Following law school, Judge Sheldon participated in the E. Barrett Prettyman Legal Internship Program at the Georgetown University Law Center. In that capacity, he was trained in criminal trial and appellate advocacy while supervising upperclass law students in the representation of criminal defendants in the Law Center's Clinical Programs. In 1976, he was hired by the University of Connecticut School of Law as a professor of law and appointed director of the Criminal Clinic. He worked at the Law School until 1991, teaching courses in criminal law and procedure, establishing and operating the Moot Court Interterm Program, and training and supervising upperclass law students in the representation of criminal defendants in the Trial and Appellate Divisions of the Criminal Clinic.

Judge Sheldon was appointed to the Superior Court by Governor Lowell P. Weicker, Jr. in 1991. In his twenty years of service as a Superior Court judge, his assignments included terms in the civil and criminal divisions of the Hartford, New Britain and Litchfield Superior Courts as well as a four-year term pioneering the Complex Litigation Docket in Waterbury. He has served as chair of the Civil Electronic Benchbook Committee, co-chair of the Education Committee, and a member of the Rules Committee, the Civil Division Task Force and the Civil Jury Instructions Committee.

Off the bench, Judge Sheldon has coached the mock trial teams of the Canton High School and the Canton Intermediate School, conducted educational programs for Russian judges and lawyers as vice-chair of the Connecticut- Pskov Rule of Law Partnership, and co-taught a course in Law and Forensic Science at the University of Connecticut School of Law. In 2009, he received the Connecticut Bar Association’s Henry J. Naruk Judiciary Award and was named a Distinguished Friend of Education by the Connecticut Association of Schools. Judge Sheldon was appointed to the Appellate Court by Governor Dannel P. Malloy in October 2011. He lives in Canton with his wife, Diane, with whom he has raised their four children, Graham, Conor, Rowan and Cameron.