The challenges of being a digital nomad for the first time

Nomadic Samuel pondering

When I think back to my first long-term backpacking trip I took across South East Asia I can’t help but smile. Travel back then was far simpler than it is now. Armed with my trusty backpack I set off to explore a sizable chunk of SE Asia. With nothing but pleasure on my mind, I carried a small wardrobe of clothes, simple point and shoot camera and very little else. When I wanted to eat I ate; when I wanted to explore I explored; when I wanted to sleep I slept; when I wanted to relax I relaxed. With nothing more than merely my internal compass and desires as my master, I set off and did things on my own pace as my bank account slowly dwindled.

These days things have changed in many ways. This is the first time I’m hitting the road as a digital nomad trying to create a successful travel blog. Although I would rather be doing nothing else other than this, I’m also facing a new set of circumstances and challenges I’ve never encountered before. In years past, when the internet was down in my flophouse, I gleefully went outside and explored. I could always send an email later. Lately, I’ve been finding getting a decent connection is often challenging. The internet is literally the lifeblood of my business; without it nothing flows. Sometimes I stare blankly at my screen fixated on the swirling page icon to load with the anticipation of a dog in the middle of a Pavlovian conditioning experiment; when it does load I feel like doing a cartwheel and giving a colossal high five to the first stranger I encounter.

I suppose what I’m really trying to convey is that I’m finding it challenging at times balancing work with pleasure. Sometimes I find myself cooped up in my guest house when I’d rather be out exploring. When I was teaching in South Korea I was resigned to the fact that I’m there to work and save money; however, now that I’m visiting new places by the day/week I’m often feeling the urge to spend the entire day exploring as opposed to parked in front of a computer. It’s been a unique experience for me so far. On the one hand, if I travel to my heart’s content, I’ll get behind on projects; however, if I decide to spend too much time online I’ll feel an extreme sense of guilt and anxiety for not doing enough of what I’m most passionate about in my life – travel. I’m still searching for the perfect balance. I’m somewhat resigned to the fact I may never find it – burning the candle excessively on both ends at times.

Nomadic Samuel wearing a conical hat and backpacking for the first time

The one thing I can’t get out of my head is this question I internally asked myself the other day: “Does travel actually get in the way of running a successful online business and potentially even a travel blog?”

It’s something I’ve been pondering quite seriously. I’ve tentatively come to the conclusion that in certain circumstances NOT traveling is actually better for workflow and productivity – even when the work I’m doing is related directly to travel.

All of the random thoughts I’ve been having related to this subject have left me questioning my motives for being on the road. Did I enjoy travel in the past because of all the new cultures I experienced, exotic foods I ate, and the friendships I forged with locals and other backpackers? Or did I really relish not having to work – feeling a sense of freedom and autonomy – while breaking out of stifling routines? I feel the answer to these questions may lie somewhere in the middle. Β Deep down I know it’s best not to compare travel experiences.

I’m considering a lot of different options (including basing myself somewhere for a significant period of time) that will allow me to rekindle the love I have for being on the road along with all of the new associated responsibilities of earning money online. I feel this is a sink or swim period in my life. I’m not keen on teaching English again given that I’ve done it for several years. I enjoyed it well enough, but to be perfectly honest, I did it more for the experience of being abroad and saving for travel than I did for the love of the job.

There are moments that I long for the carefree backpacking days of my youth; however, I realize that period of my life is now clearly over. In many ways I’m chartering waters I’ve never sailed before. Travel has shaped and plied me into a new person over the years teaching me to be a more patient person. I’m somewhat anxious now about my future but I’m going to follow my dreams because I’d rather fail at my own life and fall flat on my face than to just settle for something less. And so the journey continues… πŸ™‚

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  5. says: Tara

    Travel just isn’t the same as a digital nomad, is it? I teach online and must have a reliable Internet connection daily. My favorite tech toy on my last trip was the rented mifi in France. Such a time saver!

    Great post…thanks for sharing.

