In the last years, artificial intelligence (AI) safety gained international recognition in the light of heterogeneous safety-critical and ethical issues that risk overshadowing the broad beneficial impacts of AI. In this context, the implementation of AI observatory endeavors represents one key research direction. This paper motivates the need for an inherently _transdisciplinary_ AI observatory approach integrating diverse retrospective and counterfactual views. We delineate aims and limitations while providing hands-on-advice utilizing _concrete practical examples_. Distinguishing between unintentionally and intentionally triggered AI risks (...) with diverse socio-psycho-technological impacts, we exemplify a _retrospective descriptive analysis_ followed by a _retrospective counterfactual risk analysis_. Building on these AI observatory tools, we present near-term transdisciplinary guidelines for AI safety. As further contribution, we discuss _differentiated_ and tailored long-term directions through the lens of two disparate modern AI safety paradigms. For simplicity, we refer to these two different paradigms with the terms _artificial stupidity_ (AS) and _eternal creativity_ (EC) respectively. While both AS and EC acknowledge the need for a hybrid cognitive-affective approach to AI safety and overlap with regard to many short-term considerations, they differ fundamentally in the nature of multiple envisaged long-term solution patterns. By compiling relevant underlying _contradistinctions_, we aim to provide _future-oriented_ incentives for constructive dialectics in practical and theoretical AI safety research. (shrink)