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Digital Nomad Lessons: What I Learned from One Year on The Road

2015 was a very strange year for me. I began the year in great enthusiasm. Quit a superb job late in 2014 [Read: How I Quit My Job to Travel the World NOT!], to take up an assignment in a small heritage town in South India, and I thought things would just fly on from there. Only, as has often been the defining trait of my not-so-short-anymore life, things didn’t quite pan-out as planned, and I ended the year far, far away from where I’d imagined being. The things about trying something new though is that it always brings about new lessons, and tests your mettle. So here’s a small list of digital nomad lessons I learned from my first year on the road.

  1. Set S.M.A.R.T. Objectives and Establish a Schedule:

S.M.A.R.T. is one of those annoying acronyms right out of a B-school textbook, that I hate from the deepest depths of my bowels. I’ve never been one for schedules, discipline, objectives and goals. I’ve generally taken great pride in not knowing what I’ll be doing 2 weeks down the line. You’ve to admit that’s got its own charm; but this year has (begrudgingly) taught me how incredibly vital it is to have measure-able, track-able objectives and work towards them in an established, regular manner. We venomously hate routine, but our brains are hard-wired to function to a schedule of some sort, and no matter how hard most of us would like to rebel against the idea, the possibility of achieving optimal productivity without some sort of a schedule or calendar is virtually impossible. It may work for some, and I doff my hat to them, but it doesn’t work for me at all and that’s one thing I’m determined to fix this year.

Same goes for objectives and goals. If you don’t know what the end product is, or at least have SOME vague idea of it, how do you expect to work towards it? So Digital Nomad Lesson #1 – Set Objectives, Set a Schedule and STICK BY IT!

S.M.A.R.T Objectives

  1. Identify Your Skill-set and Gauge sale-ability

I own a third-world passport. I am not going to whine about my nationality or the state of my currency because I’m obviously proud of where I come from, but take a gander at any digital nomad group on social media and you will see how weakly represented we are as a nationality in this space. The problem is two-fold:

i) as a nation (India), we ourselves are not very open to the concept of remote-work. Most of our major employers do not encourage it, and generally tend to look at it with discomfort and apprehension. This is slowly changing, but is still a long way from becoming commonplace. Naturally, the opportunities domestically are very limited.

ii) it becomes infinitely more difficult to pitch your skill-set to an overseas third-party employer on a contractual/freelance basis. Freelancers from Asia in particular have become rather notorious for offering substandard work at ridiculously low rates (seriously guys, who writes a 1000-word piece for $0.01?).

To summarise, what I mean to say is that if you aim to make it as a digital nomad, you’ve already got your work cut out; to add to that, if you come from a third-world country, like I do, then you’ve really got the odds stacked against you.

Make a list of the things you are good at (and when I mean ‘good at’ I mean ‘professionally good at’. Being able to type one complete sentence in English may not qualify). Your job doesn’t end here.

You then need to figure out if your skillset has market value — both locally and internationally. If not locally, then figure out how open people overseas are, to hiring somebody of your profile for a gig, as opposed to hiring somebody local.

  1. Grow Your Skillset and your Market Value

I can’t emphasise enough on how important it is to keep innovating and updating your skillset as time progresses. If you are amongst the few that has a robust skillset and gets off to a good start, it’s very easy to become complacent and sit on what you have; but the best of our lot are the ones that are always vigilant, constantly networking and quick in identifying an opportunity to grow into. Some valuable resources for self-taught courses:



Once you’ve done your groundwork, your real work starts. Find prospective clients and start actively pitching to them. Where you find your work depends on your particular speciality, but there are a few good/decent portals I use mostly for ‘writing’ and ‘digital media’ gigs. Here are a few to get you started:

Freelance Writing Gigs

Travel Blogging

What My Average Work Day Looks Like

There are obviously plenty more portals to find freelance work, and if you have a specialised (read: rare) skillset such as say, coding for instance, you’ll find a lot of specialised portals with much better pay and intensive projects. It’s a tough grind – you’ve been warned!

  1. Do Not Trust Lightly and Completely

You know those travel bloggers that keep talking about the ‘kindness of strangers’? Well, I’m not saying they are wrong or misleading, I’ve had my fair share of those experiences; but there’s a hidden danger in reading these stories. You start romanticizing the ‘kindness of strangers’ and you want to/end up believing that everybody’s kind, fair and honest. Unfortunately, that isn’t the case. One of the biggest pitfalls of freelance work is that the income is unpredictable and high-risk. Firstly, it will take you ages to find decent clients, and even then, you’ll come across people who don’t pay on time, or don’t pay at all.

Some of the worst experiences I’ve had are working with friends, who promise you the world, and apparently do brilliant, life-changing work, but haggle and cheat and delay and negotiate for every penny they owe you for your services. The sad part about these scenarios is that you don’t only lose time and money, you also lose a friend.

