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The 65-year-old said despite reaching the milestone, he had no plans to stop.
"It started when I was about 10 — my father was taking us to all the airports.
"We also had afternoon teas for top-dressing pilots and I’ll never forget going for my first ride in one of those planes."
He started flying as a teenager.
Since then Mr Kean has experienced the best and worst parts of the industry.
In 1974, after the airstrip was established at Centre Bush, near Winton, a Tiger Moth crash in Tapanui left a man in a wheelchair.
This was followed by a fatal Tiger Moth crash which killed two people.In 1978 four people in a Cessna 180 were presumed dead, after it vanished between Northern Southland and Riversdale.
The plane and their remains had never been found, he said.
"The worst part about the first one was coming back from the search and the family were standing at the fence and they still had hope."
Adventures in the air also provided plenty of good memories such as flying in a small plane to Noumea, which was "a laugh", and completing 13,000 trips across Foveaux Strait.
The installation of lights on the Stewart Island airstrip in the 1980s made life "a lot easier" when conducting ambulance flights to and from the island.
"There was no other way to get a pregnant woman or a sick person off.
"We did 150 lifesaving evacuations."
On all the evacuations the plane was guided using a compass and stopwatch in the dark, Mr Kean said.
"I also flew all of the groceries, the milk, the paper and kegs of beer, which used to weigh 63kg and we’d carry nine at a time!"
A highlight of his career had been flying float planes around Fiordland in the early 2000s.
"I’ve seen some changes since — I’ve been doing it all.
"Everything now is on the phone, even the aeronautical maps.
"GPS has made flying extremely easy."
The responsibility of being a pilot or flight manager was still stressful though.
"You just take it in your stride, I suppose. You can’t afford to lie awake thinking about it too much because then you don’t sleep and then you’re a dangerous pilot."
He planned to keep flying for as long as he was physically able.