There were some successes - he has been offered roles four times - but all have been rescinded as the country went through yo-yo lockdowns and the unemployment rate crept up.
"All I want is to pay my bills, provide for my son, and afford little luxuries like coffee or ice cream," Oliver told the Herald on Sunday.
"I just want to work, regardless of what it is to help pay the bills."
Oliver, who lives in Auckland's North Shore, began his search for work in his field in sales and account management, in which he has more than 20 years' experience.
But facing brick wall after brick wall, he has looked for any sort of work to help pay the bills - relying on the support of friends to help him through tough financial times.
"I have applied for supermarket shelf packing, bus driving, fruit picking, cafe work, rubbish collection, retail. You name it - I have applied for it," he said.
Oliver was rejected from some of these roles and told he was over-qualified.
"All of this requires hours of input, research, tests, dedication, effort.
"It's a strain on your stress levels, mental health when there is zero effort from the hirer and no reason given when unsuccessful."
Oliver, who is single dad to a 7-year-old boy, said after his redundancy money dried up, he had to dive into his house deposit savings to keep him afloat - that has meant giving up on the dream of home ownership.
"The benefit barely covers my rent and child support. It is not enough to survive on let alone actually pay regular bills like petrol and food. It doesn't cover the basics of living."
Latest figures show New Zealand's unemployment rate at 4.9 per cent in the December quarter - a drop from 5.3 per cent on the previous quarter.
But economists have also warned that data could be noisy because of conflicting impacts of Covid-19 such as closed borders restricting immigration.
"We've seen a sharp fall in the number of people out of work, or wanting more hours to work ... today's report was truly remarkable," Kiwibank's chief economist Jarrod Kerr said when the figures were released in March.
Oliver says he's received a lot of help from family and friends but he's also become isolated.
"Stress levels have been through the roof - it's a significant strain on mental health with a constant worry about living costs, unstable accommodation and the need to move without having the funds."