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May 09, 2019

Jessica Woolsey – fearlessly reinventing, building community and encouraging others to try new things

Jessica Woolsey is athletic, compassionate, a community builder and a paradigm shifter. And this just scratches the surface. She is a huge supporter of active women, inspiring and encouraging women to get out there, be active and try something new. We were stoked to catch up with Jessica. Here’s how she does it.


1. Start building confidence early through sport

When Jessica was younger she was a gymnast. Through her sport, she learned how to be confident in her own skin and to love the strength she gained both physically and mentally as a result. She realized that her body was her foundation for being able to do what she does – living a healthy and active life was possible because of her strong body. Building this confidence in her abilities at a young age has served Jessica well and allows her to be and do all that she does today in adult life. Celebrating and sharing this love of sport, strength, and body is what Jessica does when she meets young woman every day.


Jessica participated in sports at the grassroots level. She grew up on a military base where there were lots of activities offered – dance, girl guides, figure skating. When Jessica went to high school, she wanted to play football. There wasn’t a girls’ team so she played with the boys. The first few weeks were rough because she had to prove herself to the boys – that she was just one of them. But she took it all in stride because it was what she wanted to do – so she just did it. The experience was an eye-opener for the boys just as much as it was for her. They underestimated her but it wasn’t long before they realized what she was capable of doing. Solid friendships were built and Jessica is still friends with these guys today.


2. Surround yourself with good people and good vibes


Snowboarding is fun, supportive and motivating. Jessica started snowboarding in high school and learned quickly. She got a job at a resort so she could be close to the sport. She admits it was a little intimidating at first – starting as a teenager, in the high school environment takes some inner strength. But she always rode with a crowd – mostly boys – that were a little better she was. This pushed her to try new and challenging things – and to just keep going. The lesson she learned was to surround yourself with good people and good vibes – it’s about having fun and using the vibes.



3. Join a community and see what you can do together

Jessica boarded with the guys and it pushed her to learn and progress. But this is not always a comfortable environment for some girls and women to try something new. Jessica was also part of an all-girls snowboard camp – supported by the Women’s Snowboard Federation. They brought 50 women together of all abilities on the hill, building a community of support for Ontario female riders. The Park Days camps were all about bringing girls together and showing them what they could do together – having fun, supporting each other and embracing the sport of snowboarding. It’s all about the vibe – you just can’t help enjoying the feeling of being a part of something so positive, supportive and friendly.


The world of women’s snowboarding is expanding in leaps and bounds – quite evident when watching the talent that participated in the 2018 Pyeongchang Winter Olympics. It is a very supportive environment – as depicted in the Full Moon film that stars female riders who were inspired by the early iconic boarders and who are inspiring the next generation. Watch the trailer and find the film here. Be inspired to get out there and try this energizing, fun sport and be part of a supportive community.



4. Give back and make a difference

Another great program that Jessica is aware of and is part of the empowering aspect of the boarding community is called Chill Foundation. The founders of Burton Snowboards started Chill for at-risk youth – inspiring youth through boardsports. Through Chill they have reached more than 20,000 youth through each of the board sports – skate, snow and surf. They are in 13 cities across North America and affiliated in programs in Europe, Australia, and Asia. They are teaching young people through sport, how to build resiliency, reach their full potential and see that there is a path out of their current circumstances. 



5. Challenge yourself with new sports


Always up for a challenge and ready to try something new, Jessica took up wakeskating. She says it’s the best thing she has taken up for summer.


Wakeskating is like skateboarding behind a boat. The big difference with wakeskating over other board watersports is that riders’ feet are not attached to the board – just like on a skateboard. The rider holds a cable that tows them behind the boat – perfect for doing skateboarding-like tricks on the water.


Jessica became part of a crew of women who joined forces to promote wakeskating and support each other as the sport progressed. This group calls themselves The Wakebabes. The Wakeskate Tour wasn’t promoting the women’s division so The Wakebabes did it for themselves. They created a website and used social media to get the word out – check them out on Facebook and Instagram.


The goal of The Wakebabes is not only to progress the sport for women but to push each other and support each other on tour. The Wakebabes are also encouraging others to take up the sport by providing opportunities like Girls Ride Days and clinics to extend their reach and give women a chance to try it in a supportive environment.


To see what wakeskating is all about, check out this video from The Wakebabes.


What would Jessica say to her 13-year-old self?

Seventy percent of children leave organized sports by age 13 (Don’t Let Youth Sports Hijack Your Life). It’s a tough age – there are social pressures, burn out, academic pressures, confidence issues – many reasons why kids have had enough by the time they hit 13. So what would Jessica say to her 13 year old self?

"You did it well kid. I wish I would have tried lots of things earlier on. Being a well- rounded athlete is a good way to be – try things and don’t be shy."

Jessica’s advice to other women

"Get involved, be confident in your own skin, feel the vibe, share the vibe and have fun."

Jessica is very involved in encouraging and inspiring other women to get involved in the sports that she loves – helping women to overcome barriers to participation. A lot has to do with confidence and being able to try new things. This is a big reason for having women specific snowboard events. It can be intimidating to ride with the boys. Some girls will only do the bare minimum. By building the community vibe it helps women flourish in the sport. Everyone is there for different reasons but they are all there just to be there together – to learn, progress, and have fun.


The snowboarding community is a great example of an empowering environment for women to thrive. It’s about giving women the skills and confidence to participate and develop and then having them share that vibe with more women.



Check out Athlete Advisor – your online business directory for all things active. Rate and review your favourite boarding program or race. See what others have to say about the ones you’d like to try.


Find or start a group or event. Organize an all female event. Visit our SWSCD Hub.


Explore fresh thinking, inspiring articles and advice on our Snowboarding activity page.


Share your story about your favourite boarding activity directly on our Discover blog or by using #seewhatshecando in your social media posts. Whether you are training for a competition, or trying a board sport for the first time – we want to hear how you DO.



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