      1. says: Tara Ross

        I understand that! However I do try to batch my work so that certain days are a lot more work than others. This allows for more exploration and less “daily grind.” πŸ™‚

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  7. says: Drew Meyers

    I’ve been working remotely / traveling since 2010…and it gets incredibly hard often times. I recently joined the Hub Seattle because I’ll be here for a couple months, and I have found I’m exponentially more productive when I’m in an environment where everyone else is working than I am sitting alone. I consider myself pretty dang self motivated – but it’s certainly easier to stay constantly motivated if you are around others who are equally or more driven than you are. While traveling, it’s hard to find that type of environment..

    1. Drew, I think you bring up a great point here. I think to improve yourself you should surround yourself with those who are equally (if not) more motivated. Standards are often raised when you’re witnessing other people doing inspiring things.

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  10. Nice post.
    My boyfriend and I are planning on hitting the road in about a year but currently living in the Dominican Republic. We’re starting the blog now to get a head start and also because we’re technically in a “traveling” situation.
    Right now work seems normal because we’re home and should kinda have a job so we’re hoping to get into the travel and work balance before we even start vagabonding….
    High expectations I know. We’ll keep you posted on that elusive balance if you do πŸ™‚

  11. Good luck! I am also trying to find a way of traveling more and work less. I am based in Cambodia, but as I have a full time job it is sometimes difficult to build my blog or travel more. I think the main thing is that you need to do what you enjoy doing and if teaching isn’t for you, then you should try and do what you are passionate about. If you are failing, which I am sure you won’t, then at least you have tried.

  12. I share a lot of your thoughts here Sam. I’ve been nomadic for a little over two years but a full time blogger for just 5 months. I’ve found it a struggle to balance life and blogging. I actually utilize house sitting assignments to substitute my accommodation costs and they have provided the opportunity to catch up on any work that I’ve fallen behind with. As my blog slowly grows so does my work load so I’m currently searching for my own ‘sweet spot’, hope you find yours! While you’re searching can you keep an eye out for mine!!

    1. Charli, it sounds like you’re doing well balancing things now. I agree with you about new challenges coming about as your blog and other online commitments expand. I remember the days when I just had this one blog and it was my main focus; that seems so long ago!

  13. says: Stephen S.

    Hey Sam,

    I’m asking myself some of the same questions, as I starting my long term travels in a just a couple weeks. I’m wondering if the fact that now I’ll have to “Work” from the road change my perceptions of travel, and take out some of the love and joy I felt for it in the first place.

    I loved this post, and I’m sure it will work itself out in the ens. Cheers mate.

    1. Hey Stephen,

      I think it honestly does take a bit of the joy out of travel. I remember back when I was a carefree backpacker. Deciding what clothes to wear, what to eat and where to go were the challenges of the day πŸ˜‰ Now sometimes I find myself staring in front of a computer screen when I’d rather be outside.

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  16. says: Emma Spires

    Thanks for the honest and inspiring article – a very enjoyable read. I think it resonates with anyone who is trying to juggle working online with travel. It would be great if you could keep us posted on your progress and what you have found works for you, whether that be staying in one place for an extended period of time, or something else. Good luck!

    1. Thanks Emma,

      Since I’ve posted this article I’ve been based in Chiang Mai. Being in one spot is certainly nice from a work perspective but I have to admit I’ve had itchy feet more often than I’d like to admit.

  17. says: 2 Digital Nomads

    Good luck mate, it’s not easy job but very doable. Being working in digital agency and working online for over 15 years, making money online is doable for sure but needs strategy before anything. So, once you know your strategy, things will be easier. Safe travel

  18. It must be so tough to force yourself to sit down in front of a laptop instead of enjoying the surroundings. You shouldn’t forget why you’re blogging and that is because of your passion for travel.

    I’ve met a travel blogger recently who said “Oh, I’m so sad I can’t come to this ‘travel bloggers networking event’ because of travelling.” Oh boo hoo! Travel blogger problems?

