When he was 12, at the request of his mother, Smalls' master sent him to Charleston to hire out as a laborer for one dollar a week, with the rest of the wage being paid to his master. The youth first worked in a hotel, then became a lamplighter on Charleston's streets. In his teen years, his love of the sea led him to find work on Charleston's docks and wharves. Smalls worked as a longshoreman, a rigger, a sail maker, and eventually worked his way up to become a wheelman, more or less a helmsman, though slaves were not permitted that title. As a result, he was very knowledgeable about Charleston harbor.