Lily Oswald’s college education took her to Oregon, California, back to Oregon and then finally to Utah.

Her career aspirations swiveled from Las Vegas tattoo artist, to architect, to city planner.

But when it came time to settle on a job after finishing her master’s degree, Oswald was selective about where she wanted to go, despite the limited job market for planners.

She wanted to return to southwest Colorado. She wanted to live in a small community, where the volunteers you build a trail alo...