Based on international comparisons, Singapore students have a rather unique profile of competencies and are generally strong in academic domains. However, in this volatile, uncertain, complex, and ambiguous (VUCA) climate, the nation is constantly emphasizing the fostering of twenty-first century (21C) and social–emotional (SE) competencies to develop the younger generation and future-ready citizens. Buttressed by our recent meta-syntheses on the development of various competencies in Singapore, this chapter will provide a greater understanding of the journey to develop 21C and SE competencies among Singapore students from a policy–research–practice nexus. A synthesis of key policy movements is provided as background context, followed by five themes that highlight the successes and gaps of 21C and SE competency development in Singapore. While Singapore’s journey is certainly distinctive, the chapter offers three implications gleaned from the insights and from international literature for other educators and policymakers interested in fostering such competencies.