After graduation he began the study of law in Windsor, under the direction of Oliver Ellsworth, and at the same time taught an academy.

In February, 1795, he was elected a tutor at Yale College, and on March 12 began his duties succeeding James Gould, of the Class of 1791, in the instruction of the sophomore (2nd year) class, and at the same time continuing the study of law with the Roger Sherman's son-in-law, Simeon Baldwin (Yale 1781).

He united with the church in Yale College by profession of his faith on May 1, 1796, and ever after made the advancement of the interests of religion a prime object.

Sherman would serve as the representative of Norwalk, where he also practiced law, in the Connecticut General Assembly in the two sessions of 1798.

He did comparatively little office-business, but devoted his time to the trial of causes in court, and he also for more than twenty-five years attended the state legislature as an advocate in cases pending before that body.

He was deeply interested in the administration of justice as provided for by legislative enactment, and many of the statutes of the state in the realm of municipal law during his active life were drawn up and their passage procured by him.

He had been actively interested also in the steps preliminary to the call of the Convention, and was the author of the Report to the Connecticut Legislature, of the Committee which had recommended the appointment of delegates.

His legal knowledge, his thoroughness and independence, and his inflexible integrity contributed to make his tenure of this office highly successful.

Her will, made in pursuance of her husband's, bequeathed their homestead, with an endowment fund to the First Ecclesiastical Society of Fairfield.