 In an era where education opportunities were limited in small Maritime towns, Sobey left school after Grade 8.However, he had an entrepreneurial mindset, and at age sixteen enrolled in a business college.In 1924, he persuaded his father to expand the store to carry a full range of groceries and the family began expanding, opening stores in the nearby industrial towns of New Glasgow, Trenton and Westville, as well as the university town of Antigonish.