Every step forward Ryan Steiskal makes in his career, he knows the support of the University of Wisconsin Oshkosh art community is like a wind at his back.

The Milwaukee artist, who grew up in Neshkoro and graduated from UW Oshkosh with a fine arts degree in 2015, said even nearly a decade removed from finishing his last class, the faculty and staff continue to provide support and encouragement.

And there’s plenty for his former teachers and classmates to applaud him for. Not only has Steiskal been making a living as an artist since 2019, but this spring he made Wisconsin State Fair history, becoming the only two-time winner of the annual Fairtastic Poster Contest.

His work earned him the top prize in 2020 and now again in 2023—the latter of which was an even greater achievement than the first, given that for the 10th anniversary of the contest his competition was a field of only previous winners.

“I feel really good about it,” he said of taking the top honor again. “I dedicated like three months to that piece too, like nonstop. It feels very good to have that time and energy and come back around and be the first ever to do this.”

As the Fairtastic Poster Contest winner, Steiskal’s colorful illustration will be printed on posters and postcards on sale throughout the Aug. 3-13 event. Proceeds benefit the Wisconsin State Fair Park Foundation. He also won a cash prize as first a finalist and then the winner and will be at the fairgrounds for four days illustrating for the public.

While it’s his second win, it’ll be his first time getting to take a victory lap around the fairgrounds a few months later to soak it in. Back in 2020, he was named the Fairtastic winner shortly before the start of the pandemic which led to the cancellation of that summer’s state fair.

When not drawing dairy cows and cream puffs, Steiskal has earned his living through commission work and selling his original pieces since giving up service industry work four years ago. After having always had a job outside the art world to pay his bills, he decided at least once he had to try giving it a go through art alone.

Giving him confidence, as always, was the art community of which he’s a part—including in Oshkosh.

“All the teachers I’ve ever had and the support from them made me feel like maybe I can in some weird way make something out of something I actually care about,” he said. “At the very least try.”

Steiskal credits one UWO educator for helping get his start in an art career. It was Joseph Peterson, now an associate geology professor, who years ago needed illustrations to go with a paper he was publishing about dinosaur behaviors. He enlisted Steiskal and now, more than 10 years later, the two continue to work together. A new Peterson paper about a Jurassic reptile will soon be submitted for publication, complete with artwork by Steiskal.

Other UWO employees continue to offer support in one way or another, he said. Sometimes it’s passing along a job opportunity, sometimes it’s just words of encouragement through an email or social media comment. They include the art department’s Craig Clifford, Susan Maxwell and Gail D. Panske.

“The faculty, they’re really great. … So well informed, so engaging, so supportive,” Steiskal said. “It’s one of those things where you never want to let them down. It motivates you to keep pushing forward. They gave you this push and this support and you want to make it meaningful.”

“My motivation is never to be the world’s greatest artist,” he said. “I just want to be able to always improve just for myself, for my own satisfaction. There is something special about putting your heart and soul and time and energy and sometimes sweat and blood into a thing just for that satisfaction. (And) sometimes it gets recognized, sometimes it doesn’t.”