Photo: Trey Ratcliff, New Zealand.

On The Road: How To Produce Great Work While Traveling The World

“I was surprised, as always, by how easy the act of leaving was, and how good it felt. The world was suddenly rich with possibility.” That’s Jack Kerouac in On The Road, written in 1951 – decades before the Internet and mobile computing made it possible for us to live and work from just about anywhere.

Yet, 60 years on, with more flexibility than ever, the inertia of the familiar keeps many of us from buying that plane ticket, negotiating with our boss, and structuring a life rich with adventure and mobility. So what’s the secret to taking the plunge?To find out, I coordinated a series of interviews with a few experts who regularly pull off this sort of thing: Rolf Potts, acclaimed travel writer and author of Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel, Chris Guillebeau, a  successful blogger and author (The Art of Non-Conformity) who has visited 177 countries, and London native Alex MacCaw, who spent a year traveling and writing before joining Twitter as a programmer.

What prompted you to take the plunge?

Alex: Well, I had spent some time in San Francisco working on a startup and was a bit burnt out. So, I decided to take a year off to travel, get a book published, and ultimately ended up moving to the States. It was either that or go to university or get job. And I’ve always been very bad at doing things I don’t like.

So, I pitched the idea of writing a JavaScript Web Applications book for O’Reilly and submitted an outline and they went for it. There was no advance but I had this naive belief that if I got published, it would increase my chances of working in the US and moving to San Francisco. So, I bought an around-the-world plane ticket and went for it. It was an amazing year, and one of the best decisions I’ve ever made. I can’t understand people who wait for their retirement to travel. I’d much rather optimize for experience than short-term wealth, and take the plunge.

Alex MacCaw’s round-the-world itinerary.

Have you found it tough to stay focused and regimented? Any tips on managing yourself vs creative output vs travel schedule?

Rolf: For me it’s always been a challenge to stay focused and regimented. But if you can’t, it’s impossible to be creative and productive when you travel. My best strategy is to maintain a daily discipline, where I am writing every single day — even if it’s just one sentence. Often I’ll find that that first sentence is the most difficult task, and once you’ve created a sentence, it’s easier to create a paragraph, a page, a chapter of writing. Without that discipline and compulsion to create at least one sentence a day, I wouldn’t be nearly as productive as I have been.

I can’t understand people who wait for their retirement to travel. I’d much rather optimize for experience than short-term wealth.

Chris:  Yes, it’s tough. That’s why you have to make it a habit like anything else. One thing that helps is to continually focus on deliverables, not time schedules. On any particular day I may be anywhere (right now I’m writing these answers from the island nation of Nauru, the world’s smallest republic). Therefore, the actual schedule may vary quite a bit from day to day or week to week.

However, every day I try to keep working away on things regardless of location: another 1,000 words for my next manuscript, another outline for a new business website, a column or freelance piece, and so on. At the end of the day, I know I’ll be dissatisfied with myself if I haven’t made sufficient progress.

I also give myself rewards that are tied to accomplishment. I love to read the New Yorker, New York Times, Economist, and other publications, so when there’s an article I’m especially interested in, I’ll make myself save it until I’ve accomplished something more productive.

If you’re traveling solo how do you get feedback when you’re stuck – any tips or methods for this?

Chris: When I get stuck, I think it’s more a question of motivation than anything else. The best way to recover, in my experience, is to ask myself what’s going on and find the root of the problem. Am I just jetlagged or otherwise tired? Am I ready to be done with this project? What do I feel like working on?

Don’t get me wrong, you may not always be able to work exclusively on things you feel motivated by. Completing big projects, like writing a book, require a constant tradeoff of short-term enjoyment for long-term fulfillment. Nevertheless, I try to spend much of my creative time on projects or tasks that I am genuinely excited about. This usually gives me more energy to keep moving along to the next project or task.

Photo: Chris Guillebeau, Dubai.

Alex: I think traveling by yourself is great. It forces you to talk to people, get advice and make friends. I applied the same principals to my last book, basically half of it was crowdsourced. I put the book up on a GitHub repository and people submit pull requests the whole time. I think it’s a good idea. You have someone driving the project but getting a lot of input really helps even when you’re by yourself. Using tools like Google Talk and chatting with friends helps. Sometimes I would put together a Google doc with an idea, and send it off to various friends for feedback.Where do you create on the road?

