In 2004-2005, Barry served as a judicial law clerk to Judge Clarence Brimmer of the United States District Court for the District of Wyoming. Currently, Barry has a very diverse work schedule. He serves as Deputy County Attorney in Johnson County, Wyoming, is a partner in Crago Law Offices, and manages the Willow Creek Ranch outside of Kaycee, Wyoming. Barry is also a freshman Republican legislator for House District 40, which covers Johnson and Sheridan counties in Wyoming. Barry and his wife Kristen have two daughters – Lily and Caroline