Adventure Lifestyle Budgeting & Finance Interviews

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.

Budgeting & Finance Inspiration Interviews Planning & Logistics

Don’t Bother With The Whole Sponsorship Thing

A few weeks back I joined seasoned round-the-world cyclist Alastair Humphreys for a coffee in a secret location in central London (OK, it was the British Library canteen) in order to chat about bike trips — specifically, bike trips that could be made for under £1,000 and within the average annual holiday allowance. It’s all part of Al’s excellent #Adventure1000 project for 2014. What follows is an edited transcription of exactly what we discussed. Enjoy…

Alastair: My Adventure1000 interview today is Tom Allen – cyclist and filmmaker – chosen solely because of his beer can stove, about which more later… Could you start by outlining the biggest expedition that you’ve been on?

Tom: The biggest expeditions I’ve been on were cycling from the UK to Armenia over eight months, cycling around the Middle East and Africa for seven months and I’ve also done trips in Mongolia for two months and down the West Coast of the U.S. for two months as well.

Six pannier setup

Stopping for the night in the Nubian desert

Storm coming in...

Alastair: This is the sort of question that’s hard to answer and generally quite irritating when you get asked it, but I think it’s quite important: could you try and give just a couple of the highlights, the sort of things that you’ve really loved about these big adventures?

Tom: I think the biggest thing is the fact that you wake up in the morning and you have no idea where you’re going to end up at the end of that day, and you have no idea what you’re going to see or who you’re going to meet, that’s kind of what adventure means to me anyway. It’s the unpredictability and the surprises and the unexpected, and the knowledge that it’s very, very rarely a bad kind of surprise. You know, it’s usually pretty positive stuff.

Alastair: So let’s talk about your first big bike trip. Why did you choose to do that? Why didn’t you, say, go for a long walk or climb a mountain? Why did you decide to cycle?

Tom: Well, the reason I decided to cycle was, firstly, because it wasn’t about a physical challenge and I thought that a long walk would be a lot more gruelling than riding a bicycle, and as far as climbing mountains and stuff like that’s concerned, that wasn’t really what I was interested in. I was interested in exploring countries, meeting people, exploring cultures, and I wanted as much versatility in my means of transport as possible, and with the bicycle you can carry everything you need, but it’s not on your back, it’s on your bike, and that’s a lot more pleasant way of doing it.

You’ve also got a massive range of distance that you can cover in a day, from as little as you like to up to, on a really good day, maybe a couple of hundred kilometres.

Alastair: And what were you doing directly before you set off on that trip?

Tom: Before I set off I spent a year planning the first trip, which is way too much planning to be quite honest, but it got me to begin. I was working as a freelance website developer. I’d finished university for about a year when my friend Andy came up with the idea. I was at a bit of a loose end, wasn’t convinced that I was doing the right thing career-wise, and just wanted to do something a bit different while I was still young and uncommitted and had that freedom.

July 2009

Alastair: Before you went, you had a year of planning and daydreaming. During that year, what were the main worries you had about that trip, and what were the worries that perhaps family were trying to impose on you, and then how did those worries compare to any problems you actually had during the journey?

Tom: I got massively bogged down in the intricacies of bicycle mechanics and what might go wrong mechanically. Massively, I mean ridiculous. And so I spent most of that year researching bicycle parts and deciding what would be the ideal components – you know, the ideal brakes, the ideal suspension, the ideal carrier rack and all this kind of thing. And I didn’t really pay much attention to the routes, I didn’t really pay much attention to the realities of how it would be to be living on the road, and I had no experience to go on in that respect either.

And so I was really just researching something I didn’t understand very well, and I guess the reason why was to try and build up confidence in something which I really didn’t have any experience in.

Alastair: How much training did you do for setting off to cycle around the world?

Tom: I did no training whatsoever. I didn’t even finish building the bike until the morning I left. I didn’t have time, because the last few weeks of preparation were so frantic in terms of getting the stuff, getting the gear together, that I didn’t actually have any time to test any of it.

Travelling Light

Alastair: I remember the night before I set off to cycle around the world, my bike pump just arrived in the post, and I undid all the packaging and threw it all in the bin, then realised I’d thrown away the little nozzle bit that does the pumping, and my Dad had to empty the entire house’s bins over the back lawn to find this nozzle. I didn’t do any training either, on the assumption that you can have too much of a good thing and there was plenty of time to get fit along the way.

Tom: Yeah, I think when it becomes a lifestyle, and especially when it’s not trying to do anything particularly athletic, you can afford to go a little bit slowly at the start. You can afford to break yourself in a little bit more gently. The more time you’ve got, the better, obviously. The funny thing is, for shorter trips training makes more sense because you’re more time-restricted and your ability to pull the trip off depends more on your fitness in the first place, whereas if you’re going off for months or years, you’ll be as fit as you’ll ever be within about the first month, regardless of how fit you are to start with.

