Cassie Sharpe thought she was done with skiing. The Canadian freeskier had earned her two Olympic medals in women’s halfpipe (gold at PyeongChang 2018 and silver at Beijing 2022), started a family, and thought she’d already ridden into the sunset.

“I’m good. I don’t need to go back. I’m happy to be a mom,” Sharpe recalls thinking after giving birth.

But in January 2024 — two years after her retirement and five months after giving birth to her daughter, Louella Duke Dorey — she started thinking that maybe the mountain was calling.

“I was watching X Games, sitting in the living room, holding [Louella], I was watching the girls [compete] and I was just like, oh, maybe I'm not done,” Sharpe recalled. “Maybe I go for another [season].”

Sharpe and her husband, Justin Dorey, a fellow halfpipe skier who competed at the 2014 Winter Olympics, discussed what it would look like if she were to go back for a season and how they could make that work. She chose to do summer training in New Zealand after seeing the spring training posts from her fellow halfpipe competitors.

"It kind of slowly ignited it into being like, 'OK, maybe we’re going to go to New Zealand and really put a push on it,'" she said.

Sharpe returned to routine training, and her training regime progressed as her daughter grew. Once her daughter weighed 15 pounds, she knew she could lift 15 pounds in the gym, and so on.

“It was a pretty quick turnaround once I decided that [I was going to return to skiing],” Sharpe said. “I was like, ‘Yeah, I think we can make this happen.’ In January, it was pedal to the metal. … I was still breastfeeding.”

The gym for the Canadian national ski team is only 30 minutes away from where Sharpe lives in Squamish, British Columbia. She would bring Louella to the gym, where her brother, Olympic snowboarder Darcy Sharpe, would care for his niece while Sharpe trained. Sometimes, Louella would be bouncing in the Jolly Jumper along the squat machines as Sharpe worked out. Like mother, like daughter.

Two months after she resumed training, Sharpe found herself on her skis for a film shoot mid-March of 2024.

“A lot of people don't think about the other pieces of being a mother,” Sharpe said. “I have to … make sure that she's taken care of, as well as me being strong enough to do what we're doing. … It was a funny juggle to do, but so well worth it so far.”

She has a great support system. Dorey works from home, and his mother steps in occasionally to take care of Louella during the six months she spends in Squamish each year.

Sharpe’s mother, Chantal, took a leave of absence — and later retired in July 2025 — from her job to go on the road with her and take care of Louella.

It’s not easy for the Olympian to bear the financial costs of traveling with her mother and daughter. To help cover expenses and compensate her mother for being a nanny, Sharpe has partnered with B2ten, a Canadian non-profit that provides funding and coaching support for Canadian athletes, and makes content for other brands such as Air Canada and Lululemon.

In addition to navigating finances, Sharpe has had to navigate the emotions of traveling with and without her baby. When she competed in her first World Cup event in New Zealand in September 2024, Sharpe and her daughter were extremely ill from the flu. It was the first time Sharpe realized she had to prioritize care for herself and Louella over a competition.

The learning curve continued. Sharpe’s first big trip away from her daughter was a World Cup event in China in December 2024, when Louella was 16 months old. While Louella did fine without her mother, Sharpe missed her daughter dearly.

She doesn’t have as much time as she did before Louella arrived as she strives to be both a worthy competitor and a mother who’s “very present and loving.”

At the same time, Sharpe recognizes the freeski field has become more competitive. At 33, she is one of the oldest competitors.

“A lot of the girls in halfpipe are seeing these other girls [in big air] that are doing bigger tricks and, like, you have to do the bigger tricks to be able to compete with the big dogs,” Sharpe said.

Eileen Gu is one of those girls raising the bar. She’s already won Olympic silver in freeski slopestyle and big air at these Games and has won 10 of her 11 World Cup halfpipe appearances since the last Olympics. At the last Olympics in 2022, Gu took home two gold medals (halfpipe, big air) and one silver (slopestyle).

Sharpe and Gu were supposed to compete at X Games Aspen 2025, but Gu pulled out after a couple of hard falls during training.

“When we got up there, [Gu’s] name wasn’t on the list," Sharpe recalled. "The aura of the whole contest changed."

After receiving the news, Sharpe's first move was to text Gu and wish her well. The next thought to cross her mind? The door is open.

Sharpe ended up winning the competition. That’s when she knew she was back in her groove.

“I was like, ‘Oh, my god, I just won X Games as a mom. That's so cool,'” she said.

That win had Sharpe setting her eyes on the next prize: qualifying for Milan Cortina 2026, which she successfully did. According to her, anything “above that is all bonus.”

Sharpe will take her first runs of the Milan Cortina Olympics on Thursday, Feb. 19, when the women's freeski halfpipe contest opens with the qualifying round. The final is scheduled for Saturday.

“I have two Olympic medals, I obviously want to perform well, I obviously want to do the thing. But [qualifying for Milan Cortina] was my base." she said.

"To me, success is making it to the Olympics. So I'm just happy to be a part of it.”

NBCOlympics.com's Shawn Smith contributed to this story.