The digital media landscape has changed radically since I took an interest in it in the late 1990s. One could say that we both grew up and diversified together during this time. This chapter delves into my curatorial, research and artistic practice, revealing various approaches to interactive arts and performance through extending the human body with wearable devices and other technologies expanding the senses, and blurring physical and virtual. The practices explored here feature a variety of approaches for making and presenting performance and interactive media, as well as enhancing the experience for the audience. The chapter takes a winding path, exploring the edges of conventional performance practices and perspectives within a technological context. It picks up in some ways from previous chapters on related practice areas in Chap. 13 on hyper/transhumanism and Chap. 14 on art performance and VR.