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Interview: An Inside Look into ‘The Headline Tour’ with Jillian Dawn

by Jacklyn Lipscomb and Mari Washburn

Nashville- based artist Jillian Dawn believes the key to success is to stay true to yourself, no matter the cost. Originally hailing from Mansfield, Massachusetts, the 24-year-old singer songwriter is paving her own distinct path in the indie pop realm with flares of country and rock sounds that leave listeners eager to hear more. Writing from real life experiences, her lyrics are raw and authentic, allowing each release so far to provide an honest glimpse into Jillian's world.


Embarking on her first headlining tour this summer, we caught up with Jillian ahead of her stops at City Winery in Boston on 7/29 and the Mercury Lounge in New York City on 7/30 to chat about her experiences on the road so far.



Alternative Lately: For anyone who doesn't know, you are currently in the midst of The Headline Tour, how have the shows been going so far and how does it feel to be headlining?

Jillian Dawn: It's been a crazy time. It's been so much fun. It feels so great to be able to do a headline tour with a band. I've never done that before, which is very fun. I've done a lot of acoustic shows and I've traveled all over for acoustic. But, to have a band and to play my songs the way that they are supposed to sound feels amazing. This month is actually insane and I can't believe it's almost over. It's very sad for me. We've been prepping this for what feels like forever. I was in LA in the week leading up to the 15th- I was there for a week and then I immediately went back to Nashville. I moved into my new place, played Nashville, and then on Saturday I drove 10 hours to DC and did a little Sofar Sounds show in DC. And then yesterday, about 24 hours ago, I got back to Massachusetts after driving from DC to Massachusetts. So it's definitely been a lot of traveling, but I'm at this point in my life and my career where I feel like I don't mind doing it all. I love it. I love traveling. I love being on the go. But definitely, I'm learning a lot of different things on tour, like what not to do this time around, which is fun and good to know for hopefully another headlining tour in the future.


Absolutely! A good learning experience. Have there been any standout moments so far?

Hmm. Definitely a lot of things that I would only know really. When I was in LA, I skipped over a song, so I was like, oh, that's fun. When I'm in the moment on stage, I'm there, but I'm also not there, if that makes any sense. It's kind of an out of body experience when I perform. I'm doing the motions of everything while also trying to live through it. So I think my favorite part about at least LA was that I got to see a lot of my college buddies there. I'm doing a lot of older songs that I worked on in school, so a lot of people knew the lyrics. My standout moments was when anyone was singing along with my music and singing along to the songs. “Vices” specifically is a song that I did at school and a lot of my friends knew that one. And then Nashville, honestly, the entire show was a standout moment for me. I've only been there for about two years and having all of my friends that I've acquired while I was there and just a bunch of new people that I didn't even know come to the show meant the world to me. It meant like, Hey, I think you're doing something right by living there. And post show too, there's certain things that have stuck with me. There's a song I play in my set called “Fool Me Twice”, and it's not out anywhere. It's just a song that I do live with a band and it's a very emotional one. A girl that was at the show texted my friend and was like, “Hey, what's that song that Jillian sang about her ex? Um, it goes like this” And she literally quoted the entire chorus just from hearing it at the show. And I was like, that's crazy! That's exactly what I want people to do every show that I play. That was a highlight for me. There's been so many- seeing my friends, meeting new ones, and getting to play the songs the way that they're supposed to sound are all my main standouts at least.


That’s amazing! Going back a little bit, you are originally from right here in the state of Massachusetts. Growing up, what made you realize that you originally wanted to pursue music?

That's a good question. I'm from a very sporty town. I grew up playing sports and there's not a lot of opportunity for music around these parts. I started in music doing musical theater when I was younger. And my earliest memory of professionally singing was when I was five years old. I sang the national anthem at my dad's golf tournament. I know it wasn't good, but it was funny. It was like a big, um, what's it called?


Oh, like a megaphone!

