Jamie was in the real estate business from 1969 through 1984 specializing in commercial real estate sales, leasing, and development. Starting in 1989, Jamie also worked on his personal real estate development. Throughout his career, Jamie was involved in volunteer work through the Spokane Chamber of Commerce, Spokane Valley Chamber of Commerce, Eastern Washington University, and the Pi Kappa Alpha fraternity.
Jamie was a founding member of the Law Offices of Wolff and Hislop. Which served as the roots for Wolff, Hislop & Crockett, PLLC. In 2023 Jamie retired from the practice of law and voluntarily resigned his license to practice law in the State of Washington.