Reflections on 1,000 Days as Digital Nomads

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The rain spat at the car as we drove down the grey motorway through thickening traffic towards the airport. The thermometer was reporting temperatures of 5ºC outside and as we stepped from the warm steel cocoon and into the harsh air, we felt winter’s icy fingers burrowing their way through our skin to touch our bones.

Twelve hours, three movies, two meals and a taxi ride later, we collapsed into bed. As I fought a migraine brought on from the oxygen deprived airline air, we gave in to the fuzz of tiredness clogging up our brains—that exhaustion particular to the traveller that makes even the most threadbare, rock hard bed seem like an inviting cloud of heavenly comfort—and fell into the heavy sleep of the walking dead: deep, dreamless and very black.

The next morning, we woke to find ourselves in a hip little apartment in South Beach, Miami. Outside, the glorious Florida sunshine warmed the world to a most acceptable 25ºC. Stepping out into a world of Art Deco architecture, string bikinis and sidewalk cafes—a million miles from the cold we’d left behind—we felt that rush of freedom that has not dimmed in the 1,000 days we’ve been doing this.

It’s a peculiar sensation that sneaks up on us when we least expect it. Hanging out the washing and and gazing over the morning Myanmar mist, watching the world wake up, you’re suddenly aware that everything is exactly like it should be. That the world is perfect in all of its imperfection.

Csikszentmihalyi labeled this sensation flow: Often felt through focused activity, it’s a feeling of oneness with the world, where time moves differently, the ego dissolves and you are a part of something larger than yourself. A moment of peace amongst the chaos and confusion of survival.

It’s a feeling of deep satisfaction; a “Holy shit, this is my life!” moment. And it’s wonderful when it happens.

But it doesn’t happen every day.

Us covered in mud at the Dead Sea, Jordan
Us covered in mud at the Dead Sea, Jordan

In Which An Ugly Truth Becomes a Beautiful Reality

The fact is, those moments are earned. They come as a result of many hours of planning, decision making and facing up to our very real failings.

Our lives are not what you may consider perfect. They are certainly not the advertiser’s version of perfect. We don’t spend the day lying in hammocks sipping margaritas. We actually work very hard—often 12 hour days for weeks on end—the key difference being that we work on the things we choose to work on, to the point that it’s almost impossible to call it work without laughing at the absurdity of it.

But if we do find ourselves doing work that we don’t like, we have no one else to blame but ourselves. We can’t get angry at our boss, or the company, or the world in general. It was our choice and is our responsibility.

We frequently fight with our often crippling indecisiveness because of this total control. There is nothing quite so debilitating as knowing that absolutely anything is possible. Like an earth-sized pure white canvas waiting for colour, where should you make the first stroke?

Before, it was possible to go days without deciding anything—from the breakfast we ate, to the road we took to work, to the work itself, to the TV we watched when we got home—all of it happened out of a mixture of habit and order.

For us, the most difficult thing we’ve faced in our first 1,000 days is not the practicalities that we worried about before we left, but the self doubt. It’s the not knowing what the right thing to do with our business is, deciding on which risks we should take, and facing up to our financial situation (if you graphed our income and outgoings, it would resemble the Hulk Coaster at Universal Studies, loops and all).

But somehow it all works out.

And then there are those moments.

Simon working at our beachfront villa in Koh Lanta, Thailand
Simon working at our beachfront villa in Koh Lanta, Thailand

Is It Worth It?

Unequivocally, yes. But it comes with costs.

If you decide to go down this road—whether that’s as a long term traveller or as a digital nomad—you will do so much more than you have ever done before. You will find yourself in situations that are difficult, crazy, comic, awkward, challenging, exhilarating, and enlightening.

This freedom is intoxicating but it changes you, which only makes going home harder. Old friends will move on—marriage, kids, new careers—or, worse, they will not have changed at all while you will be someone totally different. Most won’t even be that interested in your travel stories and you’ll struggle to fit back in.

The people you know will think you’re crazy, even if they don’t say anything to you directly. This is an unconventional path, and it breaks unspoken rules and traditions. You’ll certainly find out who your real friends are.

