Work and travel? 10 pros and cons of freelancing on the road

Is work and travel by freelancing for you? Is work and travel by freelancing for you?

While Sarah and I managed to accumulate a small pile of cash from selling everything we owned before leaving on our nomadic adventure, we knew we were going to have to work and travel if we wanted to do this for the long haul. Not only did we need to cover our travel expenses, but we also had two mortgages to service, and the rental income didn’t cover the repayments.

When we got to Thailand, about five weeks into our trip, I managed to get a job teaching English in Chiang Mai. It was only 16 hours a week which gave me plenty of time to explore the area, but the pay was ordinary by Australian standards at $US9 per hour. That meant while I made enough to enjoy living in northern Thailand, it didn’t even come close to covering the mortgage repayments back home.

It was during our two month stay in Chiang Mai that Sarah started working online as a freelance writer. She signed up to a couple of freelancing websites and began applying for writing jobs. Despite having no experience as a writer, in no time at all she managed to acquire several clients via Upwork. Initially she was working for roughly the same amount of hours as I was, for roughly the same hourly rate, but the opportunity for growth was obvious right from the start. We saw other freelancers charging much more than we were, with a number of regular clients willing to pay for good content. We knew if we did a good job in the early stages, received good reviews and five star ratings from our clients for our work, we’d soon be able to increase our rate substantially.

When we left Thailand we spent a couple of weeks travelling through northern India before settling in Abu Dubai with a friend of Sarah’s for a month. It was during this period we started to really attack the freelance writing opportunities available to us on Upwork, and before long we had had four or five clients each, and were charging $US20 per hour. Within three months of leaving the UAE, travelling through Europe and settling in France, we’d upped our rate to $US35 per hour and had even more clients. Now we were earning enough to work and travel, while covering our mortgage commitments back home.

It sounds perfect right? Within 4-5 months we were earning enough to travel the world while covering our mortgage repayments back home. But is work and travel everything it’s cracked up to be? Here are 10 pros and cons of freelancing on the road that you should consider before quitting your job to work and travel.


Location independence

Working away on the blog in our 4-berth soft sleeper

Working away on the blog in our 4-berth soft sleeper

The obvious benefit to being a freelancer is you can do it anywhere. There are so many online freelancing opportunities that you can literally be anywhere in the world while working for a client who is based somewhere else in the world. For example, I started looking after the social media platforms of a Canadian company who sold men’s grooming products online. We had clients in Australia, the United States, New Zealand, the UK and other countries around the world, all while working from our laptop in Southeast Asia and Europe.


Not only can you work from anywhere, but you can work at any time during the day or night. As a traveller this is the perfect situation, because you want to be out exploring as much as possible. The last thing you want is to be travelling through countries you’ve dreamed of visiting, only to be stuck behind your laptop all day every day.

It can be lucrative

Depending on your skillset, freelancing can be quite lucrative. Despite having no formal writing qualifications or experience, Sarah and I both managed to secure long term work for $US35 per hour in fairly quick time. Imagine how much we could charge if we had specific skills and formal qualifications? For example, I see scientific writers, designers and coders charging upwards of $US100 per hour. If you dedicate yourself to acquiring these skills before leaving your home base, you can lead a very comfortable existence as you work and travel.

Choose what you work on

Unlike at a regular job where you work for someone else, as a freelancer you can pick and choose the projects you want to work on. If you’re offered a job and it doesn’t get you excited, politely decline the offer and look for something else. Imagine trying to dictate to your boss at a 9-5 job what you are and aren’t willing to work on. That kind of attitude would see many people fired before too long. As they say, variety is the spice of life, and as a freelancer you can choose your clients and the projects you want to work on.

You are your own boss

You won’t have anyone telling you what to do or when to do it. Of course you’ll have agreements in place with your clients about when the work will be delivered, but how you achieve those goals is totally up to you. Start work at midday by the beach, stay at home in your underwear all day, stop for an hour or two to hit the gym or catch a movie, the choice is yours. There will literally be no-one looking over your shoulder while you work.

Work life balance

Chris, Sarah and a sleepy Jack on our tour boat

Chris, Sarah and a sleepy Jack on our tour boat

If you’re smart about your work, you can enjoy a wonderful work life balance. We’re travelling with our three year old son, and it’s amazing that Sarah and I get to work from home (wherever that might be at any given moment) and spend so much time with him during his formative years. We also get to take a break and go away for a few days or weeks when we want, start and finish when we want on a daily basis, and spend more time with each other than we ever did back home in Australia.


