Hailey Whitters Looks to Write a New Musical Chapter with “Living the Dream”

It’s 9AM on a Friday morning, and Hailey Whitters sounds more awake than anyone living smack dab in an unending pandemic should. She’s just returned from a walk with her dogs, dogs that woke her up far too early for her liking. But it’s ok. The coffee has already started kicking in.

Plus, she wouldn’t mind sitting in this moment for a little while.

“Everything feels like it is fitting into place right now,” gushes Whitters, her contentment coming through loud and clear over the telephone during an interview with American Songwriter. “In both my career and in my life, everything feels right. There were times when I didn’t know how I was going to get here, to this place.”

Indeed, as Whitters releases Living the Dream Friday (February 26), the songstress with the vintage vibe in a place where she, at times, forgets the moments not too long ago when she was ‘ready to quit and hightail it back to Iowa.’ 

And, in a way, it does feel like a lifetime ago when Whitters was a ‘brokenhearted, frustrated waitress in Nashville,’ giving twelve years of her life to the legendary ten-year town, in the often-desperate hope that she could still somehow score her big break as a singer/songwriter. In a last-ditch effort to ignite her solo career, Whitters released The Dream in February 2020, with the help of the royalties she was making as a writer on the Little Big Town cut “Happy People.”

“I remember feeling very down at the time,” reflects Whitters, who moved to Nashville when she was just 17 years old. “I released (The Dream) fully independently while I was still waiting tables. I mean, I had no publicist, no label, no management. It was all very indie. I then put out the song ‘Ten Year Town’, and it was that song that spurred all of this momentum for me.”

Now, when she looks back on The Dream, Whitters says she sees a record that was completed during some of the lowest and darkest points of her life. But these days, her life is simply not low or dark anymore. Hence, she made the decision to release Living the Dream, a deluxe edition of her breakthrough album, The Dream, made up of collaborations with some of the artists that had a hand in getting her from there to here.

“Because of people I got to tour with like Jordan Davis and Maren Morris and Brent Cobb, I was able to literally hang up the apron strings and do country music for a living, at a time where I was beginning to give up on so many of my dreams,” says Whitters, who has also gone on to notch cuts as a songwriter for legends such as Alan Jackson and Martina McBride. “The love that fellow artists and my fans showered on The Dream got us here.”

Written and recorded over the span of the past year, Living the Dream not only continues the story of the album that changed everything for Whitters, but also now serves as a reminder to all those who battle every day to make their Music City dreams come true.

“I wanted to show them, in song form, the full circle moment that I find myself in at this very moment,” says Whitters. “I wanted to show that a waitress could quit her job and do music for a living and perform at the (Grand Ole) Opry and hear her song on radio and collaborate with her heroes.”

Whitters does just that on ‘Fillin’ My Cup,” an addictive little ditty she was able to record with four of her musical heroes who make up Little Big Town. “To hear their voices on mine, acapella and in the studio, was so very powerful,” Whitters says of the recording of the song, which has already racked up more than 5 million streams globally since its debut.

And then there was the phone call that informed Whitters that the almighty Trisha Yearwood was also ‘down to collab’ on the Living the Dream album. “Oh, I was jumping and screaming in my kitchen,” Whitters says with a laugh. “I mean, these are the artists I have always looked up to, and I put my dream asks out there expecting to be told ‘nah.’ And they were actually coming back to me saying ‘absolutely, let’s do it.’”

Living the Dream also allowed Whitters to go into the studio with two of her songwriting heroes, who have now become her dear friends.

“That day was supposed to be a four way write, and one dropped out, and we were like, ‘sh**, let’s write anyway,’” Whitters remembers of the session alongside Hillary Lindsey and Lori McKenna that ultimately turned out the song “How to Break a Heart.” “It’s kind of a female empowering anthem, a girl gang, kick the man kind of song. Hillary (Lindsey) and Lori (McKenna) will now get on the phone together and its always a 3-hour call, and it always includes wine. (Laughs.) I feel really lucky to get to know them in this way.”

She also says she feels very lucky to feel so at peace at the moment.
“Making the Dream was my last-ditch attempt to get everything going, because I had truly lost the magic of Nashville and music in general,” Whitters concludes. “But now, I feel like this is a way to close that chapter. And now, Living the Dream showed me the magic again. It’s been an encouraging and validating process that once again reminded me that it’s important to do what you believe in… and what truly matters.”

Photo credit: Harper Smith

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