The question of Heidegger’s reflections on technology is explored in terms of ‘living with’ technology and including the socio-theoretical notion of ‘entanglement’ towards a review of Heidegger’s understanding of technology and media, including the entertainment industry and modern digital life. I explore Heidegger’s reflections on Gelassenheit by way of the Japanese aesthetic conception of life and of art as wabi-sabi understood with respect to Heidegger’s Gelassenheit as the art of Verfallenheit.