A topical challenge for algorithms in general and for automatic image categorization and generation in particular is presented in the form of a drawing for AI to “understand”. In a second vein, AI is challenged to produce something similar from verbal description. The aim of the paper is to highlight strengths and deficiencies of current Artificial Intelligence approaches while coarsely sketching a way forward. A general lack of encompassing symbol-embedding and (not only) -grounding in some bodily basis is made responsible for current deficiencies. A concomitant dearth of hierarchical organization of concepts follows suite. As a remedy for these shortcomings, it is proposed to take a wide step back and to newly incorporate aspects of cybernetics and analog control processes. It is claimed that a promising overarching perspective is provided by the Ouroboros Model with a valid and versatile algorithmic backbone for general cognition at all accessible levels of abstraction and capabilities. Reality, rules, truth, and Free Will are all useful abstractions according to the Ouroboros Model. Logic deduction as well as intuitive guesses are claimed as produced on the basis of one compartmentalized memory for schemata and a pattern-matching, i.e., monitoring process termed consumption analysis. The latter directs attention on short (attention proper) and also on long times scales (emotional biases). In this cybernetic approach, discrepancies between expectations and actual activations (e.g., sensory precepts) drive the general process of cognition and at the same time steer the storage of new and adapted memory entries. Dedicated structures in the human brain work in concert according to this scheme.