Claire Pomykala is a 26-year-old bike tourer and accidental influencer who walked away from a $115,000 tech job because it made her feel physically and mentally unwell—and replaced it with a loose mix of guiding, bikepacking trips, and independent projects. (livingbybike.com/@livingbybike)
Claire traces her path into cycling back to a campus bike co-op that offered an unexpected sense of belonging. Soon after graduating college, she skipped the traditional next steps and biked from Atlanta to Baltimore, then spent nearly six months riding solo across Europe. What began as an escape from jobs and expectations turned into a long-term way of life, including later trips across the U.S. and New Zealand.
She explains what makes bicycle touring distinct from other forms of travel, why it creates a more immersive and uncomfortable experience, and how her social media following grew at the exact moment she stopped traveling. We talk about her brief time in tech, where she jumped from $15/hour jobs to a six-figure salary despite having little background in the field: a position she describes as largely meaningless and difficult to tolerate, but financially useful, as it allowed her to save money, quit, and return to a more flexible lifestyle.
Now, Claire earns money through a combination of leading occasional luxury bike tours for a company, organizing her own smaller (and shockingly affordable) bikepacking trips, and occasional brand partnerships. At the same time, she’s trying to maintain distance from social media, even as it remains her primary source of clients.
We also discuss her essay “I’d rather be kind of poor than work most jobs,” the tradeoffs between stability and autonomy, and her preference for time-rich, flexible living over a consistent paycheck, even as she acknowledges the uncertainty that comes with it.
Full transcript: dirtbagrich.com/claire
Recorded in April 2026.
Transcript
This is an AI-generated transcript. Typos and mistakes exist!
Blake Boles (00:00)
Claire Pomykala, welcome to Dirtbag Rich.
Claire Pomykala (00:03)
Hello, thanks for having me.
Blake Boles (00:06)
When in your life have you felt the grossest and also the most alive?
Claire Pomykala (00:13)
So there was a stretch of days in New Zealand when I met a new traveling partner on the adventure and we were like, yeah, we just need to start wild camping more often. It’s easier when you’re with someone.
I think there was three days in a row of wild camping and it was really long distances. it’s like, you know, 100 kilometers a day, fully loaded, half of its mountain biking trails. First night camping at the tallest dune. It’s a mountain biking park. So we get sand in all of our gear. It’s just like impossible to get rid of the sand. It took me like months afterwards to get rid of it in my sleeping bag. Next day, we’re camping wild
camping at the side of a rest stop on this kind of freeway in New Zealand. And that second night, a car pulls over so a man can basically take a leak and he gets to the trees and he realizes that our tent is like two feet away from him.
And so he just zips up his pants and just like leaves immediately, almost peeing on my friend’s tent, not mine, but my friend’s. And then I think the next day was another 60 miler. And I remember just at that point there was sand, sweat, dirt. it’s just the grime is just, you know, accelerating every single day. ⁓ And it was awesome.
Blake Boles (01:20)
Wow.
Claire Pomykala (01:42)
It was really awesome, but I remember just being so happy to like have a bed and a shower. I don’t even know when that happened. I think I found a warm showers host actually. And it just felt so divine.
Blake Boles (01:51)
Yeah, yeah. Right. I think about that all the time, how being out in these like, kind of these ridiculous situations we put ourselves in, like a big part of the payoff is coming back to civilization and just being like, this is why couches are awesome. This is why warm food is awesome. Showers. Absolutely.
Claire Pomykala (02:08)
Yeah. Mm-hmm.
It’s really the showers for me. It’s like, I don’t mind getting dirty. I actually do love getting dirty, but I also love getting clean.
Blake Boles (02:21)
That’s a good one. How long was that New Zealand trip?
Claire Pomykala (02:25)
think it was about two months, which is not enough time for New Zealand. It’s a pretty long country.
Blake Boles (02:32)
Yeah. And you are 26 today. How old were you on that New Zealand voyage?
Claire Pomykala (02:38)
Hmm, I think I was 24. Yeah, think I was 24. Yeah, I think it was a year and a half ago, something like that.
Blake Boles (02:44)
Okay, not too long ago.
And this was not your first rodeo. This was not your first long bike tour.
Claire Pomykala (02:56)
Yeah, it was my fourth rodeo.
Blake Boles (03:01)
And maybe just for people who don’t know much about bike touring or cycle touring, or they’ve seen some psychotic looking person on the side of a busy road with a bunch of bags strapped to their bike. Can you just break down what you think bicycle touring is or what separates it from other kinds of bicycling?
Claire Pomykala (03:20)
The bicycle touring, think, is a way to more intimately experience another land and culture. Because being a regular tourist, feel like, has a certain degree of separation compared to bicycle touring. Because when you’re bicycle touring, it’s hard to escape the bad parts of where you are. And the bad parts could just literally be like rain. Like New Zealand, way more wind and rain than I thought, you know? ⁓
Blake Boles (03:42)
Hmm.
Claire Pomykala (03:50)
you don’t really have to feel that but when on your bike you feel everything you Meet everyone like I mean I remember at one point in New Zealand I was trying there was like a little farmer stand with you know fresh juice and stuff from some local and I didn’t had like only really large bills and then I see this post man come around I wave him down I’m like, I exchange money with you so I can buy juice right now?
And I gave him like probably a New Zealand 20 and he gave me an equivalent of basically quarters or whatever back. But it’s like bicycle touring puts you in so many more unique and like raw experiences. So the tourism aspect is it’s less curated. ⁓ You really get like a full variety of experiences. And I just think you have such a more profound and intimate understanding of where you are.
Blake Boles (04:32)
Hmm.
Claire Pomykala (04:47)
because it’s hard to escape all of the good and the bad. It’s kind of just all thrown at you from the land, the weather, the animals, people, just everything.
Blake Boles (04:57)
Hmm. I really appreciate that definition of, of bicycle touring as like travel intimacy. what separates it from the word bike packing? feel like a lot of people get confused about the distinction.
Claire Pomykala (05:05)
Mm-hmm.
Yeah, okay, so for me, think bikepacking is way more focused on just nature. I feel like bikepacking is all about getting as far, like not always, but like it’s further away from people, just more connection to nature and it’s usually shorter. So I think bicycle touring has probably more of a focus on culture.
But I would say bike packing is just like, just need to get in the woods and just hear only the birds. And that’s how I rehabilitate myself before I go back to my nine to five.
