When Taylor Swift turned 18, she was handed a life-altering birthday card.

“I was devastated,” Swift recalled. So was Andrea who had supported and nurtured her daughter’s musical talents since birth.

“There would always be an escape hatch into normal life if she decided this wasn’t something she had to pursue,” Andrea told Entertainment Weekly back in 2008 when her career was only really beginning to take off. “And of course, that’s like saying to her, ‘If you want to stop breathing, that’s cool.'”

After all, Swift’s mother had been on the road with her since 2006 when she’d made her singing debut onstage at the Grand Ole Opry. They had even moved their family in 2003 when she landed a record deal with Sony/ATV Publishing.

It had been her daughter’s dream to go further into the music industry and she, along with her husband Scott Swift, desperately wanted her to succeed. So the opportunity being pulled from beneath her daughter had a profound impact on the entire family.

But the devastation wouldn’t last long because she turned 18 years old later that year, in December 2007, and celebrated with a birthday party. While Chesney hadn’t been in attendance, his promoter was and handed Swift a card.

It was from Chesney and it read, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.”