Women Involved Series: Olivia Round

Olivia Round is on a daily mission to make friends with fear. She uses her talents as a writer and artist to cultivate empowerment and compassion, and one of her greatest joys is exploring this world by bicycle.

In 2011, at the age of 21, she rode her bike alone across the United States. She’s currently writing a memoir about that epic, transformative trip.

Tell us about the introduction to your #bikelife and why it was a monumental decision for you-
My first hero on two wheels was my mama. She was one of the very few people in my hometown of Ketchikan, Alaska who cycled on the soggy, narrow roads while I was growing up.

There was no bike shop, and no “bike scene” to speak of, so my mama was regarded as a very brave eccentric. I wanted to be just like her when I grew up: I wanted people to think I was a brave eccentric, too.

What inspired you to take to riding across the United States as a way of healing?
For reasons that remain unclear, I developed a fear of sexual violence at a very early age. I was never physically harmed or molested in any way, but somehow I learned that rape existed and that the perpetrators were usually male, and that lead to me developing a phobia of men. I was constantly worried about rape, and because I was obsessed with it I started to see it everywhere: on the news, in people’s stories, in books, movies, etc. Sadly, that fear of being sexually assaulted as a young girl was totally legitimate. I remember learning in high school health class that one in four young women are assaulted before the age of 18. That’s 25% of all females in America!

So, my fears kept being corroborated. They got worse and worse. By the time I left home and attended college, my phobia of men was debilitating: it’s hard to function when you’re terrified of half the human race. I knew I had to do something drastic, something to shake myself out of this scary mental rut and prove to myself that the world wasn’t as bad as I thought it was.

I decided that riding my bicycle alone across the United States would be the perfect medicine. And boy, it was! I don’t think I realized it at the time, but looking back I see that I needed to reprogram my brain. I needed to spend time on my own, away from my friends and family, to sort myself out mentally. And, to be at the mercy of the world. I’m so glad I did it. That trip wasn’t easy, but it was essential.

Preparing for a bicycle tour can be challenging, especially for those new to the concept. How did you prepare?
I didn’t do much physical training, that’s for sure! I had a full-time job and didn’t have much time to ride, so I didn’t worry about it. I just focused on route research and getting the right gear. Rather than training beforehand, I allowed myself to train on the road: for the first week, I didn’t ride more than 30 miles per day. By the second week, I would ride up to 50 miles per day. I had the whole semester off from school to do the trip, so I wasn’t in a hurry once I got started.

What would you say were the most challenging aspects of your trip?
Dealing with my fear was definitely the hardest part. I’d get triggered by stupid little things: someone yelling at me out of a car window, or getting cat-called while passing a construction site, etc. Once the situation was over, my fear would stay with me, hovering behind me like a ghost. I was always looking over my shoulder and trying to get myself to calm down.

Sleeping alone in a tent was the hardest. Don’t get me wrong, I love camping. Anytime I was in a designated campsite I was okay, but if I tried to stealth camp (just pitch a tent in a secret place at the side of the road) I was up all night in a nervous frenzy. Which didn't make for a good ride the next day. You need sleep in order to cycle!

Did you have any unexpected surprises that resulted in positive outcomes during your tour?
Hell yeah! Every damn day. I learned this country is populated by 99% kind, generous, good people. There were so many times that I needed rescuing, in some way or another, whether I’d lost the route or lacked a place to stay or needed to hitch a ride due to dangerous road conditions. It was mesmerizing how often someone would turn up at just the right moment and offer just the right assistance. I called them “angels,” and I refer to that experience as “road magic.”
What was the best part of your solo bike ride? A town you visited, a life lesson learned, people you met?
I loved having a clear mission in life. Every day I woke up and knew what I had to do. I can’t tell you how liberating it is to throw all your energy into something and see yourself making progress. It’s addicting. When the trip ended, after 5 months of travel, I felt lost. After riding my bike all day every day, I didn’t know what to do with all my free time.

I learned how important it is for me to have a clear goal, and to always have a big, exciting project to work on. I was born with a lot of focus and energy, and if I don’t channel them properly then these gifts can work against me. I start doubting myself, worrying, letting anxieties get the best of me, and spiraling downwards into depression. With a purpose in life, I wake up every day so thrilled to be alive!

Also, I learned the importance of meditation. When I felt scared on the road, I had to clear my mind and focus on the present moment, rather than “what could happen next.” Daydreaming about worst-case-scenarios is unhelpful. You’ll find yourself panicking about hypothetical things, instead of enjoying what’s really happening.

When you started out riding, what were some handling skills that challenged you? Do you have any suggestions for what helped you grasp them?
Oh my goodness, YES! For the life of me, I could not figure out how to stand up in the pedals in order climb steep hills. I remember cranking my way up my first mountain pass in Oregon, panting and straining but keeping my butt firmly in the saddle. Another touring cyclist, an older man, zoomed downhill past me, fully loaded, and shouted, “Stand up! Rock it out!” He was gone in a flash but I knew what he meant. I felt so disheartened that I didn’t know how to stand up in the pedals, and that maybe it meant I wasn’t a real cyclist. It took me over two months and a dozen more mountain passes to get the hang of it: only in Missouri’s Ozarks did I finally succeed. And thank heavens, because those Ozarks are wicked steep!

The trick was revealed in what that fellow tourer had shouted at me: Rock it out. You have to stand up, lean forward, and allow your bike to rock side to side as your upper body sways in the opposite direction. It’s terrifying, but you soon realize that gravity is on your side and you’re not going to fall over.

