The complexity of the sustainable future of mankind is not just the battle for better world or better tomorrow but a process which will take much more from humanity, shaping our needs to guarantee our presence through daunting challenges. The philosophy, observation and research have been supported by the system theory, systems thinking, analysis and synthesis of an engaged academic work. This work wants to address some of those inconvenient questions on where we are heading to, looking at the current state of systems dynamics, across disciplines. Many researchers, on a global scale, have contributed to the creation of this publication, which wants to be a testimonial of the never ceasing reflection on the challenges that will need to be addressed now, to shape sustainability in our societies, tomorrow.