In this paper I will outline some of the practical experiences and theoretical concerns that have informed some 15 years of research into the relationship between human creativity and technology. I will discuss a number of approaches to the design of effective creativity enhancing systems and identify the key theoretical concerns that have informed the practical research. Finally, I will present some conclusions about the nature of human and synthetic creativity arising from my published work. At conference the paper will be presented using a variety of audio-visual illustrations. Keywords Ambiguity, collaboration, complexity, discontinuity, posthumanism, randomness