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But after his eight year relationship ended in July, keen to make a fresh start, he quit his marketing job for a charity and bought a shipping container on a decommissioned farm just outside the town – spending $4,000 buying and transforming it into a humble home.
“For everyone, 2020 has been a bit crazy," Jay said.
“Splitting up with my partner was my catalyst for change and living simply was always something I wanted to do. I had a house, a wife and an office job, as well as a very standard life. I never really signed up for that, it kind of just happened."
“My marriage ending was such a big change already, that living simply was just the next step," he said.
“So, I asked the owner if I could buy and move into the shipping container – renting land and utilities from her. She agreed and I began living there from July."
The basic space was nothing new for Jay, who opened a pub based in two shipping containers called The Outdoor Inn, with his business partner Matt Nolan in March last year a job.
“When we were working on the bar, I saw how convenient and useable shipping containers are," he continued.
“After that, using one for a home seemed to be the perfect fit."
And his $4,000 outlay bought Jay the container and luxury fittings, including a kitchen, insulation, storage space, a bed and an attached 6ft x 4ft shed, containing his bathroom – with a shower and toilet.
“Despite the restrictions on the hospitality industry this year, saving money wasn't my main motivation for doing this," Jay said.
“But saving £700 a month is certainly welcome."
And while the shipping container lies on an “exposed" part of the farm, Jay has not had to forgo all modern comforts.
“It's not 100 per cent off-grid. The location itself would be, but I do have a water feed from the farm and I do have an electricity supply, which is constantly running," he said.
“I also use a fan heater for circulation, because shipping containers are prone to condensation and moisture build-up, so that helps with that problem."
“I've insulated the walls, too, and have another heater, so that really helps now we're coming into winter," Jay said.
Most of the time, Jay lives alone in the compact but bijou space, but he has entertained at the container, not only inviting some friends over for a few beers around his fire pit outside, but also letting them stay over.
And everyone has praised his new digs and his minimalist lifestyle in an idyllic setting, away from the hustle and bustle of the town centre.
“My friends really understand where I'm coming from with it. I don't have as much in the way of possessions as I used to," Jay said.
“I still drive to work in a company van, but I have stripped a lot of unnecessary stuff away and that's brought me real joy. The things that I have in the container serve a purpose."
It has its downside, too.
“I do have to take my clothes to a launderette in town but, basically, I have everything I need to live comfortably," he said.
But, Jay did confess that his sister Leanne Jennings was alarmed when she heard that he was living in a shipping container on farmland.
“I think she had an image in her head that I was in the container with nothing inside. You know, maybe a mattress on the floor with no electricity," he laughed.
“When she saw photos of it, I think she was relieved to see that wasn't the case at all," he added.
And while Jay sacrificed many luxuries, he did keep some treasures – including his TV, mobile record player, which is now his most prized possession.
“Music is one of my big passions. The record player in the shipping container takes up a good amount of space, so that shows the importance it has in my life," he continued.
“In normal times, I'd be going to gigs and festivals, so this is the closest I'll get to that for a while."
Even with winter closing in, when most of us reach for our home comforts, Jay has no regrets about pairing down his life.
“There is definitely something to be said for simple living. I think people can, to a degree, become obsessed with material items and possessions and the way society is, it becomes a big part of your life," he continued.
“It feels like there is never an end to it, you always want more," he concluded.
“Yet, when you strip it all back, you can find yourself really enjoying yourself by living simply."
“I walk a lot more than I used to. I read a lot more and listen to way more music. In fact, I have ended up doing far more of the things I really enjoy. I'll definitely be here for the foreseeable future – I love it."