The Challenges of Going From A Gap Year to Digital Nomad

I recently wrote about why I don’t regret quitting law to travel and it seemed only fair, as I make my final preparations for my next travel plans (where I’ll be heading back to Latin America for at least the rest of the year), to present the flip-side of the story because long-term travel isn’t always sweetness and light. The truth is that I’m excited for my next adventure but I’m also a little freaked out because I had my worse travel year yet and I’m not keen for a repeat performance.

Overall I love my travel-work lifestyle yet there are frequent moments when I really do stop and ask myself what the hell I’m doing with my life. My brother recently asked me if I was happy and, in all honesty, my answer wasn’t a definitive yes or no. The best I could articulate how I feel is “It’s complicated.” To many people that might seem crazy, ungrateful and even a fairly bit spoilt. I get to travel the world – full-time. Surely there is no room for doubt? A week later, I read an amazing article (I’ll share the link below), that completely summed up how I was feeling, why I didn’t spring out of bed every day like I was Happy from Snow White and the Seven Dwarfs and why sometimes I lose sight of what I’m doing. All of these recent thoughts have culminated into this post – transitioning from gap-year to long-term travel and the challenges in-between. So let’s go back a bit…

Deciding to go from gap year to full-time travel is a huge decision

I’ve always been a bit of an extremist – I run hard and fast or not at all, I work 16 hours a day…or binge watch TV, I party until 10pm or 6am. I rarely seem to find the middle of the road. So, I guess I could have foreseen that I was either going to love or hate travelling with a passion. It turned out I loved it. But therein lay a problem. Many people I have met on the road set out on their one-year…one summer…one month global adventure with a very solid plan to return home. For the vast majority of people, it’s enough. They take the memories and the return to “real life”. I had intended to do the same. Except six months into my trip I began to panic. I didn’t want to go back. Not to the country I’d been living in for three decades and not to the job and career that I’d fallen out of love with.

I remember sitting on a beach and making myself a promise. I wouldn’t go back until I was ready – until going back was something I really wanted to do. I was comfortable with my decision. I was spending under budget and I was fortunate enough to have some savings in the bank that I could turn to. I still didn’t have a solid plan but I had an intention and that was enough at the time. Five months later I got to India. With a non-existent nightlife and a recent experience of travel burn out in Southeast Asia, I started to think more about what I wanted in life other than “not going back”.

While I was a lawyer, I had started to write. It was pure hobby, but somewhere in the recesses between sleep and a full-time job, I’d bashed out 90,000 words of a novel. I worked on it at weekends, late at night, on holidays. It was a hobby that gave me genuine delight. So what about that, what about trying to write? Sat in a cafe in India, sipping on 50p chai, I applied for my first freelance job. And I got it! Woo-hoo – I was going to be paid $3 for 600 words. Wait?! What? Yes. It was a rate of pay that should be illegal, but sat in that cafe in Delhi, with time on my hands and a passion I was already working on for free, why not? It would pay for all my meals that day if nothing else. And so it began.

Building up a digital nomad income is hard

When September 2011 and the one year anniversary of my gap-year came around, my original promise to myself to travel until I was ready to go home had morphed. I’d made myself a different promise – to focus on my writing for six months and see if I could generate some real income. My goal wasn’t compatible with a fully-nomadic lifestyle. I would need a base – a solid wi-fi connection, a desk and a place I could hole up for a while, which led me to a Troglodyte cave house that I rented in the small yet idyllic French village of Montsoreau.

For three months I sat and I wrote. I pitched, I hit deadlines and I started to earn a not-too shabby (by travelling and freelance writing standards) income (above $3 per article, anyway!). But with my hands freezing from the cold and my wanderlust burning stronger than ever, I knew I had to return to the road. I was 18 months into my “gap-year” and I still didn’t want to go back to life as I’d known it. And so, I bought a one-way ticket to Mexico. My stint in France had taught me that I could make a living from writing but landing in Mexico I came to realise that the success of the business model I’d worked so hard to build was based on volume. It was a “write-em fast, sell-em cheap” style of work that sucked away my interest, my creativity and ultimately wasn’t for me. As I slowly wound down my work from one client after another, I found myself with a lot of time on my hands and a lot of places to explore. With abandon and little concern for my ever diminishing savings, I travelled freely, partied often and whittled away over half a year of my life. It was fun at the time, but it was an indulgence that was expensive and wasn’t taking me any further forward in life.

