Professional Development

8 things cycling trips have taught me about being a solopreneur

In 2016, I flew across the Atlantic, joined a group of strangers, and rode a bike from Paris to London along the Avenue Verte. I was not an experienced cyclist, I didn’t have a traveling companion, I was the only American in a group of 20 Italians, Germans and Australians, and it was wonderful. I wrote about my trip in an article called “10 things cycling from Paris to London taught me about work,” originally published on LinkedIn in 2016.

Since then, I have been on two more cycling trips: from Amsterdam to Bruges in 2017, and from Passau to Budapest in 2019. I’m always on a budget, and I have squeeze them in between working and taking care of my three kids, but I make these trips happen because I love them so much.

During this time, I also made a big career change, leaving my 10-year position as Director of Marketing & Communications for Charlotte Mecklenburg Library to start a consulting firm in 2018. So, upon returning from my Passau to Budapest trip, I decided to write a new article – this time from the perspective of a solopreneur.

Here are eight things cycling around Europe taught me about being a solopreneur.

  1. Place value in relationships

On my first trip, from Paris to London, I became friends with my cycling companions despite our differences in nationality and language. Several of us were traveling alone, including Anita, a newly retired schoolteacher from Cologne, Germany.

The Paris to London gang

For my 2017 trip, I reached out to the group to see if anyone wanted to join me – and Anita said yes. We discovered that despite our 20+ year age difference and different nationalities, we made good roommates and travel companions. So, for my 2019 trip, Anita agreed to join me again.

When I left my job to become a solopreneur, the thing that bolstered me the most during the transition was relationships. Having worked in the same community and industry for going on 20 years, I had developed a lot of friendships and professional relationships. For the first few weeks after I left my “day job,” I filled up my calendar with coffees and lunches. I said “yes” to invitations and reconnected with people I hadn’t seen in years. I discovered that relationships matter – not only because they can help you professionally, but because human connection is a necessary part of finding meaning in your work.

For example, one of the first leads I received after starting my business was from a woman I had interviewed for a job at the Library but did not hire. Even though she didn’t get the job, I was impressed by her talent and potential, so I met her for coffee and stayed in touch. After I left the Library, I was surprised and touched when she sent me an RFP for communications consulting for her organization.

  1. Be your own guide

When I first began planning my 2019 trip, I thought I knew what I was getting into. It was my third cycling trip and my second by boat and bike. But whereas my previous cycling routes had been guided, led by an experienced cyclist who knew the terrain; these would be self-guided. Second, the boat was much larger, making it harder to get to know my cycling companions.


The boat, my rental bike, and a page from our route book

Becoming a solopreneur was like transitioning from a “guided” to a “self-guided” career path. I went from an organization where I knew everyone to a larger, more open field. To help compensate for this, I sought out coaches and mentors who gave me practical tips and confidence to try new things. I also found books, podcasts and articles to guide me in my journey. These inputs helped both when I had unexpected downtime to fill, and when I got busy and overwhelmed. Just like I needed a variety of tools to get to my destinations on the bike trip, I needed a combination of resources to find my path and grow my business.

  1. Be a problem solver

The other big difference between my 2019 trip and previous bike trips was the fact that Passau, the starting point, was nowhere near a major airport. I first considered flying into Munich, but it was expensive, so I flew into Prague. Then I had to get from Prague to Passau. I considered taking a car, but decided the train would be more economical, environmentally friendly and scenic.

Walking to train station in Prague

I thought I had planned everything perfectly. I booked my train ticket in advance. I flew in the day before to allow time for sightseeing in Prague, then went to bed early so I could get up and catch the 7:30am train scheduled to arrive at Passau at 1:30pm. After that, I had until 4:30pm to reach my boat, which was only 15 minutes from the train station.

At first, everything went according to plan. After some minor difficulty finding the right platform in the Prague station, I made it to my train and found a seat. I thought I could relax for a few hours before I had to change trains in Linz, Austria. However, an hour after we left Prague, a train attendant came into our car. “My English is not so good,” he said, “but there is a delay. There has been an accident. Police and emergency.” My first thought was that I hoped everyone involved was okay.

