Meet Kendyll Hillegas | Illustrator and Artist

We had the good fortune of connecting with Kendyll Hillegas and we’ve shared our conversation below.

Hi Kendyll, what led you to pursuing a creative path professionally?
Well, an artistic career wasn’t something I planned on. So it feels strange in some ways to say I pursued it. I only ended up majoring in art because I happened to take a drawing 1 class as an elective and really enjoyed it. Then after college, I tried one or two approaches to turn that into a career, but quickly gave up. It’s difficult to actively pursue what you can’t even imagine.
For the next few years, I worked in a variety of jobs (barista, SAT tutor, community organizer), and basically never picked up a paintbrush once. I remember thinking of art in the past tense — something I used to do. At the same time, I was struggling with some ongoing chronic health issues. Eventually they became significant enough that I had to make some major changes to the shape of my daily life, giving up my full time job, and switching to contract work that I could do from home.

At that same time, I gradually began making art again after a 4-year hiatus. I shared some of it online as a way to motivate myself to complete paintings when I was stuck at home. With time, things grew organically — I began selling prints, tackling more ambitious work, doing commissions, and eventually transitioning to full time commercial illustration. At some point within that first year or two, it was like something clicked and I realized a creative career was a goal I could work at and pursue, in the same way that I had worked at learning to draw. Up until that point, it had felt like creativity and art making were pursuing me, and that I was repeatedly running away from them. Deciding to actively pursue a creative career felt like a massive postural shift, but also the most natural thing in the world. 

Alright, so let’s move onto what keeps you busy professionally?
Most of my client work involves commercial packaging illustration (Jukebox, Good Culture, Coca-Cola, and others), and publishing/editorial work as well (mostly magazine and newspaper illustration). I do incorporate other things, like video content, pattern design, fine art, and even teaching a class here and there, but packaging/advertising, and publishing are my bread and butter. Which is great, since I love working with clients.

My favorite projects are the ones where there’s a high level of creative alignment between the client and I, where we’re both working hard to bring a shared vision into existence. That’s one of the things I love most about getting to work with values-driven companies, and clients who share a desire to make something really authentic and creative. It requires me to be on my game when I’m in the studio painting, but also to keep that posture of curiosity, and openheartedness and collaboration, even when we’re doing something like going over revisions.

And since I genuinely love painting, it makes the career side of the equation feel connected to the whole. Because at the end of the day, whether it’s a piece of fine art, or a commercial illustration, I am getting to spend my time painting, which is an incredible privilege.

Did building a creative career feel easy? What’s a creative accomplishment you’re proud of?
Building a regular creative practice, let alone a creative career, definitely did not feel easy. I was not one of those people who had a clear vision and goal, and just doggedly pursued it. It felt a lot more like stumbling around, looking for the next right step. Something that I am continuing to learn is that there’s no absolute, no rule, no guide that I can always use regardless of context, to find my way. It’s an evolving landscape. And even if I tackle one challenge, I’ve only really learned to tackle that challenge, it’s not a formula I can necessarily apply whole-cloth to the next one. Actually, it’s very similar to painting in that way. Yes, there are skills and expertise you acquire through practice, but every single painting is a new problem to understand, a new journey to go on.

To that end, I might feel proud of how a particular painting turned out, but truly, the way I feel in those moments, is probably more accurately described as grateful. It always seems to me that there are so many aspects of a painting that were not fully in my control. The only thing that really feels in my control is the ability to be honest with myself about my feelings, and limitations, and to try to take steps in the direction I want to go. When I can do that, especially if it frightens me, or feels like a risk, or has failed I the past, I feel proud.

What’s a piece of advice about creativity that made an impact on you? What advice would you give to someone just starting out in a creative career?
The poet Mary Oliver has a frequently quoted line that summarizes her advice for living a good life: “Pay attention. / Be astonished. / Tell about it.” This has always really resonated with me with respect to painting. Creating realistic, representation work requires me to pay very close attention, and I almost always find that I’m astonished by what I see.
Whether it’s a portrait, or a packaging illustration, noticing and becoming immersed in the details feels transcendent. I think if I have any innate skill, it’s this — the ability to closely observe, and feel wonder as a response to what I see. At that level, everything feels magical and charged with meaning. So even if I’m painting a realistic strawberry for the 47th time, it feels fresh and new because I have never painted *that* strawberry.

In terms of advice that I’d share with someone else, without knowing context, it’s tough to get anything specific so I guess I’ll just pass along my favorite part of that Mary Oliver poem, and add my two cents: pay attention / be honest / prioritize action. Pay attention, and be honest with yourself about where you are, what you want, and what is getting in the way. Come up with an idea, and try to take action on it as quickly as possible, even if it’s not perfect. Then, pay attention to what you learned, and do the whole thing over again. Also, try to make friends with other people on parallel paths.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
There are so many people I want to put on this list! I love saying thank you, and acknowledging when someone has had an impact on me, so I keep a very active (and long!) shoutout list. Here are a select few:
1. Carly Menasco, my sister (a painter and tattoo artist) — she gave me a set of watercolor pencils and a pad of paper when I was at my lowest, stuck at home, sick and feeling very isolated. Even though I hadn’t painted in years, when she gave them to me, she said “Henry Matisse painted from bed, you can too.” I’m not sure whether I would have started making art again without her.
2. Trina Bentley, owner of Make & Matter (a packaging design firm) — she was one of the first art directors to bring me on to large scale commercial illustration projects, and has become a friend and creative collaborator over the years.
3. Jessica Hische — She was one of the only folks talking openly about commercial illustration pricing back in the early 2010’s. Her original “Dark Art of Pricing” PDF had a big impact on how I priced my work, and how I understood the commercial value of art. Then once I eventually hit a ceiling and felt like I had gone as far as I could go, I reached out and she very kindly agreed to connect with with me directly. Even though we make very different kinds of work, Jessica has been a concrete image for me of what it can look like to succeed, how I can keep pushing myself, and that it’s possible to do all this and enjoy it, and have a family.
4. Art Camp, my little circle of art/illustration friends (especially the OG crew, Fabiola Lara, Fran Meneses, Grace Miceli, Missy Dunaway, and Louise Barry) — Back in 2020, Fabiola Lara and I started talking semi-regularly on the phone. Then, we eventually did an in-person get together with Fran, spending a few days in the woods cooking vegan food and painting. Then the next year, Grace, Missy and Louise joined and Art Camp was born. We do monthly check ins (most of the time!) and try to get together in person regularly. Having a group of peers to problem solve with, grow with, and learn from has been incredible.
5. My Family — My partner, Eric who has supported me every step of the way, even when it was not at all clear where things were going; my daughters (6 and 4) who have made me braver, and more willing to put my heart on the line. They inspire me to keep growing, and keep passionately pursuing meaning, connection and beauty.

Website: https://www.kendyllhillegas.com

Instagram: kendyllhillegas

Youtube: https://www.youtube.com/c/kendyllhillegas

Podcast: I host ArtLab, which is a show about creativity, feelings, and the process of making art. https://tinyurl.com/4jsddvdf

Image Credits
Good Culture — Pack Design and Art Direction: Make & Matter Design; Food Styling and Photography: Amanda Perez
Jukebox — Art Direction: Emily Woods, Laura Zander; Branding and Packaging Design: Interact Brands