"I needed to make a decision pretty quickly and I think it was the right one," said Hesson after he was appointed Black Caps' coach in July. "With coaching, you've got some real longevity in the game."
In 1998, his decision began to pay off. The then 23-year-old Hesson became the youngest person to attain an NZC level three coaching qualification and put it to immediate use, becoming coaching director at Otago Cricket.
During the five years he spent in the position Hesson was in charge of older and wiser men, an experience which held him in good stead when he earned his maiden view of the first class scene.
As assistant to two-time national coach Glenn Turner at Otago, Hesson honed his coaching craft under a man who led New Zealand to their first-ever series victory in Australia.
Hesson was making a name for himself within New Zealand coaching circles and he began to be noticed at an international level, too.
In 2003, he was appointed by the ICC as national coach of Argentina in their bid to reach that year's World Cup. The venture was ultimately unsuccessful but Hesson showed promise, leading the South Americans to three wins after they had previously lost 31 straight games.
The promise was parlayed into a promotion with Otago two years later, with Hesson selected to succeed Turner as coach of the first class side.
Hesson repaid the faith shown in him by Otago Cricket by breaking a 20-year trophyless drought for the province, first winning the one-day competition in 2008 and following it up a year later with Twenty20 glory.
Now the province in which Hesson had spent his whole cricketing life was starting to seem small.
Hesson's success had put him on the radar of NZC and he led New Zealand A on various tours, but he wanted to make a quicker contribution at the highest level of the sport.
Frustrated with inaction when Buchanan began his overhaul of the NZC coaching system, Hesson grasped an opportunity for growth. He accepted a two-year contract as national coach of Kenya, initially unperturbed by turmoil on and off the field in the fledgling cricket nation.
After 11 months in charge, though, Hesson abruptly left the post after his young family fell victim to an attempted car-jacking and a grenade exploded near their house in Nairobi.
"There were a number of challenges - dealing with administration and tribal issues and, obviously, security," Hesson said. "Some of those experiences were great, some not so good, but certainly very valuable."
That tumultuous time hardly made him hot property but, when John Wright left his post, Hesson was selected from 39 potential candidates and appointed to his "dream job".
Just five months later Hesson has full autonomy but, during the last week, that dream must have felt like a nightmare.