In a world of increasing emphasis on well-being, positive education, articulated as the teaching of skills of well-being alongside academic ones, can be a vehicle for educating both the mind and heart. The Singapore education system is moving towards a future curricula, C2015, fostering student-centric and values-driven education. This demands continued engagement of the whole-child through a co-constructive journey, a school ecosystem that encompasses total curricula and whole-school approach, and a future-oriented perspective with multiple pathways of excellence. Mindfulness is a crucial lever for enacting qualitative transformation by enabling individuals and systems to be skilful architects of internal and external changes. It confers clarity, autonomy, and congruence that motivates, calibrates, and informs action. This paper delineates a whole-school approach to cultivating dispositional mindfulness through teaching, embedding and living it. An exposition of mindful schools is given, including but not limited to mindful teaching, learning, structures, and relationships. These mindful components interact to form a collective greater than its summation, instilling a culture and climate that can be self-sustaining. Ultimately, mindful schools can serve as the foundation for positive educational curricula (e.g. character strengths, resilience, motivation), furnishing a pathway towards student flourishing.