Sustainability connotes the possibility of a ‘system’ or ‘design’ to continue into the future when it works harmoniously with the environment, social, and economic factors. Is that Utopian thinking? For instances, in sustainable buildings design, the designers could and have to initiate a dialogue with the natural forces: sun, wind, water, land (soil), materials, and other resources available, renewable and non-renewable. The original theoretical premise of ‘Sustainability’ was to afford the needs of the ‘present’ without compromising ‘future’ generations’ ability to meet their needs, ALL WITHIN AVAILABLE RESOURCES. Considering the rapid changes in lifestyle and comfort notions, thanks to modern developments and connectivity, how many of our readily afforded resources in the environment are really renewable or how finite they are? That said, is the concept of ‘Sustainability’ or ‘Sustainable Design’ unsustainable, ambiguous or a theoretical illusion? If yes, can Regenerative or Net Positive Energy, Energy + design paradigms ameliorate the jinx, and how?