategic guidance can become either a negative or positive influence on career development. Such guidance was best expressed as self-reflection on structured play. With much learning thought to be self-directed, the study's implications for social change are economically and educationally important. Results suggest that corporate trainers must replace maintenance learning that is transportable to lower wage locations with innovative learning that encourages resourceful self-directed learning. Educators must make room for story-based self-reflection, the heart of self-directed learning. Recommendations for implementing entrepreneurial learning are provided.