Blake Boles (05:41)
Hmm.
Mm-hmm.
Got
it. Yeah. So it’s like wilderness backpacking, a short wilderness backpacking trip, but using a bicycle instead of just your legs. Yeah. Whereas bicycle touring is often more connected to cities or more populated areas and you’re more likely to interact with people.
Claire Pomykala (05:58)
Mm-hmm. Yeah.
Yeah, it’s just bicycle touring is usually just a longer duration of time. So there’s way more of a touristic aspect of it. Because even if you’re not even near people, you’re still in another country absorbing all of the elements of that, or maybe not in another country, but another state part of the world. So I think there’s just more emphasis on a relationship with a new place for bicycle touring potentially.
Blake Boles (06:16)
Hmm.
Hmm.
I want to keep moving backwards through your timeline and then later we’ll jump forwards from from New Zealand to the present moment. But what were the other three big tours that you went on before New Zealand?
Claire Pomykala (06:47)
⁓ Okay. Okay, so basically my first tour was from Atlanta, Georgia to Baltimore, Maryland. And that was right after I graduated college. ⁓ I gave all my stuff to my mom who drove down after graduation. And I was like, okay, when my release ends, I’m gonna bike home. And that was my test run to see if I actually liked bicycle touring because…
I mean, I was biking home, so it was a one and a half month journey. After that, I went to London because I only had one international friend that I was close with. He lived in London. So I was like, okay, I’m gonna start in London. ⁓ And as someone who’s never, who had never traveled internationally alone before, I was like, I think England will be a pretty good starting point. Everyone speaks English. It’s not too far away. I feel like it’s a pretty mellow. ⁓
like starting point for international travel.
Blake Boles (07:43)
Mm-hmm.
Claire Pomykala (07:44)
And I just kept going on from there as long as I could. I think I spent four and a half months. I spent about two months in all of England. I did a whole circle. Then I took the ferry to the Netherlands, just went all the way down south from the Netherlands until like Tuscany. And then after just basically going straight south on the Rhine River for the most part, ended up in Barcelona, met someone and did some van travel and went to Gibraltar in Portugal and came back and then I was home. And then the third tour,
was
after, which is over a year, because those two tours had about a month in between, the Atlanta to Baltimore to Europe, there was about a month in between of rest. About a year and a quarter later, I did a group bike tour, which was my first ever group trip. And we biked from Baltimore, Maryland to San Francisco, California. And we alternated van days. So we were all on road bikes. And all of our gear was in vans and just circled driving days. So we all biked like…
over 3,500 miles each most likely. ⁓ But the total mileage was over 4,000.
Blake Boles (08:50)
just like to highlight how hardcore this is that at age 21, 22, you bicycled within the US, like cycling within the US is hardcore. Like it’s dangerous often. It’s not made for cyclists. That’s, that’s like a pretty rough start in my opinion. Uh, and then, and then Europe, like going for like four or five months and doing this mostly solo.
Claire Pomykala (08:56)
Yeah.
Yeah
Yeah.
Yeah.
Mm-hmm.
Blake Boles (09:15)
and
going through all these countries where you don’t speak the language. I know lots of people do speak English in those countries, but still, ⁓ what prepared you to leap into this so passionately, so drastically at such a relatively young age?
Claire Pomykala (09:19)
Mm.
Okay, I think prepared is kind of an incorrect word for here because it was, I was mostly motivated by like, I mean, I was, I had an interest in travel for a long time, but I was primarily motivated by negative things. I did not want a job. I did not want to go get a master’s degree. I didn’t know what I was doing. It was all of this kind of anger, frustration, like that pushed me.
Blake Boles (09:49)
Mmm.
Claire Pomykala (10:02)
I was like, well, I’m going to run away from my problems. And that’s why I just kept biking until I was like out of energy, out of money. ⁓ By the end of my bike tours, because I was about six months total. I mean, if you include the Atlanta to Baltimore and the Europe, that was almost exactly six months of living on a bike ⁓ right after college with, you know, that one month in between the two.
But I was just trying to postpone that transition as long as possible because I was so incredibly jaded after college. ⁓ I just wanted like nothing to do with normal life for a long time.
Blake Boles (10:36)
Hmm.
How much do you want to do with normal life these days, Claire?
Claire Pomykala (10:47)
I don’t really know. It’s ⁓
It’s I’m constantly going back and forth on a lot of things, I feel like, because I don’t want to be super normal. But there are normal things that I want. Like I like having the place that I live. But I also want to be able to leave that place in a moment and not have to worry about it. So it’s I’m trying to find my creative, happy medium.
Blake Boles (11:12)
Hmm.
Yeah, we’ll circle back to the present moment and its many dilemmas. Just to dwell on the college years, what did you study and did you have like a pretty positive experience in college? You said you left like really not sure what you wanted to do.
Claire Pomykala (11:24)
Mm-hmm.
Yeah, so I studied public health and I think I studied that because it was a projection of everything that I needed as an individual. ⁓ And I was like, well, that should be my career because I want to know these things. But what I actually wanted to know was how to heal myself. I think that I should have studied something else. ⁓ Like I like public health a lot. I think it’s so foundational and so important. But the one thing that they don’t really tell you is
Blake Boles (11:43)
Hmm.
Claire Pomykala (12:03)
like what work will look like in that field. And like, I’ve come to learn that I’m someone that has to be physically engaged with like the things that I’m working on. ⁓ I can’t be on a computer five days a week and that is a lot of public health jobs. It’s being on a computer and it feels like a collective hallucination, just being on a computer nine to five. ⁓
Blake Boles (12:06)
Mm-hmm.
Claire Pomykala (12:27)
So yeah, when I graduated college, I was so jaded because one, I learned the healthcare system is just a poor, ⁓ my gosh, a for-profit system. It doesn’t really prioritize the health of citizens a lot of the time. And I was like, why would I wanna work in a field where everything’s set up against me and a lot of the entry-level jobs don’t pay much and look really boring? ⁓
Blake Boles (12:39)
Mm-hmm.
Claire Pomykala (12:54)
and like all of these things. And I also was so jaded because I went to a rich kid school and like I was a financial aid student and I just wanted to go to the best school that I could go to. And I went to like, yeah, a private rich kid school. And I think the hard part was when I graduated college, the whole goal is, okay, now you go start your career. And I had my first job when I was in seventh grade. So I had been working like,
know, seasonally part-time from seventh grade until I graduated college. But I was surrounded by kids who the only first job they ever had was like their internship, their sophomore or junior year. And the whole goal of college is, yeah, getting that job.
