10 Brilliant Dallas Women: Artist Haylee Ryan Doesn't Paint by Numbers

Welcome to 10 Brilliant Dallas Women, a pop-up online series about 10 awesome women making Dallas a better place to live. 

Haylee Ryan has a policy that when an opportunity lands on her plate from out of the blue, she seriously considers it. And that’s more or less how the 29-year-old ended up on the side of the road in Oak Cliff, collecting branches to use as supplies for her art class at Hogg Elementary. Six years ago she was living in Oregon, apprenticing for artist Glenn Ness and working at a non-profit benefiting the homeless, when she received a call asking her to return home to teach art at her high school. Her immediate instinct was to politely decline. “I was like, ‘I’m so sorry, I’m having a great time,’” Ryan says. But then her belief that every door opens for a reason kicked in, and she agreed to move back to Dallas. Although that job fell through, it sent her down the career path to teaching, and after several years as a full-time teacher, she now works two days a week at Hogg. The rest of her time is spent on her own artwork; as a member of the executive board at Art Conspiracy; and as half of the band Sister, the other half being her best friend and roommate Amanda Page, with whom she shares a Dalmatian and half of a duplex a short bike ride from the school.

Although Ryan wouldn’t dream of choosing between art and music now, art was her first passion. Shortly before her grandfather passed, when Ryan was 9, she gifted him her complete collection of drawings. At that time he made her mother promise that Ryan would never give up on art. That promise has kept her going during the rough periods, when a more stable, lucrative job has often sounded like the sensible choice. “Times when I was like, ‘Maybe that was just a childhood dream,’ my mom hears her dad’s voice in her head and she says, ‘No, you can do it. Let’s do it,’” Ryan says. Even as she speaks openly about the struggles and self-doubt inherent in the life of a working artist, she is bubbly and almost ethereal. Ryan fits right into a discussion of brilliant women in Dallas; she practically emanates light.

In those early drawings and paintings Ryan gave to her grandfather, her love of the human figure emerged, and it still dominates her artwork to this day. “Always, always, always I’ve drawn the human figure,” she says. “I cannot get away from people’s faces.” She sold her first portrait in the 9th grade. There are other constants in her work as well, one technique in particular being a form of layering. She first explored it in her senior art show, which featured paintings that looked pixelated up close and hyper-realistic from a distance. Then, recently, she completed a series based on polaroids of her grandmother when was young. “I know my grandmother now, but I know her as a grandma. I don’t know her as a hot ass, mackin’ with the boys. I don’t know her. But that is her.”

She was initially attracted to the muted and pastel tones of the photos from the ’60s and ’70s, but then as she painted one scene — showing her grandmother, aunt and uncle on the beach — she fell into her love of layering again. “I started painting the dark parts of it, the shadows, just to lay it in, and I stopped to change colors … You could tell that it was them, you could tell what was going on, but you could also see the background through,” she says. “These two layers that were completely separate, just magically mixed together. My eye filled in the rest of those empty spaces. [It’s about] how your mind fills stuff in, about memory. I have this certain information about a person, but there are all of these pieces that are missing.”

As a senior in high school Ryan expanded her creative outlets beyond visual art when she taught herself guitar. Around the same time she met Page, a singer, in her church youth group. “It’s pretty funny because we’re not attached to that world anymore at all,” Ryans says. “But it brought us together.” They’ve played together ever since, and their musical endeavors really took off when Ryan was a freshman at University of Dallas, albeit under unpleasant circumstances. Ryan had gone there to play softball and basketball but quickly suffered a head injury that prevented her from playing any sports for a year. She channeled her frustration into art and music, focusing on both with a renewed fervor. Even when she had healed, she didn’t return to the field. “I was devastated at the time … but if I hadn’t gotten injured, it would never have created that space for me,” she says. Ryan and Page’s latest musical incarnation is Sister, a harmony-filled blues band; they just played their first show at Twilite Lounge in June.

Their travels, both separately and together, have heavily influenced their first batch of original music. During her first teaching job at a school in Cockrell Hill, Ryan grew close with a group of teachers on an exchange program from Spain. She ended up using the same program to travel back to Spain with them when their visas ran out, and taught there for a year. Since returning home, she’s switched to teaching part-time to make room for her own art and her new passion for traveling. She and Page just got back from a six-week trip to Europe and Iceland this summer. “People look at me when we tell them the stories of the things we’ve done. They’re like, ‘How? You’re a teacher!’” Ryan says the explanation is simple: They stay with friends, and she runs her checking account down to zero with every trip. She adds that this lifestyle choice may come at the expense of car and home repairs. “We’re not luckier than anyone else. We make a certain amount of money and we choose how to spend it.”

Ryan finds inspiration for her classroom art projects in her personal life, but also more unusual places. “Sometimes it’s in the curriculum, most of the time it’s not,” she says, laughing. On the first day of school this year, she wanted to come up with something to hook the students in immediately, rather than the typical get-to-know-you activities. With funds for art supplies tight, she landed on the idea of having them paint on nature. “I looked like a crazy lady ... It was bulk trash day and I was collecting branches off the side of the road, putting them in my Honda Element,” she says. “My brother chopped down all this bamboo from his friend’s creek and we shoved it into my car. It was sticking out 6 feet — I drove on the highway with that. The kids carried it in with me and I just let them go nuts. I said, ‘No rules. Just paint it. But you’re gonna work together.’ We used it to decorate our school. It looks amazing.”

When Ryan isn’t at school, she’s either sitting at a bar or a coffeeshop with her sketchbook, sketching strangers — “Sometimes I show them later and they’re like, ‘You’re creepy. But that’s cool. Can I have it?’” — or working in her bedroom, which serves as a makeshift studio and is completely covered with oil paintings hanging up to dry. “My friends were giving me a hard time the other day that I should not be painting with oil paints in my room because it’s so unhealthy,” she says. “I go to sleep right next to them like an idiot.”

Last year Ryan also joined the executive team at Art Con, shortly before their main event in November. She had initially hoped to participate as an artist, but she wasn’t one of the 150 artists randomly selected to create work for auction. She had just switched to teaching part-time, and was worried about supporting herself. This, in her mind, could have potentially been her first big break. “I had thought, ‘OK this is cool, the ball’s rolling, I’m gonna get some exposure, I’m gonna meet a lot of people,’” Ryan says. “I cried [when I didn’t make it.]” But shortly after that, something better came along: She was invited to join the executive team. And when several artists no-showed at Artist Day, she got to participate anyway. Anxious that her painting wouldn’t sell, she asked her parents to attend and bid. But in the end, she didn’t need their help: Her painting of a Native American was one of the highest-selling pieces.

“There’s no way to explain it, but it always works out,” she says. This pattern that keeps repeating itself — whether good luck, fate or simply the natural course of things — reminds her of the effect of layering in her artwork. Daily, she’s torn between her passion for teaching, for music, for art, for travel, for philanthropy: “Up close [all of your experiences] just look like a mess,” she says. “But then you back up, and you’re like, ‘Ohhh.’ It’s a challenge to live in the moment and not be freaked out.” Ryan will keep adding layers of experience, even as they sometimes overwhelm, or seem to send conflicting messages — she was just accepted to the 42 Mural project in Deep Ellum and Patagonia is next on her list of must-visits. She knows that history will repeat itself, and someday, between her eyes and ours, the picture will look complete.

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Caroline Pritchard studied English at Kenyon College in Gambier, Ohio, and in 2012 returned to her hometown of Dallas, where she spends her free time seeking out new places to roller skate and play pinball.
Contact: Caroline North