What it’s Actually Like to Freelance While Traveling The World

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I’m sitting on the train from Prague to Berlin, in one of those stuffy 6-person compartments Czech Rail seems to love. I’m with Geoff, his sister Jenn, and her husband Terry, and we’re headed to Germany’s capital for a few days of sightseeing before Jenn and Terry head back to their life, kids, and jobs in Alberta. They’re joking around…Jenn has a glass of red wine from one of those mini airplane-sized bottles, and I can sense the excitement that comes with visiting a new country, a storied city in recent history.

While Geoff catches up with his sister and brother-in-law, I have my headphones in. I’m trying to finish an article I promised to a client, am blasting a Spotify concentration playlist to stay focused, and am crossing my fingers I can enjoy a long weekend with family that has traveled across most of a continent and the Pacific Ocean to see us.

Try as I might, it doesn’t happen, and I end up lugging my laptop with me around most of Berlin. Instead of managing to take a few days off as I’d planned, I end up trying to finish the article in a Starbucks across from Checkpoint Charlie, at the top of the Reichstag building while the others visit the dome, and on Saturday evening at St. Oberholz, the de facto digital nomad HQ of Berlin.

By the end of their trip, I’ve managed to get in some quality visiting time, but it’s not enough by a long shot. And I feel like a complete ass because of it.

It’s hard to write this post without sounding like a complete whiner…that’s certainly not my intention. But I was recently asked to write an article that brought my thoughts about all of this — quit your job, get some freelance clients, and travel the world making money from your laptop — to the surface.

And here’s what I think: that dream, which a lot of people make money from by selling the concept through their blogs, social media, and with actual products and coaching services, was for me, a steaming pile of BS. Like our friend Adam said, maybe freedom is a myth.

I wish I could say that train ride to Berlin was the first time, in our two-plus years of full-time travel, that my freelance work completely took over our lives, but the reality is it happened all the time. Despite the abundance of FOMO-inducing stock photography showing people happily typing away in the most improbable situations — at the beach, on a mountain top, right before jumping into a canoe — our trip to Berlin is a way more accurate picture of what my life has been like as a freelancer traveling the world.


Nothing about this picture makes sense to me. Photo by Dave Meier via Stocksnap.


The whole point of this exercise, and I would expect of anyone who wants to quit their jobs and travel the world, was to have more freedom and control over our lives.

Not being able to spend time with family who’d flown across an ocean to be with us does not qualify as freedom, and neither does seeing little more than the inside of a café in every city you visit.


Before we left Canada, people would ask me why we were leaving: why trade good careers, secure income, and a nice apartment for the risk and uncertainty of permanent travel and an unknown path to earning an income.

My answer back then was that of someone who hadn’t done it before, but it still stands. I  am massively privileged to have been born who and when I was. Canadian women are no longer limited to bank teller, teacher, nurse, librarian or secretary, like many in my mom’s generation were. Through no effort of my own, I was born in a country with free basic education, healthcare, and one of the most readily-accepted passports in the world. Through dumb luck, I was born to educated parents with steady jobs, with no abusive or addictive tendencies, who filled my childhood with sports, art, encouragement, and extracurricular activities. I grew up trusting the police, not experiencing racism or prejudice because of my sexuality or religion, and not having to worry more than any other woman does about physical safety and sexual assault. And then to top off all of that, the Internet became a thing during my life, and Wifi became widespread enough that it became actually possible for the first time in history for many people to work remotely.

That’s a long-winded backstory to my answer, which is this: for someone who’s always had an adventurous and wandering spirit, has marketable skills that can be done remotely, and is interested in entrepreneurship: why wouldn’t I?

Honestly, it seemed like a waste of all that dumb luck and good fortune to not take advantage, and try to become a digital nomad.

While I can’t speak for Geoff, two years later I’d probably make the same decision to leave, but I also have an answer to the “why wouldn’t we” response I had back then: because it’s really damn hard.

There’s a big group of digital nomads and bloggers in Oaxaca right now, and we’ve been having a great time with them, connecting over street food, drinks, and coffee-work dates, and talking about life, politics, travel and – yes – business. One friend mentioned she’s often asked by readers what her advice is for people who want to do what she does: travel constantly, build a digital nomad business, that kind of thing. And her response didn’t really surprise me: don’t.

Going to an office everyday and letting someone else worry about revenue, taxes, computers, registrations and lawyers…that would have been way easier. Better? From my perspective, over 800 days in on this journey, I’d say probably not. But I know Geoff would probably think long and hard before giving the same answer, and I often worry that I’m dragging him along on this journey.

There’s a lot about this life of ours that I genuinely, wholeheartedly love. I don’t actually mind that we work more now than I ever did back in Canada. I like working. But freelancing while travelling, at least the way I was doing it, was not at all what I expected, and it certainly wasn’t living the dream as it’s often made out to be.

While I’d never tell people not to do it, if that’s what they really want, I would caution anyone to think long and hard before making the leap into the freelancing digital nomad lifestyle, because it really is pretty hard to make enough money, to balance life with work, to find good clients, and to do all that while planning housesits, flights, and Airbnb stays around the world.