Blake Boles (13:37)
Hmm.
Claire Pomykala (13:42)
And I was just like, what the hell did I go to college for? already been working. And I was so burnt out from having to work longer than all of my classmates, so jaded because there were things that future employers will never see about me. ⁓ So I was just really angry, I guess, about this system of
education and like life and the cost behind it all. Like all my classmates were so excited to start their careers and I was just like I’ve been working since middle school. I’m tired. Like I’m tired of this.
Blake Boles (14:14)
Hmm.
Hmm. Mm-hmm.
Did you ever consider any ⁓ people facing or frontline health positions like nursing or other medical? No? Okay.
Claire Pomykala (14:32)
No. No,
I would never be a nurse. Never.
Blake Boles (14:35)
Why
is that? You know, they’re more on their feet. That’s what made me think of it.
Claire Pomykala (14:41)
I just don’t, I just never felt called to it at all. It’s, I think it was, it’s just like the structural aspect of health. It’s, I would say it was what really caught my eye. ⁓ Like certain regulations, laws, things that we consume. I’m more interested in the kind of preventative things about lifestyle and all that kind of stuff rather than blood work and heart rate.
Blake Boles (14:54)
Yeah.
Yeah.
And I think anyone who checks out your sub stack newsletter will see that you are a very big picture systems thinker. You’re interested in many things. So that, really lines up. you did have someone introduce you or maybe a few people introduce you to the joy of cycling in college, right? ⁓ what, what, ⁓ just give me like one, one moment that really opened your eyes.
Claire Pomykala (15:14)
Yes. Yeah.
Mm-hmm. Yes.
Yeah, the moment, okay, the moment that opened my eyes was I…
made a friend during COVID, we started biking together, and he was like, let’s go to the campus bike co-op after our ride. And I’m like, okay, whatever. I mean, this is during COVID, by the way. So this co-op technically was allowed to keep operating during COVID, because it was in a garage, which meant that it was technically outside, which meant that we could technically still hang out, and despite everything being shut down. ⁓
Blake Boles (16:01)
Nice.
Claire Pomykala (16:04)
And so it’s like this one kind of hidden gem workaround for being social during a pandemic. Everyone’s wearing masks, obviously, here and, you know, doing their best to stay outside in the co-op space. But anyways, we go to this ride or we finish our ride and we go to this little workshop and it’s pretty much all men. It’s like six men, you know, of all different ages, know, like undergrad, graduate school. And there’s me and I’m just wearing this like neon, like spandex outfit.
just like these, it’s just like not even a shirt. It’s just this like sports bra, crop top and like spandex shorts. And I just remember walking into this environment of like exclusively men and not feeling like the odd person out or any kind of way.
I mean, I think a lot of women would, know, if you’re wearing like a skin tight neon outfit and you meet a bunch of men you’ve never met before, you’re like, like, is this going to be fine? But everyone was, didn’t even like look at me any differently, didn’t talk to me any differently. Everyone was so nice and normal. And I think I’d been missing that from every, like literally every other social group I’d ever been a part of in college.
Blake Boles (17:17)
Hmm…
Claire Pomykala (17:18)
from the arts people
Blake Boles (17:18)
Mm-hmm.
Claire Pomykala (17:19)
to the rowing team I was on, it felt like there was always this weird energy ⁓ one way or another that I couldn’t define. But this group of people, it instantly felt like, it’s like, hey, like we like, like we all like the same thing. So we’re happy that you’re here. And that was end of story. And I just kept showing up because the energy of it was just so fantastic. ⁓ I just think it’s really funny because I think
I know a lot of women don’t get that experience. I know a lot of women think of it as like a very hyper, pro masculine environment, but mine was the exact opposite. It was open table, like felt like radical, like equality. No one really cared like who you were, what you looked like. It was just your character and intentions. And that’s what kept me going back for all of COVID. And just, that’s what really spiraled me into the bike world and bike
Blake Boles (18:08)
Hmm. Mm-hmm.
Claire Pomykala (18:17)
community.
Blake Boles (18:17)
Hmm.
That’s cool that it was the sense of belonging and inclusion that you felt so clearly so quickly that really made it stick for you. And I surmise that people who show up to a cooperative, you know, kind of place where everyone needs to chip in. It’s not just a bike shop. It’s not just like mountain bikers hanging out. I imagine that that has a positive effect on making everyone feel welcome.
Claire Pomykala (18:23)
Yeah.
Mm-hmm. Yeah, that’s true. definitely is a cooperative. Yeah, the whole nature of that is different than a shop or something else.
Blake Boles (18:47)
Yeah. Okay. So you discovered cycling in college right after college. You’re like, I don’t want to go get a job and certainly not in a computer job in the public health field. I was trained in. I’m going to go cycling instead. You cycle back to Baltimore. You survived cycling the United States, you know, the wild West and you pop over to Europe. at what moment does your, your social media, ⁓ what do you want to call it? Career presence?
Claire Pomykala (19:06)
Yeah
Mm-hmm.
Blake Boles (19:17)
to start to bloom. When do people start paying attention to you?
Claire Pomykala (19:21)
the very end of my trip around Europe. That’s when I like I had a couple of videos go viral and I was finishing my trip in Europe and that’s when it really took off and I was like I was like oh crap like my trip is ending now what do I do?
Blake Boles (19:39)
no, I’m getting popular. What do I do?
Claire Pomykala (19:41)
Yeah, I’m like, my life’s gonna become boring. And now everyone wants to follow me. Because the timeline was bike trip from Atlanta to Baltimore, then across Europe, that’s when I got popular. And then I came home and got my job. And then it was a year and a quarter of working my job before I biked across the United States. it was, yeah, right when I was coming home.
really popped off. don’t know the social media career is such a loose term because I’ve made very little money from it but I would say that’s when the concept of money started started so that was probably early 2022. Yeah.
Blake Boles (20:24)
Tell me more. What do mean by the concept of money started for you then?
