This critical paper utilises selective education writings by John Dewey as the basis for considering how a strengths-based and personalised view of habit and embodiment could effectively thrive as part of an enhanced health and well-being focus in schools. The paper centres on Dewey's belief that habits when allied to continuity and interaction could help children to integrate experiences in ways which enable them to constructively evaluate the contribution of health and well-being to their education. The paper concludes by reviewing how the connections between habit, embodiment and health and well-being could be pedagogically strengthened.