Little is known of the personal lives, background or training of English medieval shipmasters; it has to be assumed that they went to sea as ordinary seamen, possibly with familial connections, and learned the trade ‘on the job’. There was no system of apprenticeship and, in the fourteenth century, no guild to control their qualifications. Of their professional lives, once they had their own ship, rather more is known from records of their appearances in court, charter-parties and other surviving documents.

Having gained sufficient experience at sea, an ambitious seaman looking to be a shipmaster, had four options: to persuade a shipowner to take him on as a waged employee, to enter a shipowning partnership with merchants or financiers, to charter a ship on his own account, or to buy his own ship. Each option offered advantages and disadvantages, each had its own modus operandi, and in each the shipmaster's position varied under the several available codes of law.

During the period under examination, the differing views on commerce and on the master /servant relationship in common and merchant law, and the competition for business between their courts and the admiralty courts, led to considerable confusion. Although common law was absorbing from the law merchant the concepts of trust, service contract and partnership, there was always some doubt about which law would offer a shipmaster a more sympathetic hearing in cases concerned with a disruptive or non-cooperative partnership, or any commercial dispute.