And the 64-year-old has seen more sides than most in his profession.
His teaching career began at Waimate High School in 1977, and he was the head of commerce and a dean by the time he left in 1989.
He went on to become assistant principal at Waitaki Boys’ High School before going to Logan Park High School in 1997, where he became deputy principal and acting principal.
His life took a slightly different direction in 2000 when he became the director of Youth Services and the Dunedin Secondary Schools’ Partnership, and was employed directly by schools as the Otago Secondary Principals’ Association secretary.
"I left Logan Park deliberately for a job that I thought was going to have a lot of challenges, but it was also going to be exciting because it was quite unique.
"It involved a group of schools working together in partnership alongside specialist education services and ultimately the Ministry of Education.
"The reason I’ve stuck at it for the last 18 years is because the job has changed dramatically through that time — it’s created different challenges.
"I’m responsible for ensuring that 12 Crown entities — that’s the 12 Dunedin secondary schools — are co-ordinated in a way that we can best achieve positive outcomes for all our students, particularly the ones that could be struggling."
Mr Wilson said secondary schools worked as closely together as Tomorrow’s Schools would allow them, but the government legislation was designed for schools to be independent entities that competed against each other.
"There is always a tension with that legislation.
"But in Dunedin, the schools still continue to work very closely together around [education] programmes."
That close relationship was largely down to the work the Dunedin Secondary Schools Partnership did, he said.
"Our outcomes continue to be the best in the country and that’s because we are operating a co-ordinated programme and we are working very closely with the community."
Looking back on his career, there were many things he was proud of, but the one that stood above all the others was establishing a sabbatical leave scheme for teachers while he was working at Waitaki Boys’ High School, he said.
Four years later, the initiative was implemented by schools across the country.
"I’ve had an opportunity to innovate and I’ve been grateful for that."
Mr Wilson said his "official last day" would be January 28.
Despite retiring, he planned to continue working on a couple of education projects that were close to his heart.
He said he and his wife also planned to do more travelling and look for new and interesting things to do together.
"I’m also keen to get my golf handicap down a little bit."
Ellesmere College principal Gavin Kidd, of Leeston, has been appointed to replace Mr Wilson.
