After graduating from the University of British Columbia where he received both his bachelor of arts and law degrees, Barry spent several years practising law with small firms in Victoria. In 1981, he became an instructor in the School of Business at Camosun College, where he taught courses including real estate law, local government, business law, administrative law, and tourism law. During that time, Barry authored textbooks for some of these courses—Administrative and Municipal Law (1996), An Overview of Local Government in B.C. (1998), and Applications of Tourism Law (2000)—and created an Internet-related course for students taking business law, a required course in the business administration program at Camosun. In addition to his teaching duties, Barry was chair of the marketing, management and public administration department for five years before his retirement in 2005.