Understanding the digital society transformation is a rather fascinated challenge, especially for the future. This naturally, provokes numerous tangible and intangible assets that have to be properly handled in order to catch the right social dynamic trends direction. This however is also requiring an agile & holistic study approach towards a resilient future. In this sense, the idea of the present work is to briefly outline a comprehensive study on the problem, organized in the last few years. The results are mostly based on crowdsourcing analysis, encompassing more than hundred expert beliefs from about fifty countries, spread among five continents throughout the world. Both matrix-based morphological scenario planning and dynamic system-of-systems risk vs utility assessments are implemented in the analytical process. The obtained results are further validated, using pseudo-periodic stochastic probability assessment and verified via simulated mixed reality experiments with human factor active multimodal role. Being somewhat prognostic, the presented findings are not claiming for total comprehensiveness, but rather for producing a fruitful analytical pool with some useful recommendations that will be finally understand when the forecasted period is reached.