We recently connected with Matteson Gregory and have shared our conversation below.

Matteson, thanks for taking the time to share your stories with us today Can you open up about a risk you’ve taken – what it was like taking that risk, why you took the risk and how it turned out?

I was always the shy girl growing up. I never put myself out there or was the first to raise my hand in class. So the fact that I wanted to be a singer seemed impossible. But there I was dreaming of being a singer. Writing songs in my room after school. I knew that once I graduated high school I could start my dream. My mom was always supportive of my dream and would always hear me singing in our staircase at home. She was always pushing me to put myself out there. Telling me that my voice was important. When my senior year started, my mom made me promise that I would perform at least once. Whether it was a talent show or the choir senior showcase, she wanted me to put myself out there. I agreed and when the choir senior showcase came around, I auditioned. The best part of that was I was able to be apart of the choir senior showcase. The bad news was that because not enough people auditioned, they had to cancel it. I was upset since I had worked so hard to make it happen. And I also promised my mom. A few days later, my choir director came up to me and said that he felt bad having to cancel, but he wanted to see if I would want to perform my song for the school assembly. That would mean I would sing my song in front of the entire school. I was so hesitant, but I knew that I made a promise to my mom. So I said yes. When the day came, I was so nervous. I couldn’t think straight and I just kept thinking the worst case scenario: no one will clap for me. The assembly started and they called me up to sing. I walked up slowly, took a deep breath, and started singing into the mic. I wasn’t even done with the whole song when people started cheering and clapping for me. I was shocked. After I finish the song, I looked around at all the people who were cheering and standing up for me. I also saw my mom over by the bleachers crying happy tears. That was the moment I knew that this is what I wanted to do. And most importantly, I can do it.

Matteson, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Music was always around when I was growing up. My dad played in rock bands, and our family get-togethers usually turned into karaoke nights at my grandparents’ house. I was that kid who would jump up to sing ABBA or try to strum along on my dad’s guitar. When I was twelve, my dad officially taught me how to play, and that’s when I started writing my first songs.
I was ready to chase my dream. I entered a local talent show in my hometown, but instead of the big debut I hoped for, I ended up getting kicked off stage. It was devastating and made me question if this was really for me. But even after that, I never fully stopped. I kept writing songs in my bedroom, quietly keeping that dream alive.

Everything changed my senior year of high school when I performed at my school assembly. That moment gave me the confidence I needed to believe this path was meant for me. From there, I started booking coffee shop gigs wherever I could, taking trips to Nashville to meet other writers, and eventually connecting with my first producer which led to releasing my own music.

What sets my music apart is its honesty, I write about the real, unfiltered parts of growing up and figuring yourself out. My songs blend the heart of 90s storytelling with a modern indie pop edge, often inspired by the same kind of humor, emotion, and nostalgia you’d find in Friends or Sex and the City.

I’m proud of how far I’ve come as an independent artist building everything from the ground up, finding my sound, and connecting with listeners who see their own stories in mine. My upcoming EP, releasing next year, captures that journey it’s about change, self-discovery, and learning that it’s okay to still be a work in progress.

If there’s one thing I want people to take away from my work, it’s that your story doesn’t have to be perfect to be worth telling sometimes the best parts come from the moments you almost gave up.

What do you find most rewarding about being a creative?

The most rewarding aspect is connecting with my fans. I love when fans tell me I have made them feel better about themselves and that they have a voice in this world. I was always the quiet girl growing up and I always felt like people would talk over me. Or maybe I just let them. Now I know that my voice matters. And I want my fans to know that they matter too.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

The biggest lesson I’ve had to unlearn is that I need to make everyone happy. Especially being an artist. For a while I would always try to make the kind of songs that I thought people wanted. Like writing love songs even though I had never been in a relationship. I learned that no matter what, I cannot be everyone’s cup of tea. I know that there will be people who don’t like my music, But there are people who will love my music. The most important thing is that I write what I know and focus on the people who love that.

Contact Info:

• Website: https://mattesongregory.com
• Instagram: https://www.instagram.com/mattesongregory/
• Facebook: https://www.facebook.com/mattesongregorymusic/
• Youtube: https://www.youtube.com/@mattesongregory
• Soundcloud: https://on.soundcloud.com/S3cWSHhkSVW5sgaI4e
• Other: TikTok: https://www.tiktok.com/@mattesongregory

Image Credits

Photographer- Drake Huckstep