How To Travel Full Time While Working On The Road (Includes Q&A With A Veteran Of 9 Years)

Today’s article includes a Q&A with Nora Dunn, a Canadian who sold everything (including a busy financial planning practice) in 2006 to embrace her dreams of long-term immersive travel. She runs, a blog dedicated to the art of making travel financially self-sustaining, and has written several books on various aspects of the lifestyle – in short, she’s a real expert on combining work and travel.

Her expertise is particularly relevant right now. I no longer rent a property. I possess only one bicycle (yeah, I know!). And everything I need to live fits into either a 75-litre backpack or a pair of bicycle panniers, depending on what’s more appropriate at the time.

Not only that, but my working life travels with me too. The work is either location-independent or tied to the act of travelling itself – recent ongoing examples include shooting a feature-length documentary, editing video, writing blogs and books, setting up websites, even launching a new touring bike and co-ordinating a Kickstarter campaign.

I’ve designed my work so it doesn’t matter whether I’m in in Argentina, Australia or Austria. Today I’m in Angel (Islington), next will be Armenia – and after that, America. (All alliteration accidental!)

I really believe combining work and travel has never been a more achievable aim for a great many people. But it does require a fair bit of groundwork and a knowledge of what’s possible and realistic. This post aims to introduce some of these ideas.

So, without further ado, over to Nora, who’s much more of an authority on the subject than I am…

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Firstly, thank you, Nora, for agreeing to do a Q&A for the blog. Why don’t you tell us a bit about yourself and your experience combining work with full-time travel?

Thanks, Tom! It all started in 2006, when I sold everything I owned (including a busy financial planning practice) to embrace my dreams of long-term immersive travel. Annual 1–2 week vacations weren’t cutting it for me any more; I realized that in order to do the things I wanted to do in life and around the world, I couldn’t afford to wait another 30 years for a conventional retirement, at which point I might be unwilling or unable to travel like I really wanted. I had to do it now.

As for the process of combining work with full-time travel, that was an evolution. Initially I had no idea how I’d make ends meet; I had a loose plan to take a course with Outward Bound in Costa Rica to become a qualified outdoor education instructor. It never happened though, since my travels took me in another direction (and then another, and then another…).

But shortly after hitting the road, I realized that my lifelong penchant for the written word plus my laptop and an internet connection could equal a living as a freelance writer. The sale of my business provided a (small) 2‑year stream of income that I used to float my expenses and travel lifestyle while I built my new career as a writer on the topics of travel, personal finance, and lifestyle design.

Developing my niche happened naturally (although not without lots of hard work); I wrote about finance for travel publications, I wrote about travel for finance publications, and I wove lifestyle design throughout. Once I realized my own website could be more useful than just as a glorified travel journal, I combined these three topics on my site to teach people how to travel full-time in a financially sustainable way.

Yours seems an increasingly common ambition – to remodel a jobs and career to incorporate travel. But for a lot of aspiring bicycle adventurers, the journey comes first, with work often seen as something that needs to be put on hold – hence, we save up, do the big trip, and reluctantly return to work at that end. How would you suggest we reframe the two things to exist together? What are some of the options for combining them?

Where there’s a will, there’s a way! But sometimes, that way involves a little compromise.

One of the compromises an aspiring bicycle adventurer might concede to in order to incorporate their careers into a full-time/long-term travel lifestyle would be to travel more slowly. Instead of conquering a continent/country/whatever in a specific period of time and riding hard each day, consider setting shorter goals so you’re not on the road constantly, and take some more time off along the way so you can allow time to work.

Slow travel has an added benefit of being more culturally immersive and rewarding, as well as ultimately cheaper (for example you can get access to cheaper – even free – medium/long-term accommodation options).

Many of us who are planning long bicycle journeys spend months or years saving up money, reorganising our lives, and preparing to leave. In terms of creating opportunities to make a living while travelling, how would you suggest we approach things during this preparation time?

If you are planning on making travel a lifestyle (with income opportunities) instead of a fixed-duration trip (as in a vacation), the entire scope of your preparation and reorganization changes.

First off, you’ll need to decide what to do with your stuff, such as selling or storing it. There are also logistical things to address such as cancelling services and organizing your affairs and finances to travel long-term/full-time.

Then of course, you’ll need to develop a strategy for earning money while you’re on the road. Despite the fact that I figured my income stream out along the way, I wouldn’t recommend following my footsteps; I always advise people to have a strategy in place, and if they’re starting a new business or career I advise them to have that foundation established before they start travelling.

As for saving money, that doesn’t change; you need to save money! However the amount you need to save might be less if you have an income stream. Here’s some food for thought with regards to what you should save up for long-term travel: How Much Money do you Need to Travel Long-Term?.

(I also discuss all these matters in detail in Working on the Road: The Unconventional Guide to Full-Time Freedom*).