He then explained that I would have to get off at a station called České Budějovice to change my ticket for a later connection. I was worried, because I don’t speak Czech (I had been practicing German for this trip), and my time was limited. He told me to get off the train and look for the “City Center.” After much confusion, I discovered he meant the station’s “Information Center,” where I was finally able to change my ticket. But now the next train was delayed. By the time I got to Linz at around 3pm, after bouncing back and forth from counter to counter with tears welling behind my eyes, I realized that no train would get me to Passau by 4:30. My only choice at this point was to go by car. So, I quickly did some troubleshooting in my mind and decided to take an Uber for the one-hour drive from Linz to Passau. I made it to the boat in the nick of time.

I faced similar unexpected challenges when I became a solopreneur. Because of the unpredictable nature of running your own business, I felt like I could never sit back and “ride the train.” I needed to continually troubleshoot, try new things and adjust to changing circumstances like getting a new client, having my workload unexpectedly double, or writing a proposal on a short deadline. To deal with these unexpected changes, I had to think on my feet, stay positive and make the best of every situation even when I was feeling overwhelmed.

  1. Know your limits
Enjoying the scenery on my “day of rest”

Once I got on the boat, we got into a routine of traveling down the Danube and spending our days cycling and visiting different cities. About halfway through the week, after spending a full day exploring Budapest, I realized that I was mentally and physically exhausted. I felt overwhelmed during the morning briefing about the day’s cycling route.

I said to Anita, “I don’t feel up to leading us today; do you mind if we join some others and follow them instead?” She was fine with the idea, so we approached some people from our boat who welcomed us into their group. Not only did we benefit from their knowledge of the route, we had an enjoyable time getting to know them. I felt immense relief at not having to navigate that day, and it allowed me to mentally recharge so that I could lead us again the next day.

As a solopreneur, I have had similar experiences. It can be exhausting to be “the boss” all the time. So for some of my projects, I have had the opportunity to join a larger team where I can provide leadership without being solely in charge. This has been a wonderful experience because it gives me a break and provides the enjoyment and collaboration of working with a team.

  1. Prioritize your time

Each day was about 30 miles of cycling, and with the help of maps, GPS and daily briefings, we were able to guide ourselves. As the week progressed, we fell into a pattern. I would get up early for coffee and breakfast, letting Anita sleep in. Then I’d shower and get dressed while she ate. Then I’d sit around while she got ready. As a result, we were usually one of the last pairs to leave for the day’s cycling route.

Not surprisingly, we were often one of the last pairs to get back to the boat, and we had limited time for sightseeing along the way. Finally, on the night before our last cycling day, I suggested to Anita that we needed to get up and going earlier. She wasn’t thrilled – she’s retired and doesn’t like to get up early, but she saw the value in giving ourselves more time.

The next day we got up early and were part of the earlier crew of cyclists. It was a good thing we did, because this ended up being one of our most challenging days of cycling. The last few hours required a lot of uphill riding directly into a head wind, with temperatures in the mid-90s. But at least we had time to enjoy sights along the way.


Vineyards and villages along our route

This directly relates to a lesson I learned as a solopreneur. After I left my traditional office environment for a home office, I knew that I would need to be disciplined with my time. I continued to set an alarm in the morning and track my time spent working. To encourage healthy habits, I also gave myself time for “self-care” during the day such as exercise or meditation. All of this helped to keep me focused and productive after I left the structure of an office environment.

  1. Stay true your goals

The main reason I started going on bicycle trips was for the sheer enjoyment of seeing a new place from the back of a bicycle. However, as I visited all these new countries on my third trip, I found myself feeling disappointed that I didn’t have more time to stay in one place and explore.

