Scott's forensic attention to detail is legendary in sailing circles. His best laid plans had involved defending his Olympic title at Enoshima Yacht Harbour this summer.
Then he'd immediately jet to New Zealand where he'd join forces with Sir Ben Ainslie's quest to win the America's Cup for the first time.
However, recent months have proved that no good plan is a great plan without last-ditch revisions.
It now means in the space of four months next year, he'll switch from calling tactics for Ainslie to being the master and mate of his own fate, as he seeks to retain the gold he won in the heavyweight Finn dinghy four years ago.
"It's probably best to say it's not ideal but it is what it is," said Scott, who is one of more than 1,100 athletes on UK Sport’s World Class Programme, funded by The National Lottery.
"I've never considered having to make a choice, I couldn't make that decision so hopefully I can get both done.
"The Olympics is a personal endeavour but in the America's Cup you are just a cog in a huge engine, I love doing both but I’m no less hungry for Olympic gold.”
Ainslie won four Olympics between 2000 and 2012, keeping then world champion Scott out of the team in London before focusing on his America's Cup ambition.
And it's a blueprint Scott remains determined to follow. Indeed the F1 style appliance of science required to challenge for sport's oldest trophy is only benefiting his Olympic campaign, despite the compressed timescales.
"My sailing career is changing, and the Olympics is still a massive part of that. I’m now in this dual role where I badly want to win both,” he said.
"When you’re part of an America’s Cup team, you’re working day-to-day with the world’s best sailors with an incredibly broad range of skillsets.
"That’s always very useful to draw from and take little lessons back to your Olympic sailing.
"I think historically that’s why sailors have been so successful in combining the two.”
Ainslie names all his boats 'Rita' while Scott prefers 'Gangly Bean Head' - a childhood nickname which he scribbled on the hull of his Rio boat in black sharpie.
He admits to struggling with the expectation of his last Olympic campaign, he'd dominated his class in virtually every regatta in advance.
This time around he'll be arriving in Tokyo under the radar, with the America's Cup regatta not due to conclude until late March.
"There were people who were guilty of pretty much hanging the medal around my neck before it had been done, which was frustrating,” said Scott, whose Rio gold was one of 864 Olympic and Paralympic medals won since National Lottery funding began in 1997.
"In the last cycle, the pressure I put on myself built with almost every single event I went to.
"I had this run of success into the Games which obviously made people say: ‘It’s a done deal, you’re going to do it.’
"But my response was always: ‘Well, you really don’t have any idea what it takes for us throughout the week to win.’
"I suppose I put an awful lot of pressure on me and perhaps that's why I had some serious thoughts about whether I wanted to commit to another Olympic campaign.
"But I really wanted to be able to do it again despite all the challenges, I’m glad I’m hanging around."
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