If you fail at your digital nomad job, you’ll have to pivot

The next year I started over. I realised that in order to follow my dreams, I had to decide what it was that I really wanted. Simply “to write” was too nebulous a concept. After all, I’d been writing all day every day in France and it hadn’t fulfilled. Did I want to write for magazines (not as easy an egg to crack as writing for online), did I want to write for my blog (and, if so, how the hell do you monetize such a beast in an increasingly crowded space) or did I want to return to fiction (which guaranteed no money upfront and possibly none down the line either but was most likely to fulfil my writing passion)? There was also a further temptation – I’d been in contact with a major US publisher about writing my travel memoir.

Ask me what I wanted (and still want) and the answer is “all of the above”. Yet there simply isn’t enough time in the day to pursue them all effectively. And so I found myself at an impasse. As I struggled to find focus, my daily travel conundrums continued at pace in the background. I was in Asia trying in earnest to manage a life of full-time travel and full-time work. I spent my days brainstorming, pitching, writing and re-writing. I spent my evenings figuring out where I was going to sleep, where I could find wi-fi, plotting the best route to avoid the bulk of the monsoon and wondering when the hell I was going to fit in time for any real sightseeing, fun and even the occasional meal sat somewhere other than in front of my laptop. In short, after a few months of “starting again” my head imploded…and it wasn’t pretty. I worked myself into a tense mess of self-doubt.

What was I doing with my life? I wasn’t earning a real income (by real, I was looking at my friends at home), I wasn’t travelling well because I was existing under a constant cloud of guilt that I shouldn’t be lying on a beach but rather working and, when I did settle into a wi-fi zone, I’d berate myself for not being outdoors – what really is the point of being in the Philippines if all I was going to do was sit inside a cafe? I felt like a failure on every level.

You might miss Old World structure in your New World lifestyle

I never planned to travel for more than a year and that turned out to be one of my problems – I didn’t have any plan at all. As my gap-year came and went, and I didn’t report back for normal duty, I was wandering free, I was winging it and I wasn’t always winning. Travel has absolutely changed my life – it had opened my eyes to so many possibilities including most fundamentally that there is a different, more fulfilling (for me) lifestyle beyond wishing away my Monday to Friday on the promise of enjoying Saturday and Sunday. That was a lifestyle I knew well.

Stepping away, I’d seen the potential of something new, but what I didn’t have was the roadmap for how to navigate it and how to make it work. The temptations of travel weighed strong against my need to work full-time. But how could I juggle both? Did I simply go to the office 9 to 5 in Manila, write everything I could then spend weekends in places like Batad exploring the Rice Terraces? Wasn’t that a formula I’d broken out of (albeit with a more satisfying day-job and a more exotic thrill for weekends)?

What about mixing up the schedule – work when I felt like it so long as I got a certain amount of stuff done each week. I tried it, and it simply led to working more hours than I did when I was a lawyer – because the to-do list I crafted was enough for an entire 10-strong team of writers, not just me. I still don’t have the roadmap for this new path that I’ve taken but with every trial and error attempt, I’m getting closer, I’m finding more balance and I’m getting happier. Taking that decision not to go back to what had been my past life, I wish I’d had a list of the challenges I was going to face. Not so as to avoid them, but to be better prepared. If you’re contemplating taking a similar path, here’s my warts and all view on the challenges of transitioning from gap-year to full-time traveller.

You’ll worry about money a lot

Absent a trust fund, most people have to work to sustain their travels. There are multiple ways to do this and for most long-term travellers, that means some sort of freelance work online. This is a vast topic that I won’t go into here, but the challenges are plentiful and you shouldn’t underestimate how much time you will spend pitching for work, making financial plans that rarely come to pass and flat out looking at your bank account in dismay. Yes, travelling in cheaper countries helps, but as a freelancer, for every hour you sit on a beach, it’s an hour you don’t get paid. And let’s not even think about the possibility of getting sick for a week or needing a 2-week repair on your laptop.

People will want to talk about money a lot

There’s also a very strange break in the social norm that comes with long-term work and travel – so many people shed the taboo about money and seem completely comfortable asking you how much you earn. I get it, you’re intrigued (because you want to know if you could do it too), but seriously?! You’re a complete stranger and you’re the 12th person to ask me this week. