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. He subsequently practiced as a solicitor in several Courts of Chancery, King's Bench and Exchequer. 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. After practicing for several years he was raised to the bench in 1821, as Second Deemster, upon the appointment of John McHutchin as Clerk of the Rolls and following the resignation of John Christian, Heywood succeeded him as First Deemster in 1847. 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.
Personal life
John Joseph Heywood was the second son of Robert Heywood and Elizabeth and was the half-brother of Calcott Heywood, also a Member of the House of Keys and a Captain in the Royal Manx Fencibles. 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. Heywood was twice married. His first wife, Elinor, pre-deceased him in 1820 following which he married Elizabeth who pre-deceased him in 1843. His marriages produced one daughter by each wife. John Heywood was the last of the male line of the family resident on the Isle of Man. Through his father Heywood inherited Bemahauge Farm, which today is Government House, the official residence of the Lieutenant Governor of the Isle of Man. Governor’s Bridge, which is near to Government House was originally known as Heywood’s or the Deemster’s Bridge after Deemster Heywood. The bridge gained its present name in 1920 when it was first included in the T.T. course.
Death
Heywood had suffered the effects of ill-health for many months prior to his death. He passed away aged 66 at his home on Saturday 26 May 1855. He was survived by both his daughters.