Purpose: Fostering the skills necessary for self-directed learning (SDL) competence could be considered the most essential goal of formal education, especially due to uncertainty and changing conditions -- exampled by the COVID-19 pandemic. Importantly, SDL competence can afford a person the ability to adapt to changing social contextual conditions, thus facilitating personal growth and development -- even in the face of volatile and rapidly changing social contextual conditions. The aim of this study is to explore, theoretically, the contextual quality of educational experience necessary for learners to secure adaptive meaning-making: in order to meet the demands of our changing world. Design/methodology/approach: To date, research has failed to comprehensively identify exactly what type of educational experience is necessary for such an adaptive meaning-making process during SDL. The present theoretical paper attempts to redress this concern. Findings: Highly contextualized educational experience is necessary to enable contextual-specific, adaptable, meaning-making. Two constituents of contextualized educational experience are proposed: contextual-specific information available during the educational experience; and contextual-specific meaning schemes resultant from the educational process. Originality/value: This novel work presents an important argument that education should encourage learners to construct knowledge that is adaptable and transferable to their context, rather than automatized knowledge that is not adaptable or transferable. This is a key concern for persons who face rapidly changing social contextual conditions and therefore should be given consideration in both the design of education and in further research on SDL. Like a vaccine in an arm provides a certain protection against COVID-19, fostering our populations' SDL competence is fundamental for affording persons with an ability to meet the demands of our rapidly changing world.