VanLife Dev

Van Life Beginnings: How One Journey Rewrote My Future

September 14, 2025 | by Josh

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I’m writing this from a swanky hotel room in downtown Chicago. After more than 18 months of living and working in a van full time, little escapes from life on the road like this remind me of the comforts I’ve given up. A toilet that is close but not next to my bed which flushes. Lights left on without checking to see how much battery is left. A constant 70° temperature no matter the time of day. I’m able to forget about the survival calculus and just focus on whatever screen is in front of me. I have been looking forward to these things for the last several days and it is, admittedly, quite relieving to be casting off those concerns.

View looking out in the middle of downtown Chicago

I am in town for the week to attend my company’s annual onsite meeting and it will actually be the first time I’m meeting all except 1 of my co-workers. About 8 years ago my life was a cycle like this on repeat. I was a business process consultant and I traveled to cities throughout the US every 3 weeks — staying at nice hotels, shaking hands in polite conversation, and working from large conference rooms in sky scrappers high above the city. When the week was done it was back to my townhouse in Austin where I’d bounce between work calls and house chores throughout the day. Everything was taken care of by the time the work day was over so when I closed the laptop it was straight to hanging with friends or whatever fun I had planned for the evening. It felt like I was living the dream and, honestly, I was. I was very grateful to be in such a comfortable situation and I did my best not to squander it.

In my 5 years at that job I always fantasized about leaving to go explore the world unconstrained by days of the week but I kept that dream at bay. How could I give it up? It was too perfect of a situation to just leap into the unknown. A lot of times when I traveled somewhere new I’d extend the trip to sneak in a weekend of adventure — thinking that I was having my cake and eating it too. As a kid, I barely traveled. In fact, I didn’t leave the southeast US until I was 19. So, all of these new places just tempted my curious mind every time.

Naturally, when one trip was ending I was already thinking about the next one and how it should be on my own terms — a place that I wanted to go and stay as long as I wanted. The picture I painted in my mind was thrilling and adventurous but it meant doing it without expense reimbursements. Traveling with a corporate card was easy and it was safe. Trusting a dangerous, unknown world without a lifeline just seemed foolish.

This juxtaposition left my heart wanting to take that leap but my brain doubting that there was a rope to catch me before I hit the ground. However, I would soon be pushed, without a choice in the matter. Just as the pandemic started to grab hold of the globe my company went from 25 employees down to just 10 and I did not make the cut. It was my first time being let go from a big boy job and since I felt like I had been given a gift to be there in the first place I put up no fight when the phone rang that Friday in March of 2020. My boss was a good guy and I knew how much it pained him to be making each one of those calls. The decision had been made and my luck had run out.

Since the world was in complete lockdown and I had squirreled away some money I didn’t stress over it. At first, I used my extra time to chip in on community projects. Through the local makerspace we were 3D printing PPE parts for first responders and a community outreach project needed a technical person to create  a website to provide information about COVID services available in Austin in a variety of languages so I was able to help out there as well. These efforts felt way more important than automating bank loan application processes so I instantly felt better about how I spent my days. Then, I took the next year+ rediscovering my passions and motivations for living. I spent my time working hard on the things that mattered to me. I would go to bed late and wake up early coming up with solutions to problems I had challenged myself to solve. During this time I dedicated a lot of time to several projects that I considered turning into full-fledged business. There was only one that I was passionate enough to pursue and I continue to work on to this day. It’s a climbing app called Craglog. I also climbed a butt load and beyond the point of bloody fingers. I’d only stop when I had tried every beta sequence I could conjure up. I pushed myself to exhaustion on my terms and with the things that truly mattered to me.

This period redefined what living life meant to me. I knew I had to get back to a salary pretty soon but I wasn’t going to do it without being who I was and being challenged the ways I wanted. I found a startup where the goal was to expand access to prenatal care in underserved areas by creating a virtual ultrasound machine. In short, ultrasound examines could happen anywhere the mother-to-be lived and the doctors could conduct their exam from where ever they were. We were tackling a major problem in healthcare deserts. It was very fulfilling work which allowed me to make it through long days under tight deadlines that we faced on a regular basis. You can check out this article if you want to read about one such occasion.

