Simeon Olcott graduated from Yale College and practiced law in Charlestown, New Hampshire. He began his career in public service as a selectman and provincial legislature member, later serving as a judge of probate and moderator for Charlestown's town meetings. Throughout the American Revolution, Olcott held judicial positions in both Vermont and New Hampshire, including Associate Justice of the Vermont Supreme Court and chief justice of the New Hampshire Court of Common Pleas. His career culminated in federal service as a U.S. Senator.

Simeon Olcott's career is marked by a series of judicial appointments and a consistent alignment with Federalist principles. Despite lacking explicit economic policy stances, his judicial roles suggest a deep commitment to legal frameworks and stability. Olcott's approach reveals a calculated alignment with opposing factions on certain issues, hinting at a strategic balancing of interests. His family connections, particularly his son's military career, add another layer to his multifaceted political identity.