This presentation explores how architecture and painting can be activated as operative companions in addressing the crises of planetary life through artistic thinking. Departing from Maurice Merleau-Ponty’s notion of a pictorial rationality grounded not in completion or control but in investigation, the research proposes an investigative rationality that practices rationality as an ongoing activation of imagination, doubt, and intuition. Rather than separating art and science into distinct spheres, the work treats both as modes of thinking-with matter, sensation, and form. At the center of the inquiry lies the figure of the chiasm, understood as an intertwining of visibility and invisibility, interiority and exteriority, perceiving and perceived. Drawing on Merleau-Ponty’s concept of the universal flesh, the presentation suspends a subject-centered model of perception in favor of an objective phenomenology of impersonal subjects, where artworks and buildings participate as agencies with operative vitality (energeia). Architecture and painting are approached as sensual–abstract apparatuses that disclose the world according to their own modes of operation. Through analogical thinking informed by Renaissance treatises—particularly Leon Battista Alberti’s theory of painting and Vitruvius’ account of architecture—the presentation stages a series of chiasmatic encounters. Painterly and architectural operations such as circumscripto, ichnographia, compositio, orthographia, luminum receptio, and scaenographia are rearticulated as performative masks within a theatrical framework inspired by the canovaccio of commedia dell’arte. In these staged constellations, historical artworks and buildings function as personas, allowing painting and architecture to converse without collapsing into resemblance, preserving difference within analogy. The presentation unfolds as a compacted fabric rather than a totalizing argument, emphasizing weaving, knotting, and masking as figures of thought. By foregrounding gerunds—seaming, tracing, radiating, masking—it frames architectural and pictorial practices as temporal processes that bind appearance and operation, abstraction and materiality. In this way, architecture and painting emerge not as objects of representation but as ongoing practices of dwelling in a sensuous, planetary world marked by crisis and becoming.