Dirk VanDerwerker attended Carleton College in Northfield Minnesota where he recieved his B.A. in English on June 9, 1978. Following his graduation, he worked as a grain merchant for Cargill in Sioux City up until his enrollment into the University of Iowa in January of 1980, where he pursued a M.A in Journalism and received it in July 1981. During his time at the University of Iowa, he worked for the University's student newspaper, The Daily Iowan (DI).

He worked for the DI as a full time photographer from Summer 1981 to August 1982. He also wrote a few articles for the DI before his employment with them. After his job with the Daily Iowan, he was a staff lecturer at the University of Wisconsin-Platteville in the Communications department for two years, and then moved on to become an Assistant Professor in Communications at Oklahoma City University for one year.

He went back to reporting shortly afterwards, working as a reporter for the now defunct newspapers of Bernando News in California, Hampton Chronicle News in New York, and Eden Prairie News in Minnesota.