January Country Rookie of the Month: Alana Springsteen

Alana Springsteen has an old classical guitar she found in her grandfather’s garage at the age of seven to thank for her first foray into music.

“He didn’t even play guitar, but from the first second I saw it, I was drawn to it,” the Virginia native tells Billboard, calling just before heading out to perform as part of Luke Bryan’s annual Crash My Playa festival in Cancun, Mexico.

Her grandfather gifted her the guitar, on one condition. “He said I could have it if I promised to learn how to play it,” Springsteen recalls. “I begged my uncle to come over on weekends and start teaching me chords.”

By nine she started writing songs and a year later was making trips to Nashville. By age 14, she had signed her first publishing deal. Last year, she released the two-part EP project, History of Breaking Up, via Sony Music Nashville/Columbia. Now 22, the member of CMT’s Next Women of Country Class of 2023 is gearing up to release her three-part, full-length debut album.

On March 24, she will put out the project’s first installment, the six-song Twenty Something: Messing It Up, spearheaded by fiery single, “You Don’t Deserve a Country Song.”

When she walked into the writing session with Mitchell Tenpenny, Geoff Warburton, Michael Whitworth and Will Weatherly in early 2021, Springsteen was healing from a tough romantic breakup and was intent on writing about moving on.

“You can’t really say that title without smiling,” she says. “I wasn’t in a really good place after my last relationship ended, and this guy was the same one I wrote a lot of History of Breaking Up (Part Two) about. He broke my heart and it was not a good situation, which is why It made sense to me to kick off Messing It Up with this song. It doesn’t come from a place of anger or pain, but from a place of deciding to put myself first. I realized I was giving my ex a lot of power by sitting in regret and heartbreak, so I walked into that writing session very intentionally.”

Chatting with Billboard, Springsteen discussed her upcoming project, her new song and her time in Nashville.

When you first came to Nashville, what were your first co-writing sessions like?

I first came when I was 10 and started co-writing with Sherrié Austin and Will Rambeaux. It’s so funny looking back because I’m like, “What must they have been thinking when they saw this 10-year-old walk into a room like, ‘Here’s this idea I have. Let’s write a song’?” But I never questioned it, and just knew it’s what I was born to do.

We wrote a breakup song, believe it or not. I remember they were like, ‘Have you been through a breakup?’ I drew from stories, and movies and books. Then I met people like Bart Herbison at NSAI and Tim Fink at SESAC, just early believers. That’s one thing that is so special about Nashville. People, for the most part, genuinely want to help you get connected.

What does songwriting mean to you?

That was really a big deal for me. I mean, when I found songwriting, my whole world changed. Songwriting is how I make sense of the world. It has been my therapy. All I wanted to do was be a country artist like those I grew up on, like Shania Twain, Taylor Swift, Carrie Underwood and Keith Urban. I love the way country music can craft a hook and take you on this journey through song.

Mitchell Tenpenny was a co-writer on “You Don’t Deserve a Country Song.” You’ve also toured with him.

We met while writing this song and that led to a cool friendship. He’s got a few other moments on this upcoming album, which is exciting.

As a co-writer, a vocalist, or both?

I don’t want to give away too many details, but he’s definitely all over this record.

Do you already have all of the songs written for all three portions of Twenty Something?

I always leave room to change things. I write in real time, so I’m keeping room if something really special comes along, but I have pretty much the record planned out.

Last year, you released the two-part project, History of Breaking Up. Your upcoming album, Twenty Something, has three parts. What appeals to you about making these multi-part albums?

I think there’s just something really cool about creating this body of work and letting fans digest a lot of songs. Twenty Something is, as a whole, about kind of the messiness of your 20s. I’m only two years into my 20s, but I’ve already learned so much about myself and experienced so much change. I know I’m not alone in that.

When I wrote the song “Twenty Something,” I started to see that a lot of the music that I had written over the past few years fit into three separate categories. I wanted to compile them and take it step by step and take my fans along with me on this journey.

What can fans expect from the music on the upcoming portions of Twenty Something?

There are songs on here that call out my struggles, areas that I’ve messed it up, which a lot for me has been in the areas of love and relationships. It’s pretty vulnerable. But then there are moments where, if you’re lucky, you start living your purpose and start figuring things out. I think your 20s are a mixture of all of that. I hope that people can just find a little bit of themselves in this record one way or another.

What is the first concert you remember seeing?

The first concert I went to was Taylor Swift’s Speak Now Tour in Charlotte, North Carolina. I’m a huge Taylor fan. Growing up, it was like she was telling my stories. She was writing from such a young age, that encouraged me that I could do the same thing. I’ll never forget what it felt like watching her on that tour, the way she shared that moment with her fans. It was beautiful to watch and I’d never seen fans react to an artist that way.

Do you have a favorite music book or podcast?

I love the [podcast] And the Writer Is…, that one’s always really fun to listen to, to get into the mind of writers and learn tips from people that I look up to in the field. I’ve also been reading a book called 101 Essays That Will Change the Way You Think. I’m making my way through it. I feel like I’ll read a paragraph and be like, “Oh, wow, I need to spend a week just sitting with that and figuring out what it means to me.” So it’s one that I pick up, whether I’m on a plane or in the van on the road. But it just gives me something to think about.