Simon started skiing at the age of two in Whistler, BC, a town that puts a lot of emphasis on skiing, so he quickly came to love the sport. Simon grew up watching the pros at the time perform tricks in the park and backcountry and got inspired to follow suit. From a young age, Simon began learning tricks on the trampoline and exploring the mountains, while developing new skills with friends. At 12, Simon would tag along with the local freeride club to make new friends and shred around the mountain. It was at 13 years old Simon experienced his first-ever competition. The following year, Simon joined the Blackcomb Freestyle Club to be part of a structured program.
As Simon improved his skiing and his knowledge of tricks expanded, he transitioned from the local freestyle club to the provincial team where he would travel and compete around BC and Alberta. At that time, there was a push to get slopestyle and halfpipe skiing into the Olympics which introduced some new opportunities. A national development park and pipe team and Canadian national team for halfpipe was then created. Simon was a part of the development team until 2012 where he eventually qualified for the Canadian National Halfpipe Team.
Simon began to train with sights set on the 2014 winter Olympics. As the games approached, he got some of his best career results, including 4th place at an Olympic qualifier. Unfortunately, it was not enough for Simon to attend the games that year but he was still hungry to improve, landing on the podium at a World Cup event at the end of the 2014 season. The next season, Simon had his first win at a major event, taking superpipe gold at the 2015 Winter X Games in Aspen, Colorado. After dealing with a new injury that spring, Simon qualified and attended the 2018 Winter Olympics in PyeongChang, Korea. In 2019, Simon was the FIS World Cup Overall winner, taking home the Crystal Globe. In 2021, he took second at the World Championships in Aspen, Colorado. Now, Simon has his eyes set on Beijing 2022.