Following multiple disruptions and crises, global education stakeholders grapple with the issue of how to prepare learners for a future wrought with uncertainty and unpredictability. During the COVID-19 pandemic that caused global school closures, disruptions to learning occurred in differing scopes and magnitudes across different countries. International organisations reported that some students have incurred a 1-to-3-year learning loss, which might have ramifications on their holistic development and, further down the line, their socioeconomic prospects. An equitable solution must be sought for the world to move beyond recovering to flourishing. This article attempts to elucidate the underlying principles of Singapore's education system through Dewey's concept of democracy and education, defined from an apolitical stance. For Singapore, democracy is also balanced with pragmatic meritocracy, which is upheld as a means to provide equal opportunities for all, regardless of socioeconomic background. This paper describes Singapore's democratic and meritocratic society, setting the backdrop for an education system that seeks to develop its citizens into resilient, values-anchored, and lifelong learners ready to confront the challenges of the future.