Riding Through the Storms: Lessons Learned from Taking Risks on a Cycling Adventure

Discover the Power of Pushing Boundaries and Embracing Challenges on the Road to Self-Discovery

Eleven years ago, on a random day at the office, I decided to sign up for a week-long cycling trip in Napa Valley, California. But I literally had no business doing this for several reasons:

1. I wasn’t a cyclist, outside of the occasional spin class.

2. The only bike I owned at the time was an old hybrid Trek.

3. The daily mileage for the trip was about 50-60 miles—a manageable distance for a cyclist, but please reference #1.

4. This trip involved sleeping in a tent for seven nights, and I’m more of a “sleep in a real bed” kind of girl.

I’m really going to blame one of the physicians I worked with at the time for this entire trip. He and his wife were avid cyclists and often talked about their amazing adventures and trips all over the world. I guessed he was at least fifteen years older than me, so surely I would be fine, right?

Outside of booking this biking trip with little experience, I didn’t go into this completely unprepared. I had some training time, which was mostly done in the gym or on a smooth, paved path because I’m not a complete lunatic—who wants to ride in traffic on an actual road? Did I mention that while the trip was indeed in Napa Valley, we actually started this bike adventure in San Francisco, where we had to ride on real roads with moving traffic?

Regardless of my utter lack of experience and haphazard training methods, the trip was on. I didn’t have an actual road bike to ship from Maryland, so I figured I would just rent one for the trip in California. My saving grace was the fact that, while I was going on this trip alone, I wasn’t completely alone. Everything was arranged by Adventure Cycling: the route, the campsites, and fortunately, a van to carry my gear because I don’t think I would have survived biking with my tent, sleeping bag, and clothes for the week.

This was my first solo adventure, outside of the random strangers that would ride along the route with me. As a very low-risk taker and a more reserved person, it was a big deal to go so far out of my comfort zone. I was on a very tight budget for this adventure and needed a place to stay for one night after I landed in San Francisco before meeting the group. I read about hostels and figured, why not? Inexpensive and pretty close to where I needed to be in the morning to get my bike—how bad could it be?

It was dark when I arrived in front of the hostel, and I started to doubt this entire decision, especially when I saw the shared bunk room where I was going to sleep with seven other random women. I don’t think I slept the entire night, and I also never realized that some women could snore so loudly. The absurdity of this entire decision hit me, and I literally had to choke back laughter as I listened to all these random people breathing and snoring. At that moment, I wanted to go home and get some rest in a room where I wasn’t afraid someone was going to steal the only clothes I had to wear all week. I also questioned God about everything happening in my life as I stared at the ceiling most of the night.

As soon as the sun started to rise, I was up, showered, and ready to leave the hostel to explore the city a bit before picking up my bike for my first day of riding. I was so nervous that I couldn’t even eat breakfast. Why did I think this was a great way to spend a week off?

But as soon as I walked outside and saw the Golden Gate Bridge, my nerves turned into excitement. The weather was gorgeous, and while I was slightly worried that my lack of real hill training would be an issue (in San Francisco… not intimidating at all… haha), I knew I could somehow figure it out.

“Figuring it out” became my motto for the entire trip. I had to figure it out when:

1. I picked up my rental bike and realized I wasn’t super comfortable with the bike or how to use the gears. Not a great situation considering San Fran is just slightly hilly.

2. I wasn’t sure how to handle riding in traffic—sometimes heavy traffic.

3. I couldn’t pitch my tent because I really prefer sleeping on a real mattress in a hotel or cabin.

4. I woke up to a semi-soaked sleeping bag and clothes/gear because it rained all night. Dry didn’t matter because we had to ride the 50 miles along the Pacific Coastal Highway that day despite the weather. Who really likes wearing dry clothes and underwear anyway?

5. Oh, and I did get that flat tire I was hoping to avoid on the trip.

The thing is, despite the one rainy day and all the figuring it out in between, there was a lot of beauty. There were the miles and miles of vineyards; small towns with the best-stocked high-end gas stations I’ve ever seen; an amazing lunch at the Culinary Institute of America; the wondrous redwoods; and with each mile I pedaled, my confidence grew that I would somehow manage to make it to the end of each day’s ride.

It was an experience that taught me a lot about myself and others:

1. You are never alone. You might feel alone, but there are so many good people that will show up for you. Whether it was helping me set up my rental tent, giving me biking tips, or simply sharing a meal, my fellow bike companions got me through over 200 miles of riding.

2. You are more capable than you realize if you just put yourself out there. You can do hard things. There are a million things that you are more capable of than you realize. The first step is putting yourself out there and being vulnerable to try.

3. It’s okay to be the absolute worst at something. At the end of the trip, the coordinators gave out some acknowledgment awards. I think I got “Most Improved,” which, considering all things, is pretty awesome.

4. Taking risks can grow your abilities. I’m not exactly a known risk-taker, but I do recognize that sometimes a calculated risk can really challenge and help us grow. If nothing else, it’s a lesson.

5. There is no easy path. There were a few days, like the one it rained, when I really wished there was an easier option to get to my destination. Yet, as with most things—including improving your health—there usually isn’t a super easy path; it requires effort, and sometimes that’s not fun.

6. Ride on, even in the rain. Life can be hard—really heartbreakingly challenging at times—but keep riding and have faith that at some point the rain will slow, and things will change.

I recently purchased a used Specialized Dolce cycling bike to get back on the road after a ten-year break since that trip. Jumping back on my own bike just happens to coincide with my 7-year-old daughter really loving bike riding. Watching her speed down the street with pure joy on her face, and having my dad “time her ride” (she is just a smidge competitive… ha) makes me smile. I can’t help but wonder if someday we might have a biking trip adventure in our future. Life’s ride can be unpredictable, but what we can all do to improve our overall wellness is keep going the distance. You’ve got this. Ride on.