Early Life
Pickering was born in Salem, Massachusetts to Deacon Timothy and Mary Wingate Pickering. He was one of nine children and the younger brother of John Pickering (not to be confused with the New Hampshire judge) who would eventually serve as Speaker of the Massachusetts House of Representatives. He attended grammar school in Salem and graduated from Harvard University in 1763. Salem minister William Bentley noted on Pickering: "From his youth his townsmen proclaim him assuming, turbulent, & headstrong."
After graduating from Harvard, Pickering returned to Salem where he began working for John Higginson, the town clerk and Essex County register of deeds. Pickering was admitted to the Massachusetts Bar in 1768 and, in 1774, he succeeded Higginson as register of deeds. Soon after, he was elected to represent Salem in the Massachusetts General Court and served as a justice in the Essex County Court of Common Pleas. On April 8, 1776, he married Rebecca White of Salem.
In January 1766, Pickering was commissioned a lieutenant in the Essex County militia. He was promoted to captain three years later. In 1769, he published his ideas on drilling soldiers in the Essex Gazette. These were published in 1775 as "An Easy Plan for a Militia." The manual was used as the Continental Army drill book until replaced by Baron von Steuben's Regulations for the Order and Discipline of the Troops of the United States
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“... business training in early life should not be regarded solely as insurance against destitution in the case of an emergency. For from business experience women can gain, too, knowledge of the world and of human beings, which should be of immeasurable value to their marriage careers. Self-discipline, co-operation, adaptability, efficiency, economic management,—if she learns these in her business life she is liable for many less heartbreaks and disappointments in her married life.”
—Hortense Odlum (1892–?)