This chapter discusses how learning to be wise in practice arises through the range of educative experiences that individuals encounter, engage with and from which they learn. It presents findings from an analysis of the interview data from individuals who were identified as being exceptional in their paid work activities. These informants provided accounts of their learning and development over the course of their lives, discussing the experiences they had at work and their learning through educational provisions in institutional and/or workplace settings, and from other encounters. The analysis focused on the informants’ experiences reported and are perceived or deducted to be aligned with the development of wise practices in problem-solving and effectively responding to challenges and demanding situations at work. The findings highlight the importance of personal engagement in occupational practices and the affordances (i.e., invitational quality of opportunities) provided by and interactions with peers, colleagues and other encounters in workplace, educational and community settings. While the development of practical wisdom was reported as being highly individualised, there were often features that converged in the informants’ careers. These included (i) learning by doing/exposure; (ii) learning from experience; (iii) reflection on practice; (iv) problem-solving; (v) learning from mentors and role modelling; (vi) learning from others/different perspectives; (vii) listening and observation; (viii) on-the-job; and (ix) educational provisions. The informants were from a range of social and cultural backgrounds, and occupations and had experienced diverse work life transitions (including a change of job or career). Yet, they were committed to active and intentional learning and development of work processes. Such personal commitment and personal engagement enabled them to develop profound understanding and effective practices of the professional environment in which they worked and its problems.