The perspective we’ve gained is invaluable. We’ve become aware of our own misplaced outrage and we see how so much of the world is constructed around the need to blame someone for something, itself rooted in feelings of powerlessness. When we own each decision, we’re in control and these feelings of helplessness are replaced by those of determination.

You’ll gain a broader view of humanity, a more accepting disposition, and a realisation that we all take this fleeting and futile fight far too seriously.

Finally, you’ll never want to work for anyone else again.

Simon working at our hilltop villa in Koh Lanta
Simon working at our hilltop villa in Koh Lanta

The Practicalities

Or worry, but know that worrying is as effective as trying to solve an algebra equation by chewing bubble gum[1]

We have wasted so many hours worrying about things that turned out not to be a problem. Everything we have worried about has worked itself out, one way or another.

We’d tell you not to worry, but you will anyway. Just know that almost everything can be sorted out abroad and that the important thing is to get out there and find out for yourself what things you should be worrying about (it’s never the things you are worried about).

You’re not your job.[2]

The modern Western world builds its identity around the work you do. How many times have you asked or have you been asked: “What do you do?”.

It’s never: “What excites you?” or “When was the last time you felt truly alive?” or “What would you do if you didn’t need to earn money?”

This is fine if the same answer works for all these questions, but if it doesn’t and you decide to become a Digital Nomad or a Travel Blogger, you may feel an existential lack of identity. We still find it hard to explain what we do to people who aren’t like us because we do a little bit of everything.

Going out of our way to meet others in the same situation helped us feel part of something. Being a Digital Nomad is a thing. Running a travel blog is a thing, even if many people don’t get it. The mutual reinforcement of finding others making their own crazy choices work can be very reassuring.

Welcome to the asylum.

You’re not how much money you have in the bank. You’re not the car you drive. You’re not the contents of your wallet. You’re not your fucking khakis.[3]

Pack light and go for quality over quantity. Make sure that the things you do buy are the very best you can afford, especially your work gear, but remember that your stuff is a tool to be used.

Ask yourself if you really need it and if you don’t use it regularly, ditch it.

Deadlines and things make you creative.[4]

Creating while constantly moving can be difficult, so our pace has slowed in the last 1,000 days. It’s possible to maintain as we move around, but to really create and move the business forward, we found that we need to stop for a while and focus on the work.

I’m not afraid of death; I just don’t want to be there when it happens.[5]

In 1,000 days, the worst thing that’s happened to us is that we were pick-pocketed and lost $30.

The world isn’t that scary and people are generally good. We can’t count the number of times random strangers with nothing to gain helped out these two dumb, lost-looking gringos.

Our moped broke down three times in Thailand. In each case, someone popped up out of the blue to help us out (we also left the keys in it multiple times and it never got stolen, but don’t tell the rental agency).

Yee Peng lantern festival in Chiang Mai, Thailand
Yee Peng lantern festival in Chiang Mai, Thailand

The Next 1,000 Days

Here’s a question we get asked a lot: “Do you plan to settle down?”


  1. The original Sunscreen  ↩
  2. Yeah, I know. But everyone’s allowed to quote Fight Club once on their blog.  ↩
  3. Or twice.  ↩
  4. Jack White, Creative Genius  ↩
  5. Woody Allen, apparently.  ↩


  1. What an inspirational post. I’m not a digital nomad but I do travel quite a lot and love it. I’m not sure however whether I could do it full time. Love love your photos, wow great places. I hope to get to Jordan this year as well.

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  2. Congrats – You are one amazing couple! But of course the effort has to come from both of you…I wish I had a supportive/interested life partner too.

    By the way, given the current global rise in temperatures, have you got accustomed to not having an air conditioner around at times?

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  3. I like the idea of this lifestyle, but are you not sacrificing the chance to build a fulfilling career at home? I know most people have rubbish 9-5 but surely there are some good jobs worth staying for. Do you not think you re missing out on this?

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    • We feel that we are building a fulfilling career on the road. By working for himself Simon has had far more flexibility to choose he work he wants to do and has moved from web design to iOS app development which he loves.

