We caught up with the brilliant and insightful Chesca Lilly a few weeks ago and have shared our conversation below.

Chesca, looking forward to hearing all of your stories today. Do you wish you had waited to pursue your creative career or do you wish you had started sooner?

There’s a degree to which it just gets down to defining “career”.
I’ve been hobby-drawing since before I can remember; even my previous off-the-cuff dates for when my brain switched on and I consider myself to have “become an artist” (fourth grade, drawing every Warrior cat from their book descriptions along with their family trees), but I keep finding work from earlier and earlier despite thinking it’s all been lost by now.
I’ve always had my own projects: stories I’ve wanted to tell, characters through which they can be told, and the drive to hone my craft so that I can make them real. That journey will be one that I’m always taking. But I didn’t start making money from it until shortly before the pandemic.
I was, at that point, on a STEM track in college, figuring that I’d listen to my parents and try to secure a job that made money to support my hobbies. I kept up with my drawings throughout that time, and was starting to reach a point in my trajectory where I needed to start finding other avenues of income. So I thought, what the hell, I’m a student, I can draw, and I’ve always, ALWAYS, wanted to be one of those artists that could work primarily off of commissioned work.
That’s what that first step was born out of for me. The timing was extremely fortunate, too, because a few months after my very first commission (to a client that has since become a very dear friend of mine), the pandemic hit, and everything in STEM for me disappeared. My lab job, my apartment, even college itself, all of it. But I’d proven to myself that I COULD do it, I could take steps to make art my actual life, and I knew that I had to flip myself around to make the practicalities into reality.
I don’t think I could have done it any other way. The timing was too good, and the mistakes I made during the first portion of college where I was feeling out what independent adult life meant for Me are ones that I wouldn’t take back, especially knowing now what was coming.

Chesca, 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?

I’m primarily an illustrator and character designer. I like to make very pretty pictures, especially of complex designs and compositions, pushing the line between “too busy” and “simplistic” to find a sweet spot where the design is both efficient and fun to look at. I’ve recently been dabbling with product design, generally accessories and game assets, but I’ve been making book covers and story illustrations for indie projects for several years now.
I’m most at home with digital media, but I’ve been known to experiment with mixed traditional media especially for on-the-spot commissions at conventions, as they make for great personalized souvenirs. I’m working on ways to break out into that market more officially so that I can share that side of myself with the world as well.

How can we best help foster a strong, supportive environment for artists and creatives?

As an educator, I’m biased towards solutions that the educational system can facilitate. I think there’s so much potential there, to help foster a love for the arts early on, but also to better help young people not only transition into the industry, but to give a more honest and up-to-date look in terms of what that process looks like.
I’m still on that journey myself. But I’m building up to a position where I can BE that person for the next generation of students. It’ll take effort to avoid fossilizing, and I think that’s the main issue I currently see with the current guard of teachers: an unwillingness to adapt once they’ve found the school from which they will one day retire. We all need to stay willing to keep up to date, keep trying new things, and integrate new paths once they begin to legitimize and appear naturally in students. It’s a systemic change, largely invisible, not immediate, and requires constant effort and vigilance. But what real, lasting change isn’t?

What’s the most rewarding aspect of being a creative in your experience?

There’s something inherently tactile about the arts, and the way that it showcases progress. If you work mostly in physical media, there’s often a physical mountain too, a verifiable field of work that you can stand on and see the path you’ve cut on your hike up to your current vantage point. Anyone that’s taken a few studio classes can tell you that the artifacts left behind by these classes–materials and sketches and finished pieces and progress photos and failed experiments–quickly fill every nook and cranny of an artist’s living space.
As a digital creator, the same goes for my digital living space. Every hard drive I’ve ever owned has had a hefty portion of it dedicated to my software and brushes and assets and files. My WIP posting history, my screenshots, every aspect of creation (before it reaches another person, even) is a piece of data that shows me where I’ve come from, and far away my starting place was.
And yet, when I revisit old work, after the feelings of struggling and embarrassment have faded enough for me to look at it more kindly, like the work of one of my student’s, I find myself falling in love with it all over again. The growth is marked, but sometimes, the drive and love and passion can be even stronger looking back at more earnest phases of my life. It’s a way to remember what that earnestness feels like, even when the technical aspects of the work aren’t where I’d want them today. It’s a deeply personal journey, but it’s why even if I never make a penny from it, I’ll keep climbing that mountain.

Contact Info:

• Website: https://cinalilli.carrd.co/
• Instagram: cinalilli
• Other: Tumblr: @cinalilli
  Bluesky: cinalilli.bluesky.social

Image Credits

Photography in last photo by Leo Di Frasia