Wi-Fi issues

One of the most frustrating problems with work and travel are Wi-Fi issues. Back in Australia, either at home or in the office, we had a strong and consistent Wi-Fi connection at all times. It very rarely went down, and if it did a quick call to our provider would have the issue fixed in no time. On the road it can be much different. In some parts of the world a consistent internet connection can be hard to find, while in other parts of the world getting Wi-Fi issues resolved can be incredibly frustrating. We’ve had to go in search of a Wi-Fi connection to get work done plenty of times, with cafes, restaurants, libraries and tourist centres our go-to locations. In France when the Wi-Fi went down at the house we were housesitting, it took three weeks for us to find someone who could call the provider, explain the situation and have them send someone out to resolve our issue.


More often than not you'll be working alone

More often than not you’ll be working alone

Working as a freelancer can be a lonely experience. One of the great positives of working a regular job is the bonds and friendships you form with co-workers. As a freelancer you’re often working on projects alone, and the isolation can be a real issue for people who enjoy interacting with people. With workspaces opening up everywhere you go, where you can rent a desk on a weekly or monthly basis alongside other freelancers, there are solutions available. But it’s not always like that, and you may have to get used to the loneliness if you want to be a freelancer full-time.

You still have to get your work done

It’s true you get to set your own hours, and you can do other things as mentioned in the Pros section above, but you still have to get your work done. I’ve read plenty of articles about freelancing where people make it sound as though you never have to work, but nothing could be further from the truth. If you want to earn a good wage, you’re probably going to have to work just as much as a regular 40-hour a week office employee. So if you want to get out and about during the day, that’s awesome, but just remember you’re going to have to put in a shift that night to earn the money you need to sustain your travels. You’ll need good time management skills, and be able to block out distractions. It takes time to find your groove, but with perseverance you’ll eventually find the right balance for you.

Carry your office with you

Our tech kit (minus the go pro)

Our tech kit (minus the go pro)

Depending on what you do, you’ll have equipment that you’ll need to carry around with you wherever you go. At a bare minimum that means a laptop, mouse, power cord and hard drives. Some freelancers need to carry other equipment like cameras and tripods. It also means being very careful that your equipment doesn’t get stolen, and having insurance in case of theft, loss or damage. If something happens to your equipment and you’re not able to replace it quickly, chances are it won’t be long before you’re feeling a financial strain. Be smart with your equipment, keep an eye on it at all times while moving from one place to the next, and make sure it’s insured.

Inconsistent income

One month you might be rolling in cash, while the next month the work could dry up. That’s the reality of freelancing I’m afraid. Some people are lucky to have clients who have consistent work for them, but for many it’s a constant process of searching for work. Unlike working for someone else, you must go in search of your own work. This time spent is unpaid, and rejection can be deflating for some. You need to be dedicated to the chase for clients, and move on quickly when those jobs you really want slip through your grasp.

Work life balance

I’ve put this one in both the Pros and Cons sections, because freelancing can be a poisoned chalice. While it may seem like the perfect way to spend more time with your family, doing all the things you want to do and spending less time working, it can actually go the other way for many people. Because all you need is your laptop and an internet connection, people fall into the trap of working all the time, and that defeats the purpose of traveling, right? We’re so connected with our Smartphones and laptops that we find it difficult to put them down when we’re freelancing. Because of the inconsistent income stream, we feel as though we have to take every job that comes our way, and that leads to even longer work hours and burnout. Plan your work life carefully, learn to walk away from the laptop, and give just as much priority to your leisure time as you do to your work time.

The world has opened up to such an extent that more and more people work and travel full-time. The idea of living a comfortable nomadic existence while experience a diverse range of cultures and countries is not as far fetched as it once was. In fact, with opportunities like housesitting, couchsurfing, carpooling, hospitality exchange and work trade making long term travel cheaper and more accessible than ever before, it’s now easy for people willing to take that initial leap of faith.

Freelancing is one way to make full-time travel possible, and with a little dedication, perseverance and commitment, you could soon be living your travels dreams while earning enough money to sustain your lifestyle indefinitely. It just takes getting over the initial psychological hurdle that the comfort of a 9-5 job creates, but once you realise it’s not as hard as you might think, you’ll wonder why you didn’t quit your job and go travelling much, much sooner.

3 Comments on Work and travel? 10 pros and cons of freelancing on the road

  1. I love travelling solo but I decided to take paying customers with me and share the discoveries and build our collective online photo archive. Guiding photographic tours is a lot of work and adds stress to the journey but it allows me to spend more time travelling and documenting the regions in photos.

  2. Thanks for this deep insight into freelancing on the road. When we dream about this kind of life we tend to imagine that it’s the perfect life. But as you say, you still have to work. And working at home is quite difficult, it’s easy to get distracted and at the same time it’s easy to get into a routine of working all time, forgetting to take breaks…
    I’ll keep in mind your advice: plan your work life carefully, learn to walk away from the laptop.
    Laia recently posted…Northern Thailand by motorbike (1): coming out of my comfort zoneMy Profile

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