Why Taylor Swift’s Success Makes People So Uncomfortable

Why does Taylor Swift’s success seem to bother people so much? A recent story from Max Greenfield about a private conversation he had with Taylor years ago says a lot about the ambition that has driven her from the beginning. Taylor has never been particularly interested in pretending she doesn’t care about success, and after nearly two decades of backlash, cancellations, overexposure narratives and predictions of her downfall, she just keeps getting bigger. In this video, I’m unpacking our complicated relationship with ambition, why extreme success can inspire so much resentment, and why Taylor Swift has never seemed interested in making herself smaller just to make other people more comfortable. She always wanted the ocean.