This chapter presents findings from the study of professionals working in international organisations and public sector institutions. Previous studies of wisdom development have tended to focus on a few disciplines and on students in higher education. Also, whilst there has been active discussion of addressing wisdom in education, empirical studies of practitioners have been less frequent. Yet, practical wisdom is often identified as a skill needed by professionals involved in various fields to make better decisions. This includes working with experts from different fields and across organisations to achieve those outcomes. The kinds of decisions that need to be made require taking into account a wide range of personal, situational, and societal factors when developing solutions to complicated problems. Therefore, our study focuses on professionals and their experiences of becoming wiser during their careers in their challenging international work environments. The recently developed Holistic Wisdom Model is used as a theoretical background. The chapter employs the Holistic Wisdom Model to analyse what kind of experiences have facilitated expert learning and enhanced their ability to act wisely. The chapter presents findings from the study of 12 experts working for international organisations. Findings from thematic analyses of interviews demonstrate how the experts have used their capacities actively to engage with different dimensions of the holistic wisdom model throughout their lives and careers. Their accounts provide a rich insight into how tightly the different dimensions of wisdom and learning are intertwined in these instances of work activities.