Beating All the Odds, Nashville's Hailey Whitters Is Finally 'Living the Dream'

As difficult as Hailey Whitters' journey to a country career has been, it's also easy for her to measure. She can do it by counting her stops at Nashville's most hallowed institution, the Grand Ole Opry.

Her first experience came when she was a starry-eyed 15-year-old visiting from small-town Iowa. Sitting in that darkened auditorium, she first dared to dream.

"I saw the curtain come up and the lights go on," the 31-year-old artist tells PEOPLE, "and that was the moment that I was like, I am going to do this for the rest of my life."

Her next fateful visit: At age 27, a 10-year Nashville dweller, still undiscovered and almost ready to give up, she bought an Opry ticket in a desperate attempt to keep the dream alive.

Staring at the stage where she longed to be, she says, it hit her: "I knew that I still had a little bit more in there."

But two more years still had to pass before the best Opry visit of all: Aug. 7, 2019, the day she didn't have to buy a ticket. Of course, you don't have to when you're making your Opry debut.

As she waited side stage to go on, Whitters recalls, Sally Williams, the Opry's general manager at the time, sidled up to her and whispered: "It's going to go real fast. It'll be over before you know it. So when you're up there, take a moment. Soak it up."

Whitters says she embraced the advice, pausing between her two songs to truly feel the power of the mythic center stage. Indeed, the moment was fleeting — "I started to realize what I was doing and I started freaking out a little bit" — but no matter. Ever since, many more savor-worthy moments have been rushing into Whitters' climbing-with-a-bullet career.

Just this month, she celebrated her first award nomination, for CMT breakthrough video of the year, and she earned a coveted performance spot on the awards show, singing current single "Fillin' My Cup." Also in June, the Opry is devoting a spotlight to Whitters for the entire month as the first member of its 2021 NextStage class, which honors a select group of "exceptional talent."

"It's so impactful — the Opry taking a chance on somebody like me and introducing me to their fans, to their audience," says Whitters. "It means a lot to me, especially this early in my career."

It's telling that Whitters measures her career start as only two years old even though she's been a part of Nashville's music scene for 14 years. Those first 12 years, though, were filled with the frustrations of every struggling artist, scrambling for gigs, competing for attention, knocking on industry doors, and patching together enough part-time work to pay rent and eat.

Whitters arrived in Nashville with the single-minded determination to be a country star, imagining herself selling out arenas and lining shelves with trophies. She'd grown up the oldest of six children in Shueyville, Iowa (pop. 772), writing and singing her own songs and teaching herself guitar. Her mother was the one who introduced her to her mecca with that first memorable trip to Nashville when she was 15.

But the dream and reality collided soon after Whitters enrolled at Nashville's Belmont University as a music business major and she began pounding the pavement. "I was kind of a terrible student because I was just wanting to do music," she says. "I just really dove in headfirst and started booking shows, booking co-writes and really trying to learn as much as I could about the industry while still going to class. I was going for it."

Yet all through college and once out on her own, she had daily lessons on just how punishing Nashville can be to the countless wannabes who flock to the city.

"I remember everyone always says Nashville's a 10-year town, and when I hit year 10, I started looking around me, and looking at my friends back home," she says, "and they're all married, on baby two, baby three, buying a house, settling down. And I was starting to look around and I was like, what do I gotta show? I'd gotten a little activity as a songwriter, but I really wanted my artist's career to be further along at that point. So I started really having some come-to-Jesus moments, just some heart-to-hearts with myself. Like, what do you want? What are you here for? What does this dream mean to you? Because you're giving up a lot to be here, and it has to be worth it to you."

Though her love for country grew out of the genre's fiddle-and-twang branch, Whitters for a time even walked out on the pop limb, just hoping to gain any foothold. "I pushed myself to be very pop-country, and I did a project," she recalls, "and it just did not feel like me. And I was like, I cannot sell this. If this is what it takes, then I'm out. That was when I decided, if I fail, I'm gonna fail on my own terms, but that will mean more to me than trying to be somebody that I'm not."

That second, pivotal trip to the Opry helped Whitters rekindle her resolve. And this being Nashville, she ended up channeling all of her frustration and longing into — what else? — a song: "I'm 12 years into a 10-year town / I'm too far in to turn around / Too old to go back to school / Won't be much longer, I'll be old news / I thought I'd be a big star now / I'm 12 years into a 10-year town."

