James Forten was a sailmaker as was his father. He went to work with his father as soon as he was old enough to walk and talk.

It was the sailmaker's task to make and to repair sails for ships both large and small, some making trans-Atlantic voyages and others hugging the coast of the new thirteen states. The ships carried food, supplies, and people. It would be the sailmaker's job to very carefully measure each sail that was needed and to understand how the sails handled when the ship was underway. Without good sails, the ship was worthless. Along with making sails, sailmakers were also asked to make just about anything else you can make with canvas. Forten made tents, tarps, and floor coverings. Once, he even attempted making a cover for a piano.

Sail lofts were on the upper floors of warehouses because ample space was needed for marking out the plans for each sail and laying down the canvas to be cut. The upper floors didn't have support beams for the building so the whole floor space could be used for laying out the canvas. Only the smallest sails could fit up the stairs to the loft; so most sails had to be hoisted up the outside of the building and through an open window.

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