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Traveling and working online
We’ve been nomads since 2015, but didn’t start building location-independent, online careers until 2017. When we started transitioning into digital work, we both completed various projects as freelancers before eventually founding our company in 2018.
Traveling and working online are both full-time jobs. In our early years of digital nomadism, we tried a variety of living situations (including renting, work exchange, and housesitting) and learned a lot about balancing the two.
Our failed attempts at “working away”
At that time, we started using a site called Workaway that connects people with projects (hosts) with volunteers. This seemed like a perfect way to travel, meet people, be part of cool initiatives and keep costs low as we built up our digital skills and project experience.
Through Workaway, hosts offer room and board to volunteers in exchange for 4-6 hours of work per day doing various tasks (this may have changed since 2017). Projects could include anything from basic property maintenance to posting on social media to restoring vintage sailboats, and there were hosts all over the world offering interesting opportunities.
While there are many people who have had lovely experiences using this site, we were unfortunately not so lucky! In our first exchange, our host had agreed to have us build a new website and online presence for her farmstay business, which would have been a great portfolio piece for us. However, when we arrived, she insisted we perform only farm-related tasks because “that was the experience she wanted to give her Workaway volunteers,” and that a website just “wasn’t relevant” to her needs. Though we love working outside, it was really important to us to dedicate time and attention to building our skills for remote work, which we knew could support our lifestyle in the long term from anywhere. This was frustrating but we were able to complete the exchange quickly on civil terms and continue on our way.
At the next Workaway, we had agreed with the hosts to complete the 4-6 hours of work per day in the afternoons, and dedicate our mornings to online work. While this seemed to be a solid solution at first, it became apparent our hosts didn’t like that we had other things to do besides be available at the house and devote our attention to hanging out with them and completing projects. I remember the woman being on the phone with her friend, and though I don’t speak Dutch, I could understand what she meant when she exclaimed “Dat is niet Workaway!” Needless to say, it was clear this wasn’t a good fit either, so we packed up our bags and went back out on the road.
It didn’t seem we weren’t cut out for Workaway, but at least we tried. Living in close quarters with strangers while trying to balance their projects with building our new careers created too much tension – at least in that context. After two failed attempts, we needed to find an exchange setup where we wouldn’t be so subject to a host’s whims or expectations about how we should spend our time.
Finding our way to housesitting
Housesitting, on the other hand, turned out to be exactly what we were looking for. We could still provide real value through an exchange (i.e. caring for homes and adorable pets) while having the independence and space we needed to focus on our work. There was a clear understanding of responsibilities on both sides, we got to experience new places, spend time with animals, and most importantly, we had the privacy and quiet we needed to actually build our remote careers.
In years prior, I had housesat for people I knew in my hometown, but heard about housesitting websites where people had profiles for doing these sorts of exchanges. I don’t remember why we picked MindMyHouse, but as soon as we signed up we started applying for sits. With a brand new profile and no testimonials, we had our work cut out for us to stand out from the competition.
Our first housesitting gig
We finally got a chance to break into the online housesitting world with a month-long stay in a small hill town in Bulgaria, taking care of 4 dogs and 5 cats. Maybe it was because the homeowner liked our application letter, or maybe it was because there weren’t a lot of other applicants – we’ll never know – but we didn’t care! We were thrilled to get this opportunity to make a good impression and visit a part of the world we’d never seen before. At this first-ever sit we encountered a major piece of important information: I cannot live in a house with fleas.
We discovered this after a week or so living in the cottage; I had been getting bit all over my calves and ankles and the itching was starting to drive me nuts. Kory wasn’t having any symptoms like mine and I thought I was going crazy. Eventually I actually caught a flea which was both a moment of gratifying vindication and exasperating helplessness. If fleas don’t bite you, they’re no bother… but I might as well be a cat to them, so living with blood-sucking roommates was getting extremely uncomfortable. And if you’ve ever dealt with fleas, bed bugs, lice or other parasitic pests, you know it’s not an easy or quick fix!
While our host’s friend helped us to acquire some flea treatments for the cats, these treatments can’t do much to stop the flea population from reproducing if they have already moved in. I spent the next few weeks just trying to keep them at bay – vacuuming like a madwoman, spraying everything with apple cider vinegar, sleeping in a tent, and testing out every “proven flea trap” or “flea remedy” I could find online. At the time, leaving the sit didn’t even seem like an option, so I just toughed it out until the end of the agreed upon timeframe. Our last day was exactly on my birthday, November 15th. I remember taking the bus back to Sofia, the capital, and feeling like it was a happy birthday, indeed!
Housesitting now
We’ve come a long way since then… though funnily enough we had a run-in with fleas while housesitting in 2024. Luckily for us, the elderly cat who had brought them to the house in the first place had already passed away before we actually got to the sit, so our only charges were the garden and houseplants. With the help of some neighbors, we left within a few days of arriving – the same day I managed to catch 5 fleas within 10 minutes while trying to drink my morning tea 😳
It was one of those strange moments where life shows you just how much you’ve grown. Here I was, facing the exact same problem that had made me miserable for weeks during our very first sit, but this time everything was different. While I had a moment of feeling trapped and desperate, instead of scrambling for DIY solutions and sleeping in a tent, I packed our bags.
I had the experience to recognize the situation immediately, the confidence to prioritize my wellbeing, the immediate backup and full support from my partner, and most importantly, we weren’t afraid to communicate with the homeowners and leave. What had once felt like something I just had to get through was now a clear signal that this particular sit wasn’t right for us – and that we had the right to go.
In many ways, the experiences we’ve had housesitting between 2017 and 2024 were directly responsible for that growth and change. Being a housesitter has taught me so much about communication, boundaries, trusting my gut, what I want out of life, and what it means to “do the right thing”; not just for other people, but for myself.
No matter how luxurious a location might seem, or perfect a pet might be, housesitting is not glamorous… it’s messy and human and real! And that’s what makes it so special. Though over the years, our housesitting experiences have gotten easier, more exciting and more fun – in fact, after a particularly amazing sit in Sète, France, we started using a little motto when making life decisions: “Sète-r-better!” to remind us how beautiful life can be and that there is always room to receive more of that beauty.
In recent sits, we’ve been enthusiastically welcomed in (and invited back) to homes in places where we’d previously struggled to even find housesitting opportunities. It’s really pretty incredible to look back at where it all started, and see how that first gig evolved into many new adventures, right up into the present moment. It feels good to still be falling in love with sweet animals and beautiful scenery wherever we go.
Dear Reader…
Have you ever had to pivot from a travel or work situation that wasn’t working? What did you learn from it?
What’s been your biggest ‘growth moment’ while traveling or working remotely?
For those who’ve done housesitting or similar exchanges… what was your most challenging (or unexpectedly educational) experience?
How do you balance being flexible and adventurous with protecting your own wellbeing and boundaries?
What’s your ‘Sète-r-better’ moment – a time when travel showed you how beautiful life could be?
If it’s in your pleasure, please comment below!
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