Schotland received a B.A. from Columbia in 1954 and an LL.B. from Harvard in 1960, where he was a member of the Harvard Law Review. He also attended Wadham College, Oxford, from 1959-60. Schotland then spent a year as a research assistant to Professor Paul Freund of Harvard, working on the History of the U.S. Supreme Court. After clerking for Supreme Court Justice William Brennan from 1961-62, he entered private practice in New York City. He joined the faculty of UVA in 1964, becoming a full professor in 1967. He taught courses in such subjects as Administrative Law, Constitutional Law, Legal Methods, and Corporations. In 1968, he became Chief Counsel to the Securities Exchange Commission Institutional Investor Study. He departed UVA in 1970 to become Associate Dean of Georgetown University Law School.