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Skateboarding Through Life, All the Way to the Olympics

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If you make it to the Olympics, it is pretty safe to say you have made it to the top of your game. You have arrived! It’s an amazing achievement, and the Olympic athletes make it all look so easy, so effortless. But what we don’t see is what it took them to finally get there – it’s a long road, full of bumps, bruises, and setbacks. Of course, most people who start down that path never make it to the triumphant finish line. Yet somehow, a special few do finally make it.

In Roam Media’s Boundless series, Episode 5 – Colorado Skatepark Tour with Annie Guglia, the Roam team meets up with just such an aspiring Olympian, professional skateboarder Annie Guglia. In the 2021 Tokyo Olympics, skateboarding is finally making its debut, and Annie aims to be one of the competitors. And she has fought long and hard for the chance. The Tokyo Olympics website calls her out specifically as someone who is “breaking barriers in women’s sports,” adding that “the Montreal-born athlete is a role model for future generations of women skateboarders.”

Annie, now 32-years old, is a three-time Female National Champion skateboarder. She started early in high school, where she fell in with a group of skaters and became hooked. These girl skaters called themselves the Skirtboarders and skateboarded around Montreal in the early 2000s. They were kind of unusual because, at that time, the sport was composed of literally nothing but edgy teenage boys. But Annie was sure she could someday become a terrific skater herself.

However, to make it all the way to the top takes a special kind of person, one with certain important characteristics. Natural talent won’t cut it on its own. It takes so much hard work and determination that many naturals simply give up when it is time for the tough work to begin. A true champion has to be a striver, someone who both knows what it is going to take and is willing to give all that it’s going to require. The natural question then is, how is this kind of person trained and formed? How does a person learn to develop the necessary resilience and perseverance?

According to Annie, in her case, these qualities grew naturally from the sport itself. As she says, “Skateboarding is such a good self-development tool.” So many aspects of skateboarding translate naturally to her entire life, particularly the patience necessary to practice difficult tricks over and over until she gets them right. And also, the resilience necessary to get back up, not just from the first fall, but from all of them. Even professional skateboarders at the top echelon still need constant practice and experience many falls as a natural course of events.


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In fact, the Roam video begins not by showcasing her amazing skateboarding tricks, but by showing some pretty spectacular high-speed falls and spills. It’s demonstrating the importance of always getting back up and trying it again – and if you wipe out again, you get right back up. Annie’s voiceover reinforces this message of how much the sport of skateboarding has tested her and molded her into being such a strong person. All these important lessons carry over into real life, not just when you are on the board.

The short film follows Annie and fellow skateboarder Alexis on a trip through Colorado in her RV. She describes Colorado as a sort of “temple for skateboarders,” with its many skateboard parks surrounded by the famous Colorado backdrops of natural forests and snowy mountains. There is no doubt that Annie is a very strong, self-motivated person, but of course, no one stands alone – collaboration is a big part of how she operates. Alexis is someone she deems “the perfect adventure buddy. Having him around is gonna help me push myself more.” So while they are good friends, they are also helping each other to achieve even more. Annie realizes that not all the motivation to push harder has to come from within – certain others can help with that also.

The two of them drive from park to park, and each stop is at a remarkably different skatepark where they each get on their boards and let loose. The video captures the jumps and tricks, the different paths and obstacles, and some of the sheer joy she seems to radiate from being on her board in her element, doing what she knows she is excellent at. The Roam videographers have a hard time keeping up with her – they are also on wheels to better capture the action, but they seem sometimes stuck in a slower gear than Annie is as she flies past them at top speed.

There is a yin/yang element to skateboarding in Colorado because the skateparks are always in the city, but they choose to drive out into the forests to spend the nights surrounded by the trees, silence, and clear, star-strewn skies. One gets the impression that this is part of her approach also – after the loud, intense workouts in the cement parks, she can then retire to a completely different environment and let the peacefulness of the natural world rejuvenate her to come back well-rested for the next time. She says that in the city, the job is to chase the best park, whereas in the backcountry, it is completely different. It’s a chase to find the best views.

They skate their way through Breckenridge and Leadville, and then in Frisco, she meets up with her friend, professional photographer Celia Miller, for a skatepark photoshoot. Celia becomes the director, deciding the best angles to shoot, and Annie breaks out all her stunts. We see grind and slide tricks, footplant tricks, air-grab-ramp tricks, kickflips, rail-slides, you name it. One gets the idea that this collaboration with the photographer is another facet of Annie’s workflow – it’s bringing in another member of her extended team to help her learn to look her best and most impressive. Even a sport as solitary as skateboarding benefits from multiple fresh inputs from outsiders.

Annie can get philosophical about her skateboarding passion, and she sometimes feels that it is honestly a metaphor for freedom. “When you get a skateboard, you can do whatever you want with it… there’s a billion possibilities!” It’s like getting into the van to begin a new adventure, “You can take any road and end up wherever you want to be.” Her board and her journey are indeed a metaphor for life.

About Annie Guglia

Annie Guglia is a Canadian skateboarder and LGBTQ rights activist. She made her debut appearance in the Olympics at the age of 30 representing Canada at the 2020 Summer Olympics where skateboarding was also added in Olympics for the very first time. During the 2020 Summer Olympics, she competed in women’s street event.

About ROAM Academy

ROAM exists to inspire, educate, and activate your life of Adventure + Purpose. Founded by the world’s best adventure athletes, photographers, and filmmakers, ROAM brings a new voice, straight from the icons themselves, to the world. Through educational videos, original shows, mini-documentaries, audio experiments, and community events like the annual ROAM Awards, we strive to energize and encourage our audience and members. ROAM’s mission of providing quality storytelling and education is designed to spark something within, creating a simplicity of motion that draws people toward living in the now. Their ultimate goal? To encourage and support everyone in our community to ROAM toward a life of Adventure + Purpose.

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