Today we’d like to introduce you to Claire Pomykala
Hi Claire, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
In 2021 I graduated college with a degree in public health and had no idea what I wanted to do with my life. I felt burnt out, jaded by the public health system, career prospects, and like I needed to break out of some mental cage I was in. I had recently gotten into biking and had heard of people who would go on these things called “bike tours” where they’d cycle for months on end and explore somewhere new. My senior spring semester of college, I was only enrolled in 9 credits (I believe) and was working three part time jobs- I did this so I could save up a healthy chunk of money to go on my first bike tour, which was 1.5 months of cycling from my college apartment in Atlanta, to my parent’s home in Baltimore (tour #1). During this senior year, I also became part of the campus bike co-op and learned a wealth of information about cycling which provided me with enough knowledge to start planning my first tour. After that first tour, I had some cash leftover (plus some graduation money) and I used that to buy a new (used) bike and some better gear to embark on a 4 1/2 month bike tour in Europe (tour #2). I posted photos and videos during tour #1 to keep my friends updated about my journey, and as tour #2 went on, I thought to myself “maybe I should see about becoming an influencer”. With no social media background, I began posting photos and videos and experimenting with content creation, constantly waffling with the idea of whether or not I wanted the attention.
When I came back from my Europe bike tour (January of 2022), I started working for a remote Silicon Valley tech startup as a product/community manager. It was a wildly random job to end up in my lap, but it was the only thing I could find, and I was out of money from traveling. I worked that job for 1.25 years, planting my roots here in Baltimore, tring to make sense of the end of an epic journey, the beginning of a new job, and the shaky platform my life was placed on.
The Ulman Foundation reached out to me in 2023 to advertise for a cross USA bike tour that would raise money for young adults fighting cancer, and I saw that as my ticket out of my tech job. Working in tech paid me a large sums of money, but I was isolated, hated my work, didn’t respect the founders of the company, and felt like I wasn’t contributing an ounce to society or to my personal development. It was a mental health nightmare, and I was looking for a reason to quit. So when the Ulman Foundation reached out to me to advertise for their trip and sign up for it, I did, and spent the entire summer of 2023 biking from Baltimore to San Francisco with 11 strangers on my first group and van supported bike tour. I forgot to mention that a stray cat remarkably fell into my life in the fall of 2022, so I found a subletter to rent my apartment in Baltimore for a reduced rate to take care of my cat- this is quite important because I love my cat, and all of my travels require that I find someone to take care of him!
I came back home from that trip, was “funemployed”, and keen on attempting to build my own business. I reached out to various bike companies, dabbled with YouTube, made a website, and planned my next tour to New Zealand for just a few months later. I was eating up my savings, excited and nervous to take such a risk on building a business while not knowing an ounce about what I wanted to do or how to do it.
I bicycle toured New Zealand, explored Australia, then came home in March of 2024 (my next subletter was leaving and I had to come back to take care of my cat) and immediately began searching for a job. I had been somewhat directionlessly trying to build my own brand, not having a soul to talk to and eek out any advice. It seemed safer to find some part-time work (I became a bicycle tour guide in Washington DC) and spend the corners of my free time continuing to build my business, which I still hardly knew if I wanted to do. At times I wished to find and apply to what would be a “dream job”, but then I remembered that it’s not guaranteed that you’ll get the job you apply to, and it’s not guaranteed you’ll like it once you start.
During this transitional phase, some followers from my Instagram asked if I ever considered leading tours. I pondered it, but was very hesitant, because after cycling across the USA for 2.5 months with strangers, I knew how bad (and good) those dynamics could be. I took the multiple messages from strangers as a sign that I should give this thing a go. So I created some $45 tickets to lead a trip completing the length of the C&O Canal over 3 days, making my guinea pig customers aware that this was a very experimental trip. A dozen things went wrong over those three days, but despite all of it, I came home feeling hopeful and excited about leading more. I realized that maybe this is what I wanted to do, what I was supposed to do with Living By Bike.. I led two more trips that fall, and now that it is 2025, I am hoping to lead half a dozen trips, and maybe even a bike tour.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
None of this has been a smooth road in the sense that I didn’t even know I was going to be starting a business to begin with! A bunch of my followers were asking me to lead trips and I decided to give it a go in May or April of last year. Even that first trip wasn’t smooth in a very literal sense. We biked the length of the C&O Canal (180+ miles), which is a gravel trail, and it rained every day on that 3 day trip. I forgot my rain jacket (which was really embarrassing as the guide) and I was losing participants like flies. I was late to the start of my own trip, and when I got there, I realized one of my guests was a no-show. Another guest got a stomach bug on day one and left the very next morning. Another guest was having mechanical issues and was so fed up with the weather that she decided to leave at the end of the day on day two. On day three, one guest was having knee issues and had their parent pick them up about three quarters of the way through the day. Essentially, I was expecting to start off and end with five guests, but I only ended with one at the conclusion of the trail. It was embarrassing, but I was also happy to have gotten almost everything that could’ve gone wrong out of the way. After leading that first trip, I set up many more procedures and standards to make sure that all the rest of my trip would go smoothly.
