Hailey Whitters Honors Perseverance With Deluxe Album Living the Dream

Playing Nashville
Photo Credit: Harper Smith

When Hailey Whitters wrote “Ten Year Town,” she was starting to lose faith in her dreams of making it big in country music. She’d written songs for Alan Jackson, Martina McBride and Little Big Town, but was still waiting for her own star to rise. “I’m 12 years in to a 10 year town,” she confesses in the heart-opening track, which kicks off her self-funded 2020 album The Dream. She didn’t know it then, but the unflinchingly honest song – about surpassing the time limit to “make it” in the competitive Nashville music industry – is also the one that catapulted Whitters from waiting tables to establishing herself as an artist. “Ten Year Town” helped her achieve many of the goals that come along with country music stardom, from going on the road full time opening for the likes of Maren Morris and Little Big Town to making her Grand Ole Opry debut.

“I really felt like I was living the dream,” Whitters tells Audiofemme of the her “career changing record” and the success that followed. “I was getting to see all these bucket list moments happen and these dreams that prior to this record I had really questioned – ‘Am I going to get to do this?’ ‘Am I going to get to see some of these dreams come true?’ I feel like that record really changed that for me and made that possible.”

Watching the way in which her life was transformed as a result of The Dream, producer Jake Gear (then Whitters’ boyfriend and now her fiancé) suggested making a deluxe edition, appropriately titled Living the Dream, set for release on February 26. The project features five new songs in the form of collaborations with Trisha Yearwood, Little Big Town, Jordan Davis and singer-songwriters Lori McKenna, Hillary Lindsey and Brent Cobb, each of whom Whitters attributes to playing a distinct role in her career.

The new collection begins with “Fillin’ My Cup,” a jovial take on the highs and lows of life and the people who make it all worth it, elevated by Little Big Town’s spirited harmonies. The Grammy-winning group played a significant part in The Dream, as Whitters used the royalty checks she earned from the band’s 2017 single “Happy People,” which she co-wrote with McKenna, to fund the album. On “Fillin’ My Cup,” their voices support potent truisms, like “You can’t appreciate the sugar if you never had the salt.” “It’s one of those lines that reminds me that this is all part of it. Take the good, take the bad, keep going, it’s going to swing back your way,” Whitters says. “All those saltier moments are the ones that come out and make life sweet.”

The native Iowan also called upon one of her childhood idols, Trisha Yearwood, to duet with her on the witty “How Far Can It Go?” an observational look at young love that would fit seamlessly on any ’90s country playlist. “Trisha’s a hero,” Whitters professes, saying she grew up “studying her records.” “She really inspired me to want to do this in the first place, so to have her on it is a huge dream come true.”

Meanwhile, Cobb, who has also taken Whitters out on tour as a supporting act, appears on the bluegrass-influenced “Glad to Be Here,” which finds the two singers on the grateful side of life, while the songwriting dream team of McKenna and Lindsey lend their talents to “How to Break a Heart.” Davis brought Whitters along as an opening act on his Trouble Town Tour in early 2020; here, he helps bring Living The Dream to a free-spirited close through “The Ride,” a tribute to the “burned out believers” and dream chasers. “It’s about moments. It’s about having some of those goals and dreams and getting to see them and appreciate the ride that gets you there,” Whitters notes. 

The young visionary has been intentional about honoring the journey throughout her career – because it’s those honest glimpses into her resiliency that helped her finally reach her goals. “Ten Year Town” showcases her determination (“I didn’t come this far to only go this far”) as well as her hopes (“This next song could turn it all around”) via defining lyrics that can apply to anyone still waiting on their big break – and for Whitters, eventually proved to be prophetic. “That language is very candid. It feels like a page out of a diary,” Whitters says. “Those are lines of persevering and continuing to keep going.”

Perseverance is an integral element of Whitters’ journey and subsequent success. The bright-eyed singer has begun to realize how even the simplest of life’s moments are complexly connected. She’s got some permanent symbols on her skin to remind her of that – visible in the video for “Fillin’ My Cup,” as she sticks out a thumb to hitchhike in a pageant-esque wedding dress. She sticks her thumb in the air, revealing a small tattoo of the letter “D” (honoring her late brother Drake) on her wrist and a delicate prairie rose in the crook of her arm, both symbolizing the deep connection she has to her hometown roots. The prairie rose is Iowa’s state flower, Whitters explains; Gear and her creative director Harper Smith, who sketched the design as a logo for The Dream – are also from the Hawkeye State. “I jog back at my parents’ house on the highway and I see the prairie roses in the ditch, and it always makes me happy,” Whitters says. “It makes me think of Iowa and makes me think of heartland.”

She and Gear had decided to get matching prairie rose tattoos after the album that ultimately changed the trajectory of Whitters’ career was complete. “It makes me think of that record that Jake and I built from scratch. It’s become a very meaningful symbol to me,” Whitters reflects, identifying how her roots are connected to her creative ambitions. “The more I’m forced to create, the more I’m forced to think about some of that stuff. I feel like I’m unraveling these layers that are freaky almost, how much they are intertwined.” 

The newest tracks on Living the Dream are Whitters’ way of expressing gratitude for her time here on earth, the people who’ve shaped her experience, and the dreams she’s carried in her heart that continue to unfold before her — passing that feeling of hope onto each person she reaches through her music. “I think in the most simple sense, living the dream to me is realizing how lucky we are to be alive,” she says. “I was looking at the people in my life who have died and who’ve died young. It was a big lesson in perspective to be able to look at that and think ‘How lucky am I to get to be a human being in this world and live and hurt and cry and laugh and love?’ It’s about feeling vulnerable in all those areas and in all those things.”

“My hope is [that] it shows those dreamers: this is what can happen when you don’t give up and keep going, keep chasing the dream,” she adds. “I hope it’s a story of inspiration.” 

Follow Hailey Whitters on Instagram, Twitter and Facebook for ongoing updates. 

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