Jessie Wilson Captures Her Three Years in Nashville on Debut EP ‘How ‘Bout We Find Out’

Jessie Wilson packed up from her native Alabama just over three years ago to follow her musical dreams. Once an elementary school teacher, Wilson admits that she feels something when she’s on stage that she doesn’t feel anywhere else. The feeling that strikes her when someone connects with one of her songs is something she can’t replicate.

So when her move to Nashville was full of highs, lows and in-betweens, it was those feelings that she continued to chase that kept her rooted in Music City, continuing to chug along until she had music of her own to release that capture those emotions. Then came March 24th and the release of her debut EP, How ‘Bout We Find Out,

As she weaves her way through tales of bad decisions, loss and the end of a relationship, Wilson carves out a sound that is undeniably hers; unique in the same way that her musical heroes carved out their niche in the country music world.

We chatted with Wilson all about How ‘Bout We Find Out, as well as her move to Nashville, staying busy on the road, her plans for the rest of the year and more!

Pro Country: Your website lists artists like Miranda Lambert, Ashley McBryde, Lori McKenna and Morgan Wade as influences on your music. What do you love about their way of writing and presenting songs and how has that served as an influence on you?

Jessie Wilson: I love the way they all write songs and tell stories. Ashley writes very true to herself, and I think that’s what’s most captivating about country music. I love Miranda’s grit and the powerhouse female vocal that I feel we need a lot more of. Lori is very songwritery and a great storyteller. Morgan has grit and a unique voice. I feel she’s very unique. I feel I’m very unique, and I used to feel kind of weird about that when I was younger. Being from Alabama, I’ve got a different kind of voice, and not a lot of people were very unique there. I relate to Morgan in that aspect. They’re all unique in their own way.

PC: You began playing guitar at 17 years-old. What was it that drew you to the instrument and drew you to start writing songs?

JW: I’ve always loved music. I was apparently humming melodies at two weeks-old. I asked my mom if she was sure that I wasn’t just going “goo goo, ga ga,” but she insisted that I was humming songs [laughs]. I was raised singing karaoke at a bar/pool club that we went to every summer.

When I was in high school, Taylor Swift was a big thing. She was my biggest role model at the time because she was one of the only women that could play guitar, write her own music and sing. That really motivated me. I don’t know how true it is, but I read an interview where she said she learned guitar from YouTube, so every day after school, I got on YouTube and taught myself how to play. I’ve never had any lessons, it’s just something that’s raw and real inside of me.

PC: You moved away from Alabama three years ago to Nashville. What emotions were you feeling as you were moving so far away from home and immersing yourself in Music City?

JW: I feel like when people talk about chasing their dreams, they always talk about the glamorous parts. It’s very hard; it’s been a roller coaster of emotions.

When I graduated high school, my mom wanted me to get a degree before I moved, and while I did, I ended up staying in a long-term relationship with a guy for longer than I expected. I was waiting around, twiddling my thumbs and just playing around Alabama and Georgia on the weekend. I finally got sick and tired of it, and what I identify as God was a strong voice in my head that said “Now’s the time” at 5:30 in the morning. I was getting ready to go teach at my elementary school that day. I told my principal, finished out that year and came here.

Since I moved here, I’ve dedicated my whole life to this. There was no other 9-5, this has been it and the way I make an income for myself. I’ve had to figure out how to be a full-time songwriter and musician independently. I always tell people that I hope their first year was better than mine; I experienced the pandemic, weeks later, my dad passed away, and then weeks after that, my long-term relationship ended, so it was very “Welcome to Nashville.” Everything in me was screaming to go home and give up. It was hard to go through those things while also pursuing music. I always say the happiest and saddest times of my life have been here. There’s a lot of experiences you go through chasing a dream, but I wouldn’t change a thing. Despite the tears that have come along with this journey, I’m happy.

PC: You mentioned your career as an elementary school teacher. Is there any kind of pressure, internally or externally, that you feel with making the choice to leave that career to pursue music full-time?

JW: There was a lot of pressure. To be a teacher, you just have to go to school for a certain number of years, and then bam, you can be a teacher. As long as you have a great interview and a great person, you’re going to get hired. When you dive into music face first, there’s no Holy Bible as the guide; you just come here. Aside from my step-brother and his family, I only knew one person here. I’ve learned that a lot of my friends came here knowing people. It does help to do that, but I was tired of excuses, I was ready to go. I wasted enough time in Alabama. There’s been a lot of pressure with figuring this out and wondering if I’m doing all of this right. You just have to trust your gut and heart and tell yourself that you’re doing the right thing. I’m putting out beautiful music and telling my story. It’s not my job to figure out how I’m going to “get there” one day, wherever “there” is. I just want to keep enjoying the journey and feeling good about what I’ve done when I put my head on my pillow at night.

PC: What went into the decision to have “Business of Bad Decisions” serve as both your debut single and the first release from your new EP, How ‘Bout We Find Out?

JW: I felt like it had a lot of energy. A lot of people had been waiting to hear my sound and my music. It’s kind of funny, I’m usually a very emotional, deep writer, but I liked how fun and sassy this song was. It wasn’t as deep as “Never Even Got to Say Goodbye” or “That’s What Mommas Are For,” but I loved the energy of it. This song was really my breakup story. I came from a place where people felt like you can’t admit when you’ve made a mistake, so especially with me being a former teacher and worship leader, I felt like this song shows that we’re all human and we can all make bad decisions. It was a truth that I really needed to share.

