How I Work On The Road, Pt I

Work while traveling on the road
Work on the road

I’ve run a digital enterprise on the road for the past few years, and it’s been more of an evolutionary process, instead of one that simply happened right away.

I’m currently in the surf town of Muizenberg, 30 minutes south of Cape Town, South Africa.

I’m volunteering as a duty manager at a hostel, trading my four days of work for a bed in a dorm, cheap food, and free coffee.

This allows me to stay for free on the road, while providing me enough time to enjoy my surroundings and spend sufficient time to maintain my own business.

I’ve run a web design and development agency for over 15 years now, starting when I was in Toronto, Canada.

While I’ve since relocated to Melbourne, Australia, my work has remained constant, and I’ve added knowledge, skills and smarter services along the way.

When I tell fellow travellers about my trip, and that I run my own business on the road, providing me the means to travel, they’re usually impressed and want to know how they can do the same.


Some Realities About Traveling

It sounds dreamy. You roam the planet, anywhere from remote, exotic landscapes, to bustling urban metropolises. You encounter a litany of intriguing personalities, making heaps of new friends along the way.

While these are readily possible and all very nice, each of these elements contribute to the single-most thwarting energy of any trip: Distraction.

You require a certain degree of discipline and self-motivation to work on the road.

I.e. – You have to get your work done!

If you have clients or an employer, you need to be able to communicate with them, and deliver on time and within budget. If you have a publishing schedule – e.g. when writing a blog – you have to adhere to practical release dates.

It’s easy to be stuck in transit without communication for days, whether there is a lack of signal, infrastructure, or your battery dies with no means to charge it.

It’s even easier to meet a cool crew of new people in some awesome place and be invited along to see sight after sight, or go out night after night. It’s a lot of fun!

Being organised, making the occasional sacrifice to stay in instead of make road trips or party, and ticking things off your daily task list will all help.

You have to remember it’s not quite a holiday. Your trip is happening because you’re working for it, and out of that there should be a natural respect for that work and the people helping pay your way.

Crime and safety are two other important considerations. For the most part, you’ll be in foreign locations, more dangerous than what you’re used to. Robberies, muggings and even kidnappings are common. You need to be careful, for yourself and your belongings.

Travel insurance is crucial. Services like World Nomads offer low cost travel insurance and benefits for every region in the world.

I recently broke a tooth off on a hard South African biscuit called a rusk. Over $700 of dental expenses later I have a new crown on my tooth, and I recently learned my claim was accepted and would soon be paid for.


Some (Nicer) Realities About Traveling

If you can handle getting your work done and take proper precautions for your health and safety, there are some enduring reasons to travel and work on the road.

First off, most places you visit will be incredibly inexpensive compared to where you’re used to. For instance, I live in Australia, recently named the most expensive country in the world. Everywhere is significantly cheaper than Australia! If you’re from Europe, North America or Brazil, you will find similar savings.

This means you don’t have to work as much and/or make as much as you would otherwise have to in your home city. Money goes a long way – food, drink, alcohol, transport.

Accommodation can be the most expensive variable, but you can book a bed in a nice hostel dorm for anywhere from $10-20 a night. I usually research hostels on Hostelworld and find popular ones with high ratings in a good area. If you don’t like the sound of bunk beds, just try it out! You get used to them pretty quickly. There are female-only dorms in a lot of places, and upgrading to a private room still works out much cheaper than a hotel room.

The advantage of hostels is meeting a lot of people, and having access to better trips around the local area.

If you’re really stuck for coin, you can do what I’m doing in Muizenberg – offer to work in exchange for room and board.

Just make sure you’ll still have enough days and hours to get your work done and sufficiently enjoy yourself.


Getting To Work – What Can I Do?

If you love the idea of working on the road, but have no idea what you could actually do, there are lots of options.

My own means was quite simple, as it’s an extension of the same work I’ve done since 2000: web design and development. What’s allowed me the freedom to travel more and more has been setting up my business in a way where most of the nitty gritty work is performed by people and companies to whom I outsource many tasks. This adjusts my role to handle bringing in leads, sourcing what clients want, issuing instructions to my developers, and handling all the work that isn’t able to be outsourced.

When I first started in the web business, I was putting in 80-100 hours of work a week, but over the past few years, including a study of Tim Ferris’ The Four Hour Work Week, I’ve since learned to delegate and free up a lot of my time. I’ve cut out most of my hands on hours, freeing me up to work on my own projects as well as bring in new work, and I’m in a much better space because of this.

If you’re in the creative arts, such as a designer, developer, illustration, video editor, writer, etc… You will be able to set up something similar.

If you’re not – or would rather do something else – you have options:

  • Set up an online store
  • Set up a website that gains traffic interested in your offerings, with the purpose of driving people to affiliate sites, where you earn commissions on sales. Enough traffic and you can look into ad revenue as well
  • Set up a popular social media resource to the point where brands pay you money to share them
  • Envision a venture, a service or a project that you’re interested in developing. Find an awesome domain name. Set up a landing page to start tracking interest. And begin building it.
  • Consult. It can be anything from professional advice, to mentoring, to online tarot readings
  • Teach a language


Building a Digital Enterprise

Landing pages are useful for any of these options, or for freelance professionals such as designers. They drive traffic and leads to your offer or information, and if set up properly can liaise you directly with those interested in what you have to present. You can run ad campaigns with targeted traffic, and utilise retargeted ads to follow up on anybody that visits your pages or website.


In the next part of this series, I’ll show you how to rapidly build a new idea by thinking of a domain name and putting up a quick landing page to start capturing interest and feedback.

Once you have the confidence that your idea might work, you can start making those travel plans and work towards them.

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