"I took the plunge and then I was down in my life and hated it for several months," said the rider who will compete in the Big Save Elite Road National Championship road race in Napier tomorrow. His trip across the Cook Strait ferry got delayed yesterday because of stormy weather but race organisers were confident he would arrive.
For someone who has built a reputation as the best hill climber in New Zealand, Bennett had arrived in Switzerland as an apprehensive teenager amid uncertainty and fear surrounding his living arrangements.
His best-laid plans to ride for a team in Switzerland went pear-shaped a fortnight before he left Nelson but, because he had booked his flights, there was no turning back.
It was snowing when he landed at the airport and the Swiss rider who picked him up informed Bennett he wasn't going to stay at his house but flat with a stranger.
"I had no team, the guy I was going to stay with was in his 50s and didn't speak English, and I was told he was into having relationships with younger men.
"So I had just got off the plane and I was already shitting myself. So, you can say, I was motivated to become successful pretty quickly," said Bennett, adding his homosexual middle-aged flatmate turned out to be "a pretty nice bloke in the end".
But the early ragging process in pursuit of a contract, never mind a pro-tour one, is something that will be forever etched in his mind.
"It was the right thing to do but I used to be travelling around with my bike on the trains to go to tours," he said, mindful of the frustrations of defending New Zealand road race champion Joseph Cooper, of Wellington, who claims he does everything a professional rider does except pick up their lucrative cheques.
"I was fresh out of here [Nelson] with no lodging, no money and scrounging around for food to survive - to keep my chances alive."
The break came for Bennett in France two years later when he turned pro with Trek-Livestrong in 2011, after pocketing some cash through a couple of wins with a French team, VCC Morteau-Montbenoit.
"I'm in my fifth pro season and pretty settled on the pro-tour and moving up in the world and finding confidence in being away from home," said the bloke who left footprints for a rash of other young Nelson amateurs to carve a niche with VCC Morteau-Montbenoit.
Stints with Radioshack Nissan-Trek (Luxembourg) and Leopard (US) followed in 2012-13 as well as Cannondale Pro Cycling (Italy) in 2014 before he joined the Dutch team of Lotto NL-Jumbo.
Bennett's status now ensures he doesn't have to scrimp it out while plying his trade abroad, living in the same area as other Kiwi pros such as Greg Henderson (Lotto Soudal), Sam Bewley (Orica-GreenEDGE), Jesse Sergeant (AG2R Mondiale) and Patrick Bevin (Cannondale).
"I've had it tough, so I live in my own apartment now and I don't have to live with four or five other cyclists or do something shitty like that," he said, hoping his girlfriend will spend several months with him in Girona this year.
Consequently, Bennett thoroughly enjoys returning home this time of the year to soak up family and home comforts of riding at the nationals.
"Riding in New Zealand is more fun whereas with the pros you're on the handlebars and there's pressure all the time."
Ironically, it's his first trip to Napier for Bennett whose only foray into the Bay was at Wairoa when he visited his brother, Joe, who used to work there as a vet several years ago.
In fact, he's only competed at two nationals in the North Island - finishing runner-up to former Radioshack teammate and three-time elite winner Hayden Roulston in 2013 in Whanganui.
Packing only 60kg on his 1.8m frame, Bennett fancies himself on the bigger alps of Europe.
"Short hills make courses a lot more competitive. The fastest guys struggle on the hills but I need European mountains to make a difference."
Having tackled the Cashmere Hills of Christchurch during four nationals, he juxtaposes it with the unfamiliar Napier Hill and anticipates there won't be much difference from his perspective.
Frankly, he feels it'll boil down to "who has the legs after 180ks" because it can go either way.
Coming downhill in the last 7.5km loop of the hilly circuit will require as much dexterity because speeding up too much or slowing down to an over-cautious approach may both close the gaps for the leading riders with the peloton in pursuit.
However, Bennett is realistic about his chances of winning this weekend because he is "a very long way away from peak conditioning".
Back into it here "for just the love of it", he is hoping to hit top form for the Down Under Tour in Adelaide from January 19-24.
Bennett's love of riding stems from mountain biking. He went on to compete in the 2008 World Championship in Italy.
"It was good fun and I still like hitting the trails," he said, before switching to gruelling but seductive road racing in 2009.