After graduating college in 2015, Friedman began working at the "Statesman Journal", in Salem. In 2016, his coverage of the Malheur National Wildlife Refuge standoff for "USA Today" and an investigation into officer misconduct in Oregon prisons earned him the Rookie of the Year Award from the Society of Professional Journalists, Oregon Territory Chapter. In 2016 he was hired by "The Oregonian" as a state capitol bureau reporter. He later moved on to covering Portland City Hall.