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This paper examines holistic education initia-tives of two high-performing education systems—Finlandand Singapore. This qualitative analysis captures a phe-nomenological schooling experience of holistic educationunder the two systems. Our conceptualization of holisticeducation focuses on two key dimensions: transformativelearning and community engagement. Indications oftransformative learning were observed through the(un)structured play activities that students engaged in. Forcommunity engagement, we examined the imperatives thatunderpin community engagement initiatives that studentswere exposed to. A sociological explanation of this accountdiscusses the context that shapes approaches to holisticlearning, and how changes in schooling approaches mirror-changing educational landscapes in both Finland and Sin-gapore. Implications on Singapore’s holistic education willthen be drawn