If you look closely at Matthew Kramer ’09’s recent illustration (pictured above) for “The New York Times Book Review,” you’ll see that none of the lines in the drawing overlap with one another. “I like the idea that each of the individual lines comes together to form a character, in the same way that letters form sentences,” Matthew explains. “So in my style, I never intersect the lines. I don’t know if I’m going to stick with it as a rule forever, but that’s kind of a defining feature of my drawings.”

This distinctive artistic style – where each element is intentionally separate yet comes close enough to form a cohesive whole – is also reminiscent of Matthew’s journey through Wheeler and Hamilton, and beyond. Each meaningful experience throughout their lifetime has led into one another, but when we retraced those footsteps together, it was decidedly not a linear path.

Matthew was a Wheeler lifer who didn’t particularly like school, at least not in the conventional sense, “but I liked Wheeler.” They were most at home in the moments between classes – literally – as they explored hallways and “hidden” passageways as they moved in unexpected ways across school.

Matthew remembers regularly arriving early to Lower School Art to help Teacher Ann-Marie Gillett set up supplies for that day’s project. “That was my favorite thing to do,” they say. “Art was always the place where I felt most myself.”

They also appreciate the teachers at Wheeler who helped them discover their own route across campus (and eventually to a career), including English Teacher Annie Funnel and Paige Stites of the Mathematics Department, who were both great mentors, and Art Teacher Leah Grear, who reframed how they thought about art and success.

When Matthew applied but didn’t get into Wheeler’s Studio Art Program, Ms. Grear “helped me realize there isn’t one track to succeed in the arts,” they reflect. “You don’t have to follow a single prescribed path.”

For Matthew, who went on to minor in Studio Art at Vassar, that path actually led them to pause on art for a bit after college. It wasn’t until they attended a community event called “Friends Don’t Let Friends Stop Making Art,” that they were drawn back in. They began by creating small cartoons and enjoyed it enough to keep going.

From there, Matthew, who is dyslexic, took another unconventional step (at least for a visual artist), when they decided to pursue an MFA in Creative Writing at Brown. “The writing programs were funded,” Matthew says with a small laugh, “so I convinced them I was a writer.” The program opened doors to artist residencies in places like Paris, Italy, and Maine, and also allowed Matthew to take illustration classes at RISD, where they learned how to navigate the professional illustration world.

Along the way, they began securing illustration gigs and drawing longer-form projects, like graphic novels, as they developed their economical and yet expressive visual style. True to their MFA, Matthew describes the line-by-line approach of their work, which beyond the Times has also appeared in such major publications as “The New Yorker” and “The Iowa Review,” as a process that’s closer to writing than traditional drawing.

“Everyone has a style already inside them,” they say. “If you draw every day for five or 10 years, a style would come out. The people who make art, like me, aren’t the most talented – but we’re the ones who don’t stop.”

Which brings us back to a sense of success. While Matthew has now illustrated for renowned publications, they measure achievement less by prestige than by freedom.

“I pay all my bills making my art. I do what I want with my time,” they say. “Most people are not doing what they want to be doing with their lives. For me, success is having freedom to do what I want with my time.”

It’s advice Matthew shares with today’s Wheeler students, especially those who feel uncertain or out of step with traditional expectations. “There are so many weird jobs out there,” they say. “If you start now, by the time you’re 27, you could be doing it. Don’t do something you hate instead, because you’ll just keep doing it.”

Matthew also encourages students to look outside of themselves. As a self-described nomad who spoke to us from their current location in Mexico City, travel has become central to their life, creative practice, and (of course) how they see the world. “Get out,” Matthew says. “There’s so much to learn, and so many ways to live a good life.”

In looking back for this story, Matthew now sees Wheeler as a place that inspired and educated them, but with the room (and the less followed paths from room to room) that they needed.

“There were other ways through, and Wheeler supported that,” they say. “That made all the difference.”

You can see more of Matthew’s work on their website.