    1. Hahaha, that’s a good point Natalia. It’s important to remember why you’re doing this in the first place. I’ve often thought travel bloggers who are enjoying their travels the most are the ones who seldom update their blogs πŸ˜‰

  19. Hi Samuel! I really enjoyed reading your insight to the world my hubby and I have just entered. Although we’ve been traveling full time for just over 12 months now we only started our blog in February. Its nice to get inside the thoughts of a more seasons blogger and traveler to know what lies ahead for us.

    Thank you for allowing us to get inside your head πŸ™‚

  20. says: Mike

    Good luck! I just started my blog as I will be leaving to teach English in Spain for a year (at least). I haven’t monetized mine yet, and I’m not sure if I will down the line. I’ve enjoyed blogging much more than I expected since I started it though. Have fun with being a digital nomad! It will be challenging, but rewarding too! Maybe we’ll cross paths in our travels someday.

  21. says: Abby

    I miss being young and free lol. Let us live vicariously through you guys! And I’m not worried one second you won’t be a grand success. If not, you’ll do something else. Have fun!!

  22. Really good post Sam – you certainly don’t have the same freedoms trying to run a travel blog whilst on the road as the normal happy-go-lucky backpacker that’s for sure. I’ve found it hard to maintain a balance of travel and work (and I’m sure I’m not the first), but you guys have each other to bounce off which is really cool!

    Good luck with it, and keep us posted on how you get on!

  23. Great post Sam. Really insightful.
    Have you found yourself on the internet for an entire day, or are you still getting out each day to explore? I would love to reach a point to be doing what you’re doing but of course there are some unexpected hurdles to jump once you reach a certain point. Thanks for pointing them out and writing this article.
    Keep up the good work. (try to mix it with a good dose of play)

    1. says: Samuel

      Thanks Nick,

      I’ve been finding we’ve been staying longer in each destination that in the past (roughly a week) allowing us to travel slower. We typically pick one activity or place to visit for the day and then spend the rest of the time working.

  24. says: Ryan

    Wow Sam, what a deep look into the inner workings of a seasoned traveler. Thanks for sharing this. It seems like this happens to many of the travelers I know after a very extended period abroad. And you are right, from my experience it seems so much more difficult to keep up productivity and consitency. Seems like running a travel blog would be easier while not traveling! Eithe way, I believe you’ll find a sweet spot somewhere if its time to stay somewhere a little while and rekindle that travel mojo!

    1. says: Samuel

      Thanks Ryan!

      I’m really looking for that ‘sweet spot’ and I’ve actually come closer to finding it after posting this article. I think admitting how frustrated I was helped me take a better look at how I was doing things.

  25. says: wanderoneday

    I’m glad that it turns out the life of a perpetual nomad isn’t everything it is cracked up to be. I don’t mean that in a negative way, but more as a consolation to those of us who stay in one place for most of the year, traveling for vacations and day trips instead of as a lifestyle.

    I’ve always wondered how people feel without a solid “home base”, because as much as I love to travel, I really like knowing where “home” is. Are nomads that different than I am? Or does everyone need a sense of place sometimes?

    I look forward to reading about your decisions, to see how permanent wanderlust reconciles with the desire for reliability/stability!

    1. says: Samuel

      Thanks, you really bring up some great points here. I think the perfect balance for me eventually will be to alternate between backpacking and basing myself somewhere throughout the year.

  26. Thanks for a very heartfelt and truthful post Sam!

    Having travelled as backpackers for 2 years, and now teaching English in order to fund another trip….and trying to build up our website, we have a rough idea of what you’re feeling! We have a question running through our minds as well: Will we want to sit in our guesthouse and write posts?..when the whole world is out there waiting for us to see it?!

    I guess we’ll find out when we take off in July.

    Thanks for the insightful post Sam πŸ™‚

    1. says: Samuel

      Thanks Dariece!

