He is a gun Optimist racer. The Optimist is a single dinghy, but McCutcheon is coming to the end of his time in that boat, which is for junior yachtsmen.
He is ranked fifth nationally in that class with the club nationals to come over Easter off Kohimarama which will determine if he heads up or down the ladder in his Optimist swansong.
McCutcheon got into the sport when he was just 9, courtesy of his father, and naturally he lives right near the water in Cheltenham, with Wakatere his home club. That is where the racing takes place tomorrow, so he will know the conditions and what the wind gets up to.
Westlake is one of the top sailing schools around, ranked fourth nationally in 2015, with Kerikeri the big guns. Under the coaching of Phil Davies at Westlake, McCutcheon gets plenty of sailing time in different boats. If it is not the Optimist, it is the Starling, and the team does a lot of racing in the 420.
"Sailing three boats, they all have their different aspects, so you need to control them as well as doing other boats and gaining experience," says McCutcheon.
It is not quite true to say McCutcheon is out on the water every spare moment he gets. He generally takes Mondays and Fridays off to catch up on his studies and give his body a break, but the rest of the time he is out here doing what he loves.
McCutcheon is a four-time national champ, and has represented New Zealand abroad. Think Australia, Antigua, Bahrain, Bermuda and New Caledonia. Not bad for a 14-year-old.
People underestimate how taxing sailing can be, especially when you are a one-man operator much of the time. McCutcheon admits he is wrecked at the end of a day's racing, trying to keep control of a boat that is at the mercy of the elements. Regatta racing is demanding too.
"Consistency is a big part of racing. You really want to minimise those high numbers and stay consistent throughout the regatta."
He knows all about Westlake's rich yachting history, with the likes of Dean Barker and 2001 YSPOTY winner Michael Bullot old boys. So there are plenty of role models for the class of 2016.
"It's definitely been a good influence on me both as a sailor and as a person. It's like a sport for life," says McCutcheon.
Now he has his sights set on the 2017 Youth Olympics and longer-term, the 2024 Olympics are very much on this determined young sailor's horizon.