This chapter presents a multidimensional framework for rethinking successful education, emphasizing the development of future-ready learners in Singapore. It highlights the importance of integrating economic, social, and environmental contexts into educational reforms aligned with Industry 4.0 and 5.0. The framework focuses on three core purposes: lifelong learning, meaningful lifework, and responsible living. Innovative pedagogies, student agency, and community involvement are central to fostering creativity, resilience, and social cohesion. By addressing global challenges and local needs, Singapore aims to cultivate adaptable, responsible, and competent graduates capable of contributing to a sustainable and interconnected future.