The artist and principal author has been creating art works in multimedia through the semantic association of ideas into concepts, as a means of exploring the efficacy of hypermedia for a conceptual art practice. This is particularly evident in the developments apparent in the ongoing 'Deconstructing Duchamp' project, where 'flocking' behaviours have been applied to Duchampian digitised items to observe the familial relations within, and key to his work, at play. Following this project, a second work 'Shift-Life' has proceeded to further develop the idea of allotting animal-like behaviours to electronic data items giving them the appearance of possessing a basic intelligence. By then observing their response to our physical interactions we can glean a clearer understanding, from their inter-relationships, of a complex conceptual framework. While Marcel Duchamp offered the art world one of the most complex and formative pieces of art ever, initiating the shift of values from aesthetics to idea, Charles Darwin developed the theory of evolution, the 'big' idea of survivability through adaptation. Shift-Life was created as part of the national Darwin 200 project for the international bicentenary in 2009. It is a complex system of virtual life-forms struggling to survive in an environment made volatile through human interaction. Central to this installation work is the artificial life ecosystem as a self-sustaining, self-reproducing equilibrium of creatures and plants living in it. The general behaviour of each organism was more sophisticated than for the Duchampian creatures in that they were equipped for survival strategies and the reproduction of progenies. An exposition of the Shift-Life program is therefore presented followed by reflection on both projects and future directions for this collaborative research where potential emergent behaviours are concerned.