Rolf: I’ve done some of my best work in tiny, dumpy hotel rooms. The important part isn’t the comfort so much as the isolation and the ability to focus entirely on the task at hand. Sometimes dumpy hotels are better than nice ones, since I work faster and more efficiently when my goal is to get outside and experience something nicer by the end of the day.

I’ve done some of my best work in tiny, dumpy hotel rooms.

Is there a country or region you felt more creative or inspired in?

Rolf: I don’t know that the country affects creativity so much as the person does. If you can maintain discipline in the Australian Outback, for instance, you can maintain that same discipline if you travel to Bangkok or Paris or 50 miles from your hometown. I’ve done a lot of writing in  Thailand — it’s where I wrote my first book, “Vagabonding” — but I feel like the work I did there wasn’t exclusive or unique to that place. I’ve worked well in Paris, and in hotels in Peru and Egypt, and in my house on the Kansas prairie. Location is less important than self-discipline.

Alex: Cambodia was incredible, a country filled with amazing temples, scenery and food. I wrote a portion of the book on a little desert island just off Cambodia called koh rong samloem. We only had electricity for 2 hours of the day (powered by solar panels), so I had to turn my screen brightness right down and try to make the laptop’s battery last as long as possible.

Photo: Alex MacCaw, Cambodia.

How do you fight feeling out of sorts while being constantly on the move?

Chris: I tend to go back to a lot of the same places while en route to new places. For example, I visit Hong Kong at least 3-4 times a year. Each time it’s only a short stay, but I know it well. Whenever I arrive in HKG and head to the city, I follow a routine of revisiting a few favorite areas and trying to visit at least one new area every time I go. The mashup of foreign and familiar helps with inspiration. My theory is that a certain amount of change is good, but not so much that your whole rhythm is thrown.

Any advice for someone nervous to do something like this?

Alex: I would start by rationalizing your fears and put them into context. Then work out what you’ll regret more in the future when looking back — not taking that incredible adventure while you could, or living the rat race you were stuck in? Often fears seem trivial with that perspective.

How did all this risk of travel and creation work out?

Alex: For me, it turned out really well. The book’s been published, I’ve moved to San Francisco and have my dream job at Twitter. I’ve accomplished all I initially set out to do and more. However, to be honest I never really saw this as much of a risk. The worst case scenario was that my bid for the US failed, that I would be back doing consultancy in London and my savings depleted. In the large scheme of things, that’s not a big deal at all. In the end, I believe you make your own luck to a large extent. It’s just a matter of reaching out, and taking that initial leap of faith.

More insights on: Disconnecting, Risk-Taking

Jake Cook

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Jake Cook is an entrepreneur, professor, and writer. A co-founder at Tadpull, he also teaches Online and Social Media Marketing at Montana State University. He’s fascinated by the intersection of design, technology and creativity. Follow him at @jacobmcook.
load comments (33)
  • Chris

    Traveling alone is also a great way to break out of a creative funk. Last month, I spent two weeks in Brazil, Argentina and Uruguay — places that I had never been and where I did not speak the language — and came back recharged.

  • Rod

    Great article. Very inspiring. One of the best things I’ve done was to travel the world after university. Then found a job that gives me enough time to travel throughout the year without being stuck for months on end in an office.

  • Adam Dale

    Some great tips here! I’m currently travelling around the U.S.A and have a photography blog to cover it.. Please check it out

  • Jake Cook

    Hi Rod
    Great point on taking a break after university – thanks for the note. Any tips on how you negotiated your job to let you travel?

  • Jake Cook

    Adam you have some great pictures. Hope the rest of your trip goes well.

  • Rachel

    I wish I had those guts. I want to just do it. I wish I didn’t have a loan or I would be all over this…

  • Rod

    Hi Jake. The office is shut during Christmas/New Year, Easter and in the summer 3 weeks. In addition we get a couple of weeks off which we can take whenever possible. And let’s not forget the long weekends which I try to take advantage of. This gives me a well balanced work and travel year.

  • Logo Design

    Good Article on the Great traveling, i do love to travel, so this tips would be useful for me!