      That’s the hardest thing to deal with by far! When you’re traveling you’re not working on your sites and when you’re working on your sites you’re not travelling πŸ™‚

  27. Hey Samual,

    Eloise and I are definitely finding that travelling is getting in the way our quest to full-time digital-nomadism. It’s changing the way we run our lives, as well as how we travel. I feel you 100% regarding the internet being the lifeblood of your business. We’ve missed some time critical advertisement deals during a big travel stint up in the far north of India, literally no Wi-Fi for hundreds of miles. Now, with our business plan and direction, we simply cannot be out of internet range for more than 24 hours. I find this a tad annoying, and against the whole principle of why we went travelling in the first place. To escape all the bullshit of the ‘work life’ and the cliques that go with it. Lucky I enjoy the rocky path to digital nomadism and attempting to become fully location independent. πŸ˜‰ Even if it does mean that our ‘travelling’ has slowed down massively and we need to go places with Wi-Fi and electricity!
    Keep plugging away bro! πŸ™‚


    1. says: Samuel

      Hey Stu,

      I totally feel you. It’s kind of a shame we’re so reliant on wifi. I’ve been discussing with Audrey how much we’d like to go to Myanmar soon; however, we’ve heard that the internet is so bad that if we do want to go we figure we’ll need to base ourselves somewhere before and after the trip to get ahead and get caught up on work.

  28. Good for you and good luck Samuel. You’re way ahead of the curve already. I hit some of the same roadblocks too. We’re in France and use it as our homebase to travel out to other places in Europe but i feel cooped up with m y blog and gorwing that sometimes that my site-seeing gets curtailed by one more job, one more new advertiser, one more edit. aaaah. Plus, with three kids in tow ranging in age from 5 to 16, it seems like there is no balance. p.s. we’re heading to Thailand in a few months and i’m worried about lack of internet access. I’m actually really scared about it… In some ways i think it was easier when I was working as an english teacher and doing odd jobs for a few months at a time and then travelling for a few months at a time. With this digital nomad mentality i am constantly in work mode. But it’s all worth it!!! isn’t it?

    1. says: Samuel

      Hey Annie,

      I certainly think it is all worth it in the end! At least, I sure hope so…LOL

      Thailand surprisingly is quite well equipped in terms of internet from my previous experiences traveling there.

      I hope you’ll find the right balance when you head there soon.

  29. Hey Samuel!

    Great article, it is the ever present dilemma for the digital nomad and you are right it is all about balance and flexibility. Technology helps! While on the go seeing the sights I have the iPhone handy to record my thoughts and a pen & paper as well.

    There is nothing more fun than writing a travel post whilst in the midst of it all. I’m sure you’ll find your balance. There are many of us who do it, you just have to find what works for you.

    Good luck.


    1. says: Samuel

      Thanks Kylie,

      I totally agree with you. I’m personally finding that travelling (as opposed to teaching) is really helping me get into the projects I’m working on more.

  30. I’m leaving to backpack the world, starting my journey as a digital nomad, in less then three weeks. I’m hoping to travel for years to come, travel blogging and writing. Currently I’m making enough money to sustain my travels as a writer and I can write (mostly) without the internet.

    I’m sure it’ll be hard to want to work on my adventure but I’ll find my balance as I’m sure you have.
    Take care,

    1. says: Samuel

      That’s exciting news Wil! Best wishes…

      I think that as you go along you’ll find ways to work more efficiently to make it all work out for you.

    1. says: Samuel

      Thank you Jennifer!

      It’s been more challenging than I anticipated. At first I thought I’d be replacing my teaching hours with travel and still working during my free time to get projects done, but it hasn’t quite worked out that way πŸ™‚

  31. says: Maria

    Lovin’ the honesty Sam and like the idea that you may stop for longer periods – it’s purely selfish of me, if you stop you’ll feed me more intel on a place I too have seen but didn’t have time to stay in or a place I’ve not yet seen and I’ll be better armed for the day I do. Could you mix it and stay 30 or 90 days in one location then move on? That might offer balance and as a reader it would give me a chance to vicariously explore more of a specific region.