Claire Pomykala (20:28)
Like every once in a while a company would be like, ⁓ do you want this product and promote it? And I didn’t know anything about.
brand deals, I didn’t know anything about social media marketing in the slightest. So it was very experimental, pretty much almost no money being made, but I was like, there’s something here to work with. I’m not really sure what’s happening, but I’m gonna just entertain it. ⁓
And it’s been a very, very slow build for me, this social media career. It’s just like the Wild West, honestly. Things are changing all the time. Half of it is ⁓ like a pyramid scheme. I was trying to figure out my place in this crazy environment. Do I even like this? What’s happening right now?
Blake Boles (21:25)
Yeah, and
it’s a very screen-based environment, which is part of what you were running away from.
Claire Pomykala (21:30)
Yeah.
Exactly. Exactly. So I was just like, I don’t know what’s happening, but I’m here.
Blake Boles (21:36)
Yeah,
yeah. Okay. And that social media success, did that lead into the job that you that you landed at the end of your time in Europe?
Claire Pomykala (21:48)
No. So the job that I got was actually through a friend that it was at this like random tech startup that wanted to hire my friend and she was like, I can’t do it, but I have a different person who you might like. And I was in London when I was emailing this company. So I was at the very beginning of my Europe, my Europe bike tour when I was interviewing this company. ⁓ So like,
I think they hired me because they were thinking, if this chick can bike around 10 countries in Europe alone, she could clearly be a product manager somehow. ⁓
Blake Boles (22:28)
I don’t understand
Claire Pomykala (22:29)
I don’t either.
Blake Boles (22:29)
that link, personally.
Claire Pomykala (22:31)
I don’t either, but they hired me. ⁓ For context, one of the interview questions was, you know what the cloud is? And I was like, what, the clouds in the sky? And they still hired me. So I think they were like, she went to a good school and she can be self-sufficient while traveling internationally. So she’s a problem solver, but I’m terrible at technology.
Blake Boles (22:34)
Okay.
And they hired you. Huh. Yeah.
It’s fascinating. I wonder if it really just was like university credentials or the personal referral or maybe the social media. But like you said, it was before you really got big on social media. Anyways, you got a tech job and up to this point, you had worked mostly like entry level or service jobs since you were 14 years old, right?
Claire Pomykala (23:20)
Yeah, like camp counselors, lifeguards, tutors, ⁓ in a library, in a lab. Like, I had a dozen jobs before I graduated college.
Blake Boles (23:28)
Yeah.
Yeah.
So not exactly big money in any of those positions, if I’m guessing correctly. And then what, what was dropped into your lap? And if you’re willing to say like roughly how much money did you start getting paid all of a
Claire Pomykala (23:35)
No. Yeah.
Oh, I went from making, you know, whatever, $15 an hour to $115,000 a year.
Blake Boles (23:51)
How did that feel Claire?
Claire Pomykala (23:55)
Good, but mostly bad. Because, well, the nature of my job sucked. ⁓ I spent 40 hours a week making so much money, but I hated every hour of work. And also the work that I did was completely meaningless. It was purposeless. It was just theatrical. And everything that I did basically went into the… ⁓
Blake Boles (23:58)
Why?
you
Claire Pomykala (24:22)
the online wasteland and I was doing just meaningless work that did nothing to help the world, but I was being rewarded for it.
Blake Boles (24:32)
And are you being
hyperbolic when you say meaningless and it didn’t help the world? Like, did you really think that whatever products you were developing were absolutely useless or even destructive?
Claire Pomykala (24:44)
⁓ I think it was an ego driven company based off of somebody who wasn’t as successful as his friends.
Blake Boles (24:51)
Okay, so it’s kind of like someone
lost a bet or something. They’re like, I’m going to make a product, I’m going to make it incredible and they’re not doing it for like the right reasons or to really serve people or to really solve some important problem.
Claire Pomykala (25:00)
Yeah, I think
that a lot of people just wanna be the next like Zuckerberg. People want to just be this like this new force in the world of tech. And they’re just grasping at this million dollar idea, right? And then they think to themselves, I have a million dollar idea. But we don’t even need these million dollar ideas. Like what we need is to not have…
Blake Boles (25:07)
Hmm.
Claire Pomykala (25:27)
like poison in our food, you know? Like we don’t need this new, like this new cloud technology that’s gonna revolutionize a million things. this company ultimately, I think was made, like we were told that this was a product that was going to you know, the cloud systems and all these so much easier for so many companies. ⁓
And I hardly even understood it, but I think that’s just my lack of understanding of tech. Like if I can’t touch something and feel it, it’s going to be really hard for me to know what the hell is going on. But, know, the company wasn’t doing anything meaningful. Like I had friends doing meaningful work, getting paid 45K a year. And I’m just over here doing something that I know is not actually going to help people. Like based on how
a lot of things were going on in the company. just felt like, yeah, very theatrical. I was pretending to work all the time and most of the work that I did do just never worked out. So it’s just this constant theater of having a nine to five. And then you tell people, I’m a product manager for a tech startup and everyone’s eyes light up and…
Blake Boles (26:35)
Hmm. Mm-hmm.
Claire Pomykala (26:48)
you’re getting paid like what feels like dirty money, honestly. mean, I don’t have the kindest of things to say about the tech industry if you can’t already tell, but it’s just like my work, like the value of my work was not $115,000 a year. And I was one of the lowest paid employees, you know?
Blake Boles (26:57)
Yeah.
Hmm.
This is a quintessential David Graeber bullshit job. This is pretty much what he described in that essay. ⁓ so this begs the question, since you had had summer camp jobs or tutoring ⁓ jobs that I presume were more interesting and meaningful and you can see direct impact, like what made you take this job? Did, did you have more idealistic hopes at the beginning? Were you curious? Were you just like, I want to see what it feels like to earn this much money.
Claire Pomykala (27:15)
It is.
Yeah.
⁓ I didn’t apply to any jobs after college. So when this one fell into my lap, I was like perfect. I was like.
Blake Boles (27:45)
Because it gave you money or just because it was a
job and you’re like I probably should get a job at some point and here’s one
Claire Pomykala (27:49)
Basically,
basically it was like, okay, I didn’t have to apply. I had an interview, I didn’t have to apply. That’s awesome. It’s gonna pay me $115,000. That’s awesome. I’ve been a financial aid kid. I got my first job when I was really young, so I would like to not be poor for once. Because that gets really exhausting. And I I have student debt. was like, I can’t afford to pass up this job. It’s just like, that would be so bad.
