He studied law under the guidance of Pennsylvania’s attorney general Benjamin Chew and began his law practice in 1761. However, he could not do well in this endeavour.
Looking for a career change, he entered the public service later in 1761 and was appointed secretary to the Provincial Council of Pennsylvania Indian Commission. In this position, he worked to make treaties with the Delaware and several other tribes.
He was made the customs collector for Salem, New Jersey, in 1763. During this time he tried his hands at operating a business venture, but could not find success.
He worked as a librarian for a year in 1764.
Public career suited him well, and in order to seek better job prospects he went to England in 1766 to secure the position of commissioner of customs for North America.
In England, he met the would-be Prime Minister Lord North, his half-brother The Bishop of Worcester, and the painter Benjamin West. His acquaintance with Lord North enriched his knowledge about politics and the working of governments, while he learnt painting from Benjamin West.
He returned to America in 1767 as he could not achieve the original goal of securing the position of commissioner of customs for North America.
In 1771, he became the director of the Library Company and held this post for two years.
He returned to public service in 1772 when he got appointed as a Customs Collector for New castle Delaware.
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In 1774, he shifted to Bordentown where he became an Assemblyman for the New Jersey Royal Provincial Council.
His success in the public service gave him the confidence to revive his legal career and he was admitted to the Royal Council of New Jersey in 1775.
In 1776, he resigned from all the posts he held under the government of the British Empire as they conflicted with the revolutionary causes he believed in. He was selected as a delegate to represent New Jersey in the Second Continental Congress on 22 June 1776.
He voted for independence on 2 July 1776 and participated in the independence debates with several other delegates. He signed the Declaration on 2 August 1776. His stint with the congress was brief and he left in November the same year.
He was appointed by the State of Pennsylvania to serve as a judge of the Admiralty in 1779 and held this position till 1789. He also served as a judge of Pennsylvania’s U.S. District court for one term from 1790 to 1791.
He also composed many songs and ballads, including the highly acclaimed "My Days have been so Wondrous Free" which he had originally penned in 1759. His other famous compositions include ‘The New Roof’ and ‘The Toast’.
As a writer, he published several essays with an underlying political motif, the notable of them being ‘A Pretty Story’ (1774), ‘The Prophecy’ (1776), and ‘The Political Catechism’ (1777).
He is credited to have designed the first American flag and he contributed to the designs of various important seals and symbols for the newly independent U.S.
In 1776, he participated in the vote of independence and independence debates, and signed the Declaration of Independence on 2 August, becoming one of the 56 delegates to do so.
He claimed in a 1780 letter to the government that he had designed America’s first flag that consisted of thirteen white stars in a background of blue, and thirteen red and white stripes. At that time the government did not acknowledge his claim, but later on it became an undisputable fact that he was the designer of the first American Flag.