There isn’t a lot you can do once you find yourself in this situation, so the best advice I can give you is ‘prevention is better than cure’. I’ve found out the hard way, it is extremely vital to protect yourself legally as a freelance or remote worker. In most cases, feel free to demand a pre-payment or set up milestone-focused payments through a third-party instrument like Escrowwhich will add at least some sort of protection to your interests. 


I’m really sorry to piss all over several thousand parades all at once, but you have got to be both incredibly talented and incredibly fortunate to step into this realm and have everything fall into place for you right away. There’s a very long and weary road waiting ahead of you. Be prepared for 2 years of back-breaking work, with no respite, no rest, no favours, extreme austerity, countless rejections and 50 hour work-weeks becoming the norm! It may not necessarily end up being that bad for you, but I think it’s important to be mentally prepared for the worst (and then smile at how easy it looks later).

  1. Hedge Your Bets/Always Have a Back-up Plan

I am currently in the midst of trying to figure out my way forward and what I want to do with 2016, but let me tell you I’ve already started weighing my options and doing a mental SWOT of each. The problem with being a jack-of-all-trades is that sometimes you have far too many options and you end up incredibly disoriented about what path you want to take in life. Sometimes that isn’t such a bad thing, but every once in a while it is important to sit down and review Lesson #1, and see what route is most likely to lead you to the overall goal or objective you set for yourself.

Walking off the beaten path is no stroll in the park…well sometimes it could be, but you can’t always bank on it. Because there is no precedence, and no ‘one way to success’, unlike some of the more tried and tested ways of life, you will make a lot of mistakes, and that is OKAY, so long as you continue to learn from them and keep eliminating them. You will have moments of acute self-doubt, loathing, despair and “WHAT THE FUCK AM I DOING WITH MY LIFE”, and each of those moments are legitimate, and acceptable – it is ok to feel that way…momentarily; but then you shake it off and get right back to work.

Every time you feel sorry for yourself, remember the words of all the people that thought you were so brave to be able to do what you wanted to do; remember how each of them secretly wished they had the balls to do what you do (even if they never said that explicitly), and remember that even if you fail, it’s okay. You went out and you tried your hand at something most people go through a lifetime dreaming about. You’ve always got the rest of your life to play safe, live comfortably, and write another self-proclaimed expert piece on digital nomad lessons you learned! For now, it’s okay to take risks and want to fly! Good luck and Godspeed 🙂

Digital Nomad Lessons - Workplaces Look Like This

The Brighter Part About a Digital Nomad Life – Beer at Your Work-desk!

PS. If you have been through a similar situation in life, I’d love to hear about it. Also, if you read this and decide to take the leap, I’d again want to hear all about it! I once received a note from a reader about how one of my posts gave her the courage to make a decision she’d been oscillating about for months, and I think I still hold on to that note every time I wonder if I want to continue investing so much time and resources into this. You know what to do! The comments box is open, or you can always drop me a note on email! Hope these Digital Nomad Lessons help you prepare better for your journey than I was 😉


  1. Thank you for this! I own a third world passport as well and deciding to do the shift to a nomadic lifestyle this year. Your post is very helpful (aside from it hitting home)! bookmarking this for reference 🙂

  2. Dear Sanket, thank you for sharing this motivating passage! I totally understand you when you speak about being a holder of a 3rd world country passport, I myself is one of them. Here, in my country (Ukraine) people also deliver high quality services at some 0.0000… money. And I also believe that there are always good options if one starts looking for them.


    • mm

      Frankly, I’m alarmed at the number of people willing to work crazy hours for peanuts. It brings down the market value of the entire industry, but I agree, if you look long enough and learn to look in the right places, you’ll find good things, eventually 🙂

  3. I find it genuinely interesting to hear honesty about digital nomadism from those who are deep in it. Ironically, I think most digital nomads make money “selling the dream” but it’s important to know the reality if you’re preparing to step off the proverbial cliff.

    I’ve been thinking a lot about getting deeper into freelance – and have been lucky to score some jobs on Upwork so far – but am hesitant to leave behind all forms of regular hourly pay in favor of a completely digital nomad life. I think perhaps a balance of the two might be the way to go for me. Maybe a part-time/casual job 20-30 hours and freelance otherwise. Just some thoughts. We shall see I suppose!

    • mm

      Yep. You make a lot of sense, Michelle. If you’ve got a good thing going, it makes sense to build relationships and some steady freelance income on the side instead of just taking the plunge unprepared. I think a lot of people believe that they need to just quit cold-turkey, if they really want to do something. Law of inertia I guess – they believe they can’t and won’t do anything about it, until they find themselves thrown into the deep end (or throw themselves).

  4. Loved this post! I always read about bloggers or people on Instagram who have quit the jobs and are living the dream life to travel the world. It’s nice to see a different perspective, the reality of how much work and self motivation it takes. Kudos to you for being to do it and sticking to your goals!

    • mm

      haha, Ann! I actually have another post that talks about the ugly side of travel blogging nobody speaks about. I think you might enjoy reading that even more. There’s always two sides to a pretty picture – and because we as travel bloggers are expected to sell the dream, we seldom speak about the other side of the penny!

