Taylor Swift has been working on her music career since she was a teenager. She released her debut single at 17 and won Album of the Year for her second album. She also experienced major career letdowns at an early age. Swift spoke about one early, devastating moment in her career.

Taylor Swift dealt with a major disappointment early in her career

When Swift was 17, she booked an opening slot on Kenny Chesney’s tour. This was a major opportunity for her; she believed it would lift her career to unimaginable new heights. 

“This was going to change my career,” she told Time in 2023. “I was so excited.” 

Unfortunately, a beer company sponsored the tour, meaning that an underage artist couldn’t perform. The news came as a huge blow to the entire Swift family.

“[My mom] was weeping,” Swift said. “Her head was in her hands as if there had been a family emergency.” 

Swift said she was “devastated” by the news, though her career still took off soon afterward.

Kenny Chesney gave her money to make up for it

Several months later, Swift saw Chesney’s promoter. He gave her a letter and accompanying check from the country singer.

“I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you,” read the note, Swift recalled. “It was for more money than I’d ever seen in my life. I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

Not long after, Swift won Entertainer of the Year at the CMAs. Chesney, realizing her career hadn’t suffered, asked for his money back.

“So, backstage, I went up to her and gave her a big hug,” he said, per Billboard. “I said ‘congratulations, but gimme my money back.’”

Taylor Swift once shared how she deals with career letdowns 

Losing her opening spot on Chesney’s tour was far from the last time Swift has experienced disappointment. She said she responds to letdowns by working on her music.

“It’s all in how you deal with loss,” she said. “I respond to extreme pain with defiance.”

She emphasized the importance of continuing to make art through pain.

“Nothing is permanent,” she said. “So I’m very careful to be grateful every second that I get to be doing this at this level, because I’ve had it taken away from me before. There is one thing I’ve learned: My response to anything that happens, good or bad, is to keep making things. Keep making art.”