PC: You’ve said “That’s What Mommas Are For” is your favorite song on How ‘Bout We Find Outand that you have heard after shows from fans that the song has touched. What does it mean to you to have a song so personal to you connecting with people the way this one has, and how much do you enjoy those messages and conversations with fans?

JW: That means the most to me. I’ve always been kind of weird; if I would give my mom or sister a card for their birthday, I would write something emotional and ask why they weren’t crying [laughs]. In the weirdest of ways, as much as I don’t like to make people sad, when people are crying because of a song that I wrote, sharing that deep connection with them is why I do what I do. I think there’s a lot of real-world things that happen that a lot of people don’t feel comfortable talking about, but I think there’s healing in revisiting those emotions. The song reaches people from different walks of life and meets them where they’re at.

PC: “How ‘Bout We Find Out” was the third and final single release prior to the release of its EP. What drew you to have the song serve as the title track?

JW: I was trying to do a little play on words, like “How ‘bout we find out what Jessie Wilson’s about.” I was initially going to call it “Heartaches and Happiness” because of the highs and lows of this journey, but I feel like How ‘Bout We Find Out was a good play on words. I’ve been here for three and a half years, and this is my first release. I’ve been going through a lot and trying to find my identity; I enjoyed being a teacher, but I know I was born to be a musician and to share my truth with the world. I feel like people have been wanting to know what Jessie Wilson is about, so I had to show them.

The song is a good sounding, good vibing country song that I feel a lot of people will connect with. It seems to be a lot of folks’ favorite song on the EP too.

PC: “How ‘Bout We Find Out” also features Sam Banks on duet vocals. Can you talk about how Sam became involved with the song and how much you enjoyed sharing it with him?

JW: I ran into Sam several times here in town at writer’s rounds and gigs. He plays guitar and sings with Craig Morgan. There were a few people that I was interested in and a few people that I tried it out with, but I didn’t feel like it fit the song. I learned in the creative process that even though someone may be your good friend, you have to listen to the song and look at what suits the song best. I feel like Sam has such a great, traditional, twangy voice, and when he came in, it felt like magic. He nailed it, and it seemed like there was a magic between us when we were recording it. We had never done a gig or written a song before that, it was very cold turkey, but it worked out!

PC: “Never Even Got to Say Goodbye” is our favorite song on How ‘Bout We Find Out, and is a song you co-wrote with Becca Rae. Can you take us in the room and talk about how the song came together?

JW: That was one of the hardest songs I ever had to write. At most, that was a month after my dad passed away. I was thinking about cancelling the write, but I’d written with Becca a couple times. We sat on the couch with a box of tissues, and she was pulling it out of me. To be honest, I feel like I hardly contributed besides crying and telling my story, and I apologized to her, and she told me that I was writing it. She was respectful and said we could stop at any time, but I didn’t want to because it seemed like it was the right time. I’ve found that a lot of people can revisit emotions, but I’ve found that I write best when I’m writing in the present. When we finished, I loved it. I’ve been playing that song out for years, and there’s usually never a dry eye in the room. That song hits a lot of folks that have lost somebody. Losing people is never easy, but when you don’t see it coming, it makes it harder, and that was my whole mindset with this song.

PC: What do you hope listeners take away from How ‘Bout We Find Out after listening all the way through?

JW: I hope they feel a range of emotions. All five songs might not be everyone’s cup of tea, but I hope and pray that they find a song they can connect with. It could be “Business of Bad Decisions” for someone that is just getting over a breakup and wants to go through a wild, party phase. It could be “How ‘Bout We Find Out” if there’s a love interest and they’re on a lake on a boat and need a good vibing song. It could be the sadness of “Never Even Got to Say Goodbye” or the sentimental “That’s What Mommas Are For.” Or it could be about a relationship that’s not working out with “Leaving’s All That’s Left to Do.” I hope they learn who I am and that they can visualize my last three and a half years of being here. I hope they find a song that makes them want to smile, cry and listen to it again.

PC: Your website mentions that you play an average of more than 200 shows per year. How much do you enjoy staying active on the road and bringing your music to people in that setting?

JW: I love it! I was made for the stage. People ask me if I had to pick between being an artist or songwriter, which I would choose, and I would want to be an artist, because there’s a feeling that I get when I’m on stage that I never feel. It’s funny, I’m kind of a shy person when it comes to walking in front of people or in crowds; if me and a friend walk into a restaurant, I don’t usually want to walk first. But when I’m on stage, that’s the only time I want attention. My biggest compliment is to make a room be quiet. My goal is to make people listen with my talent and with the story I’m telling. Even if it’s a cover song.

PC: Along with promoting How ‘Bout We Find Out, what do you have planned for the rest of 2023?

JW: I’m working on booking right now and getting out a bit. My ultimate goal is to find a team to have around me; whether that’s a team or a booking agency. I’m completely independent, so I want to start working with a team of people that are for Jessie Wilson and are going to help me reach the next step and gear up for my debut record. I hope to get in the studio in the fall. But my biggest thing is hoping this music strikes the ears of the right people, because it takes a village.