In this special episode, hosts Kate Wolf, Medaya Ocher, and Eric Newman discuss how Big Tech dreams – from iPhones to social media to AI – have become nightmares. How did these decade-defining innovations end up making modern life feel sadder, lonelier, and scarier? And what, if anything, can we do about it? Using two recent books — Cory Doctorow's Ensh*ttification and Paul Kingsnorth's Against the Machine—as reference points, the hosts discuss labor practices, government regulation, the place of spirituality and religion, cottagecore fantasies, and how they personally navigate unplugging from the machine.