Since the early 21st Century, building a Knowledge Society represents an aspiration not only for the developed countries, but for the developing ones too. There is an increasing concern worldwide for rendering this process manageable towards a sustainable, equitable and ethically sound societal system. As proper management, including at the societal level, requires both wisdom and measurement, the operationalisation of the Knowledge Society concept encompasses a qualitative side, related to vision-building, and a quantitative one, pertaining to designing and using dedicated metrics. The endeavour of enabling policy-makers mapping, steering and monitoring the sustainable development of the Knowledge Society at national level, in a world increasingly based on creativity, learning and open communication, led researchers to devising a wide range of composite indexes. However, as such indexes are generated through weighting and aggregation, their usefulness is limited to retrospectively assessing and comparing levels and states already attained; therefore, to better serve policy-making purposes, composite indexes should be complemented by other instruments. Complexification, inspired by the systemic paradigm, allows obtaining "rich pictures" of the Knowledge Society; to this end, a multi-dimensional scorecard of the Knowledge Society development is hereby suggested, that seeks a more contextual orientation towards sustainability. It is assumed that, in the case of the Knowledge Society, the sustainability condition goes well beyond the "greening" desideratum and should be of a higher order, relying upon the conversion of natural and productive life-cycles into virtuous circles of self-sustainability