Because of a quirk in the schedule, the Canadian pilot will race her signature two-woman event and about an hour later make her World Cup debut as a four-man pilot Saturday.
Humphries and Elana Meyers Taylor of the U.S. will be the first females to pilot four-man bobsleds in a World Cup. Both will do double-driving duty in the men's and women's races at Calgary's Canada Olympic Park.
"When it rains, it pours, you know the old saying," Humphries said Monday in COP's Ice House. "It's going to be a very intense day.
"I haven't ever had to be in this situation before. I'm not able to draw from experience. No one has been in this situation, coaching staff, nobody. It's going to be trial and error. We're going to face it the best way we know how."
Humphries has logged four runs at Olympic Games and world championships, but they're spread over two days. On Saturday, the second heat of the women's race starts at 12:30 followed by the first heat of four-man at 2 p.m. local time.
So Humphries, the two-time Olympic gold medallist, and Meyers Taylor will have little time to mentally switch gears between the women's and men's races.
"I've never had to do four all-out runs in one day, let alone with limited time in between," Humphries said. "It's new for everybody, not just for Elana and I, but for the rest of the world to be in this position.
"It's not set up perfectly, but nothing ever is. You learn to adapt and overcome and this is going to be one of those situations."
The World Cup event kicks off Friday, with men's and women's skeleton and men's two-man bobsled.
Humphries asked the world's governing body of the sport in May to allow her to pilot a men's sled. With just six weeks until the start of the 2014-15 racing season, the FIBT gave her the green light by declaring four-man bobsled "gender neutral."
That allows for mixed teams and all-female teams to compete against men's four-man sleds. Humphries and Meyers Taylor, who finished second to Humphries at this year's Winter Olympics, will pilot crews with male brakemen and pushers.
Humphries and Meyers Taylor logged five races on three different tracks on the developmental North American and European Cup circuits to earn their World Cup qualification.
Neither woman raced four-man at the season-opening World Cup last week in Lake Placid, N.Y. They instead chose to compete in two-woman only and postpone their four-man debuts until Calgary.
Meyers Taylor won gold in the women's race in Lake Placid. Humphries and brakewoman Melissa Lotholz of Barrhead, Alta., were fifth.
So there is a competition-within-a-competition for Humphries and Meyers Taylor. Both want to prove themselves against the men and beat each other in their new event while they continue to battle for gold in women's races.
"We call it the battle royale between her and I," Humphries said.
"Definitely have some catching up to do in two-man. I'm not in panic-mode by any means. I've got to be able to shift my focus back and forth and sometimes it's not going to go exactly like I planned."
Her crewmen Dan Dale of Grande Prairie, Alta., Calgary's D.J. McLelland and Joey Nemet of Hamilton will all make their World Cup debuts Saturday.
"I have a lot of, you know, 'momma-ing' to do to prepare my guys," Humphries said. "We've got a lot of learning, a lot of preparation.
"We are facing the world's best teams out there and the other brakemen on the other crews, the other side's guys are fairly big and large and can be intimidating."
Humphries and her crew finished fourth and second in a pair of North American Cup races in November in Calgary. They were 17th in a European Cup race Dec. 7 in La Plagne, France.
"I can feel going down the track the strides she's making as a pilot in four-man," Dale said. "We want to give Kaillie the best push possible. Anything we can do to make her weekend easier we're here to do it."
Humphries is grateful the compressed race day will be on her familiar home track. She believes she won't have to race both events on a single day elsewhere this World Cup season.
"It's definitely easier than it would have been on the majority of tracks around the world and I'm lucky that it's here," she said.
Humphries and brakeman Heather Moyse of Summerside, P.E.I., defended their Olympic title in Sochi, Russia, in February after claiming gold four years ago in Whistler, B.C. The two women were Canada's flag-bearers at the closing ceremonies in Sochi.
Humphries will attempt a three-peat in Pyeongchang, South Korea, in 2018. The 29-year-old has won 11 of her 16 career World Cup races as well as a pair of women's world championships.
Women's bobsled was introduced as an Olympic sport in 2002 as a two-person event, while the men continued to race two-man and four-man sleds.