Although they were granted freedom from enslavement, earning a living was difficult for black Loyalists who came to Canada. Yet, over time Fortune developed two lucrative businesses in the area. She began working as a baggage carrier, transporting luggage and provisions from ships, which she would deliver in her wheelbarrow. Later, she implemented a rudimentary "wake-up call" service in which she would alert people at nearby inns in danger of missing departing ships. Fortune also imposed and enforced curfews at the wharves and the surrounding area, hence enforcing the law at early Annapolis Royal. Many consider her the first policewoman in Canada.
In time, Fortune's entrepreneurial pursuits became lucrative. Her baggage company became known as Lewis Transfer in 1841, and horse-drawn wagons replaced wheelbarrows. Fortune's grandchildren carried on the family business for the next 100 years.
Fortune's legacy continues today. The Association of Black Law Enforcers have created a scholarship in her name, and her descendant Daurene Lewis became the first Black female mayor in North America. Numerous descendants still work in the shipping and trucking business.