[1] In January 2019, Stess broke and dislocated her elbow, which required three surgeries and several months of recovery.

[18] Stess won a gold medal at the 2021 USA National Championships in the park competition, becoming the youngest champion in the event at 15 years, two months old.

[19] In October 2022, at 16 years old, Stess competed in the women's park division of the STU Open in Rio de Janeiro, Brazil, where she finished in third place, behind Sky Brown and Sakura Yosozumi.

[20] She competed at the 2022 World Skateboarding Championship in Sharjah, in the United Arab Emirates, which was postponed until February 2023, and finished in seventh place.

[21][22] In October 2023, she won a bronze medal in the park event at the 2023 World Skateboarding Championship in Rome, Italy, with a score of 90.80.