Alastair: The fact that your bottom hurts for two weeks matters less when your trip’s a year long than if your trip is only two weeks’ long…

Tom: Exactly. It’s a real pain in the ass.

Keep reading this interview at And join up for #Adventure1000 (free) if you haven’t already!


An (actually interesting) long-form interview on BBC Radio Leicester

Today I leave on a new journey, exploring language-learning in Iran. I’ll be on my way to the airport by the time this is published.

But yesterday I was invited to join presenter Ben Jackson for an extended conversation on my local radio station, BBC Radio Leicester. They were kind enough to record it for me, and I have now illegally made it available to listen to online!

Interviews Philosophy Of Travel

The World According To… Tom Allen (Wanderlust Interview)

I was recently given this list of questions to answer for Wanderlust magazine; a rare opportunity to bang on guiltlessly about my opinions and experiences.

Mountain/desert/jungle/ocean — which are you?

Some of my favourite experiences have been in the desert. Life has to slow down in the heat and dryness, and that sense of calm is a welcome opposite from the busy lives we lead at home. I love the mountains, too – they breed a unique kind of culture and help remind us of our insignificance.

Cycling the Nubian desert

First travel experience?

I took a year out after school and went to the mountains of eastern Canada to train as a ski-instructor for three months. It wasn’t the most adventurous of trips, but at the age of eighteen it certainly felt like it!

Favourite journey?

There are so many to choose from, but I keep coming back to my ride through northern Sudan. It was the year before the asphalt road was built through the region, so it was very tough going. But the remoteness ensured that the hospitality I received along the way was matchless, and the satisfaction of pulling it off was all the greater for it being such a challenge.

Nubian village on the Nile's west bank

Top 5 places worldwide?

It’s possible to have a cracking adventure almost anywhere in the world. But for landscapes, the ‘Lost Coast’ of Northern California takes a bit of beating. City-wise, I seem to keep finding myself back in Istanbul, and I absolutely loved Portland, Oregon. The most extravagant hospitality I’ve ever received was in Syria and Iran.

Flora on the Lost Coast shoreline

Special place to stay?

It’s difficult to recommend accommodation, as I usually sleep in my tent. So instead I’ll cite my personal favourite wild-camping spot, which was on the banks of a semi-frozen Lake Khovsgol in northern Mongolia.

Sunset over Khovsgol

3 items you always pack?

A 1‑man tent, a Buff, and a diary.

Campground lightshow

Passport stamp you’re proudest of?

I really like the colourful design of my Yemeni visa sticker.

Vegetable stall in Aden

Passport stamp most like to have?

Saudi Arabia. The Middle East is my favourite region of the world, but Saudi restrictions meant I had to take three boats and travel through four African countries to get between Jordan and Yemen.

Weird weather down by the Dead Sea

Guilty travel pleasure?

Pigging out on street food. As I travel mainly by bicycle, my body becomes a calorie-burning machine, so I can stuff myself, safe in the knowledge that it’s fuel for my legs.

A predictable scene in an all-you-can-eat Mongolia BBQ in Vancouver

Window or aisle?

Window in daytime (so I can see). Aisle at nighttime (so I can sleep).

Mirrored self portrait

Who is your ideal travelling companion?

I often travel alone. But my ideal companion would be a native of the country from whom I could learn the language and scratch a little deeper as a result.


Best meal on the road? Worst?

I remember one particular Iskender kebab in Istanbul — spicy slabs of grilled meat, creamy yoghurt, rich tomato sauce, all on a bed of bread croutons, and then slathered with molten butter. The worst meal was something I was given in the Nubian desert. Think of the consistency of raw egg-white, but warm and salty. Then envisage lots of unidentifiable green bits floating in it. Then imagine eating it with your hands.

Taiwanese food 3, Taiwan Bicycle Bloggers Tour 2012

Most surprising place? Most disappointing?

I was blown away by Taiwan’s warmth and modernity – I was told there that tourists came from the PRC to see ‘China as it could have been’. There honestly hasn’t been anywhere that disappointed me. I don’t do any research on the places I go, and I’d like to think that without preconceptions I’m better able to accept a place for what it is, rather than dwelling on what I expected to find but didn’t.

Cycle park 3, Taiwan Bicycle Bloggers Tour 2012

Where do you NOT want to go?

I really can’t think of anywhere that I would actively choose not to go to. Having said that, it’d take quite a bit of convincing to get me back to the French Riviera in the summer.

