[3][1][2] Following his schooling Heywood was articled to Peter Hodgson in Whitehaven, Cumberland, from where he took a position in London in order to conclude his legal studies.
[3][1][2] Upon his return to the Island from England, Heywood enrolled as a law student at the Rolls Office, Castle Rushen, subsequently being called to the Manx Bar.
It was generally accepted on the Isle of Man at the time that the appointment of Christian as First Deemster in 1823 had been achieved by way of his connection with the Duke of Atholl, and that it had been made over the head of Heywood who was judged by his contemporaries to be more ably suited to the position.
He was the nephew of Peter Heywood, who was a midshipman on HMS Bounty during its notorious voyage under the command of Captain William Bligh.
[3][1][2] Through his father Heywood inherited Bemahauge Farm, which today is Government House, the official residence of the Lieutenant Governor of the Isle of Man.