I found Jesse in a branch of Terry’s tree that I haven’t visited in a while. He’s not a direct ancestor, nor is he even a blood relative. Jesse was Terry’s 4-times-great uncle by marriage, who married Catherine GOUGE, sister of Frances GOUGE and Matthew Thomas ROBSON, Terry’s 3-times-great grandparents. Both Catherine and Frances GOUGE were daughters of Robert GOUGE and Frances HART who were Terry’s 4G grandparents. They were married in Newington in northern Kent, England on 24 Nov 1778 (just west-northwest of Sittingbourne on the road west to Chatham). “Catharine" was born on 13 Jan 1794 in Kingstown. There was a larger town of Kingsdown on Kent’s east coast, north of Dover and south of Deal, but Catherine's Kingsdown was a rural community about 3 or 4 km south-southeast of Sittingbourne. So they didn’t go far.

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By 1841, Jesse age 50 and Catherine age 45 were living in Bearsted with two apprentice saddlers, another lodger and five of their children: Frances 20, Henry 19, Ellen 16, Jess Jr 10 and Eliza 7. Their daughter Emma had already moved out and later married Samuel Wesley Copleston in 1845. Their daughter Jane was born in 1827 but I have yet to find what happened to her. From land records in 1842, Jesse owned “Old cottage” and pasture land at Cross Keys and also rented one "Invicta Villas”, an orchard and other plots of land at Mill Hill Bearsted. The 1847 City Directory and Poll Books say he was a saddler living on Bearsted Street. All this seems fairly straightforward and even prosperous, with nothing to cause alarm.

The London Gazette published 17 July 1849, issue 20999, page 2283
There are two further notices in the London Gazette regarding this. The first was published a week later on 24 July 1849:
Pursuant to the Acts for the Relief of Insolvent Debtors in England.
The following Prisoners, whose Estates and Effects have been vested in the Provisional Assignee by Order of the Court for Relief of Insolvent Debtors, and whose Petitions and Schedules, duly files, have been severally referred and transmitted to the County Courts hereinafter mentioned, pursuant to the Statute in that behalf, are ordered to be brought up before the Judges of the said Courts respectively, as herein set forth, to be dealt with according to Law:
Before the Judge of the County Court of Kent, holden at Maidstone, on Tuesday the 7th day of August 1849. …
Jessee Joy, of Bearsted, near Maidstone, in the county of Kent, Saddler, Harnessmaker, and Farmer

The London Gazette published 23 July 1850, issue 21120, page 2076
He and his family seem to have weathered the storm because the 1851 census lists Jesse age 59 living on Bearsted Street with his wife Catherine 57, children Jesse R 19 saddler, Eliza C 17, their married daughter Emma Copleston 31, grandson William Copleston and a saddler’s apprentice. He was back in business and had a second chance to earn a good living.

Courtesy of Google Maps.
In 1861 Jesse was back with his family in Bearsted, still listed as a saddler and harness maker. He was 69. Only his wife Catherine and unmarried daughter Eliza were at home along with a boarder who happened to be a collector of poor rates. Hopefully there wasn't a conflict of interest with his landlord. Their daughter Eliza died later that year, and the following year in Dec 1862, Jesse passed away at the age of 71. He was buried on the 13th in Bearsted, where Catherine joined him in 1869. His life had not lived up to his name.
Reference the No Story Too Small blog by genealogist Amy Johnson Crow for more details.
It is giving me the much needed incentive to write and publish my family stories.