In the 1980s, Stein was freelancing as a musician and composer for theatre and dance. During that time, he would work in Regina as a composer for the New Dance Horizons, where he helped them with their production management skills. 
When the 1990s came around, he took a job at the Banff Centre for Arts and Creativity, where he was the Associate Director of Program Planning, a position that led him all over Canada and the world. It was then during the early 2000s that he decided he wanted to be closer to the art.
“In the beginning of the early 2000s, I decided I would recommit to working in small arts organizations. Big biocracies are good for jobs, but you are quite far away from the actual hands-on art-making, and that’s the part I loved,” he said. “When I was faced with a career change opportunity, and there was this little cool company in Regina, I decided that I would make the plunge.”

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