Before recording her album The Dream (out on Feb. 28), Hailey Whitters was wondering if it was time to give up on Nashville. It had been a decade since she'd packed up and moved from her small hometown in Iowa to Music City. And while she'd written cuts for Alan Jackson, Little Big Town, Martina McBride and more, she was starting to feel discouraged by the industry and thought this one might end up being her last record.
"You wonder 'Is this ever going to happen for me?'" Whitters tells Wide Open Country. "I was at a point where I was kind of giving up on it. I'd been here for 10 years and I was kind of like 'Alright, well I tried. I'm going to make this one last record and put everything I have into it. Because if this is the last record I make and I hang up my hat and move back to Iowa, I want to feel good about what I did here.'"
Whitters waited tables, sold a guitar and dipped into her savings to fund the 12-track record that would become The Dream. While writing for the album, she penned the stunning "Ten Year Town," which she calls her "ballad of the dreamer," with Brandy Clark.
"I think that song was meant to be with Brandy Clark," Whitters says. "Both of us are people and artists who have struggled to fit in with the business here -- not necessarily being super embraced by 'the machine,' so I think we were able to just openly express our thoughts and the way it is without putting a filter on it."
The song, a brutally honest look at holding onto a dream when you're already "12 years into a 10 year town," earned Whitters praise from Maren Morris, who brought her on tour last year, and Brothers Osborne, who championed Whitters on social media and on the red carpet at the 2019 ACM Awards.
"[The song's] last line is 'this next song could turn it all around.' I feel like 'Ten Year Town' was really that song for me," she says.
Throughout the album, Whitters captures the simple beauty of every day life. Those precious snapshots in time were something she found herself valuing more and more while making the record.
"Anything could make me cry tears of joy or tears [over] realizing how big life is and how easy it is to take the smallest things for granted," Whitters says. "So it really inspired me to write things that I felt like said something as far as slowing down and really appreciating life at the present moment."
Album standout "Janice at the Hotel Bar," which Whitters wrote with Lori McKenna, does just that. The song was inspired by several of the women Whitters grew up with and an encounter popular lifestyle blogger Landyn Hutchinson had with a real woman named Janice. The result is a celebration of the life lessons women share with one another. ("My grandma always said a glass of red a day is good for the heart...and there's a 95 year old woman in my town who still mows her own lawn," Whitters says.)
On "Heartland," Whitters draws inspiration from Shueyville, Iowa, where she first started writing songs and spent her early years performing at local restaurants and the American Legion.
"I'm 12 years and nine hours away from that -- from home base," she says. "Writing that song and getting to go back there, both physically and mentally, has really allowed me to feel more free here."
Though she was hell-bent on moving to Nashville as a teenager, she says her career as a singer-songwriter was shaped by those days in Iowa studying liner notes on Dixie Chicks CDs and falling in love with the stories on local country radio.
"That's something that was big in the songs I grew up on," Whitters says. "They were telling stories. Like Tim McGraw's 'Don't Take the Girl' or 'Red Rag Top' or 'Traveling Soldier' by the Dixie Chicks. All these songs were telling perspectives and stories about life and I think that really stuck out to me. I feel like that's what makes country music country music."
And while she didn't realize it at the time, a lot of the songs that inspired her were written by one woman.
"The music I was growing up on, now I know a lot of those songs were written by Matraca Berg. A lot of those female '90s songs I love -- "Wild Angels," "You Can Feel Bad," "XXXs and OOOs" -- that was actually Matraca Berg. Once I got here and I learned that, I realized I was chasing her a lot of the time. I think Matraca wrote a lot of the songs that shaped me."
A lot has changed for Whitters in the past 10 years and it's safe to say that The Dream is far from her last album. But even with success, some things stay the same. She'll keep writing, looking for the next song to turn it all around.
"My goal is just to write a great, timeless Song of the Year, Song of the Decade kind of song," Whitters says. "Those songs that reach everyone and make everyone stop for a second and think about life... something that people are going to feel."
Whitters will play an album release show at Nashville's Basement East on March 10. Tickets are available here.