6 Songs That Reflect What I Learnt After 6 Months on the Road as an Aspiring Digital Nomad

It’s rolling around to 6 months that I have been living this life as a travelling aspiring digital nomad. On the road and fakin’ it till I make it.

6 Songs That Reflect (3)

No, I don’t have it all figured out. But that doesn’t bother me terribly. Looking back at every other challenge I have had in my life, I have at some point been in a space where I didn’t have it figured out. Yet, low and behold I eventually managed to overcome them.

And that is one of the many lessons that pre-nomadic life actually taught me. Yes, pre-nomadic life – while it may feel like a constant prison cell – does teach you things! And I don’t mean just how to get away with playing games all day so your boss doesn’t see, no, serious things like checking your tinder notifications on the sly.

Alright, I’m still joking. But yes, pre-nomadic life taught me that even though things have seemed so annoying. So stagnant. So intolerable, well, I have always pushed through, and had the wherewithal to get where I’m going. And that helped me to have the confidence to make a move – without having all the answers.

Lesson 1: I’m Not the Only One

Yes, as Sam Smith croons, ‘I’m Not The Only One’, but unlike him, that cheers me and doesn’t bum me out. I don’t have this whole making money online/ travelling full-time deal sorted just yet. One of the biggest misconceptions you can get coming out and mingling with other travellers and people working on the road is that everyone has it figured out – but you. But I have gradually come to understand that this just isn’t the case.

If you are contemplating heading off on a nomadic journey or aspire to be a full-time digital nomad, as I do, you probably have a lot of fear and self-doubt. Everyone does. I did, and I still do. But that’s no reason not to ‘feel the fear and do it anyway’.

Once you make the leap and find yourslef out here with other people with similar goals to yours you will realise that a lot of people don’t have it figured out. It’s important to remember that none of the people who are ‘crushing it’ now had it all figured out when they started. But they started –  that’s the key. And they never gave up.

Lesson  2 – There Are Many Ways

No two digital nomads I have met have found the exact same path to success. Some of them begin their businesses while still working 9-to-5 and start travelling when their ventures are suceessfully up and running. Some people sell up and take a leap of faith, building their business on the road and flying by the seat of their pants. Others put all their efforts into one major venture, while some have many different income streams from the get go. There are writers, programmers, coaches, course creators, drop shippers, graphic designers and You Tubers, to name a few.

There is no one way to make this lifestlye work. Life style design is a big part of being a digital nomad – it’s a lifestyle not a career. So in light of that, design your path to success, your LIFE of success. Find what works for you and don’t feel that you have to follow some formula. Take guidance from those who are successful, but you will find your own path. And Like Sinatra – it’s O.K to say: I did it ‘My Way’.

Lesson 3 – Being On The Road Can Be Social

I have never really had a full-on social life. I still don’t. But if there was anywhere that one could have a crazy-busy social schedule it’s on the road. By the very nature of being on the road, working location independent people have a more flexible schedule. This allows them to schedule their work around fun activities. And you can do the same.

Aside from that, people on the road are often travelling alone – and looking for company, just as you are. Although there are some digital nomad couples out there, they are often as much in search of company as lone travellers. As such, people are forever organising mixers, coffee meet ups, weekend trips, networking events and more. Join groups on Facebook in the area where you are travelling and where you are planning to travel next, and you will have no end of people to meet or events to attend. In short, as Michael Jackson sang, ‘You Are Not Alone’.

Lesson 4 – Not Everyone is Enthusiastic About This Lifestyle

I guess it is the nature of the human condition to be perpetually dissatisfied, but you may not realise that this even happens to digital nomads (whose lives are pretty damn exciting). Like any lifestyle, it can begin to wear thin, and after a number of years on the road many digital nomads begin to experience a number of mixed emotions – they feel jaded, tired of never having a constant location, totally over always having to say goodbye to friends (and lovers), or maybe even sick of being tied to a laptop all week.

Eventually, even the allure of the road can wear thin – and the excitement and adventure of a life of unpredictability can turn into a yearning for certainty. A lot of nomads start to feel ‘Jaded’.

But it’s not the end of the world. That is one of the great aspects of being able to design your life. A lot of digital nomads solve this by taking some massive action and changing their life drastically for a season. This can involve heading back to their home country for a few months, heading into the mountains for an extended spiritual retreat, or taking house-sitting jobs for more of a feeling of stability – as well as and the comfort of pets to look after, and some free accommodation. This is a great way to affordably take time off work, and be able to greatly reduce your output for a bit if you feel the need to chill.

Lesson 5: It Takes All Types To Make A World…..or  A Digital Nomad Community!

You might get the impression that digital nomads, entrepreneurs on the road, location independent workers – whatever you want to call them – are a type. They aren’t. They are as varied as a ‘Coat of Many Colours’

Yes, like any other community, there are similarities between individual digital nomads, but they are really such a diverse group. Probably more so than many people who share a career. Digital nomads are often engaged in multiple ventures at once, have diversely different travel histories, come from different parts of the world, and have widely different skills – really it is the most diverse community you can imagine.

Lesson 6: You Will Feel A Lot

No, I’m not being creepy, I’m talking about emotions. The travel/earn life is fraught with feeling. This might sound weird, but a lot of people live such an ordered cubicle life, they are able to insulate themselves very effectively over time. It’s safer that way, it’s comfortable. I get it. But when you are on the road, travelling, and trying to earn online, and facing every challenge that goes with that, you FEEL. All the time, such a variety of feelings. No boring emotions here – there’s an interesting medley of discomfort, fear, inadequacy, elation, complete peace, giddiness, excitement, dread, and so much more.

And what I have noticed in myself – as well as in others I have met – is that this results in a lot of people in this lifestyle chilling out a lot more. People start to become more sanguine. It’s nice. After awhile everyone begins to realise how little control they have over much of it, and so they adapt…learn to step back and ‘Let it Be’. Thanks The Beatles.


So that’s the countdown done. If you liked it, please share. But also, tell me about you. Have you recently begun your nomadic journey? Or have you been travelling for awhile? Let me know where you are at…and what you have learnt lately.

3 thoughts on “6 Songs That Reflect What I Learnt After 6 Months on the Road as an Aspiring Digital Nomad

  • November 11, 2015 at 9:13 am

    Great post! I’m around day number 55 of my six month journey and things are kind of rough. I’ve experienced all of the above emotions and it’s difficult to talk about with friends and family because: I’m traveling around the world! How could you be sad or uncertain for even a second? This isn’t my first time on an adventure like this, but somehow I’ve forgotten this part.
    Devon recently posted…How to Make Friends While Traveling AloneMy Profile

    • November 11, 2015 at 9:43 am

      Hey Devon, I totally get it. Even before i began my journey, I found that I couldn’t relate to a lot of people back home, just because they really didn’t understand my head space, and that continues as i have proceeded with my journey. A lot of nomads struggle with this, but at the same time, as our lifestyle becomes more common, I think that may begin to change – could take a while though! For now, connecting with other nomads seems to be the best way to get things off our chests, i guess. Thanks so much for stopping by!

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