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O'Brien was born in Lincoln, Nebraska. He received a Bachelor of Science degree from the University of Wyoming in 1965. He received a Juris Doctor from University of Wyoming Law School in 1972. He was in the United States Army, Ordnance Corps from 1966 to 1969. He was a Staff attorney of Land & Natural Resources Division/Appellate Section, United States Department of Justice from 1972 to 1974. He was in private practice of law in Wyoming from 1974 to 1980. He was a District Judge, Sixth Judicial District Court of Wyoming from 1980 to 2000. He was a President, Visionary Communications, Inc. from 2000 to 2001. He was in private practice of law in Wyoming from 2001 to 2002.