In the emerging digital age, futuristic visions such as human-centred Society 5.0 are becoming very relevant for many countries. In these early stages, what would lead to business executives’ happiness in such a future Society 5.0 remains under-researched. Therefore, this article aims to surface the values of business executives which could inform value creation ideation for developing Society 5.0. The study considered Singapore as a benchmark case of innovation-based competitiveness, it being one of the most progressed smart cities as per advances in the digital age. Semi-structured interviews were conducted with business executives of different national cultures in Singapore. Drawing on Maslow’s needs theory, the current research used interpretivism for thematic analysis of their lived experience narratives. The findings initiate an innovative understanding of business executives’ expectations by considering a variety of national cultures in a common location. The article offers in-depth original insights into individual business executives’ values for value creation in society. It addresses the paucity of lived experience accounts of happiness in smart cities, specifically the leader, Singapore. Thus, this research provides foundations for further study of the expectations of the individual business executive and other stakeholders.