 In 1964, he received a Master of Laws from Harvard Law School.Wollman began his career as a judicial law clerk to Judge George Theodore Mickelson of the United States District Court for the District of South Dakota from 1962 to 1963.He was in private practice of law in Aberdeen, South Dakota, from 1964 to 1971, and served as a State's attorney of Brown County, South Dakota, (in Aberdeen) from 1967 to 1971.