In the context of the fourth industrial revolution (4IR), the rapid advancement of technologies such as artificial intelligence and robotics are disrupting the existing structures of labour markets and impacting the nature of work and employment at a much broader scale and faster pace than previously. What becomes of the future of work and employment, then, can be described to be a ‘race between education and technology’ (Goldin & Katz, 2008). Consequently, one of the greatest challenges for education systems in the 4IR will be to find a way to supply a stream of the right talents and skills amidst the fast-changing requirements of the labour market. Against this backdrop, Singapore has identified the concept of lifelong learning — as manifested through the SkillsFuture initiative — to underpin recent reforms in the nation’s higher education and skills development policy, in order to meet the constantly evolving skills needs for the future. By drawing on Singapore as an illustrative case study, this chapter seeks to draw out the key challenges, pertinent trends and developments in higher education and lifelong learning, to contribute to greater clarity in proposing the way forward in the actions for societies to take, so as to win in the race between education and technology.