Wild camping in Italy

Who/what inspired you to travel? Any travel heroes?

I was inspired to travel by the nagging feeling that school and university hadn’t really equipped me for life yet. My good mate Andy was the one who brought up the idea of cycling. I can’t say I have any travel heroes, but I’m constantly inspired by the current generation of self-made young explorers who are pushing the definition of adventure.

Masters of campcraft

What do you listen to on the road? Any song take you back to a particular time or place?

I used to listen to a lot of drum & bass. (It’s awful. You’d hate it.) As time has gone by, the need to listen to music has diminished. Now, when I’m on the road, I prefer to keep my senses alert.

Turkish Road Tunnels

What do you read?

I almost never read ‘travel writing’. I read mostly non-fiction, particularly popular science. I’m not sure why. Perhaps it’s because travel is a way of learning about life on Earth, and reading astrophysics and cosmology is a way of learning about everything else.

Al Salam Camp, Luxor, Egypt

Is there a person you met while travelling who reaffirmed your faith in humanity? Anyone who made you lose it?

One of my earliest experiences was being invited to stay with a Slovakian guy who left a key in the door and a welcome-note on the table 365 days a year, whether or not he was actually there. You can go and stay a week or two at his place right now, if you want, as long as you water the garden. He’s never had anything stolen. Two weeks later, in Romania, I was invited in for the night and the following morning asked for one hundred euros to cover my stay. Luckily the former type of experiences have outweighed the latter a hundredfold.


What’s the most impressive / useful phrase you know in a foreign language?

The most useful word in any language is ‘thank you’, cliched as it might be. For impressive phrases, ‘yes ko spitak ziov asbetn em’ is Armenian, roughly translates as ‘I am your knight in shining armour’, and works really well.

Sunrise over Yerevan and Mount Ararat

What is your worst habit as a traveller?

Staying days (or weeks, or months) longer in a city than I planned.

Istanbul by night

Snowbound in a tent in Antarctica, how would you entertain your companions?

Very little beats a good storytelling session. Stories aren’t just entertainment, they’re also how we share and find security in the common elements of being human.

Camping in the snow

When and where in your travels have you been happiest?

I am at my happiest with a full stomach and a clear blue sky and a tailwind and a new border-crossing at my back.

Another epic valley

What smell most says ‘travel’ to you?

Freshly-baked bread. Or roadkill.

Bread-making in an Aden fish restaurant

Given a choice, which era would you travel in?

In a romantic frame of mind I’d probably say the fourteenth century, when legendary Islamic travellers like Ibn Battutah were wandering the globe. But in any other mood I would say today, rather than pining for a golden age that probably never was.

Shobak Castle, Jordan

If you could combine three cities to make your perfect metropolis, what would they be?

I go to cities mostly for the people, and so I’d quite like to combine the fiery pride of Tehran with the outlook and optimism of San Francisco, but in the geographical surrounds of Vancouver. That would be an interesting mix, and nature would never be far away.

Cafe in Tehran, Iran
Steepest grade in downtown San Francisco
An appropriate pavement carving in Victoria, Vancouver Island

Your turn! Copy-paste these questions into the comments and answer them:

  • Mountain/desert/jungle/ocean — which are you?
  • First travel experience?
  • Favourite journey?
  • Top 5 places worldwide?
  • Special place to stay?
  • 3 items you always pack?
  • Passport stamp you’re proudest of?
  • Passport stamp most like to have?
  • Guilty travel pleasure?
  • Window or aisle?
  • Who is your ideal travelling companion?
  • Where do you NOT want to go?
  • Who/what inspired you to travel? Any travel heroes?
  • What do you listen to on the road? Any song take you back to a particular time or place?
  • What do you read ?
  • Is there a person you met while travelling who reaffirmed your faith in humanity? Anyone who made you lose it?
  • What’s the most impressive / useful phrase you know in a foreign language?
  • What is your worst habit as a traveller?
  • Snowbound in a tent in Antarctica, how would you entertain your companions?
  • When and where in your travels have you been happiest?
  • What smell most says ‘travel’ to you?
  • Given a choice, which era would you travel in?
  • If you could combine three cities to make your perfect metropolis, what would they be?
Audio & Podcasts Interviews

Philosophy Of Travel & The Making Of ‘Janapar’: An Interview With The Sprocket Podcast

Podcasts are to radio stations what blogs are to newspapers, and — as with all things online and unfiltered — good content bubbles to the surface through persistence and collective appreciation.

These varied and portable programmes are one of my favourite things to listen to (with one ear, naturally) during long bike rides. I’ve started to consider how the medium might be used for future projects after meeting and being inspired by the couple behind The Sprocket Podcast.