  5. I’m originally from Canada, but live in Guatemala, so any time my country of residence shows up, I end up with people thinking I ought to charge less for my work. I actually had one client, who had posted his budget of $800, offer me $200 for the same job, because he said my cost of living was lower. Uh, yeah, well, my value doesn’t change just because I live somewhere perceived as cheap!

  6. Determination and perseverence is the key… I’m sure you will continue to follow your passion and pave your way to live this nomadic life.
    Good luck!

  7. I loved reading this post! As a citizen of the United States, I am fascinated to hear about your experience traveling as a third world citizen. It’s something I never thought of, and I’m sorry you have dealt with your challenges to find freelance work. I love that your blog gives your honest narrative of how your year has been. Can’t wait to keep reading!

  8. You’re right, it is important to be patient. It’s a thing that I learn everyday…

  9. Thanks for sharing! A very interesting read. The ‘OMG what am I doing with my life’ moments are frequent for me. I think I need to make some changes. 🙂

  10. Very insightful! Unfortunately, I learned from my parents that doing business with friends or family always gets hairy. I think I’ll avoid it as a whole. I love how you bring up the challenges of coming from a India vs Europe or N. America, and do agree that there should be more representation.

    • mm

      Well, it’s a lesson I learned the hard way. I actually let go of a very promising opportunity this year, because it was coming from a friend. Representation is growing, slowly, gradually…the fun thing to see now is if it’s a passing trend, or if it’s there to last 🙂

  11. Super inspiring for where I am in my life right now!

  12. This is such an inspiring and at the same time practical post! More people should be aware that there is more to being a digital nomad than just the freedom to work for yourself. There are perks, of course, but it takes hard work to get there. Thanks for sharing! 🙂

    • mm

      The more we talk about it, the more people will become aware, Liz. I’m also a little weary of people claiming I’ve such a lucky life. No, buddy! Not lucky at all!

  13. Your post is such a great inspiration. While I come from Easter Europe, I have to say I have a lot less issues traveling or working, at least as far as the EU goes. I haven’t tried working and travelling for more than a month at a time, but at least a semi-nomadic lifestyle has always had its appeal. I completely agree with your tips on having SMART goals and always improving your skill set, no matter what area you work in.

  14. Thanks for this post! I would consider myself lucky, as I am from Singapore, and own a pretty good passport and have a pretty strong currency. The mentality of Singaporeans are to have a stable job and to climb the corporate ladder, but at the end of the day, you realised that you achieved nothing in life.

    • mm

      Yep! Same, here in India too. Parents are constantly baffled at my life decisions. Can’t comprehend why I leave behind such a good scene and keep struggling to make it in this line of work, but like you said, nothing ventured, nothing gained, right?

  15. I have never heard of SMART, surprisingly! But I will definitely be using it now. Thanks so much!!

  16. This is just life changing for me as a digital nomad too. Most of the time, we work our ass off and we get underpaid. 🙁 I know that being one has its perks too but I learned to be more careful next time 🙂 Hope you can visit the Philippines too 🙂

    • mm

      I hope I can too, Jeane! I was planning on a trip to Boracay in May, but flights are far too expensive. I think I’m going to settle for Koh Phanghan instead!

  17. You did a brave move for being a digital nomad. That’s something I’m also willing to do in the future. You set good points here. Another thing that I would like to add is think big and never underestimate your self. When I started blogging, It’s clear to me what I would like to happen in my blogging career which I’m happy that it’s slowly happenning now. I’m always proud but humble and always believe in myself. Because at the end of the day. When everyone are doesn’t believe in you. You will only have your self.

  18. This post is so motivating an actually it is really moving. Leaving the job to experience something unforgettable and I think I may be the next one doing it one day, hahaha!
    + very useful tips, thank you!

  19. I have actually been writing a similar post on how to set goals and reach them! I can only say that you are right and I am experiencing that it works ! great post!
    Miriam from http://www.be-sparkling.com

  20. Great tips! Setting goals and sticking to them is so much harder than it sounds when you are working for yourself, but absolutely necessary as you found out 🙂 I like that you included #6 as a nice little reality check.

  21. Thank you so much for sharing this because I have many of the same feelings and experience. I left the corporate world to pursue my passions without having a clear idea of what exactly I would do. Loving travel and photography, I started my blog. But I still struggle to monetize it or utilize a specific skillset that I can market. What I wish I had thought about sooner 😉

  22. sticking to the schedule is very important to me, precisely being the reason why I travel alone!

  23. A lot of valuable information thank you! As an ameture digital nomad this is very helpful~!!

  24. Inspirational message ,Thanks

  25. I’m happy to see in an article tips on how to make it as a traveler. Indeed, the first step is to decide that this is what you want to do, then set those actionable, measurable goals. And stick to the plan! To many wonderful travelling years!

  26. I am so glad that you talked about the romanticizing of the kindness of strangers. It definitely does happen and i’ve met some amazingly kind people while traveling, but there are so many people out there who are not kind and like you said, are trying to take advantage of you.

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