This article attempts to conceptualise the relationship between the individual (professional) and the structural in a period of relatively radical changes in society. The challenging and revealing dialectic of such relations is analysed through the combination of auto-ethnographic reflections and archival documents showing the changes in the functioning of a council of experts in a country that experienced and coped with three fundamentally peaceful transitions: the transition from a self-managed socialist economy to a market economy, the transition from a one-party socialist system to a representative liberal democracy, and from a republic that was part of a federal state to an independent state. The Expert Council of the Socialist Republic of Slovenia (then still part of the Socialist Republic of Yugoslavia), later renamed the Expert Council of the Republic of Slovenia (at that time a liberal democracy with a market economy and an independent state), can serve as an example of the productive intertwining of individual (expert) and the structural in the formulation and the implementation of the functional transformation of the educational system. The contextualised account and assessment of the shifts that together helped bring about the independent state and its education system formation outlines the complexity and importance of reflexive governance in the times of transition, which, in itself, brings to the fore a number of relevant issues and invites and supports change in the educational system. Such an opportunity should not be missed by the country and its educators.