At the “finish line” of my first bike trip

I had to remind myself of my goal, which was to have the bicycling experience. Sure, exploring cities by foot is great, and I make time to do that on every trip. But my favorite moments are when I am exploring new places and taking in breathtaking scenery on a bicycle. Not to mention the sense of accomplishment at the end of a long route. The sense of freedom and joy is like nothing else. So, when I started to feel frustrated, I simply reminded myself why I was there and I felt better. I also took more pleasure in the experience of cycling.

The same held true when I launched my business. I didn’t have a full slate of clients lined up, and that left me feeling uncertain. But then I remembered my goal – to use my experience and expertise to help organizations – and that helped me put my energy in the right places. With my goal in mind, I began to put my message out to potential clients, and that led to more work that aligned with my goal. That in turn allowed me to take more enjoyment from my work.

  1. Don’t be afraid to ask questions

After the bike trip ended and I was on the train back to Prague, I ran across another challenging situation. I had boarded a train in Regensburg, Germany and had just gotten comfortable in my compartment when there came a barely audible announcement in German and English. What I thought I heard was that only the back of the train was going to Prague; the front of the train was going somewhere called Hoff, Germany. This didn’t make any sense, but I had to swallow my pride and ask my German-speaking seatmates if what I thought I heard was true. They said yes (probably thinking, “This dumb American doesn’t know what half of the train she’s on!”), so I took a deep breath, grabbed my bags and started walk-running back through the cars as quickly as I could.

At this point the train was moving, so I was jostled back and forth as I went. Each car was different – some were double-decker, so I had to drag my bags up narrow stairs; others had tight aisles I could barely squeeze through. I was sweaty and panicked, and there was no clear indication of which part of the train was the front or back, so I just kept going. Finally, I got to a car with some other people who had the same panicked look as me and asked if this was the Prague half of the train. They said yes, and I heaved a sigh of relief and fell into a seat.

Swallowing my pride and asking questions was a big part of becoming a solopreneur. I talked to my self-employed siblings. I talked to friends who had done consulting in the past. I asked my job search coach to transition to being a business coach, and he agreed. Even some of my clients, those who had built their own businesses, gave me advice. As I built up my business from nothing, I needed to ask questions, even when I didn’t want to admit that I didn’t know something, so that I didn’t end up on a “train” headed in the wrong direction.

  1. Allow space for serendipity

As I mentioned earlier, despite all my planning, I had to adjust to unexpected changes in plans. Some of these ended up being very positive. For example, I had an extra day in Prague at the end of my trip due to a misunderstanding with the boat and bike company.

The Charles Bridge at sunset

At this point I was tired and a bit homesick, so at first, I tried to move my flight up a day. When that proved too expensive, I decided to make the best of it and enjoy this additional time in Prague. I pulled out my guidebooks and found lots of things to do that day. I checked out the library, wandered through Old Town, ate ice cream, went to museums, booked a walking tour and enjoyed the Charles Bridge at sunset. Finding the serendipity in this circumstance helped to restore my energy and sense of adventure. It also gave me many wonderful experiences and memories that I would have missed if I’d moved my flight.

Serendipity has also been a big part of my working life as a solopreneur. The flexibility of my schedule, and my ability to work from anywhere, has allowed me to be spontaneous and spend more time doing things and seeing people I love. Last fall, I was able to spend Thanksgiving with my sister in Connecticut, catching up with extended family while keeping up with work deadlines from her guest room. This spring, when I was in Texas working for a client, I found a beautiful bike trail in Fort Worth and had a great experience riding along the riverfront. Not every unexpected occurrence is going to be positive. But being open to the potential for positive opportunities is they key to making room for serendipity.

As I look back on my first ten months as a solopreneur, I feel a great sense of accomplishment. And yet, I know I have just scraped the surface of what it means to run a business. I look forward to continuing to grow and learn as a business owner, just as I look forward to many more cycling trips in the future. If these experiences have taught me anything, it’s that life is unpredictable, messy and most of all wonderful if you have relationships, can guide yourself, solve problems, ask questions, prioritize, know your limits, stay true to your goals and allow for serendipity.

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