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Meet Jessica Healey of Austin

Today we’d like to introduce you to Jessica Healey

Hi Jessica, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
A theatre kid from Fort Worth, Texas, I’m now a singer-songwriter and jazz vocalist based in Austin. Art and perfomance have always been my greatest passions, from singing to writing, dancing, acting, and playing guitar. I studied acting at Texas State University but was pretty disillusioned by a mid-pandemic graduation, so I took up a remote sales job for more stability. A couple of years later, just as I was beginning to perform at local open mics and jam sessions, I was laid off. It felt like a sign, so I decided to go all in and pursue music full-time.

Now, I’m the songwriter, bandleader, guitarist, and vocalist of my indie-pop band, which had the incredible opportunity of performing an official showcase at the 2024 South by Southwest (SXSW) Music Festival. My music blends influences from pop, rock, soul, and jazz, drawing comparisons to artists like Madison Cunningham, Fiona Apple, Lizzy McAlpine, and Corinne Bailey Rae. Known for my brutally honest lyrics, I’ve built a loyal and engaged following who deeply connect with my unique sound. As a solo acoustic artist, I’ve also performed original showcases for SoFar Sounds and the Austin Music Love Concert Series.

Additionally, I’ve become deeply involved in Austin’s jazz scene—a development I never planned but have found incredibly fulfilling. Beyond my newfound love for the music, the friendships I’ve built in this community have been especially rewarding. I lead my jazz ensemble, the Jessica Healey Quintet, and have had the honor of performing alongside brilliant musicians like Gerry Gibbs, Mike Sailors, and Kevin Lovejoy.

Right now, I’m in the final stages of post-production for my debut EP, set to release in the spring of 2025. That project has been a huge challenge in not only committing to artistic choices, but believing in myself enough to share them. I’m so very excited to have my tunes out there for people to hear, especially the lyrics, which are the most precious and important part of my art.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Getting laid off was definitely a blow to my ego—though not as big as you might think, since I was already one foot out the door, spending more time improving my craft than attending extra meetings. However, my perspective on the news was immediately changed when the first response from a loved one was, ‘Congratulations.’ In that moment, I knew they were right: I was being shoved off the cliff, as it was time to ‘spread my little wings and take to the sky.’

November of 2023 through November of 2024 was certainly the largest period of growth I’ve yet to live out (even more than the first year out of high school, which is really saying something). And growth = pain. Self-employment as an artist means not only believing in your talents and skills, but continuing to advocate for yourself even in periods of self-doubt. It means taking on new responsibilities that were previously managed by your employer–tasks like filing for taxes, creating an online presence, marketing your business, and continuing to hone your skills to remain competitive in your field.

Some concrete challenges include adjusting to a completely flipped schedule for sleep, exercise, household tasks, spending time with loved ones, and running errands. Working from 5 p.m. to 3 a.m. instead of 9 a.m. to 5 p.m. was a major shift, and I’m still finding a balance.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
Yes!!! I love writing songs!! In my originals, I aim to write lyrics that are vulnerable–sometimes shockingly so–but never for shock-value alone. The more honest and direct they are, the more cathartic it feels to sing them, helping me process the pain that served as the impetus for the song. Additionally, cutting out the bullshit seems to hit people’s heart and challenge their minds more succinctly, which has always been my experience as a listener. A song that makes my jaw drop, whether from a surprising modulation or a phrase so unfiltered it feels uncomfortably personal, that is a winner. I believe the discomfort is an indication of a truth within myself that I have yet to confront. And this song now no longer gives me the choice to avoid it.

I also love jazz!! It’s jarring–in the best way–to be involved with two communities so different from each other in values, backgrounds, artistic visions, and lifestyles. Singing jazz as a vocalist feels more executively creative and less vulnerable, offering a refreshing break from bearing my soul at original shows. The initial framework is already laid by the composer and lyricist, so my artistic fulfillment comes from experimenting with their melody and simply enjoying the incredible sounds of the band. And these songs *were* the singer-songwriter tunes back in their day, so it feels like I’m paying homage to the genre of music that is the foundation for everything pop music is today.

What has been the most important lesson you’ve learned along your journey?
Wow. So many. I’d say trust. Trusting my ears, trusting myself. Trusting my ears to know what I like and dislike about other people’s music as well as my own. Trusting my impulses as I write new melodies and progressions, even if they challenge the expectations I previously had for myself.

Trusting myself enough to push through self-doubt. So much doubt. Finding myself around musicians infinitely more talented, skilled, educated and practiced than myself can be both incredibly inspiring and, at times, disheartening (especially depending on the time of the month). I constantly feel behind. There’s so much I want to learn, but I have to trust that I’ll get there in time and that I’m worth advocating for exactly as I am in this moment.

Contact Info:

Image Credits
Jose Velazco
Kim Yarbrough
Raul Ochoa
Valentina Loiodice

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