  • Ann Stanley

    I have a fantasy about wandering around the world. I wonder if I should make it a dream. But there’s the job, which I love, the house we just built, the kids, the dog…
    Now that I’ve said it something will shift and I’ll start to think – what will it take to make it happen?

  • Conni Biesalski

    Thanks for this! I’ve travelled a lot and been a nomad for more than 10 years, but now I am finally taking the leap to be a digital nomad, taking my new freelance business on the road with a writing career as the long-term goal. I’m a bit nervous as I’m still a bit unsure how I can manage to get work done in tropical environments with the beach or beautiful places at my feet. My first stop is Indonesia…so I guess I shall see :) If you like you can follow my journey at my blog

  • Conni Biesalski

    Wow, I love your photos! Really well done! :)

  • Jake Cook

    Hi Ann – I have a good friend who moved his whole family to Hawaii for 2 years. Here’s an article he wrote about the experience, if you’re interested – thanks for the note.

  • Catalina B.

    I’m delighted to have read this article. After traveling for one year only, to 7 countries in Asia and Europe, we produced BrightLounge, a video podcast where we interview one brilliant mind from each country we visit. The focus is on sharing inspiring stories of designers, entrepreneurs, artists and creatives everywhere around the world. Check it out at :)

  • Jane Pellicciotto

    People tend to think it’s easier for others to work from anywhere because fear is coloring their thinking. That being said, stories about working from anywhere are nearly always about writers. Though it can require contact with others, it’s mostly a solitary activity and one that uses a single tool.

    Even more inspiring would be stories about people working in fields that require consistent contact with others and possibly tools and resources not found online. And that also address how to help clients and prospects overcome the fear that you’re sipping umbrellaed drinks on a pink beach instead of working on their project.

    With services like Skype, PayPal, Dropbox and others, anything is possible. But designers, for example, who need to see physical proofs, use a swatch book or refer to their library of design books, need to shift into a different way of thinking about their work.

    Anyone know of people who have done this successfully?

  • Sebastian Neylan

    Really nice article.

  • Adam Dale

    Thank you Conni, much appreciated :-)

  • Adam Dale

    Cheers Jake.. Thank you :-)

  • Jake Cook

    Hi Jane – thanks for the comment. This was something I wrestled with in the article – that being do these free-roaming lifestyles apply to creatives outside of writing?

    I think for those that have to collaborate with clients, a tool like Basecamp from 37Signals is invaluable for managing files, timelines, communication, and expectations. Paired with the tools you mentioned there really is no reason with a bit of extra hustle that collaboration can’t take place.

    It’s a tough sell to bosses and clients though. Tim Ferris book The 4-Hour Workweek has some great step by step examples on how to tee all this up for negotiating an extended leave.

    Hope this helps!

  • Boggs Chris

    Great subject, something that has been occupying my mind more and more as I get older. Still, the unspoken subtext of almost all of these type articles is that the traveler at the center of the story, who just throws caution to the wind, is well-heeled enough to pull these things off in the first place. I don’t think that the obstacles in the way of this kind of travel are related to anyone’s inability to adapt to the demands of creative thinking on the road. I’d be willing to bet a lot more people would travel if they wouldn’t have to lose their home or starve to do it! Also, lots of folks have the money to do it, if just, and they work in an industry where the demands for physical presence are surmountable but the bosses and managers that they have to deal with quite often refuse to work with someone who is not physically present.

  • James

    This was a really great article! I finally launched my business about four weeks ago and I’ve been wrestling with how to incorporate travel/work. I’m not quite ready to take the full plunge yet, but this is ever more the motivation. So thanks!

  • San Francisco

    These sites also have a rating method so that travelers can know whether these carriers are worth flying with, & have they got a nice number of satisfied clients.

  • Katrina

    If only, if only. It seems like travel and writing go hand-in-hand, but I’d like to know what a non-writer can do to make their job more mobile. So many jobs seem to “require” physical location and I’d like a sense of how to build more mobility into careers that are somewhat location-specific. Short of becoming a freelancer, which I have no desire to do, how does one do this?

