In between her junior and senior year, high school student Anna Olesen spent a week of her summer vacation to share her mountain bike skills and experience with 9-12-year-old girls at the new Little Bellas WinMan Trails Half Day Camp. What was so cool about Anna’s involvement was her ability to relate to the girls. At 17 years old, the age gap between Anna and the Little Bellas wasn’t huge, but a lot can happen during adolescence, like deciding you want to race mountain bikes and then going for it.
A beginner pro (an oxymoron?)
During those early years, all Anna wanted to do was go fast, which — you’ll agree — is essential for a budding pro racer. The flowy, well-cared for trails at WinMan gave her what she wanted, and 12-year-old Anna seemed content to blaze around the WinMan trail system. But professional mountain biking has grown up, and modern cross-country courses are thrilling (and maybe a little scary) for their technical features. Anna would have to evolve as well if she wanted to toe the line with professional racers.
“I think it's really important to push yourself,” Anna said. “Me and my brother have started to go to some more downhill parks where I go out on the trails and study them to find the different lines so that I can get comfortable on really technical trails.”
Crashing as a skill
Racing at top speed over technical features isn’t without risk — after all, one small mistake can make the difference between first and second place. It can also lead to crashing, which is a skill all on its own, since one can hardly ride mountain bikes without experiencing at least one crash. During her week with the Little Bellas, Anna expertly managed a crash by a Little Bellas who was new to mountain biking.
“I think it was one of the girls where it was her first time riding and she crashed,” Anna explained. “You could tell she was totally freaked out and didn't know what to do. I was able to calm her down a bit, which worked really well. By the end of the week, she crashed again and was a lot calmer about it, and was able to manage it on her own, which I think was really cool.”
Crash evaluation is a vital skill to have as a mountain biker because we learn from our mistakes. But what’s more valuable is the wisdom and experience of others.
Dirt Camp Racing
2025 marks Anna’s first year with Dirt Camp Racing, a national team with programs for all racing levels, from junior to pro. Most development teams go up to ages 17 or 18, or U23, at which point racers are set adrift to navigate their careers on their own. As one of 90 team members, Anna can take advantage of the vast experience of her teammates. This is crucial because being a bike racer isn’t only about racing (or winning). In the age of social media, sponsorship gets evaluated in a variety of ways, like what kind of value a racer brings to the sponsor. It’s not just about the number of “likes” a post gets or how many followers a racer can collect, authenticity and leading by example also matter.
Social media: is it so bad?
For all the criticism leveled at social media, sometimes it can be a tool for good.
“When I got Instagram and social media for the first time, of course I started following pro racers because I thought they were so cool,” Anna said. “And so, I started following them on social media and I was seeing so much about Little Bellas. This summer — or I guess this spring — I was looking at the calendar of events at WinMan. I'm pretty involved there, and I help with a lot of different activities, like kids’ clinics and stuff. I saw Little Bellas and I was like, wait, that's what Lea and all the pros post about. So, I reached out ‘cause I thought it'd be really fun to get involved.”
Anna went all in for the Little Bellas. She spent the week working on riding different features with the Little Bellas, demonstrating the correct body position for clearing certain obstacles, and showing the skills they were learning in action. She also learned some things herself, like how to give someone time to work through a hard section of trail. Empathy is a skill — it also helps when you’ve experienced the same challenges as someone who’s struggling.
For the Little Bellas who got to ride with Anna, greatness was in the making…for them and perhaps for her. Mentoring on mountain bikes is a chance for Little Bellas’ mentors to kindle the spark that mountain biking ignites. The opposite of “you can’t be what you can’t see” was Anna Olesen for a week this past July. She came, she rode, and she showed the Little Bellas what they could be.