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  4. Such an inspiring, brilliantly written post. I love reading about people who choose their own path in life, and I’m glad to hear you’re continuing to do what you love! It’s frustrating when you tell people you have to work, and they don’t see you sitting behind your own computer, on your own time, as a job. It seems they never really understand – but then again, who cares? You’re living a hard-earned dream!

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  5. Well done! I can relate!

    I get so flustered trying to answer the question, “what do you do for a living?” Since I wear about 5 hats and they’re all related, it’s tough to explain.

    It’s also hard to complain when I’ve had a “rough” week. No one but my husband understood when I came home utterly exhausted from an around-the-world trip. My friends thought it looked like a splendid vacation.

    But it is SOOOOOOOOOOO soooooooo worth it.


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  6. Insightful thoughts put together with nice words. Me and my girlfriend are at “only” 300 days today (counted thanks to you, pisco sour time now) and while I agree with you, I think I occasionally will always feel the need for a break. Of course, the break can be on the road as well…

    Ok, will read it once more and keep on discussing the pros and cons with myself then :). Nice blog, looking forward to follow the two of you on for the next thousand(s) days.

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  7. I love this! Really inspiring post. It’s so refreshing to read the truth, good and bad, about the digital nomad lifestyle. I’m not 100% sure what the future holds for me and Andy yet, but we’re working on a few ideas. Some people gloss over things a bit and just focus on how wonderful the lifestyle is, and while I’m sure the overall balance is wonderful, it helps to see some not-so-fun truths. Congrats on hitting 1000 days on the road! Looking forward to reading about the next 1000!

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  8. Congratulations guys! Amazing that the worst thing that happened to you was that you had been pick pocketed.It proves that travel isn’t the big scary thing that most people think. It can be the best choice anyone can ever make. You two are role models and an inspiration. Keep on moving and traveling and enjoy!

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  9. Love your website and reading about all your adventures. You have inspired me to do two things:
    2020 Vision- I will be 60 years old in 2020 and have decided to liquidate my assets and travel the world for 10 years. At 70 (2030) I will retire and start to “act my age”…
    Also registered curryinahurry to blog about curry or versions of it around teh world. My interest and lifetime has revolved around food, so it is a natural fit. I have already seen a lot of the world, but looking forward to visiting the rest.

    Thanks you for your inspiration!


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    • Congratulations Dale! It sounds like a fantastic plan except that I don’t think you should ever act your age :) I love the sound of the curry website—we’d definitely read that.

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  10. Fantastic post. Thank you! This is ultimately the direction I would like to go and I’m right on the brink of starting down that path. I guess I’m just trying to figure out the technicalities now. I look forward to exploring your site more and learning more about you two. =) Also, I just want to say that your site header has to be the absolute best out of the travel blogs I’ve seen. I just love it.

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  11. Anything is possible if you really, really want something. My ultimate goal is not to spend another 25 years behind a desk. I made one step towards this goal, another one was to start writing…will see what the future brings.
    Excellent post. It’s motivating.

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  12. I am reading this on my lunch break in my 8th grade classroom. I took a year off from this job last year to sort-of travel (though I still had/have a mortgage–and a husband who did NOT take a year off) and so much of this reminds me of how I felt…last year. I had many moments of ‘wow–this is my life’. And I know that I will have many, many more. I just need to stay focused and keep my ultimate goal in mind. Posts like these help me regain that focus, and for that, I thank you.

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    • I’m glad we were able to help a little Tracy. With focus I’m sure you’ll be able to achieve whatever you set out to do. Good luck!

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  13. Love, love LOVE this post. Everything about it speaks to me. As a fellow digital nomad, living and traveling with my wife, it certainly is a rollercoaster ride of emotions. It’s crazy to think that too, considering that we have the “dream life,” but it comes with all sorts of other daily challenges that you don’t experience when falling into the system back home.

    I especially love the “This freedom is intoxicating but it changes you, which only makes going home harder. Old friends will move on—marriage, kids, new careers—or, worse, they will not have changed at all while you will be someone totally different. Most won’t even be that interested in your travel stories and you’ll struggle to fit back in.”