    1. says: Samuel

      Maria, that’s a great suggestion! I think we’ll likely find a mix of backpacking (moving quite often) and basing ourselves somewhere for an extended period of time (weeks/months) although we’ve yet to figure it out exactly…haha

  32. Hi Samuel – welcome to the life of a blog slave πŸ™‚ I’ve been on the road for six years and can totally relate. I’ve actually hit two walls, times when I either had to make some changes or quit. I never want travel to become something that I think of as something I “have to do” to earn a living. When the joy starts slipping, it’s time to reassess! I now go through a process every year of writing down my goals and then looking at every activity I do to see if it helps me reach my goals. If it doesn’t, I nix it. If it does and I don’t have time to do it, I hire someone to do it for me. I hired my sister as my virtual assistant a little more than a year ago and it was one of the best decisions I made. I also decided that any email I received that began with “Hi there” or some such generic greeting did not need to be answered, or even read. I’ve discovered the power of the delete key. If someone is asking something of me but can’t even take the time to look up my name (which is highly visible at the top of my blog), I delete the message. There are lots of solutions like this that will carve out more free time, but I really think it starts with an honest assessment of why you are doing it, where you are going, and developing a marketing plan for how to get there. In short, if this is how you want to live, you’ve got to treat it like a business. Best of luck.

    1. says: Samuel

      Thanks Barbara,

      That’s fantastic advice! I think given your experience on the road you’ve really mastered all of this over time. I really like your suggestions for outsourcing work that is important (but doesn’t necessarily have to be done by you) along with reducing non-essential components that eat away at your time. I’m slowly getting better at this myself. I know for certain this is what I want to do, so I will continue to tinker and experiment with things until I find the right balance. Thanks for being an inspiration and sharing your thoughts here.

  33. You are obviously doing something right – with a well-read site and lots of interactions – so I see how you need to keep feeding it.

    When I have been travelling for a long time, two things affect me. One is education – it depends how much I know a place – how much of the history – of what is going on now in politics, in culture – on the street – . If I lose interest in that, then everything becomes a flat landscape.

    The other is not wanting to be the customer all the time – sometimes I want to be person who gets the reward for doing something.

    I don’t think that being in one place and earning a living ‘back home on the internet’ fulfils that function – it has to be in the place I am.

    1. says: Samuel

      David, those are some excellent points. I feel the same way when visiting a destination.

      I’m really fortunate to be doing what I am right now. Even though I haven’t found the right balance, I’m enjoying life far more than I would be if I was back home doing a job I felt no passion towards.

  34. Sigh, let me know if you ever get it figured out. It’s a bit of a back and forth for me, I’ll try to stay home to work for a few weeks, but by the end of week one I’m ready to explore again. Then I go out and exhaust myself travelling/working again. You may have the right idea with basing yourself somewhere new for awhile :]

  35. says: Jacinta

    Nice to read your thoughts Samuel. We all know change is inevitable while at the same time wanting to cling to old habits in some way….it`s the human condition.
    You`ve achieved so much in a short space of time…you should be proud…but it`s always good to keep refining your goals, adapting them to your new circumstances.
    My advice would be…and I don`t know anything about your comitments re your blogs… separate the two in some way. Enjoy the travel, take your photos and videos and then take time out to bring you blogs up to date. Otherwise you are probably not enjoying the experience of travel so much if you are constantly thinking about updating the blogs and spending your time focusing on what you want to upload to the internet instead of the carefree spontaniety of following you instincts and enjoying the moment. I sent a cheap lunch on me ! Take care and keep posting those great photos/videos, πŸ™‚

    1. says: Samuel


      Thank you so much for your support! I would say that is far more than just a cheap lunch and we greatly appreciate it πŸ™‚

      Your idea of separating travel from work is a great idea. I think we’re going to do certain trips each week where we don’t bring our cameras and have no intentions of writing about it. Those kinds of moments will be just for us πŸ™‚

  36. says: Vi

    I understand you. It is so different when you are just travel and when you are trying to make online business from your travel.

  37. says: Nate

    Best of luck man! I’m about to embark on my first digital nomad adventure as well running my business down in Chile. I’ve done the backpacker thing before, and it was awesome. But I’m curious and a little nervous to experience travelling while I am still working.

    1. says: Samuel

      Hey Nate, that’s great to hear and Chile is a country I’d love to revisit again soon.

      I think you’ll find that slowing down (compared to previous backpacking adventures) and creating a work and play schedule will help with your transition.