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It was probably due to his father's influence that Henry also received the lifetime appointment as Clerk of Dutchess County on November 15, 1742. Whether he received the appointment as a political favor or not, Henry Sr. was a responsible and careful man, who worked at his post with a dedicated work ethic that he passed on to his children. In addition to his clerkship, Henry also acted as a surveyor, a skill he learned from his father, and as the manager of his Uncle Henry Beekman's estate while his uncle served in the Colonial Assembly. At his uncle's retirement from politics, Henry Livingston served several terms, himself, in the Assembly. Based on the tax rolls of Poughkeepsie, Henry was well enough to do by Poughkeepsie standards, but certainly not by Livingston family standards.