Caldwell never shirked from joining the teenage boys when they started moving to the bigger kickers and adding an extra flip to the doubles they did as kids.
Triples are the price of admission for the men, and while not unheard of among the women, the list of athletes who will try them is short: Jacqui Cooper, Alla Tsuper and Xu Mengtao are among the few who have tried them over the years. They're also among the best to ever fly off a ramp.
At the Sochi Olympics, Lydia Lassila of Australia became the first woman to land a quadruple-twisting triple flip on snow in training. The next night, she brought it to the medals round, and though she touched her hand to the ground on the landing, she won a bronze medal anyway and stole the headlines.
"That's who I'm inspired by," Caldwell said that night. "She's trying to push the sport so that girls are jumping like the boys, and she's doing it, and it's really impressive."
At freestyle world championships this month, Caldwell sent her message when she became the first woman to cleanly land that same triple-flipping, quadruple-twisting jump in competition.
"It was the first time I had every coach come up to me and shake my hand before the score even came up," said Todd Ossian, who works with Caldwell as head coach of the U.S. aerials team.
And yet, Caldwell was oh-so-close to not being able to even try that winning jump.
Aerials competitions go through a series of qualifying and elimination rounds that include only one jump each. Consistency is rewarded, and most women train a variety of double flips to make it through the rounds, then bring out their most intricate jump — more often than not, also a double — for when the medals are awarded.
Caldwell doesn't go that route. She tries triples every time she steps onto the hill.
It adds extra risk to the early rounds. When the field was being cut from 12 to nine at world championships, for instance, Caldwell didn't land her triple flip. She was able to squeak into the top nine and advance only because her degree of difficulty for the triple was so high.
"I'm OK sacrificing some good competition results to increase my consistency on the triple," Caldwell said.
The recently ended season tested the limits of how much Caldwell was willing to sacrifice. In meet after meet, from Moscow to Minsk to an Olympic test event in South Korea, difficulties with the triple kept her far away from the podium. In the World Cup standings, Caldwell finished 10th.
To her, that's more a badge of honor than a sign of failure.
"I want the crowd to feel like they know who won," Caldwell said. "I want it to be impressive. I just want people to say, 'That's sweet. That's what's deserved.' If a lot of girls are doing triples up there and I fall, there would still be a lot of girls who would do well. I'm cool with that. If I mess up, that's OK. But I want the sport to look good."