Matthew Orstad remembers the hotel room in Santa Fe, New Mexico. While his wife, a new doctor, attended a medical conference, he worked on a website with a collaborator in Huron, South Dakota. For hours they talked and wrote code using the hotel’s wi-fi and the speaker phone. “I was electrified by the experience,” he says. He could envision breaking free of the nine-to-five world.

Orstad grew up in Crooks, South Dakota, a small farming community along the rail line northwest of Sioux Falls. Surrounded by corn and soybean fields, his high school served several nearby towns and rural areas. After graduation in 1997, he moved across the state to attend the South Dakota School of Mines & Technology or “Tech,” where he majored in computer science and fell in love with a classmate named Keri Bachmeier. She graduated in 2001. He graduated the following May, and they were married in June.

“At Tech it was assumed that you would move out of state to find a job,” he says, but that option wasn’t open to Matthew. Keri had been accepted at the University of South Dakota’s School of Medicine in Sioux Falls. For the next three years, while she went to school, he worked for the EROS Data Center northeast of the city.

“As a student I figured I would a traditional job,” Matthew says, “and so did most of my classmates.” As traditional jobs go, EROS was an interesting place to work. The U.S. Geological Survey (USGS) operates the Earth Resources Observation and Science center to collect and manage satellite data. But after Keri finished her course work and accepted a residency in Mason City, Iowa about 225 miles away, Matthew had to decide what he was going to do for work.

Fortunately, the federal government is one of the most progressive employers in the country when it comes to telecommuting. Matthew’s bosses let him work from Mason City. “It was convenient,” he says, “but there was still the expectation of the 7:30 to 4:30 work day.” Like many in the millenial generation, he chafed at the rigidityof the structure which seemed so out of synch with his increasingly virtual worklife.

In Mason City, Keri and Matthew welcomed their daughter into the world, and suddenly Matthew’s work-at-home life changed. To gain more flexibility to take care of his daughter, Matthew took a leave from EROS and began freelancing. He developed websites for local clients. “But I had trouble finding the magic mix,” he says. At Tech he had learned how to program, but “there were no marketing courses. I learned nothing about how to run my own business.”

As he struggled to make it on his own, Orstad discovered an unlikely source of work. Matthew Reinbold, a fellow alum from Tech, was living in Salt Lake City and had launched his own business developing websites with complicated backend elements. Reinbold needed programmers he could trust. He began feeding Orstad work. “I knew him from school,” Reinbold says, “and I knew the quality of his work.”

When Keri finished her residency in Mason City, the couple decided to move back to South Dakota. “We are both country mice,” Matthew says, “I grew up on my parents’ farm. Keri was raised on a ranch south of Rapid City where they had ostriches.”

Small towns in South Dakota are hungry for doctors, so the Orstads had their pick of communities. They chose Wessington Springs, a town of less than 900 people east of the Missouri River in the heart of the state. “We wanted to be reasonably close to family,” Matthew says. They also wanted a community that made them feel welcome.”

“The community welcomed us with open arms,” he says, “and it’s been that way since we moved in.” While Keri goes to the clinic, Matthew continues to work from home, taking care of their daughter and lending his expertise to the community as it tries to develop its presence in the on-line world. He continues to learn more about how to market his skills and sees a business model evolving from his work with the local newspaper.

He is concerned about the declining population in rural South Dakota. Wessington Springs, for example, has lost nearly a third of its population since 1980. “Not everybody can move to the cities and have a Starbucks on every corner,” he says. “Somebody has to farm.” Maybe there’s hope in the life and work that Matthew has found for himself as a new pioneer in the heartland of America.