Free subjective choices and selections form an inevitable part of the practice of algorithmic based design and art works. Notably, this aspect of decisions made by practitioners has featured in generative art and design literature, yet, has remained obscure and has not been critically discussed. In this paper I will examine artists’ and designers’ selections through three case studies representing different typologies of decision processes. The philosophical aspect of these decisions will be elaborated following Wittgenstein’s paradox and the critical argument made by philosophers Jacques Bouveresse and Charles Taylor in that no rule, no matter how explicit and unambivalent can ever really determine its own application. The actual implementation of rule systems, therefore, is a practice in itself, one that entails finely tuned interpretations, as well as arbitrary and intuitive choices.
Finally, I will argue that this relates to what Heidegger later observed to be the original meaning of creative making, referring to the Greek word ‘Poiesis’, where the thoughtful aspect of the work and the poetic one are united in a non-separated praxis. Similar to the practice made by oulipo poets who use rule systems to enhance the creative engine of their work, I will argue that these decisions can potentially transform the practice of generative art and design to that of Poiesis in its original meaning: the free play and improvised confrontations with ever renewed unfolding situations, that eventually can lead to liberation from the rules themselves.