  • Michael Wills

    Some do but could you say what your field is? Mine is programming. I went from negotiating working alternate hours to working remotely but present for meetings. Now I have been freelance for going on 7 years with clients in several time zones in the US. Meetings are often via webex and those sometimes happen at 2am when I am overseas. :)

  • travel agents in chennai

    Define the your travel post being heed for very effort. Every news are impress to me.

  • Cheap Flights to Toronto

     I love to not work. I like to travel. I work maybe half the year, no more.

  • Dubai flights from UK

    Wow what a pic !!! It seems you are so damn creative..Why don’t you post some more pics..

  • HeadRoom Assistance

    This article is really great! I agree with the many reactions below. I think it’s worth the effort to do further research on how other Entrepreneurs of other branches deal with this. Thanks for the inspiring message above though.

  • Meaghan Blanch

    I had to go into freelance, as I decided to ride a bicycle from Vietnam to Laos, to China. Ending up in medium sized Chinese city where I could’t speak the language, it was a less then ideal way to finding a design job.

    So during the trip i started preparing for a blog, with the idea of going freelance when settled. I found slogging 8 hours a day on a bike hard to get your head around getting a start up running. My specialty is print, which for online work is difficult. So i have had to gear myself differently, work on new skills, pitch for clients, build online presence etc. All these things I never had to do before.

    The point is, it is much harder being online than I imagined, and I put in a lot of hours now doing all the seemingly ‘extra’ things outside of working on a paid project. I have also learnt a swag of new skills and figure out all sorts of challenges completely out of my comfort level . It also took some time, catching on to what other freelancers do to get work online. It is possible though.

  • Richard Demato

    Hey Jane / Jake –

    I don’t know how you’d personally define “successful”, but I’ve spent the last 14 months as a nomad and it’s been equally exciting, exhausting and frustratingly disruptive.

    I wouldn’t trade a moment of it.

    I can’t say it’s the best idea if you’re leading a startup, at least not on your first attempt at being a long term nomad. There’s much to discover in terms of building a routine and managing the disruption. I knew it was a little much when I got emotional over putting all my socks in a single drawer when I had month long temporary business apartment. Way too much time was lost packing and repacking and organizing. But it can be done if you’re not a writer. You’ll embrace Airbnb, Hotel Tonight and other travel apps such as Wi-Fi Finder.

    For me it was a passable idea because we had business partners and key collaborators in LA, SF and Boulder with a lot of business development out of NYC. The past year has taken me from LA to Boulder to San Francisco to New York to Cape Town to Miami to Yakima to Austin to Phoenix and a few others in between or on repeat. It’s been amazing from the perspective of building a network and enhancing external relationships, but it definitely makes it harder to have a fluid dynamic with your team.

    And Jake, funny you should mention The 4-Hour Workweek. I used tips from the book to set expectations at my old consulting firm and built flex hours and remote working into my contract. I then came across Chris Guillebeau’s work and took the leap.

  • Chris Courtis

    I agree that creativity can be drawn from many sources and it can vary from place to place. I think it is possible to be inspired by things you may have never thought about and that is why experiencing different cultures, places and countries can really help in inspiring the creative mindset. When I have been away travelling I always find my mind becomes more active and thoughts and ideas start to flow.

    I do think for many people though the possibility of travel and work is out of reach as there are many variables that present barriers to enjoy this sort of freedom.

  • Janet

    I taught courses online for a North American college while on the road. I taught in Athens, London, Rome, Udine, Venice, on a cruise ship, etc. Sometimes it was hard because the internet connection in the room was not great depending on where I was. So I would have to work in the lobby of the hotel on my laptop. But it was great, so fantastic! As Jake says though, you have to be very disciplined.

  • GipsyCat

    Great article! very inspiring! the world is becoming smaller and smaller, we have so many opportunities that t scares us to try anything out of the “norm”

  • Alfred

    I’ve found instead of committing to backpacking, and moving around consistently, is to base in a livable city with an expat community. You meet amazing people, it’s easy to setup and find others working online and you can take weeklong and weekend trips to explore your area. So far I’ve based from Buenos Aires, Mexico City and Medellin Colombia. Each unique experiences, and I was able to successfully work with clients in the states as well as find new clients through the expat communities.

    Here are some photo projects that I’ve worked on while traveling:

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