Blake Boles (28:14)
Mmm, mhm.
Claire Pomykala (28:18)
to not, you know, it was like, yes, this job, like I took the job knowing I probably wouldn’t like it, but I also took the job knowing that, you know, cash rules everything, money rules everything, and you, at some points in your life, you have to kind of choose, I guess, how you’re gonna manage it, and that was a jumpstart for me. Like if you think of like managing a car, that really was a jumpstart for my personal finances, and I will always appreciate that. ⁓
but I’m so glad that I’m out of that career because it was making me so sick physically and mentally. Like it was just, it was just ruining my health. ⁓ But again, my financial health was great and all that jazz. yeah. A year and a quarter.
Blake Boles (28:54)
Hmm.
How long did you stick around?
Okay, so you earned something on the order of $140,000 from working there. Not too shabby, Claire, for being in her early 20s.
Claire Pomykala (29:21)
Yeah.
Blake Boles (29:24)
And so now we’re getting into more recent history. We’re getting into your, New Zealand bike trip. ⁓ were you still working for the tech company when you were cycling New Zealand?
Claire Pomykala (29:34)
No, so basically what happened was I got roped into this bike ride across the United States and I was looking for a reason to quit my job, but there was no reason. And then this person was like, you should do marketing for this group.
bike ride across the country because they raise money for a local nonprofit in Baltimore. The bike ride starts on June 4th. I was like, okay, I told my company I want to take unpaid time off to go bike on this cross-country journey. So I had unpaid time off for the entire bike ride across the country. And then a week before the trip ended, I quit. And then, because I knew I was never going to come back, but I also knew that I wanted my health care. So… ⁓
Blake Boles (30:08)
Yeah.
Claire Pomykala (30:17)
was like, whatever. They were gonna, I had an intel from someone in the company that they were laying people off anyways and I knew I was like the least important person there. So I was like, whatever, they don’t need me or want me, I’ll just leave. ⁓ And the shit that I’ve going across the country is what was the reason to kind of leave my job. And then at that point I didn’t have my job. ⁓
Blake Boles (30:27)
Hmm. Mm-hmm.
Claire Pomykala (30:40)
But I had savings stacked up because I knew I was going to do something like this. I knew I was going to just chaotically quit and then start biking. And then I just was talking to a friend. It was like, want to go to New Zealand? It was sure. So then we booked our flights to New Zealand. ⁓ And I was just a free bird at that point, you know, watching my bank account go down, but I had been strategic about it. So I kind of, I had known for a long time working my tech job. I was just going to randomly quit one day and go for a long.
bike ride.
Blake Boles (31:11)
Hmm. And it’s really
good for funding those long bike rides. Yeah. So it sounds to me like for the majority of the time, since you finished formal higher education, you have not been working or certainly not working full time. you’ve been able to do a lot of cycling, go on a lot of adventures, ⁓ more than many people will do before they, you know, hit retirement age. ⁓ and just so people are, are aware of.
Claire Pomykala (31:16)
Yup. yeah.
Yeah.
Blake Boles (31:41)
where your income comes from. ⁓ Like what is your financial or your money situation right now? How are you making money? Is some of it from social media? And please talk about the bicycle trips you’ve been running.
Claire Pomykala (31:53)
Okay, so the main moneymaker right now is working for these luxury active vacation company. Yeah, this is one company that I work for. ⁓
you know, it’s a one week trip for these people. They spend like $3,000 to go on a one week luxury bike trip. So that’s the seasonal job that I have. That’s really the moneymaker. Aside from that, there’s seven other things that go on. I lead bike packing trips. So those are primarily in Maryland. I’m slowly going to new places too, but Maryland’s where I live. So it’s just easier to run a trip nearby.
I lead a couple of bike packing trips a year. So it’s usually three days camping, way cheaper than those really fancy vacations for that company I work for. Aside from that, I do some social media marketing for brands that I really like. ⁓ Like a recent one was Aventin, which is this e-bike company. ⁓ But I have lot of kind of casual partnerships going on, ⁓ which is both nice because it’s…
like no stress, then cashflow also means like no pay or little pay. So it’s, I don’t know, you take what you can get, you just roll with it, but I’m getting a little bit better at the social media marketing aspect of things and managing my finances. ⁓ Sometimes I sell bike things, actually.
because I’m a very creative person, one thing that my friend and I, this is almost a little secret. I’m like, should I share this right now? I have a friend who’s as creatively minded as I am, and we’re gonna be making ⁓ like cargo nets for bikes, but in fun colors because everything out there is just black.
Blake Boles (33:35)
Ooh That’s what I own
Claire Pomykala (33:39)
Yeah, there’s nothing like fun. There’s no neon green with neon red. There’s no neon pink with brown. There’s nothing crazy. And cyclists love fun colors. So anyways, it’s like, that’s a new business adventure is being creative and contributing to this fun, colorful, spunky part of the bike world. I got a thousand projects going on at once. I’m too…
This is like, one of my greatest assets is having ideas. And then also one of my biggest flaws is there’s too many of them to make happen.
Blake Boles (34:14)
Yeah,
yeah, so this is probably a difficult question to answer but how much do you work these days? if is it like Are you working all the time? Are you like that kind of like I have seven side hustles? I’m trying to be a super entrepreneur ⁓ Do you still have time to like genuinely relax reflect? Do art go on cycle trips that you don’t feel the need to document or evaluate products or whatever? Tell me how that balance is working out for you right now Claire
Claire Pomykala (34:43)
The
balance is not very balanced, but ⁓ I don’t know. I’m trying to figure it out. It’s really hard to define how many hours that I’m working these days because sometimes the work is just really fun. And sometimes the work is really boring. Like working on this project with my friend for making these cargo nets, like on one hand, it doesn’t feel like work at all because I just love making stuff so much.
But on the other hand, eventually we’ll have to start listing it online, selling it, shipping it. I mean, do I even call that work right now? Building the board for making this? It doesn’t feel like it, but it is. ⁓ I don’t know, I have a lot of fun.
Blake Boles (35:26)
Mm. Mm-hmm.
Claire Pomykala (35:31)
I do. ⁓ I would say it’s kind of hard for me to sit still. That’s definitely where the difficulty comes in for relaxation. When you’re managing seven side projects, every time you’re sitting still, you’re like, well, I could be sitting still on a computer fixing that one thing that I know I need to fix.
