4 Insights From Working on the Road

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Over the last decade, I have traveled and funded travel in many different ways. Working full-time and taking the odd long-weekend trip away. Using leave for a week or so of holiday travel, camping or road trips. Saving up for long overseas trips that take months at a time. And one backpacking trip that took eighteen months, funded by savings, volunteering, and working along the road. 

For the last two years, Kelli and I have spent most of our time in a van overlanding the Americas. Right now we spend eight to nine months of the year traveling and working on the road. We spend the rest of our time in Australia working remotely and saving money. 

During this time we have found the style of travel and the way to fund that travel that we find works best for us. Or, at least, that works best for us right now. Here are four insights I’ve come to find about working from the road.

Finding a Balance

Once, it seemed that the greatest thing in the world would be to have enough money to travel through the world non-stop without ever having to work again. Now that thought makes me feel very anxious. Over time I have come to find the balance I prefer is to work and travel simultaneously.

In 2016 after months of backpacking through Southeast and Central Asia and across Russia, I was exhausted. Tired of packing up my backpack every few days, tired of making friends and saying goodbye every week, tired of walking tours and pub crawls. All I wanted to do was stop somewhere and rest. Maybe get some work and stay put it one place, at least for a time.

Stopping to work in a hostel in Estonia in the middle of winter wasn’t necessarily ‘the’ solution. However, it was a decision that would set me on a course to find a more balanced approach to travel. And, ultimately come to find that combining long-term travel with remote work is not only achievable but also more enjoyable and sustainable.

Now I find, travel is all the sweeter when downtime is used productively to earn money or pursue projects. To look up from your laptop and find yourself in a foreign country. Ready to find a new trailhead, beach, or restaurant. Or to finish work for the week on a Thursday or Friday, pack up the van, and drive out of cell service for the weekend. We don’t get travel fatigue and we don’t (knock on wood) become jaded to our travel lifestyle. This is because periods of hard work punctuate our travel experiences.

And of course, it goes without saying that working from a beach in Mexico feels less like work than the nine-to-five grind ever did.

Expenditure Is as Important as Income

Mexican Pesos Money

This philosophy is not something I was raised with, it is definitely Kelli’s influence on our life. Her deeply ingrained need to live firmly within one’s means, combined with her background in accounting means we have an extremely thorough budget. And a multi-page spreadsheet measures every last peso, or any currency, that goes out.

If you have made the decision to step out of the rat race. To work less and do more, then it follows (for most of us) that there will be less disposable income. Luckily the logistical limitations of van life have already excluded us from accruing too much stuff. A lesson we have both learned before during our backpacking days and have readily re-embraced.

However, lots of daily costs can easily blow out your budget if you don’t stay on top of it. Thinking of costs as being comparatively cheap is a good example of a pitfall. Finding yourself in that mindset is a quick way to blow the budget.

Working on the road can undoubtedly decrease your earning power. But with careful budgeting and by tracking every cent that you spend, you can have a much greater understanding of how one hour of earnings is being used. With that understanding comes the power to more effectively choose how you spend your time.

READ MORE: How to Create a Travel Budget

The Job You Want Is Hard to Know and Harder to Find (…But It Is Out There)

From My Own Experience

When I backpacked in my mid-twenties I was always thoroughly impressed by digital nomads. Those that had pulled themselves up by their virtual bootstraps. Travellers living on the road while operating online businesses or freelancing. But I couldn’t see how anything I had to offer would ever translate to remote work opportunities.

For me, it was simply living on the road and watching how other people did it that allowed me to slowly transition into remote work. Friends teaching English in Vietnam. Discovering a program in Poland where I could volunteer to teach English in exchange for full room and board and an English teaching qualification. And finally making the decision that I wanted to prioritize my lifestyle goals and reverse engineer any sort of career around that.

When I finally took the plunge and began teaching online I was also pleasantly surprised it was a job I got more out of than many jobs that had come before. But the real satisfaction I derive from my job is that it fits so well into my life that I have decided to make about more than just my ‘career’.

Observing Kelli

I have also watched Kelli go through the process of adjusting to the realities of becoming a full-time traveler. Moving from a senior role in a big four accounting firm to finding something that was compatible with a nomadic lifestyle was difficult. Jobs that would interest her and would offer pay commensurate with her experience were not exactly everywhere. Unfortunately, the truth for accountants and many other professional service industries is that most businesses are reluctant to accept that their technical accountant will be working from a jungle in the darkest Peru and that’s understandable. 

It took her months to finally get a job. Through those months there were periods of deep doubt. As she burnt through savings with little progress to show for it. But her perseverance, flexibility, and ability to sniff out every opportunity have resulted in two jobs that have given her the flexibility to work remotely in positions that challenge and interest her.

These are specific examples related to us. But, in our travels, we have met people from all walks of life doing every type of vocation from the road. It may take some creativity, some time, and some hard work. It will probably take some low points when you wonder if all of it has been for nothing and you’re going to end up where you started (or further behind). Working from the road may seem like it narrows your choice of jobs. But, a job to suit every type of traveler is out there. The first step is trying to figure out what you need most from your job and working backward from there.

Giving Time to Your Passions

Attempting to podcast from inside the van

Right now the sweet spot for us is 20 – 25 hours a week working to keep gas in the tank. And 15 – 20 hours a week into our various passion projects. In that time we write this blog, take photographs, and work on our podcast and our vlog. Outside of this, our time is ours to devote to our life of travel. Learning, planning, driving, reading, swimming, exploring, cooking, and of course eating and drinking.

So, what we’ve come to find while trying to escape the daily grind is we are at our most content with a 40-hour work week. We just require the autonomy to do it how we want. Furthermore, some of that ‘work’ time needs to go toward projects we love and believe in. And we want to be able to finish working and invest ourselves fully in the rest of what we do that makes up our life.

What else would you like to know about our experiences? Check out our other Van Life lifestyle articles.

What have you learned working on the road? Let us know below.

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