Oberman lived and travelled through Canada, Europe and the Middle East before he returned to Winnipeg in 1973, where he received his teaching degree.
In 1975, he started working as an English, Drama and Journalism teacher at Joseph Wolinsky Collegiate, a job he held for nearly 30 years.
An important development in his career as a writer was the summer he spent at the Banff School of Fine Arts where he studied under W. O. Mitchell.
Oberman acted and directed in both film and stage plays, and toured North America as a professional storyteller.
He wrote columns and freelance articles for the Winnipeg Free Press and published children's songs, stories and poems in a number of magazines, journals and anthologies.