I had found the work I wanted to be doing but it still didn’t quench my thirst for living. My heart was happier with my new situation but not fully satisfied. I continued to pour most of my extra time into rock climbing and, after my self-awarded sabbatical, I now had a good foundation of technical knowledge. Not to mention that I was in the best physical climbing shape of my life. Since the world was opening up again I began taking climbing-specific vacations. At first, I coaxed my buddies to spots in the US like Red Rock Canyon and Smith Rock. My appetite was bigger though. I started looking at international destinations. I decided it was time to take my dream trip — backpacking around Europe. I’d heard so many stories from friends about their experiences there. When they told their stories they spoke with such a fond nostalgia. It was validation that Europe was indeed this fairytale land of castles and public transit. So, I was able to convince my team to let me work while I bounced across Europe.

It was a wild 3 weeks which you can read all about in this post but the most important thing that happened which is relevant to this story was renting a van from a climber in Mallorca. He went by Harry but probably because he knew that my American tongue would butcher his actual name. From the start he was incredibly kind. He showed me how to do all the things with the van and then suggested I take it up to the mountains on the western side of the island. The temps were going to be cooler up there and it was a beautiful place to visit in the van because I could park there overnight. So, once we parted ways I began heading up that way. I still remember driving up the winding roads, past the most picturesque Spanish vineyards, and the thrill of having my little home on wheels. The natural beauty of the mountains was breathtaking.

The rented van with sliding door openMy destination was a parking lot in Lluc and once I arrived I was able to quickly get myself settled. One of the doors had a broken lock though so I made sure to stash my valuables out of sight as much as I could. Then, I began wandering around to where ever my eyeballs wanted me to go. I made it back to the van by the early afternoon to begin my work day — I was keeping my regular hours for work so my day started around 3 in the afternoon and went late into the evening. I got my little workstation setup and as the sun was going down the park visitors began filing out. Pretty soon it was just me and 1 other van that was on the other side of the parking lot. This was the moment that it all changed for me. I had this beautiful corner of the world all to myself. Just about every visit to a beautiful place I had ever been to was crowded with other visitors. That’s just something I had come to accept and it felt selfish to complain about it. I still never complain about that. It’s everyone’s right to visit places that showcase the natural beauty of our planet. As such we should be respectful of those spaces and fellow visitors. If I’m lucky enough to experience it in solitude then I’m just lucky to have that moment for myself. That’s what this was — my serene moment in Lluc. It belongs to no one else but me. A moment I alone can forever hold onto and cherish.

I fell asleep to the sounds of nature with a gentle, crisp breeze blowing in the open window. The comfort of nature surrounded me warmer than the blanket that was draped over me. It was a different kind of peace I had not felt before. I had taken camping trips deep into the backcountry before. The comfort of nature wasn’t unfamiliar to me but what set this apart was that it didn’t require a ton of logistics and coordination. There was no packing my gear or setting up a tent. It was simple and easy. That morning I had checked out of a hostel, by the afternoon I was passing vineyards that overlooked the Mediterranean sea, then I was parked and writing code, and by the time I was sleepy all I had to do was close the laptop and lay my head down to rest. It felt criminal to be doing this while everyone I knew was going to be waking up soon to the same monotonous routine from their day before and their week before that. I recognize not everyone was envious of what I was doing but I was! I felt like an alter-ego of mine had conjured up some virtual reality fantasy for me to experience but their was no fantasy to it. I was really doing living this way.

Statue at the park in Lluc

The next morning, when I awoke, I stepped out of bed and slid open the door of the van. The sun was rising above the trees and the parking lot was still empty. Since my calls for work wouldn’t start for another 7 hours I pretty much had a full day of adventure ahead of me and I wasted no time. It wouldn’t be long before visitors began showing up so I took the opportunity to revisit some of the crowded spots from the day before. I made the whole round trip back to the van without needing to dodge a single selfie stick and barely ever hearing another voice. Once I got back I had myself a relaxing little breakfast as I watched the arriving families scuttle from their cars to the bathrooms then onward to the trails then back for their forgotten gear then back again to the trails. When breakfast was done I straightened up the van, stowed away anything that might slide around, and then I was heading off to my next adventure to do some deep water soloing down at the coast.

This one transformative night had cost me less than a stay at the dodgiest of motels and my mind was made up — as soon as I was stateside again I was going to start my search for a van and make this my new way of life.

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