Blake Boles (35:39)
Yeah.
Yeah, I think this is a theme in a lot of these, these interviews I’ve done is that a lot of people just genuinely genuinely enjoy their, their side projects, their, their, even their main work, their creative things that might end up making some money one day, but probably won’t. And so it’s hard to say like, how many hours do you work with the assumption that the other hours are somehow this like mythical pure form of relaxation, which is really not what a lot of us are looking for. We’re looking for meaningful engagement. So yeah.
Claire Pomykala (36:19)
Yeah.
Yeah, like, even I realized the other day that I’ve been doing a lot more. ⁓
kind of sculptural projects. I’m using power tools and I made a couple of videos of me just making just random crap at this welding studio that my friends have. And apparently that’s now marketing for me because my number of website views have skyrocketed like in direct correlation to when I post a video of me using an angle grinder.
Blake Boles (36:50)
Ahahahahah
Claire Pomykala (36:52)
And I’m just like at
this studio being like, apparently now I need to get more content of this because it’s having a direct impact on my bike packing sales. Crazy.
Blake Boles (37:01)
So this is a perfect
segue into your evolving relationship to social media because you had this kind of early breakout success, which you seem to enjoy. You’re like, I’m popular now. And, and what you just told me is like, wow, people like seeing me with an angle grinder. I guess this means I need to make more videos like this, this kind of like.
Claire Pomykala (37:07)
Yes.
Yeah.
Blake Boles (37:23)
gut response of like, I get the likes, then I do more of the thing like Pavlovian dog response. And so in recent time, like in the past year, I’ve noticed you’ve taken this stand against Instagram and TikTok and tell me where this came from and how it is right now for you.
Claire Pomykala (37:25)
Mm-hmm.
Yeah. Yeah.
Mm-hmm.
⁓ I think I just at one point came across a lot of YouTube videos and articles from psychology places, like regular people then psychologists all saying like basically you are becoming less intelligent because of doom scrolling and all these things. And I just kind of had this realization of like,
I love being intelligent. I love having a brain. I love having time to do things that I enjoy. I just felt so hollow posting on social media. ⁓ I wasn’t really getting as much as I thought I would get because there was this, the TikTok boom really had this illusory like,
concept that you could become rich by tomorrow. And that was happening to some people. It wasn’t happening to me, but it was always like, it’s the lottery system. Like it could be you next, it could be you next. ⁓ But it wasn’t ever me. And it’s honestly not it for a lot of people.
Blake Boles (38:49)
Hmm, mhm.
Claire Pomykala (38:57)
I was just like, I don’t like that my life is going away. Like as a child, I was always doing stuff. I was doing stuff all the damn time, like games, sports, making things. That’s what gives me life. And these apps are just taking away my ability to do all of that. ⁓
Blake Boles (39:17)
because of
your relationship with the apps, both as a consumer and a creator.
Claire Pomykala (39:22)
Yeah, because mine’s twofold, as a consumer and a creator. You’re double sucked in. If you’re just a consumer, that’s one way of being sucked in. But I’m doing both. I have to know what’s happening on these apps to stay up to date with it. And I was like, this is so much of my life gone. I don’t mind editing videos, but it doesn’t scratch that itch for me. And…
Blake Boles (39:36)
Mmm. Mm-hmm.
Claire Pomykala (39:50)
I just think it’s so messed up that, right, I’m 26. These social media came out in a time where my brain was almost fully formed, but people who are younger than me, I’m like, God damn, it’s just so messed up. People are losing their ability to have a hobby because of these apps. They’re losing their ability to read a book because of these apps. And I took a huge step back. ⁓
for myself mainly, like what do I want my life to look like? I don’t wanna be addicted to this. And I would say my doom scrolling is significantly less than it used to be. ⁓
And I have started posting a little bit because my business was born and is tied to my Instagram. So I’m trying to find the balance of like my bike packing trips. When I have a form and it’s how did you find this trip? Almost every single time it’s Instagram. People aren’t finding my trips because of Substack or because of Google search and all these other things. It’s because of my Instagram. So it’s like, okay, I don’t really wanna be here because I don’t think there is a ton
Blake Boles (40:33)
Hmm.
Hmm.
Claire Pomykala (40:55)
of good things coming from these apps, but I kind of am realizing I do have to have some kind of presence. So in order for my business to keep being alive, because it feels like if I don’t want to be on these apps at all, I almost have to give up my business. So I’m trying to figure out where I stand with all of that. I think ultimately,
One thing that’s been helpful is just posting things that I want to and not really caring in the slightest about what’s cool online. It’s just doing what I want. I think there’s a lawnmower that’s right outside of my window.
Blake Boles (41:31)
There’s definitely a
lawnmower,
All right. The lawnmower threat has been removed for now. ⁓ one of the things I really enjoyed on your sub stack Claire, you’ve posted earlier this year, 14 reasons not to become an influencer. And, ⁓ it was not nearly as popular as something you posted just before that, which is I’d rather be kind of poor than work most jobs. So in your writing career, it seems like that has really struck.
Claire Pomykala (41:47)
Yeah.
Yeah.
Yeah.
Blake Boles (42:00)
a nerve with people. Like what was inside that post?
Claire Pomykala (42:05)
my God, was just, yeah, saying I’d rather be kind of poor than work most jobs. That was really it. And I wrote that not realizing a lot of people related to it. I had no plans for it to actually blow up, because my Substack is so inconsequential. ⁓ It’s just like an afterthought, because I used to just post everything on Instagram that I was like, maybe I should do it on different platform and I’m on Substack.
Yeah, the I’d rather be kind of poor than work most jobs was basically saying like, I feel like people look at me and they’re all trying to find my lost purpose for a career. Like, I’m just a fish out of water.
Blake Boles (42:48)
Like they’re trying to help
you get back on track so you can have a nice, well-paid, good benefits job and then you’re going to be happy.
Claire Pomykala (42:51)
Yes.
Exactly,
they’re all trying to help me get back on track and everyone’s, you know, well intentioned, obviously, they’re well intentioned, but I feel like they’re not, I mean, it’s a very practical approach to life and there’s nothing wrong with being practical, like things that need to be done, need to be done.
But I’m not a practical person. Clearly, I’m not a practical person. After college, instead of getting a job, I just went to bike around Europe instead. I was like, screw all this. I’m making my own path. And that’s the kind of person I think I am. It’s just like I have a high tolerance for uncertainty. I have a high tolerance for.