What advice or suggestions do you have for someone looking to complete a long-distance tour on their own?
Get out a sheet of paper, and make two lists. First off, list all the reasons why you want to go. Secondly, list what will happen, and how you’ll feel in 10 years if you don’t go. This will either make you realize you don’t really care that much, or it will be the tough-love moment you need to make it happen.

Adventure Cycling Association, with their routes, maps, gear recommendations, and even guided bike tours, is a great place to start.

What do you love about riding your bike?

My bike is my medicine. “It’s cheaper than therapy,” my boss used to say at a bike shop where I worked last year. Within two minutes of getting on my bicycle, I’m overwhelmed by joy. This little-kid sparkly feeling comes over me, and I start making dumb noises: whooping, cheering, singing. I can’t help it. My bike makes me so happy. It feels like flying, like freedom.

What inspired you to write about your journey? Particularly what motivated you to write a book?
While I hope this book helps others, I’m actually writing this story for myself. It's like a love letter to the little girl I once was. My childhood might've been different if I'd found a book like this when I was in middle school. (That’s not to say this book is appropriate for kids, because it’s not, but at a young age I was already reading books above my reading level, with content that really scared me.)

And, I confess, a huge part of my motivation to write this book is to be understood. I spent most of my life feeling misunderstood and different, even wrong, because of how unusual my behavior was (refusing to date, turning down every slow dance, declining to hug men, etc). When I told people I was afraid of men, they’d say, “Why? What happened to you?” and I felt like I had to have a definitive answer, because otherwise I wasn’t allowed to be afraid. I want to write this book because it gives the little girl inside of me permission to be afraid. I want to tell her, “Hey, I heard you’re scared. That’s totally legitimate because this world can be a scary place. But you know what? Fear only rules our lives if we let it. So… let’s go play.

Why is it important to you to be candid, honest, and open when talking about your experience and fears?
I’m pretty open. I’ve been known to happily divulge my hang-ups, bowel movements, dietary restrictions, sexuality, and deepest fears to complete strangers. Not everyone is comfortable being that uncensored, and I respect that. But the fact that I can do it, that I want to share, means I should. Because if enough people share their stories and are honest about their experiences, it helps others heal. Honesty is inclusive, comforting, and helps other people feel like they can be their authentic selves, too. And, you know, the truth is often hilarious. I love making people laugh.

How do you feel that we, as women, can create a change in how we converse about our fears, worries, and the concept of self-sabotage either in conversation or writing?
The #MeToo Movement is revealing how much we aren’t telling each other. I’ve heard multiple stories of women being assaulted or harassed and keeping it to themselves for years while their perpetrator went on to hurt other people. A lot of other people, in some sad cases. If those early victims had come forward and said something, they could have spared others the same fate.

We need to remember that we’re all in this together. We need to be gentle with the accusers, as well as the accused. The more we can respond with compassion to both sides, the more comfortable people will feel coming forward with their stories. This isn’t “Men vs. Women,” as I thought it was when I was a kid. And harassment is not a “women’s issue.” Men get hurt, too. And no man wants his mother, sister, daughter, friend, or lover to be hurt. So, what happens to one of us affects all of us.

As far as self-sabotage goes, that’s a tricky one. People are complicated. I’m being challenged during this memoir-writing process to dig deep and write the whole truth, and it’s bringing up all these surprising revelations. For example, I spent years telling my friends that I wanted to heal from my phobia, but looking back I realize that I wasn’t ready. I’d identified with my fear for so long, I couldn’t let it go. I was afraid of who I’d be without it. It takes courage to kill your former self and let the new one have a chance. I wasn’t ready to take that step, and invite that kind of dramatic transformation into my life, until recently.

Tell us about your bike(s), what they are like and why did you choose them?

I’m a one-bike-girl, as I like to say. In 2011 I bought a gorgeous, well-maintained Miyata from a guy on Craigslist in Portland. I’d test-ridden other bikes, but when I hopped on her I knew she was the one. She felt like part of my body. I named her Miya, rode her across the country, and the rest, as they say, is history.

What do you feel deters women from getting involved with cycling?

Studies have shown that women are biologically more risk-averse than men, and cycling is currently a risky activity in the US. Providing bike lanes and bike paths greatly increases female ridership, because having a designated place to ride makes cycling safer.

What do you feel could change industry-wise or locally to encourage more women to be involved?

Bike shops are the gate-keepers. For an aspiring cyclist, a bike shop can be the most intimidating place. It holds all the answers, but they’re worried about being judged. If a shop employee is kind, supportive, and enthusiastic about new riders, they can win customers for life. Especially female customers. There’s no need to intimidate or overwhelm newbies with industry jargon and athletic pressure: just help ‘em find a bike that feels comfortable and allows them to do what they want to do, and then cheer them on. Hiring more women to work in the cycling industry is a good thing, too.

What inspires you to encourage women to ride?

I fell in love with cycling, so that’s the platform I use when I reach out to women. But, really, I don’t care if anyone else rides a bike, ever. I just want to live in a world where more people overcome their fears, have epic adventures, and surprise themselves. In case anyone is looking for permission to be a badass, I want to offer it to them.

Tell us a random fact about yourself!

I have some secret rituals to ward off bad luck (and bike thieves). One of them is to whisper “don’t go home with strangers” to my bicycle whenever I leave her unattended. Another is to kiss her handlebars after a ride.


  1. I have done nine trips by bike with my husband. I loved everyone even if it was difficult at times. I wish I started as young as you are. I am now 83 and still on the bike.. I enjoy your blog. You are a woman that I admire.


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