Born in St. Andrews, Nova Scotia to William and Flora Chisholm, Chisholm was educated at St. Francis Xavier University before moving to Halifax in 1896.

[1] He attended Dalhousie University, where he received his law degree and his first job was in a law firm headed by a man destined to be a future Canadian Prime Minister, Robert Borden.

[1] In 1916, Borden appointed him to the Nova Scotia Supreme Court, being the first Dalhousie graduate to be so named.

[2] Chisholm also wrote historical articles about past Nova Scotia justices and contributed to the Catholic Encyclopedia.

[1] In 1935, he became the last Nova Scotia Supreme Court justice to be knighted.