I don’t know, dealing with the consequences of my own actions. And I’m just like, well, I don’t like most jobs. I love doing things. Like I really, really, really love doing things. I just hate most jobs. I don’t like being told I have to ask for time off. Like I don’t want to ask to take time off to go on a camping trip one weekend. Like, are you kidding me?
That’s ridiculous. Like my boss doesn’t own my life and
You know, my generation is super screwed over because the cost of life is just accelerating and wages are not following it. So it’s like, if I’m going to be poor, let it be my choice. Like, I don’t want to be working like a full 40 hours a week to make 45k for something that I don’t enjoy while watching the cost of everything just increase before my eyes. It just…
Blake Boles (44:16)
Hmm.
Hmm.
Claire Pomykala (44:36)
If I’m gonna be, yeah.
Blake Boles (44:38)
What about your friends who are working for 45,000 a year full-time, but they have work that they enjoy and feels purposeful. Like how does that balance of time, money and purpose appeal to you?
Claire Pomykala (44:51)
I am not very, I don’t really know yet because on one hand I feel envy that they have stability and consistency in their income. On another hand, I’m not jealous or I have no envy of the fact that they still have to do things like ask for time off. Like I value my life and my quality of life deeply, like all my hobbies. Like I love my hobbies too much.
Blake Boles (45:10)
Yeah. Yeah.
Yeah.
Claire Pomykala (45:21)
And I
care tremendously more about having time for my hobbies than I do about stability of income, honestly. ⁓ So I don’t really know. It’s like, I’m kind of in a weird space right now. Because like in your book, you mentioned being high paying but low paying. that is, yeah, like high pay, low income. That is exactly the situation that I’m in right now. It’s really hard to describe.
Blake Boles (45:41)
High pay but low income, yeah.
Claire Pomykala (45:49)
⁓ But that’s where I am and I’m just like, I kind of can, like if I wanted to go biking all of next week, I could, I literally could. I wouldn’t have to go ask permission from anyone. I could just do it. I mean, I’m not going to because I have things, other things to take care of, but.
I don’t know, it’s that flexibility and being able to go places on my time and do the things that I want. I mean, there’s a lot of chaos with it. So, I don’t know, maybe one day I won’t want the chaos anymore. I’m kind of tired of it, but I think it’s still worth the experiment. One thing that I’ve tried to live my life a lot of is it’s better to try and fail than never try at all. And I’m trying.
Blake Boles (46:22)
Yeah.
Yeah.
Yeah. Yeah. I wonder if just knowing that you could take that week off, even if you never actualize it is like this huge reward in itself. Just kind of knowing that you are not under someone’s thumb and that fundamentally you have this, sense of control and autonomy and, just knowing that it’s a possibility is enough. ⁓ but fundamentally you’d rather like be at home working on your 22 different projects.
Claire Pomykala (46:56)
Mm-hmm.
Yeah, yeah, like for example, this summer, I’m gonna go biking in Canada for probably 35, 40 days. That is already over the limit of time off for pretty much every job in the United States. Exactly, you know? And like, why should I not be able to do that? That is so stupid. And I feel like, honestly, I feel like a lot of Americans, they’re…
Blake Boles (47:19)
even very swanky jobs.
like.
Claire Pomykala (47:35)
They’re just being so practical and doing the things that have to get done, because I know they need to get done, but I don’t know. We all deserve, everyone deserves so much more like a life and just really like living life. Living life right now is defined by the things that you can consume, the things that you can buy, but it’s not like the things that you do in life, like living it. And…
Blake Boles (48:01)
Hmm.
Claire Pomykala (48:02)
I feel like that’s a huge trap of the American psyche is that life, like living a good life is oftentimes measured by the things that you’re buying and you’re consuming. But that’s not at all what’s important to me. Again, the slightest. I would rather be dirtbagging in Canada, dumpster diving and wild camping than like buying this beautiful new dress just to go like, you know, to a-
Blake Boles (48:27)
Go eat some
very expensive brunch.
Claire Pomykala (48:29)
Yeah, like that’s fun every once in a while, but that’s just not what makes me feel like I’m living.
Blake Boles (48:37)
And I think this is why people loved your videos and seem to continue to love your Instagram posts because you embody that very well in many of the posts. ⁓ And more recently, you have also been like very transparent about these much darker moments where you seem to have existential dread, some serious feeling of powerlessness, really railing against ⁓ global capitalism. And it seems like that is
Claire Pomykala (48:40)
Yeah.
Yeah.
Mm-hmm.
Mm-hmm.
Blake Boles (49:06)
really an all-consuming thing for you at moments. And tell me more. Yeah.
Claire Pomykala (49:09)
Yeah, I mean, it is, yeah.
Well, at the end of the day, like the consequence of all this global capitalism is just gonna be death. That’s just really what it is. Like the death of the oceans, the death of people abroad. it’s just, these things are all, a direct correlation to.
the ending of human life in so many ways. Like, there’s no other way to describe it. And to me, it just feels completely psychotic to just keep moving forward. ⁓ I know for some people it’s like, okay, well, I gotta put food on the table. I gotta work this job. Like, I gotta do all these things, X, Y, and Z. And I feel like there’s, like, I’m trying to not tell everyone how to live their life.
because that’s not my place to do that. But the current track that we are on is just like obliteration, is what it feels like, you know, for me. It feels like it’s just, I was telling a friend it feels like there’s death around the corner all the time. And I don’t want it to feel that way. I want everyone and everything to feel like there’s life around the corner all the time. But it’s, that’s hard.
Blake Boles (50:06)
Hmm, mhm.
Claire Pomykala (50:23)
It’s hard when you see a million negative policies happening, when you see the signs of climate change, when you hear the news of the impacts of climate change locally or across the planet, all these things. just status quo, continuing with status quo, to me is psychotic. And I think that’s why
I’ve made my own life crazy because to me that feels less crazy than like everything else.
Blake Boles (50:57)
Hmm,
framing. As you like tried to step away from social media a bit more, did that change your relationship to like feelings of imminent doom at all or just you consumed it in a different way?