Now, in terms of the planning aspect in the marketing aspect I’ve had some good forward momentum, but having to figure out almost everything on your own is always going to be quite difficult. I’ve made so many mistakes and struggled with building a website, understanding YouTube, navigating brand partnerships, and all of the innumerable startup lessons & costs associated with building a business. I can remember during the holiday season this past year I was trying to make a cyclist gift guide, and because my website kept breaking, the dozens of hours of work I put into it amounted to nothing, since the blog post didn’t come out until just a couple days before Christmas, and when it was out, I had no energy to promote it- I was exhausted and deflated. At the end of the day, being both the mentor, the student, as well as the website designer, director, producer, marketer, trip planner, coordinator, trip guide etc. is incredibly overwhelming. The mountain of mistakes you make does gradually turn into a wealth of skills and knowledge. But you can only hope, with forward momentum and an unnerving optimistic attitude, that it will turn a dream into a sustaining business.
I would say the biggest struggles along the way have been: not having anyone to talk to for advice on starting a business; deep personal life challenges (personal relationships, tragic events physical and mental health, the political state of the world healthcare etc.); financial constraints; and a lack of clear direction. I frequently describe my personal life as a “dumpster fire” which trailed me for the last ten years. My personal issues have definitely postponed the development of my brand and my business, but hey, if I didn’t work so hard to have them resolved and at bay, I wouldn’t be anywhere near where I am today!
Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I would say that in the context of Living By Bike, I am most known for going on long, multi-month bicycle tours and living (and advocating for being) car-free. I’m known for being adventurous, tough, outspoken, and politically conscious/vocal about many issues going on in this world. I’m always trying to find the right balance between making fun and easy content versus intellectually stimulating political content. I specialize in remembering the people I want to associate with, the people who made me who I am and make me my happiest and proudest self. I’m not preoccupied with hotel deals, looking a certain way, or the biggest brands to exist. Everything comes back to community, to banding with the right people who share your similar values. It can be quite complicated at times, but the more I align myself with brands and individuals who share my values, rather than trading them for some kind of “approval”, the happier, more content, and more aligned I become.
As for the business born from Living By Bike, I’m (freshly) known for leading bikepacking trips in the DMV area, and hopefully beyond. They are 3-day trips along the C&O Canal and county area, but I’m hoping to lead more trips in Canada, Atlanta, and maybe even Iceland. These trips are unsupported, meaning my guests pack all of their own gear, while I supply all the trip planning, foster the community space, and educate them ahead of time on how to prepare and what gear to bring.
I most proud of listening to my intuition. For a long time, I always did what I thought I was supposed to do, never doing the things that I actually wanted to do. In 2022 I decided to start listening to my intuition 110% of the time, and to give a giant middle finger to everyone or every thought I would have that would make me feel otherwise. I cut off ties with many people who I felt were bringing me down and ditching hobbies that didn’t feel like they truly aligned with who I was. I started investigating new communities to be a part of, prioritizing my health above everything else, and chipping away at the crippling perfectionism that governed my life (and that’s really hard to do when you lived your entire life putting on a mask to conform to others expectations). So I’m very proud of myself for getting out of that mental trap. Because if I hadn’t gotten out of it, I’d probably be working a job that I hate with only two weeks of vacation a year. I probably wouldn’t have started the small business and I wouldn’t still be trying to start the small business even though I only make a couple thousand dollars a year from it. I’m a little bit delusional and I’m also really stubborn. But that’s kind of what it takes to be successful, and I just hope that in the next five years, I can look back and be even more grateful for taking the risks that I have and leaning into my intuition, rather than playing it “safe” by living a life I would hate to live.
Do you have any advice for those looking to network or find a mentor?
This is something that I’m still struggling with. Most content and travelers live isolated bubbles from one another. We are stratified across the United States and across the world and it’s hard to have conversations and relationships with people in a similar state of life. I have a couple of travel and outdoor influencers that I keep in close contact with, but it’s not many, and those relationships are not particularly deep (but of course still valuable!). There are some other small businesses in Baltimore that I’ve had some loose conversations with, but I haven’t gone too deep into those relationships because maybe I’m a little bit afraid to take up people’s time by requesting free advice- at the end of the day, we are all busy chasing a dream while managing the little amounts of free time that we have. I have worked on connecting with other similar businesses (bikepacking businesses) and like-minded people, and I deeply appreciate every amount of knowledge and advice that I have received. It’s been a journey of hide-and-go-seek to know who to talk to and what to ask them. It’s not like any of my immediate friends are starting small businesses or live a lifestyle (of outdoor and long-term travel) similar to mine, and it can cause me to feel isolated and misunderstood. Of course this isn’t malicious on anyone’s behalf (I simply feel isolated), but I’m more so trying to say that when I say that I’ve been both the mentor and the student of building my career- the classroom consists of me in my apartment- I very much mean it.
Now I have been loosely working with a business coach this past winter and I’m still figuring out if the value that I’m getting from it is worth the price that I’m paying for it. All that I can say is that this business coach is willing to give me their time and advice to help me grow my business, whereas not everyone else can. Finding help from others has been a lot of scavenging for hidden gems- which definitely has its value and place- but can feel unsustainable and unpredictable. Working with a mentor comes at a high price, and I frequently wonder if I had more/better connections to similar entrepreneurs, if I’d need this kind of help. At the end of the day, I am grateful for the help, but frequently fearful of the price tag.
Contact Info:
- Website: https://livingbybike.org
- Instagram: https://www.instagram.com/livingbybike/
- Youtube: https://www.youtube.com/channel/UCTetAFUXiO5_DFiOdsNDzZQ
- Other: https://livingbybike.substack.com/
