In doing so he followed in the footsteps of his wife, siblings, daughter and niece.
"I thought 'right, Kim, you could stay on for another five years but you might die as well'.
"If it wasn't for all the good things; the kids, the sport ... I might have gone earlier."
He says his job dealing with prisoners has made him the most relaxed he's ever been.
"If a problem is not solved by the time your shift ends, you go home anyway and the next person picks it up. I have no homework."
Whittington had been at Heretaunga Intermediate for 12 years. By the time he left he'd become the only male teacher - a burden which weighed heavily on his shoulders.
"Quite often when we got kids in from broken homes - that is families with no fathers, a lot of them got put in my room because I would be a positive male role model, which tended to load up the classroom."
He said the "powers that be" were reluctant to let him take leave, unless it was bereavement leave or something they couldn't do anything about.
"Any discretionary leave you hardly ever got off if you were a male."
Whittington said, when he started, teachers did a half yearly 'progress and achievement register' and then an end of year report.
But then came parent-teacher-child interviews each term and reports "longer than a roll of toilet paper".
He said he was often up until 1-2am each night.
Whittington's not alone in voicing his concerns about the profession. Primary and intermediate teachers took strike action in August and further action may be taken, amid stalled negotiations.
Ministry of Education spokeswoman Ellen McGregor-Reid said despite its challenges, teaching was still a viable career path for many NZ men.
But numbers remained low, compared to female teachers, in early childhood and primary education, she said.
She said the ministry had recently launched a marketing campaign to attract more Kiwis to teaching, with TV advertisements that featured male and female teachers.
For Whittington, he sees the day he got a prison job as the day he got free.
"I got out."