Claire Pomykala (51:12)
I think I definitely consumed it in a different way. I don’t know, you also just see it walking around. I mean, you do see slivers of life and beauty too, just walking around, but I mean, you just feel all this unnecessary…
these unnecessary threats and danger around you all the time, at least again, like for me. And I feel like the news or, I mean, it’s impossible to escape the news no matter how hard you try, I feel like. So I don’t know. I just finished reading Hope in the Dark by Rebecca Solnit, I think is her last name. And I think that was, I think she wrote that during the Bush era. ⁓
Blake Boles (51:56)
Mm-hmm.
Claire Pomykala (52:02)
which I was a toddler in.
But that book has been kind of helpful for still possessing hope to make the world a better place. And that’s what I’m trying to always remind myself is like, in order to make the world a better place, you have to continuously try. The minute that you stop trying is the minute you’ve guaranteed you’re no longer making it a better place. And I think, I don’t know, on one hand, being off of social media is great because I can just focus on doing all those things like this community garden that I just started going to. I I bike to try and make the world a better place and I
Social media was also a way to try and encourage other people to make the world a better place through their, you know, through realizing the connection of everything. Like I feel like biking just makes you realize how connected everything is and how coerced we all are into living a certain way of life. So on one hand, social media can be a tool to help make the world a better place. And another hand, getting off of it also does that.
Blake Boles (53:01)
Hmm.
And you have some really great posts out there about why cycling like gives people hope for the future. I recommend people go look for those. as we get close to the end here, I definitely want to hear about your recent experience in Chile. And that seemed like a just incredibly positive, healthy, ⁓ time for you. So just maybe give me a story about what a day in your life looked like and what you were doing out there.
Claire Pomykala (53:16)
Mm-hmm.
We.
Chile was split into three sections. We started in Pichulimu, beach town, just relaxing, having fun in this beach town. The chunk of it was a work away in a very small bed and breakfast vineyard ⁓ at the foothills of the Andes. That was an amazing experience. I was with my girlfriend and we were just doing this work away program and just waking up. And the job of the day was to go pick blackberries to make a pie for the guests.
And obviously, it was a short piece of time. So it’s really easy to idolize.
stuff like that when you’re only doing it for a week and a half or a week, but ⁓ it was really just the quietness and the simplicity that calmed my nervous system down so much. I live in Baltimore, which is a loud city, and Chile was an experiment for different ways of life for me. Will I like living somewhere further away and quieter? There’s tons of pros to it.
Blake Boles (54:12)
Sure.
Claire Pomykala (54:39)
It was just, I felt calmer. I was outside all the time. didn’t feel like, I mean, people just yell at you sometimes for no reason in the city. You’ll be biking and they just yell at you. And you’re like, what did I do besides breathe? So I don’t know. Chile was awesome. It’s so beautiful there. Their natural landscape is just really beautiful, at least where I was. And…
Blake Boles (54:49)
Yeah, yeah.
Yeah.
What was the third part of the Chile trip? You said there were three.
Claire Pomykala (55:10)
Oh yeah, that was just being in Santiago, just being a city girl. And Santiago was cool and all. I wouldn’t say it was my favorite city that I went to, but it wasn’t like bad city either. It was just a place.
Blake Boles (55:18)
Yeah, it’s fine.
Yeah, it’s a place people go and they fly. Yeah. Well, I’m really curious how you’re going to answer this last one, Claire, which is if people want to find you online to know what you’re up to, where should they go?
Claire Pomykala (55:25)
Yeah.
Unfortunately, the answer is Instagram. I know, I know. Well, I think I’m working on something else. think Instagram is the place for now. I think I’m still figuring, I mean, I’ve just redone my entire website, which is livingbybike.com. I finished that about a month ago, like just getting the whole thing set up and beautiful. And that’s gonna be a constant work in progress. Eventually, I would like that.
Blake Boles (55:41)
⁓ I was hoping you’d say something else.
Claire Pomykala (56:06)
to be the main place, but the traction still comes from Instagram. Like people are visiting my website through Instagram. So.
Blake Boles (56:14)
Yeah. Well, I’ll
put both of those up on the episode description, but I also really recommend that people go to what is currently called Claire’s Substack Newsletter, very inventive title, which is linked in, I believe, both your Instagram and your website. And for me, I really like reading these long form thoughts that you have. I don’t go into Instagram much or YouTube much. So that’s where I have enjoyed getting to know you more.
Claire Pomykala (56:27)
Ha
Blake Boles (56:43)
I’m delighted that you have a personal website. I’m a huge fan. want everyone to have a personal website. Yeah. Great. And if anyone is interested in cycling, exchanging less than $3,000 to cycle for a week with you to go for on one of your bike packing trips, like how do they find it? How far in advance do they need to book and what kind of trips, what length and like how hardcore of the trip are you running?
Claire Pomykala (56:48)
Yeah.
You
Sure.
So my trips are three to four days and they’re very inexpensive. Like the cheapest one’s $95, the most expensive one’s like 250. It just…
Blake Boles (57:18)
What? Wow, cool. That’s super accessible.
Claire Pomykala (57:22)
It just
depends on the trip. The one trip that’s $95, that’s because I don’t pay for any camping. It’s all free. Everything’s basically free. Then the one that’s like 250 is like, we need to book a shuttle at the end of it and pay for the campgrounds and all that stuff. So there’s a variety of things, but that is all on livingbybike.com. There is just the…
2026 tours. That’s where you find those there. I used to be on Ticket Tailor, but I am now getting everything put into one home base, which is very exciting. ⁓ But I lead about four trips a year. ⁓ And my October ones are the ones I’m really excited about because it’s peak leaf changing season. And I think people are always like, it’s too cold to go biking. I’m like, that means that no one’s going to be on the trail. And
Blake Boles (58:05)
Mmm.
Yes, exactly.
Claire Pomykala (58:12)
Yeah, and the trees will be really pretty. So those are really excited about.
Blake Boles (58:18)
Great.
⁓ I’m as a fellow guide, really happy for you that you get to share your love of cycling with people. And especially in such a financially accessible way, and you get to be out there in October in leaf season when everyone else is indoors in front of a screen. You’re doing something right. Yeah, go ahead.
Claire Pomykala (58:31)
Yeah.
Yeah, yeah, it’s a 50 % chance that
it rains, because that’s always how it is, but it is still worth it.
Blake Boles (58:46)
Yeah. Great. Great. Claire, thanks so much for coming on the podcast.
Claire Pomykala (58:51)
Yeah, thank you for having me. It’s been a pleasure talking.