Generative systems are unique in that they allow the artist to specify processes rather than outcomes. In this paper, I describe my creative approach to working with complex computational systems that I have designed and coded over several decades. These systems require certain ways of working that offer both liberation and restriction on creative practice. To illustrate how these systems work in a creative sense, I will give an overview of two recent works: Fifty Sisters (2012–2016) and The Unknowable (2015–2017). Fifty Sisters comprises of fifty 1m × 1m images of computer synthesised plant-forms, algorithmically “grown” from computer code using artificial evolution and generative grammars. Each plant-like form is derived from the primitive graphic elements of oil company logos. The title of the work refers to the original “Seven Sisters” – a cartel of seven oil companies that dominated the global petrochemical industry and Middle East oil production from the mid-1940s until the oil crisis of the 1970s. The Unknowable is a three-channel 4k video triptych. The work depicts a series of virtual flora, evolved using computer programs based on biological evolution. In each sequence evolved plant species slowly disintegrate and then reform, breaking into their fundamental component – the polygon – then reforming anew in an endless cycle of destruction and reconstitution. Both works are mediations on our changed relationship to nature and the natural in a globalised, disconnected virtual world now effectively navigated through digital media.