Here’s how it worked for me.

This post is for folks who want to try longer-term travel and are looking for solutions to the income/cost equation. I received a message from a friend of a friend, and with her permission I’m sharing her question and my response here. 


Hi Lynette, I’m a friend of [xx] and she suggested I sent you a message. I’m hoping to spend some time travelling and was wondering if you had any tips or suggestions for income on the road? I have looked into teaching online, but that would be a constant struggle of finding a quiet area, which is not always easy while travelling. If you have any advice, it would be greatly appreciated. Thanks! 


Hi Ann, I had to think about your question for a while, because I felt a bit stumped. In fact, the quiet space and the internet connection are the two things I absolutely need when I’m looking for a place to stay. (Add to that: it has to be clean!)

But then I realized, I’m not really ‘travelling’ the way lots of people travel, like a few days in Florence, a few days in Venice, sleeping in hostels to keep the costs down. I am too introverted to survive hostels, and my anxiety and lack of spatial awareness make me useless in a new place for at least a week. My travel is probably more akin to the retiree-in-Florida model, except without the pension and retirement savings. For example, I spent two months living out of a tiny tower in a town called Slany and from that home base I was able to do day trips into Prague and a few three-day trips to some other parts of the Czech Republic. But mostly, I was just working a full-time job; all pretty boring except when I took a lunch break I was going for a walk in a pretty little Czech village. So first off, I would suggest you not rule out the possibility of finding a quiet space while you travel.

I’m going to include some links now—if you use my links to sign up, you and I both get discounts.

For a few years I’ve been using Airbnb to find longer-term accommodations, and many apartments have discounts for monthly rentals. My rule of thumb is to search for places that cost the same, or less, per month as I would pay if I were renting an apartment back home. That cost limit rules out certain countries for me, but I’ve found nice accommodations in eastern Europe and the Mediterranean—those are the places I’ve been most interested in so far. I basically treat Airbnb the way I used to treat the Christmas Wish Book—always browsing and marking things to come back to later.

For shorter stays, I’ve had some luck using My most memorable stay was in Belgrade, Serbia: a riverboat moored on the Danube river but run as a hotel—I could have sat on my bed all day long, just watching the birds come and go on the river.

Accommodations in the UK are a bit steeper, even on Airbnb, but this year I’ve managed to pick up pet-sitting jobs through Trusted Housesitters and got free accommodations and met some lovely people in exchange for keeping their dogs and cats cared for. There’s a fee to sign up, but I’ve recovered the living costs many times over. The trick with this approach is getting your first gigs—once you have a few good references on the site it gets easier to get more jobs. Right now I’ve got sitting jobs lined up for this coming summer in Wales, Scotland, England, then Scotland again.

To your question of how to earn money while travelling, I’ve been working on freelancing websites for more than three years and have built up a pretty regular set of clients. In the first year, I was also working part-time in St. John’s and house sitting for friends to keep my overhead low. In the second year, I continued freelancing while doing a 25 hr/wk job in Quebec through the Odyssey program. That year was difficult because the freelance work was getting steady, so I did very little but work and sleep during that time. The freelancing started out as an extra-cash thing, but it turned into a steady income over those two years.

There are a few different freelancing sites—and the one I started with no longer exists—but the one I’m working on now is Upwork. Take a look at the site, see if there are any areas where you might be able to market your skills. I set up my profile on the site as writer and editor, but in fact what keeps my bills paid on the regular is a whole lot of transcription work. Some other sites I’ve tried are Guru and Freelancer—I wonder if they still exist!

Okay, that’s how it worked for me. I hope some of it is useful to you 🙂 Good luck with your plans!

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