Long-term bicycle travel attracts people at all stages of life, from school-leavers and graduates to those in later life who are looking for a change. How might our former work experience (or lack thereof) affect how feasible working on the road would be? In other words, do you think age and experience matters?

Age and experience matter, but not in a make-it-or-break-it kind of way; instead age and experience (or lack thereof) simply provide different opportunities.

Young travellers (under the age of 30) can take advantage of working holiday visas to stay 1–2 years in each of a variety of countries with the ability to get a job doing whatever they’re qualified for. This is a great way to develop work experience and still enjoy a travel lifestyle.

On the other hand, I started travelling full-time after 30, and I was grateful for my time and experience in the traditional work-force in Canada. I was able to put money away for (my eventual) retirement and get some general financial footing (as well as life experience) that helped me in my travels.

As for getting work on the road as an “older” traveller, that’s not difficult either. In Working on the Road, I interviewed a woman “of a certain age” (she’ll admit to six or so decades) who teaches English abroad, as well as a couple in their 40s who has no troubles getting jobs along the way as they travel full-time. They are just two random examples of a myriad of income-earning possibilities for people of any age.

Cycling often involves long periods of overland travel in remote areas where mobile working would be impractical and undesirable. How might income generation work in this case in the long term? Is it feasible, for example, to run an internet-based ‘microbusiness’ in spite of such protracted downtime? Or would another approach be more appropriate?

If you’ve got a long ride to make that will involve being offline and out-of-touch for a while, there are a few solutions you could develop:

  • Create a business that doesn’t require you to be constantly online (not always easy to do as a location independent entrepreneur but certainly not impossible)
  • Develop the business to a point where you can hire somebody to take care of things while you’re offline
  • Instead of internet-based jobs or businesses, focus on getting jobs “on the ground” between long bicycle trips

The beauty of lifestyle design is that it’s yours to design. It’s up to you to decide what kinds of bicycle trips you want to do the most, and where you want to do them, and then find the right work opportunities to complement that lifestyle. There’s always a bit of compromise here and there, but ultimately you get to call the shots.

Conversely, after weeks or months of pedalling, a lot of us feel the need to decompress and digest, which often involves staying in one place for a while. Might we use this time to find temporary work? Do you think it matters precisely where this happens to be? 

I can imagine you’d want some downtime after a long bicycle journey! I certainly do after a long stint of active travel.

Indeed, these rest stops are a good opportunity to find temporary work, for example with a working holiday visa in hand, or some transferrable skills and good networking abilities, or with online telecommuting or entrepreneurial work.

Location dictates working opportunities to an extent; for example in Asia working holiday visas aren’t generally available, but you can get a job teaching English. In most developing countries you are less likely to find a decent-paying temporary job, but the cost of living is cheap if you have an online business and are earning money in a stronger currency.

As bicycle travellers with a large degree of self-sufficiency, we can often stretch our budgets out to enviable proportions – 5 to 10 dollars a day is totally realistic. But setting up to live and work somewhere must carry overheads. How might we handle this and ensure we can actually save our earnings to further our travels?

Actually, setting up to live and work somewhere doesn’t have to be expensive – at all. For example, when you’re planning your “decompression” stops, these can be opportunities to get free accommodation.

For the first six years of my full-time travels, I travelled from one free accommodation opportunity to another, utilizing techniques like volunteering, house-sitting, living on boats, hospitality exchanges, and more. Free accommodation gigs can last from a few days to a few months, and they exist around the world.

Added benefit: you don’t need to earn as much money when your accommodation is covered! For more information, you’ll want to check out my first book: How to Get Free Accommodation Around the World.

Finally, many of us are concerned about how we might return to a more settled existence once our wanderlust is (at least temporarily!) satiated. How might the skills and experience gained while working on the road translate to a more conventional style of living?

I don’t know anybody who has had an easy time reintegrating to a conventional style of living after an extended period of travel, but it’s certainly possible (and sometimes even enjoyable).

If your work on the road is of a location independent nature, not much will change for you in terms of incorporating your career into a conventional lifestyle. For job-searching employees, although you might think you’re hurting your resume with time spent abroad, most employers I’ve spoken with view world travel and work-abroad experience very kindly when it comes to hiring. Travel experience demonstrates flexibility and adaptability, courage to face new situations, problem-solving skills, ability to cope with stressful situations, and willingness to get along and communicate with different kinds of people.

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Thanks Nora! Do check out her new guide and resource, Working On The Road: The Unconventional Guide To Full-Time Freedom*. Despite already being well on the way towards this kind of lifestyle, I bought the guide as soon as it was released, and found that it massively enhanced my understanding of what’s possible and how to achieve it.

Comments (skip to respond)

One response to “How To Travel Full Time While Working On The Road (Includes Q&A With A Veteran Of 9 Years)”

  1. Tom and leon,
    Just watched the 15 min version of Karun.
    I am touched by your love for what you do and grateful for your love of Iran.
    Babak Emadi Paramkouhi

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