Hailes began writing in a High School Plane Geometry class. He graduated in English from the University of Utah, worked on a master's degree in Comparative Literature, became a salesman and then sales manager for Highlights for Children, managed a twenty-story medical building in Minneapolis, and finally went to California as a technical writer. For the last fourteen years he has been writing manuals and training materials for companies such as IBM, Claris, Hewlett-Packard, and 3Com.