Megaphone, yeah. <laugh>. Yeah, that's my earliest memory of doing all of that. I think over time I was just invested in it. It was what I loved to do. I'm a talker and I also sing all around my house, and my parents were like, “hey, should we get her into lessons? Should we get her into music class? Like, what's the next step?” I'm very fortunate to have very supportive parents that help foster dreams for me and my sisters. They were like, if you want to do this, then pursue it.


I started writing when I was 12 in seventh grade and then started taking guitar at the same time. I took piano on and off though for three years and guitar for about one full year. After that, I was self-taught and not very good, but I could get by. I started professionally singing and songwriting in middle school. It helped being in a place where I could do musical theater and I had a lot of different parts of life to kind of pull from- musical theater, sports, and being a teenager is crazy. I just pulled content from whatever I was going through at the time, like which crush wasn't texting me back after school. That's kind of how I got into it. Everyone in my family can kind of sing, but no one pursued it as professionally or as hardcore as I have.


As you stated, you are currently based in Nashville, which is so cool. I feel like the pipeline of people migrating from the east coast to LA and Nashville is so real these days. How has being in Nashville influenced your songwriting and growth as an artist recently?

That’s a great question! I think I write a little more country than I used to. I never really did any co-writing before I moved to Nashville. Even at school when I was going for songwriting, I did maybe a total of 5- 10 cowrites in my four years at Miami. Being in Nashville is all about co-writing and I had to learn how to do that while simultaneously up-hinging my life. It's been wild. I think that I've learned to write with integrity while also writing in a commercial fashion. By that, I don't mean pop hits or anything like that, which I have learned over time. I think commercial as in writing as a job versus writing as a passion project. I do still write on my own and I definitely have those moments, but Nashville has taught me to churn content out faster, which is great. I feel like that can be like a hit or miss subject with some people because, you know, churning out content isn't the same as crafting something that you believe in sometimes. But I never release songs that I don't believe in. I’ve also learned how to write for other people. I didn't really do that before. I've had a couple writes with other artists, where I'm not the main artist and I'm not the voice that has to be portrayed, which is very interesting and something that I probably need a little more practice with. But yeah, it's been very, very interesting.


You've been releasing music for quite a few years now. You released your debut EP all the way back in 2016. What kind of advice would you give to any fellow up and coming artists who strive to embark on their own musical journeys?

My main piece of advice is stay true to yourself, as cheesy as that is. Try to surround yourself with people that will foster your dream rather than tear it down. I wouldn't be where I am without my family and without my group of friends that always push me to play, and to release my songs and things like that. Just make sure you're surrounding yourself with the people that are going to help push you and motivate you versus tear you down. With recording and things like that, just trust your gut with who you work with. If you're not getting a good vibe, then switch it up. With rejection- don't let that stop you because music is so subjective that you're going to get so many different opinions. If there's anything that you can do with rejection, you should use it as motivation. I've been rejected from in many capacities of life. But with music specifically, when I was younger, I'd send my stuff to certain blogs or meet with industry people and they'd be like, oh, it’s okay, whatever. Instead of letting that tear me down and move on from this dream, I let it motivate me. I was like, if you think this can be better, then let's see if I can make it better. Let's see how I can still stay true to myself, but also make it more professional. I just believe that if your art is going to do something, it has to be true to who you are and you should just try to stick with that. Don't lose yourself in the process. Be as authentic as you can.


That is perfect advice! Your two most recent standout singles have been “Watered Down” and “Fear of Heights”. They fit very well in that indie pop singer songwriter realm. When you are first beginning the process of creating a new song, what are some examples of the things that inspire you?