Attempting to work while housesitting...but mostly getting distracted by this guy
Attempting to work while housesitting…but mostly getting distracted by this guy





21 thoughts on “What it’s Actually Like to Freelance While Traveling The World”

  1. Yep, I know it’s tough and it’s nice to hear your thoughts on this. Thanks for mentioning my article on the subject, too. That one struck a chord with a lot of people and I couldn’t really believe the negative feedback I got — it seems some people really don’t want to believe entrepreneurship can be challenging. I know it sucks to talk about the downside of this kind of stuff, but it’s good to get it out—if not for others, than at the very least for yourself!

    1. Thanks Adam – I really couldn’t believe how negative the comments were on your article, either. We should be able to talk about the downsides of something, without being accused of whining. I think it’s important for anyone who’s thinking about this kind of life to see that it’s not all rainbows, all the time. I still love it, and I like it more now that I’m not working to tight deadlines, but there are definite downsides :)

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  3. This really is true. Now that we have location independent jobs we are way less free than before. We were in Siem Reap for 5 days before we had time to do a “half day” Angkor Wat tour. Most people do 3 full days. But it’s good motivation to get back to the time when we were more in control of our days.

    1. YES! For me, the struggle with freelancing was never really knowing when things were going to come through, and then when things were going to be due. But you’re right, because I know with location independent roles, many people have trouble setting boundaries beyond the 9 to 5. That sucks about Angkor though! I’ve been twice and the first time I did a 3-day pass, and the second time I was with Geoff and we did 1-day. If it makes you feel any better, I think 1-day is enough :)

  4. Sometimes I feel that people make big bubble of presenting how life is beautiful of traveling and living from it. We all people, no need masks, sometimes days are like shit, sometimes much better, for some need years to start living from writing, others lucky enough to reach it during couple of months:) The main things I think, no need to show things that are not real :)
    I really enjoyed to read this post, let make life real :)

  5. It’s all about perspective. Every life has struggles, whether you’re homeless, middle class and employed or independently wealthy.
    If you’re healthy and have enough to eat, everything else is small stuff. And you know what they say about the small stuff…

    1. Yep! All about perspective is totally right…unfortunately, not everyone shares this view sometimes! At the end of the day, we’re incredibly lucky and you’re right that most of our concerns are small in the grand scheme of things! Thanks Nat, and hope all is well with you! Xoxo

  6. I really enjoyed this post. Thank you for giving another perspective towards the digital nomad lifestyle. I have a well-paid job on a 9-month contract that I enjoy on the whole and that allows me time off to travel often and actually be part of the experience instead of online for most of it. On the side I blog about my travels for fun and earn little or nothing for it. Whilst I’d love to move and work abroad, having a stable income and being able to spend it on what I want is reassuring. Travel bloggers need to be careful when promoting an “escape from boring 9-5 life” – it’s not always the best option for everyone.

    1. Thanks for the perspective, Shannon! One thing I am really proud of in mine and Geoff’s life is that we’ve taken a lot of time and thought over the years to really define what our values are and what’s important to us, and one of them is definitely “freedom.” It sounds like you have a very clear idea of what’s important to you too, and are making choices that give you the stability your like! I think the key is “different strokes for different folks” – I definitely understand that full-time travel is not the ideal for most people :)

  7. Don’t know what I love more. The fact you’re being honest and talking about the struggle – I always tell people – it’s not all milk and honey running around and I try to keep my blog brutally honest. When I’m having a shitty day I say it so, cause reality of travel is as same as reality in life. I love also that you understand and are aware how in a way you are privillaged – being born in a society as yours. Truth to be told – lot of you westerns forget not all of the world has opportunities like you do. Thank you for sharing!

    Love peace and pancakes from Croatia

    1. Thanks for taking the time to share your thoughts and comment. Privilege is a huge component to being able to live this life, and I never want to forget it, because it really was luck of the draw. And you’re right that full-time travel isn’t all sunshine…sometimes it sucks trying to figure everything out and sometimes it’s really uncomfortable :)

  8. Awwww, I just saw this article today….and for what it’s worth, Terry and I did have an amazing trip and visit with both of you, laptop and all! What amazes us still, is that although you were swamped with the work you were doing then, you were ABLE to do it EVERYWHERE we went…on a train, at the Dome, in a Starbucks..you did not have to be strapped to a desk in an office like I am at this very moment (staring at my Prague screen saver).

    PS – didn’t you have a mini airplane bottle of wine on that train ride too??

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  10. This is a really interesting article! You always hear so much about the positive aspects of freelance work and so little about the negative side. Thanks for sharing such a balanced article!

  11. Oh man, thanks for this! You’ve really nailed it on the head, and freelancing while traveling is NOT as glamorous as it appears to be. I’ve figured out that it’s best to spend at least a month in one location (if possible) or else I don’t get a chance to see anything because I’m typically working.

    I hope you had the chance to step away from the computer and enjoy where you’re at – for at least a little bit today!

  12. I’ve SO been there! The last two U.S. road trips I took, I was working remotely. I thought I’d be able to catch up in places we stayed, but I ended up working in the car (and then feeling nauseous!), and got behind enough that I had to spend my 5 days in San Francisco working =( Not to mention my partner was annoyed at how much I was working and how irritable I was as a result! Never again, and now we travel much more slowly – we do a lot of housesitting too! It’s always harder when family and friends visit though, because then they see how much we are actually working and get frustrated about it. Still, I wouldn’t trade it for a 9-5 office job!

  13. I agree with this, of course!! I’m lucky though to be both employed part time and then be freelancing on top of this. As you say, always a stress when you need to work

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