Mr Connelly acknowledges he didn't make the most of opportunities when he was younger and that has contributed to his position. But he has also taken risks, owning a possum-hunting business before it became uneconomic.
For 14 years he sat on the sickness benefit. He wasn't sick, but he couldn't seem to convince authorities that he had a disability and needed extra help.
Eventually, on a visit to a Whangarei Winz office in 2005, the penny seemed to drop for one staff member, he said.
"She says to me, 'What are you here for?' She punched my number up and then her face changed. I'd been waiting for this look. I'd imagined it and dreamed about it for many years.
"She goes, 'You're on a sickness benefit but there's nothing wrong with you; you're disabled'."
Mr Connelly said his experience of Government agencies was that they didn't want to help him move out of his cycle. He also suspected lots of welfare cash got sucked up by bureaucracy, leaving the poor as "penniless" as ever.
Tiaho Trust's chief executive Johnny Wilkinson worked on him, convincing him over time that Whanau Ora's approach was different.
Mr Connelly has nearly finished a plan which has two main thrusts. The Connellys have a high cancer rate so he wants his relations to look at ways of reducing risk. Also, he hopes to bring his family together to discuss a plan for their financial wellbeing.
"I'm quietly hopeful," he said. "I want Whanau Ora to lay the foundation. It's about the future of our whanau. This is totally different from what the Government system usually is.
"It's about saying, 'What are your needs? Identify them, and how do you see them being addressed'."