Callan grew up in Aleknagik, Alaska, a Yupik village accessible only by air or boat.

At seven years old, she inherited her big brother's hand-me-down snowboard, learning on the hill behind her Upi's (grandpa's) house. Her family snowmobiled the surrounding mountains, shuttling she and her brother up to the peaks to shred down.

In 2001, she and her mom moved to Girdwood, AK, home of Alyeska Ski Resort. She began competing along with her friends in local races and qualified for a national competition. She achieved some success nationwide quickly, earning spots on the Junior World Championship Team and at 16 received an invite to the US Snowboard Team. In 2007, she won the Visa U.S. Snowboardcross National Championships and took 3rd place in the first World Cup of her career in Furano, Japan.

 

Chythlook-Sifsof spent much of the 2009, 2012, 2013 and 2014 seasons battling knee surgeries. Determined to make it to the 2010 Vancouver Olympic Games, she moved to Park City, UT to train at the Olympic Training Center there before returning from her first injury and back to the World Cup circuit in 2010. Callan was named to the 2010 Olympic team, becoming the first indigenous Alaskan to do so. She backed up the Olympic season with solid results in 2011, including silver medals at both the Winter X Games and World Cup in Arosa, Switzerland, achieving the third World Cup podium of her career.

The 2012 season, garnered two top-ten World Cup finishes however chronic knee injury plagued her through the 2014 Sochi Olympic Qualification. 

Callan chose to forgo a significant surgery in order to make a bid for 2014 Olympic Team however missed the 2014 Olympic Team by three FIS Points.

Callan retired from professional snowboarding in 2014. She was a private and professional coach for the Park City Snowboard Team and head coach for the 2021-2022 US Paralympic Team.

Callan has been an advocate for the empowerment of indigenous voices, working alongside organizations such as Protect Our Winters, Times Up, Athlete Ally, Girl Scouts of Alaska, PBS and others, utilizing her platform to further opportunities within marginalized communities.​