    Each time I go home, it’s that much more true. Yet, at the same time, I’m always amazed at how easy it is to slip right back into the routine and pattern. Especially because that’s what would make friends and family most happy!

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    • Thanks for your comment Greg. I think everyone struggles to fit back in, possibly because we don’t really want to. We left those routines behind in search of something new and like you said, we don’t want to fall back into them.

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  14. Simon,

    Inspiring is one way of putting it (your Nomadic lifestyle) and how wonderfully refreshing it is to hear that the world out there is still such an incredible place. I certainly thought so when I first packed my bag and hit the road back in 1981 – wow, that seems ages ago…! Perhaps some of your ‘followers’ would be interested in checking out my ‘Kodac Instamatic’ classic photos of the good old days where the visit to the ‘Poste Restante’ was the highlight of your month….

    I guess it’s true to say I am ‘plugging’ my latest travel business venture (also my life story) but then our likeminded friends out there on the road should to know that it is possible to return home ‘older & wiser’ and put their amazing travel experiences into day to day practise like it did. Check out my CV at and there you will see how I have successfully combined my love of travel with earning money and having a career I am passionate about….

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  15. Ahhhh, my friend. Good thoughts. Well deserved writing break. Now…. get back on that computer and get my projects done! ;)

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  16. Wow, this one really rang true! We struggle with these same issues all the time.

    Also got me to thinking – so I went to a date calculator and today is officially our 611th day on the road! Well, we visited home once but I don’t count that :)

    How long are you guys in PdC? I think we’re headed that way next month…

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  17. Very insightful, thanks for sharing. I’ve done exactly the same thing with moped keys in Thailand so I had to laugh… Have returned to the scooter and spent minutes searching my pockets for the darn things before noticing them hanging from the lock underneath the seat.

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  18. You guys, this is so beautiful and I relate on so many levels that I don’t quite know where to start. It is SO hard to create while moving, people at home won’t understand, there is no one to blame for your choices but you, etc. etc. I am only now beginning to realize the importance of the travel community and how much it means to connect with others that are having the same experiences. Thanks for putting it all into words.

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  19. Inspiring. I have one foot in both worlds as I have a husband with a day job, two teenagers, one in college and one in high school and a mortgage payment. Husband is ready to transition, but we still need to launch kids.

    Keep on traveling and writing.

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  20. LOVING this post, guys. I’m aiming to do the whole digital nomad thing come March next year – will see how it goes, although I’m not exactly sure how job opportunities will arise in that field…freelancing, I guess? More research needed.

    Anyway, the part that I really love is where you write about those little moments, the ones that aren’t big events, but where things hit you, and you have a, “holy crap, THIS is my life!” moment of realisation. I don’t have them often, but when I do, everything just feels right, in a way that it never did when I was working my 9 to 5 in the UK doing a job just to pay the bills.

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    • Those little moments are what really keep us going. I think it’s possible whatever you’re doing, but I also think it’s a lot easier to get to them when you step out of the traditional work culture. They tend to whack you over the head a little more forcefully.

      Good luck with your venture into the Digital Nomad world—if you have any questions, feel free to ask.

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  21. Wow… I love this piece! You wrote so many thoughtful, insightful things that I can completely relate to, especially about those “wow, this is my life?!” moments! Also, on the lack of identity: it’s amazing how much we tie our lives to our jobs. What we do really does define us. Having been unemployed for my year of travel, I often feel a bit silly when people ask me “what I do” and I don’t really have an answer. But you’re definitely right that you just need to take it all into perspective.

    Overall, a very inspiring article. I can’t wait to read about your next 1000 days!

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    • Thanks very much, Ellen.

      We tend to tailor our answer to the audience a bit—if it’s someone who really wouldn’t understand, then we can always just say “writer” or “app developer”.

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  22. I can understand why people ask it but why would you settle down?

    You’ll know when the time is right – it’s like anything in that way. You might just wake up one morning and think ‘yeah, this has been great, but it’s time for something else now.’ And if that happens, so be it.

    Great, honest, post.

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  23. How do you deal with bus drivers or attendants who insist you store your backpack in the storage area under the bus while traveling?

