How I Quit Quitting Jobs and Became a Digital Nomad

Last year, I decided to leave my steady high-tech job. It wasn’t because I was unhappy. I liked my job. I liked my coworkers. Most days, I even liked the work I did. I had tons of perks, a good team, and a steady paycheck. Still, more often than I care to admit, I’d find myself sat at my desk staring at a piece of content that needed to be edited, day-dreaming of white-sand beaches and bustling street food markets. 

If I’m being honest, I don’t have the best track record when it comes to holding a job. I’m not a bad employee. I think I’m actually quite a good employee. The problem is that I have a history of not being able to stay in one place for too long. I’ve quit my job so many times (five, to be exact) in order to travel that it’s become a habit. 

When I was in university, at the ripe young age of 18, I left my part-time retail job in order to participate in a creative writing retreat in Kenya. The moment I came back, I applied to go on a student exchange in England the following year, so after getting that same retail job back, I left again.

Fast forward a couple of years, I tried and failed to quit my corporate job, and instead took two months of unpaid leave in order to travel to Europe with a friend. To absolutely no one’s surprise, I immediately started looking for more opportunities to go abroad as soon as I returned. I decided that within the year, I would move to Israel to volunteer as an English teacher, and also squeeze in a cheeky three-month trip to Southeast Asia right before. And then I did what I do best: I quit my job to travel. Again.

When I was faced with the prospect of quitting yet another job last year, a job that I enjoyed, in order to travel, I started having second thoughts. How many times would I be able to find a new job when I get back? Surely, prospective employers would begin to wonder why I keep starting new jobs each year with large gaps of time between them. It’s one thing to do this in your early twenties, but this habit of mine wouldn’t be sustainable in the long run as I try and become one of those elusive “responsible adults” and establish some semblance of financial stability.

My original plan was to travel for two months in order to complete The Mongol Rally over the summer, however, the more I thought about it, the less sense it made to quit my job for a measly two months. If I was going to do it, I had to really do it. So I extended the timeline to six months, and I gave myself an objective: earn money on the road.

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The Mongol Rally, passing through Ashgabat, Turkmenistan with Freddy, our trusty Fiat Panda.

I always considered freelance writing a pipe dream, something that other people do successfully, but not me. I wondered if I had the discipline, or even the network I needed in order to succeed. Despite all the doubts, I knew I owed it to myself and my dreams to at least try. At the very least, I had safeguarded myself with enough savings to fail within my self-assigned six-month timeline.

After my summer driving across Europe and Central Asia, I found myself in Southeast Asia yet again. Except this time around, my trip would be different. Instead of spending time nursing bucket-sized mixed drinks, I would spend a chunk of my time working, honing my skills, and growing my business. I set myself a goal of gaining a new client each month. Some months I didn’t even know how I’d achieve this, but each month I magically found myself growing. The growth was slow, but it was steady.

Four months after beginning my digital nomad journey, I earned enough to cover my travel costs and save money. I was shocked. I told myself at the beginning that if I only made enough to cover my monthly spending so that I didn’t have to dip into my savings, I’d be happy. Now that I was also saving money, I felt like the world was at my fingertips. 

My six-month Asian travel itinerary quickly evolved into a plan that included a 6-12 month stint in Central and South America, divided by a quick stop to say “hello” to some friends and family in Israel and Canada.

When I was living in Tel Aviv, it was always difficult to decide whether I wanted to spend my limited vacation time traveling somewhere new or visiting friends and family back home. As a location-independent freelancer, I now have the freedom to choose both.

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Working on my work/life balance near some rice fields in central Sri Lanka. Definitely not posed.

As the COVID-19 pandemic quickly shuttered borders and stranded travelers, the Latin American leg of my intended global tour got scrapped and all my plans had to be put on indefinite hold. I was lucky enough to get back to Canada just in time after being stuck on a remote island in India (that’s a story for another day).

Though times are challenging for freelancers and salaried employees alike, I’m still able to earn regular income while in lockdown. Unsurprisingly, travel writers haven’t been in demand much lately, so that branch of my freelance business has sadly been very quiet. Being able to write for a living while so many people are struggling with unemployment or unpaid leave has made me realize how much of a good decision this was for me. Sure, my workflow can change from month-to-month, but that’s a risk every freelancer accepts. At the very least, I don’t have to rely on one source of work to earn a living, and I’m thankful for that. 

What’s next? Well, I’d like to be back by a beach sometime soon. Canada’s great, but it’s cold, people are suspiciously nice, and honestly, I’ve started to miss the salty air and attitude of Tel Aviv. Ideally, I’d like to be able to base myself in one place and have the flexibility to pack and bag and say “I’m going to Mexico for a month and I don’t have to submit any time-off request BYE.”

Will I ever go back to working regular office hours, in a regular office, with regular meetings and regular allotted vacation days? Maybe. I won’t rule it out completely. But for now, I’ve earned the coveted-yet-trendy title of “digital nomad,” and I intend to keep it that way for as long as I still enjoy it.

So, that’s my story. What’s yours? Do you need help with a story you’re trying to tell or an article you need to be written? Start by getting in touch and let’s make it happen.


  1. ปั้มไลค์

    Like!! I blog frequently and I really thank you for your content. The article has truly peaked my interest.

  2. Mikhal Heffer

    I enjoyed the blog. It’s great how freelancers can take off and work from any place around the world. It’s a great working option – as a writer, translator, and many other professions. that you can do it all online. So now it’s so easy to combine business and pleasure. Keep up!

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