Those two songs were written with very different processes, I'd say. With “Watered Down” I was flying back home after Christmas in 2021. I was in the airport and I was in the security line and I thought I saw my ex in the security line checkout, and then I did a double take and I was like, oh, it's not him. Then I thought to myself, I was like, that looks like the watered-down version of him. And then I also thought- that's a really cool idea- a watered down version of somebody. So I wrote that down in my notes and I took it to my co-writers who were the same co-writers on “Fear of Heights”- Drea Gordon, Tamara Laurel, and Caleb Oczkowski. They were like, that's a really interesting idea! We wrote that song in about three hours. I knew when we wrote it that it was special. “Fear of Heights” was written from the guitar riff. I was just messing around with that on the guitar. We were bouncing ideas off of each other for two hours and it kind of just poured out from there. So it wasn't from a specific situation, but it was whatever we came up with in the moment. When I was in Los Angeles in 2022, I sent my friends my demos sometimes, and I was in the car with my friend Sean and my friend Jake. We were talking about music and all that and my friend Sean was like, why don't you release “Watered Down”? Like, you should totally release it. It's a great song. And I was like, it’s a little more pop than what I think I'm trying to portray. It's definitely different from the stuff I just released. But I was like, you want to know what? You're right. It is a good song. I don't have to put myself in a box. I can release whatever I want to release. I can have a pop moment and then I can do a full-blown country album and then I can do a folk track or something like that. As long as I believe in the song and I believe it can touch other people, I have every right to release it.


Are there any artists that personally inspire you or those that you look up to?

Sarah Bareilles is my go-to for this question. I love her so much. She just has such an incredible career and I think she's such a great role model for young women in the industry. She's touched so many different parts of the industry from songwriting to production to musical theater. She's very interesting and a great role model to have as a woman in music. I also love Taylor Swift, Maggie Rogers, the 1975. I grew up on Carrie Underwood too, so I love Carrie.


We are Alternative Lately and we like to ask people that we have on the show what they are listening to lately. So what are you streaming on repeat right now?

My go-to song this summer has been "Cruel Summer" by Taylor Swift. I don’t know what's in that song, but I have to listen to it if I'm going to have a summer vibe. I love the band Sawyer, they are a Nashville based duo. They're sick and they're also good people. Sabrina Carpenter is great. Pretty Sister is also a great artist project and they've got a ton of really cool pop R&B songs. I've been listening to their discography a little bit and it's very interesting. And of course, Harry Styles. I am a huge Harry Styles fan.


You are making Stops in Boston and New York coming up. What can those who plan on attending expect from those shows?

The main thing I have to say is the band. I have had different bands for LA and Nashville, but this band is made up of a bunch of University of Miami alum and they're very, very talented. I can't wait to be able to play the songs that I've been playing in these cities with a band. I've only played in Boston with a band once and it was very last minute. I didn't get to do nearly as much promo as I have for this time around, and it's a sold-out show which is so exciting because I've never sold out a show in my home city. It's a lot of family friends coming and a lot of high school buddies, so I'm excited to show people that have been supporting me for a long period of time, what I actually do and what I've been doing in Nashville. There's a lot of new songs coming on this headline tour that I'm hoping to record in the fall. I'll also be playing electric guitar- I don't normally play that. I have merch too for the first time, which is new and exciting.


(Speaking of opening acts) Mia Giovina is an amazing artist. She is so professional, and she's just been a joy to tour with. She's been with me since LA and Nashville, and then she'll be coming up this weekend. She's from New Jersey and she's so talented and she's so young and like, just such a hustler. I'm honored that she said yes to joining me on this tour. And then Spencer Jordan is so amazing. He's a Nashville guy. He'll be making his New York debut, which is exciting. They are both so talented and such great people too.


We already touched on new and exciting things, but, do you have any future plans that you're really pumped about for the rest of the year or even going into the beginning of next year?

Well, I'm on the road until essentially October, but after that my goal is to hunker down and record all of the new songs that I've been playing on this tour. I have some that I've been sitting on since I moved to Nashville and I'm excited to get those in the works for hopefully, fingers crossed, a full project coming in 2024. I also have the “Come On Over Baby (All I Want Is You)” covers that kind of hit it off on TikTok that just came out last month. That's my newest release. But yeah, lots to come in 2024 with new music. I have a lot of people asking for certain songs that I'm playing and I'm just excited to finally deliver on that… That’s the plan!



 

Be sure to check out Jillian Dawn's newest release and catch her first ever headline tour- with a stops in New York City and Boston this weekend!




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