Sure, every artist’s journey is different. But there’s no one in country music — or music period — whose trajectory towards making a debut album resembles Charles Esten‘s.

“Right?! It’s been a long road, hasn’t it,” the singer jokes in conversation with Taste of Country, talking about his new album Love Ain’t Pretty — which, with a Friday (Jan. 26) release date, arrives more than three decades after the launch of Esten’s career.

From his first entertainment gig in 1988 — an appearance on a game show called Sale of the Century, where he won more than $32,000 in prizes — to a run as lead role Deacon Claybourne on the hit country-themed series Nashville, to his Guinness World Record-earning string of 54 single releases in 54 weeks, Esten has put in his 10,000 hours, approximately 30 times over.

Of course there are some disadvantages to releasing a debut album later in life (Esten is 58). He’s not expecting Love Ain’t Pretty to make as great an impact on radio, for example. But he also knows the value of bringing a backstory and an identity that no one else possibly could: Who else has the advantage of a character like Deacon Claybourne internalized into their own musical identity? Who else has had the benefit of rising to country music stardom fictionally, then doing it again in their off-screen life?

“What I learned from Deacon, I learned more from fans of Deacon,” Esten says. Over the course of the show, viewers got in touch with Esten to tell them how much comfort the hard-living, troubled and resilient character of Deacon meant to them.

“Because of how hard their life had been, or how hard their father’s life had been, or their mother’s. They just wanted to share with me that there was something cathartic about taking the journey with him,” he continues. “Once I learned that, I started to see that more in my own music. That it had to have meaning; it had to have connection. It had to have some kind of intent to help and heal.”

Esten uses the phrase “through line” a lot when he’s talking about Love Ain’t Pretty, and for good reason: He worked hard to make the project a cohesive artistic statement that, start to finish, reflects who he is. That started with prioritizing emotional meat and potatoes, the way Deacon and fans of Deacon taught him. It also mean co-writing all 13 tracks on the project and pairing a foundation of true-blue country with the rock ‘n’ roll leaning tendencies he playfully describes as going “full Springsteen.”

Esten credits producer Marshall Altman, and the musicians Altman enlisted to play on the sessions, for expertly honing in on that vision. The COVID-19 pandemic helped, too. Right before the first lockdowns hit, he started work on an album; that project quickly got shelved. Once restrictions lifted, Esten was more than ready to start work again, and his mission for what he wanted his debut album to be was clearer than ever.

“I think COVID reinforced the overall concept of: Life is hard, life can be brutal, and yet it can be so beautiful,” the singer says, when asked what that mission was. “Everything you ever suffered from the most — love was definitely tied up in that. If you lost a relationship, if you lost a person, it was ’cause you loved ’em. That’s why it hurts so much, and also why it’s so beautiful.”

Momentum grew with songs like “Down the Road” and “A Little Right Now,” which Esten points to as songs that fleshed out the album’s theme. But although he knew what he wanted the overall sentiment to be, he didn’t have the exact words to sum up Love Ain’t Pretty until he wrote the title song, which was also the last addition to the tracklist.

“By the time we were finished with it, before we go out of the room, I go, ‘This is the title and this is the first song,'” Esten says, remembering the day he wrote that song with Altman and songwriter Jimmy Yeary. “It was, ‘This is what this album is about. Love ain’t pretty, but it’s beautiful.'”

As soon as he’d written the words, he knew he’d hit the message right: And that clear-eyed confidence, borne out of decades of hard work, is another reason why Esten’s winding road to his debut album is so valuable.

“I will say one other thing about waiting so long: I remember when I was in college, I went to work in construction. I was, like, a carpenter’s helper,” the singer says. “So I got this toolbox. And I was so proud of this toolbox. I’d got, like, a hammer and screwdrivers and a drill and all these things. I was so proud because they all looked so brand new.”

“And then I got there and I see all these carpenters and their tools are all old and beat to hell, but I envied that,” he continues with a chuckle. “Mine looked so meticulously new and unused. They shouted, ‘This guy’s never held a hammer before.’ The great thing about being as old as I am now is, I look at my toolbox and it’s not that new anymore. I’ve swung that hammer many, many times, you know what I mean?”