She and tune-meister Brandy Clark (who has her own "10-year town" story) actually penned the song in Whitters' 10th year. Her producer, she says, pushed for a lyric change, for accuracy's sake. Whitters successfully fought back, all the while "thinking in the back of my head, God, I hope I'm not 12 years into a 10-year town when I make it."

But just as life can turn into a country song, so can a country song turn into life. In fact, two years later, in early 2019, Whitters was still trying to gain traction when she finally was able to release "Ten Year Town." What happened next could also only happen in country: The song about being a nobody suddenly turned Whitters into a somebody.

Critics swooned, socials buzzed, and artists — notably, Carly Pearce and the Brothers Osborne — who'd been rooting for Whitters for years rooted even louder. More tangible benefits soon followed: the invitation for the Opry debut and a call from Maren Morris.

"She invited me to go on tour, and I didn't have a manager, I didn't have a label," Whitters recalls. "She was so instrumental in me being able to hang up waitressing and to be able to commit to being a musician full time."

Whitters had been working the job — slinging beignets at a Cajun restaurant — to bankroll, tip by tip, the album that "Ten Year Town" was destined for. She and her boyfriend, music publishing executive Jake Gear, co-produced the project over a couple of years, in piecemeal fashion, because of the costs.

At one critical point, Gear had to ask her: "Do you want a ring or a record?"

Whitters didn't think twice: "A record."

"We put everything that we had into it," she says now.

Today, she has the record, with a title that couldn't be more appropriate: The Dream. Released independently in February 2020, it went on to appear on more than 15 "best of the year" lists. She also now has a manager and a label, which issued a deluxe version of the album, Living the Dream, in February with five more songs. Each new track features a guest vocalist, including Jordan Davis and Brent Cobb (both of whom have taken her out on tour), Little Big Town (already fans after putting "Happy People," a Whitters co-write with Lori McKenna, on their 2017 album, The Breaker), and Trisha Yearwood.

For Whitters, the participation of Yearwood, a childhood hero, still seems like a miracle. Their collaboration is on "How Far Can It Go?", a song Whitters, Hillary Lindsey and Nicolle Galyon wrote as a modern-day version of Yearwood's signature song, "She's in Love with the Boy."

Growing up, Whitters says, "I was singing it into the hairbrush microphone, forcing the family to sit down and watch me perform it in the yard."

Whitters had never even met Yearwood, and she knew the collab was a pie-in-the-sky ask. "I fully expected it to be a pass," she says, "but I was like, no harm in asking. Someone at my label made the phone call and she called us that afternoon, and was like, 'Guess what? Trisha's down.' And my producer and I just jumped up and down squealing."

With the vocals recorded separately, Whitters heard the mix for the first time when she was visiting her family in Iowa. "I was driving the same back roads that I used to drive, listening to her on the radio," she says, "and I just got to feel that full-circle moment. It was incredible."

Whitters has since gotten to meet Yearwood and says "she's so grounded and real, and she just feels like a friend that you've known forever. She feels like everything that I just hope to be someday as an artist."

By now, Whitters knows that sort of authenticity is what a real country dream is made of — not packed arenas or awards by the bushel. And she's determined to plot her career accordingly.

Success is "to be able to just create music that I love," she says. "It sounds very simple, but I just want to wake up and be inspired to write and to record and to perform songs that really hit me and hit other people. I don't care if it's for 50 people or 50,000. I've learned the older I get to keep my dreams simple."

Those dreams, she knows, can also be as simple as a ring. She did finally get one of those, too. Gear, who's another Iowa native, proposed last July in the middle of an Iowa cornfield.

They held off making wedding plans during the months of quarantine "because my family is gonna want to get loud and drunk and sweaty and dance — and that just didn't even sound safe," Whitters says with a laugh. "I don't know if it even sounds safe still," she adds, laughing again.

Now preparing to go on tour with Midland and appear at several premier festivals, including the Windy City Smokeout and Tortuga, Whitters and Gear have decided to put off the wedding until 2022. "I just am so anxious to get to work again," she says.

She takes note of the fact that next year will actually make a decade since she and Gear began dating. "You know, I'm a 10-year gal," she says with a grin.

These days she's liking the sound of that.