Born in North Sydeny, N.S., in 1949, Justice Pickup spent most of his young life in Cape Breton and attended Port Hawkesbury High School. He went on to study politicial science at St. Francis Xavier University, graduating in 1972, and obtained his law degree from Dalhousie University in 1975.

Justice Pickup was admitted to the Nova Scotia Bar the same year he graduated from Dal. After articling with Vincent Burke in Port Hawkesbury, he practiced with the firm LeBlanc, MacDonald & Pickup, and later Pickup MacDowell. He was appointed Queen's Counsel in 1993.

Prior to being appointed a judge, Justice Pickup dedicated many hours to community and business organizations. He was involved with the Strait Area Waterfront Development Corporation and the Strait of Canso Yacht Club. He served as director of the Halifax International Airport Authority and was a member of the advisory board for Edulaw Corporation, a national reporting service for education law.

A boating enthusiast, Justice Pickup looks forward to more days on the water and enjoying family time with his wife, Brenda, and their adult sons, Dennis and Scott.