We caught up with the brilliant and insightful Jessica Healey a few weeks ago and have shared our conversation below.
Hi Jessica, we’re so appreciative of you taking the time to share your nuggets of wisdom with our community. One of the topics we think is most important for folks looking to level up their lives is building up their self-confidence and self-esteem. Can you share how you developed your confidence?
It’s been a long and arduous journey lol. Supportive friends, loving parents, mantras in the mirror, etc. Another helpful factor has been personal follow through. I find that the more I follow through on my word to myself, the more safe I feel within the world around me.
When I feel I’m reliable and trustworthy, I feel more capable of taking on external struggles whether it be professional challenges, anxiety-inducing social situations, interpersonal struggles, etc. And as I successfully navigate my way through these unfortunate events, I find my sense of self strengthen deeper further because “Hey, look! I just made it through that scary thing!” Following through on my commitments gives me a sense of security and safety.
Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?
I’m an indie singer-songwriter and performing artist based in Austin, Texas. My goal in writing music is to be raw and real. Unfiltered vulnerability that invites listeners into a deeply personal, relatable space. My sound blends indie-folk intimacy with pop-infused melodies, jazz-inspired harmonic nuances, and striking lyrical narratives.
One of the most exciting aspects of my journey has been the surprise of it all. Four years living in Austin, and for the first 2.5 years, I was completely removed from–and rather indifferent to–the music scene. But when I was laid off November 1 2023, I began my career as a professional musician the same day. Everything I’ve accomplished up to this point has happened within 1.5 years, leaving me surprised, exhausted, proud, overwhelmed, fulfilled, and many other things all within a very shot amount of time. Performing at renowned Austin venues like Elephant Room, Monk’s, and Jupiter Supper Club, SXSW (2024), The White Horse, The Mohawk… that reality had never crossed my mind as a possibility. My day-to-day life is something I never could’ve imagined, and that’s very exciting.
Currently, I’m in the process of releasing 6 new singles which will culminate in an EP. A bold and introspective collection exploring themes of self-awareness, emotional resilience, and the complexities of human connection. Each song was inspired from a particularly visceral feeling, and I hope people experience that while they listen.
In addition to music releases, my band and I perform regularly around Austin and are expanding to larger venues and even other cities. I’m excited to get back into the studio so that we can release new music and connect with broader audiences. I’ve got a large batch of new works that explore different themes and ideas and I’m stoked for people to hear.
Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?
My previous sales experience has been probably THE most important factor in my quick transition from hobbyist to full-time professional musician. There are way too many talented artists who simply don’t possess–or make it a point to learn–the business savvy and skills necessary to build and maintain a successful and sustainable business in the music industry. I had an immediate understanding that I am a product/service to be marketed and sold, and that I am the only one who is gonna do it. That awareness allowed me to take rejection less personally and persist in building my business.
For my first 2-3 months as a “full-time musician,” I sent minimum 100 emails a week to venues, coffee shops, bars, restaurants, nursing homes, etc. Every week after that, I would email and/or call until I got a “yes” or a “no.” Cold calling and prospecting, managing the pipeline of those leads, setting time aside to make those calls, making goals for the number of gigs I wanted to book each month, those are all very boring and non-musical skills lol. But they led to my current lifestyle where I am able to invest time and money into furthering my art, and in a sustainable way.
So if I had to pick three out of the sales skills that help me, I’d say
1) Networking
2) Lead Prospecting / Pipeline Management
3) Resilience and persistence (soft skill, but still extremely difficult to come by)
Looking back over the past 12 months or so, what do you think has been your biggest area of improvement or growth?
My biggest area of growth over the past 12 months has definitely been learning how to become a decisive, confident leader with a strong vision. A year ago in June, I played at Monk’s Jazz Club with a band under my own name for the first time, which was freaking terrifying but also jumpstarted the next chapter of my career in bandleading.
Over the following months, I focused on developing my original project with a band. Scheduling rehearsals, gigs, studio sessions, etc. was a lot of extra coordination work on top of the solo career I had already established.
For a while, I was pushing the original band project really hard, but since band gigs pay less and are harder to come by than solo gigs, I was mostly paying the band out of pocket until we secured our residency at Jupiter Supper Club. Around this time, I had a huge holiday influx of corporate gigs requesting full bands.
Since then, I’ve had to learn rather quickly learn not just how to book, but how to manage multiple calendars at once, how to keep everyone happy: the client as well as the band, how to pay subcontractors in a reliable and consistent way that won’t kill me come tax season… the list goes on.
Interestingly, bringing more people into my project made me realize how essential it is for me to have clarity and confidence in my own vision. Initially, I thought being considerate meant frequently asking the band’s opinions and preferences. But over time, I’ve found that what people really value is a decisive leader who offers guidance rather than communicates uncertainty or hesitation.
Ironically, the larger the band became, the more clearly I had to know myself, my intentions, and my goals, and the more self-sufficient I’ve become. Of course, I occasionally slip into old habits of deferring decisions. But I see now that owning your creative vision isn’t selfish or “bossy” but rather how to be a good boss.
Contact Info:
- Website: https://www.jesshealeymusic.com
- Instagram: https://www.instagram.com/jesshealeymusic/
- Youtube: https://www.youtube.com/@Jesshealeymusic
- Soundcloud: https://soundcloud.com/jesshealeymusic?utm_source=clipboard&utm_medium=text&utm_campaign=social_sharing
- Other: Tik Tok : https://www.tiktok.com/@jesshealeymusicc
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