This is an era of uncertainty, during which adaptability is a key capability to survival and future success. What has Singapore done to develop an education system that facilitates its young to learn in such an era? Firstly, Singapore enhances the adaptive capacity of its education system by increasing its diversity. In particular, it is developing more educational pathways, areas of learning and types of schools. Secondly, Singapore emphasizes lifelong learning. In particular, Singapore will be focusing on providing more learning opportunities for working adults and enhancing support for mid-career reskilling. In these educational changes, Singapore has been addressing both hardware (changing policies) and software (addressing culture), in order to develop an education system that can facilitate learners to learn in an era of uncertainty. What will help Singapore in further developing such a system? This paper suggests two software "upgrades", namely "inspiration by design" and "readiness for paradigm shift". Firstly, instead of a paradigm of competence, Singapore adopts a paradigm of inspiration. In this paradigm, the aim is for students to find their inspiration to learn, and such inspiration is provided through a systemic approach. This is "inspiration by design". Secondly, Singapore nurtures the spirit of readiness for paradigm shifts in education. An example of a paradigm shift is to be ready for the advent of artificial intelligence in education. Such readiness is about reflecting on fundamentals so that the use of artificial intelligence enhances the development of real human intelligence.