This article examines the promotion of lifelong learning (LLL) in Singapore through a new national initiative known as the SkillsFuture movement. It is argued that the attainment of LLL is confronted with three key challenges, the first being the sociocultural preference for academic rather than vocational education in Singapore. Secondly, there is an absence of a strong local culture that underscores the habits of mind needed for LLL. The final challenge is the dominant ideology of pragmatism that potentially conflicts with the goal of the SkillsFuture movement for individuals to enjoy learning and pursue their passion. The article further recommends a reconceptualisation of the notion of LLL in Singapore by supplementing the skills growth model with the individual development and social learning models. The Singapore example illustrates the difficulties and prospects of advocating LLL due to historical and socialcultural conditions and practices.