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    • I think we’ve been asked a few times to put them under the bus, but we just refused to let them and they relented. Our backpacks are pretty small though.

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  24. The picture of you guys the monastary at Petra brought to mind a journey I made along the ravines that lead to it, many years ago now, with a group of Brits, Ozzies, NZ’s and Canucks. That doorway entrance behind you we all walked through on our way to Kathmandu, Bali and beyond.

    Every time I get your newsletter I get itchy feet and my girlfriend starts getting twitchy as I start eyeing my backpack :-)

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  25. Wonderfully written! I know precisely the feeling you described. For me it happens when I am “fully present,” not obsessing about the past or worrying about the future. I’m coming up on six years and like you, the way I travel has had to slow down. I just couldn’t grow the business, travel, interview people, see places, do social media tasks, manage advertising and all the other things that go along with being a travel writer/blogger and still create god content when I was in “see 16 countries in six months” mode. My travels have slowed way down – no less than a month in each country – but as a result I’m connecting with the culture more. Wishing you another 1000 days equally as rewarding.

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  26. Great post. I am a new travel blogger and it gave me a lot of insight into this new adventure I am embarking on. I agree with all the reason you stated about why you are digital nomads and you have chosen this life. ( I especially love the fight club quote)

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  27. What an honest post, not sugar-coated, but still inspirational! Most of the travelling/nomadic bloggers that I follow are from across The Pond, which I love so much that I have started talking/writing like them (awesome, you guys, freaking etc..), but it’s nice to read the writing of some fellow Brits, even though you can tell you have travelled because of your enthusiasm; I think I might be babbling now!
    What I love as well, is how you recommend quality products over quantitiy; this is something I believe in at least 80% of the time, but that I get shot down in flames because of quite a bit. Anyhoo, fab post as usual and wonderful photography-here’s to another 1000!

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  28. Congratulations to you guys! It’s inspiring to know that travel can become a way of life. Thanks for inspiration. Best of luck on your next 1000 days!

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  29. Hi Simon, first of all A very very congratulation on 1000 days of both of you being together and making Never Ending Voyage to reach at heights. By the way , it is much motivating for me to have a splash in dead sea for getting covered in Mud. I would love to do this.

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  30. Brilliant post Simon, just in time as we’re heading off to become digital nomads in Chiang Mai, glad to have this blog as a constant source of inspiration and guidance.

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  31. Congratulations on your first 1,000 days – here’s to the next!

    A fantastic, insightful, awe-inspiring post… settle down… why?!

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  32. Your guys are my go-to bloggers :) read this particular article a 2am. I am always left with a feeling inspirational jealousy.

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  33. Thank you for this nice article. Although I’m not a digital nomad and travel blogging is for the moment just a hobby, people do look at me with confusion when I talk about it. So it’s good to seek out other bloggers from time to time, whod do understand that travel blogging is a thing ;)

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  34. Happy 1000 days and nights! It is a constant source of pride to follow your adventures, and we wish you all the luck in the world – and all the best adventures! Stay safe and happy – but know that we miss you and love you very much although we are happy for you! xxxx

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  35. Perfectly worded expression of what we feel every day, but find so hard to express to others. Nomadic life is exhilarating and exhausting. It’s a constant struggle with societal definitions and norms as well as self definition. The long-term sense of cultural dislocation is, perhaps, the greatest challenge. It’s also an odd thrill. That’s a very difficult reality to convey to anyone but a fellow nomad. As we approach 2000 days, I can’t say it really ever gets easier.

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  36. This post might just be the one that has motivated me to start writing and enjoying travel blogging again. Thanks you two! And congratulations on 1000 days ;)

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  37. Awesome post! You guys inspire us so much. We’re only 306 days in, and struggling with the same indecisiveness when there are so many available options. It’s especially difficult to explain when people ask about our future plans. They exist, but they could go any one of a million different ways, and I couldn’t be happier about that.

    Thanks for continually being inspiring.

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  38. This piece of writing is brilliant Simon – so many great pearls of wisdom. I love it Congratulations on your 1000 day anniversary! And thanks for inspiring Steve and I so much on our journey. Hope to see you again soon. Maybe you could visit us for Christmas :)

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