Taylor Swift is telling me a story, and when Taylor Swift tells you a story, you listen, because you know it’s going to be good—not only because she’s had an extraordinary life, but because she’s an extraordinary storyteller. This one is about a time she got her heart broken, although not in the way you might expect.
She was 17, she says, and she had booked the biggest opportunity of her life so far—a highly coveted slot opening for country superstar Kenny Chesney on tour. “This was going to change my career,” she remembers. “I was so excited.” But a couple weeks later, Swift arrived home to find her mother Andrea sitting on the front steps of their house. “She was weeping,” Swift says. “Her head was in her hands as if there had been a family emergency.” Through sobs, Andrea told her daughter that Chesney’s tour had been sponsored by a beer company. Taylor was too young to join. “I was devastated,” Swift says.
But some months later, at Swift’s 18th birthday party, she saw Chesney’s promoter. He handed her a card from Chesney that read, as Swift recalls, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.” With the note was a check. “It was for more money than I’d ever seen in my life,” Swift says. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”
Listening to Swift share this, on a clear fall afternoon in her New York City apartment, I’m struck by how satisfying the story is. There are high stakes at the outset; there are details, vivid and sensory; there’s a twist that flips the action on its head; and there’s a happy ending for its hero. It takes her only about 30 seconds to recount this, but those 30 seconds contain an entire narrative world.
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I’m not surprised. Swift has a preternatural skill for finding the story. Her anecdote about Chesney symbolizes a larger narrative in Swift’s life, one about redemption—where our protagonist discovers new happiness not despite challenges, but because of them. Swift, as we’ll discuss, took a few hits to get here. “I’ve been raised up and down the flagpole of public opinion so many times in the last 20 years,” she says as we tuck into a cozy den off the kitchen to talk, and she kicks off her shoes and curls up onto the sofa. “I’ve been given a tiara, then had it taken away.” She is seemingly unguarded in conversation, reflective about both where she’s been and where she finds herself now. After all, while she’s long been one of the biggest entertainers in the world, this year is different. “It feels like the breakthrough moment of my career, happening at 33,” she says. “And for the first time in my life, I was mentally tough enough to take what comes with that.” This is her story—even if she’s now so high that it’s hard to believe she was ever low.
