After admission to practice law in 1974, Jim entered the general practice of law in Centralia. In 1976, he became an Industrial Appeals Judge for the Board of Industrial Insurance Appeals. He served in that position for four years.

In 1980, he left the Board to form the firm, which was then known as Rolland & O’Malley. That firm grew to become Rolland, O'Malley, Williams and Wyckoff.

In 2005 Jim left Rolland, O'Malley, Williams and Wyckoff to start another firm based on his belief that personal, empathetic representation of injured workers is the only way to run his business.

Jim is an Eagle Member of the Washington State Trial Lawyers Association and a longstanding member of the Association of Trial Lawyers of America and the Western Trial Lawyers Association.

He has close to thirty years experience in Labor and Industries (L&I) workers' compensation cases.