Through means that remain unclear (it is possible that he had been an apprentice in Jamaica or had learned while in the Navy), Wedderburn became a journeyman tailor. As he referred to himself as a "flint" tailor, this suggests he was registered in the book of trades and shared values typical of other artisans - including pride in his craft and a belief in economic independence. Unfortunately, the instability of his career made him increasingly susceptible to the effects of a trade recession, inflation and food shortages, and he was soon reduced to part-time mending work on the outskirts of town.