As soon as he finished the individual two-day section of the Coast to Coast in 2006, he decided he would try a marathon.
On September 9, he will run his 100th marathon over the Dunedin course and become the 37th member of the New Zealand 100 Marathons Club, breaking the record for the fastest to achieve the target, taking just six years, five months and eight days.
The record leading into the Dunedin event is held by Auckland's Ingrid Frost, who took nine years and two days.
Chan (53) is no stranger to Dunedin. He attended Forbury School, Macandrew Intermediate, King's High School and the University of Otago, before moving to Christchurch 20 years ago.
He was named best all-round student at King's, before graduating from Otago with a double degree in biology and marketing.
"Now I sell wine and run marathons," he said.
"They are a great de-stresser."
As much as Chan is proud of his Coast to Coast achievement, he has found running a marathon offers more of a challenge.
"You can't sit down in a marathon," he joked.
Chan ran his first marathon in Queenstown, just seven weeks after the 2006 Coast to Coast, and completed five marathons that first year.
He had heard you should run no more than four in a year, but then met Mike Stewart, the veteran Hutt Valley runner who is nearing 500 marathons.
Chan, whose most prolific year included 26 marathons, has discovered an ability to recover from races and remain injury free.
"I have had no significant running injuries. My main injuries were from snowboarding and mountain biking."
He recalls meeting running guru Arthur Lydiard, who encouraged him to build his base fitness through "long, slow distances".
"I found him to be inspirational and recall his advice to reward myself with a beer after events and hard training sessions."
Chan has completed three Lydiard Legend races since it became a marathon-distance event and will contest his fourth (his 101st marathon) on September 15, the week after the Moro-sponsored Dunedin event.
"Any marathon you finish is a good one," he said.
"You can't go into each one and expect a personal best. You're only going to break down."
Two of Chan's sons, Jonathan and Alex, have won national open fencing championships. A third son, Alex, was the youngest winner of the national senior sabre championship in 2007 at the age of 14.
A number of members from the New Zealand 100 Marathons Club will be competing alongside Chan in Dunedin next week.
Among them are Frost and Stewart.
Frost (46) was originally going to run her 150th marathon on the Dunedin course, but when she discovered it was Chan's 100th, she held one back to let him have the spotlight. She will run her 150th a week later in the Legends event in Auckland.
Frost has contested the Dunedin marathon eight times, with her first time on the course her slowest at 3hr 31min 25sec, and her fastest in 2010 in 3hr 16min.
Stewart will run his 498th marathon on the course next week, and plans to notch up his 500th in late November.
