Stephens served in Parliament from 1702 to 1727, and his political activities created financial difficulties. His effort to find employment took him to British America in 1736 to conduct a land survey in South Carolina. He briefly traveled to Georgia, and there met the colony’s leader, James Edward Oglethorpe, whom he had known in Parliament. Stephens returned to England and submitted a report of his travels to the Trustees. The members expressed delight with Stephens’s lucid style, detailed descriptions, and cool-headed temperament. The Trustees hired Stephens, then in his mid-sixties, as their secretary. They considered his appointment a perfect solution to Oglethorpe’s lack of regular updates about the state of the colony, the attitude of the colonists, and the progress of appointed officials.
Stephens arrived in Georgia on November 1, 1737, and found the new colony a hotbed of personal rivalries and factions. Colonists criticized the Trustees’ policy on tail-male land tenure (a system prohibiting daughters from inheriting land, thus ensuring that all freeholders would be soldiers who could defend the colony), the prohibition of rum and enslaved people, and appointed officials. Stephens possessed no authority to make executive decisions, but he acted as an impartial observer and used his legal knowledge to provide sound advice. Stephens laid out his observations about the colony in a series of reports that contained a wry and caustic description of the people and character of early Georgia. For the most part Stephens supported the Trustees’ policies, but he perceived future difficulties concerning land tenure. He urged the Trustees to accept full female inheritance, but Oglethorpe, who had returned to England, convinced his associates to maintain the tail-male policy. Stephens received a sharp rebuke for his efforts and temporarily experienced a decline in the confidence of the Trustees and disgruntled colonists.
Stephens hoped that Oglethorpe’s return in September 1738 would ease tensions in the colony. But Oglethorpe could not allocate enough time to handle the daily concerns of the people in addition to negotiations with the Creeks, defense concerns, and a war with Spain by 1739. He left most decisions to Stephens. At first the secretary could not act without Oglethorpe’s approval and fumed about wasted time and unanswered questions. The situation eased slightly when Oglethorpe permitted Stephens to undertake a few administrative responsibilities.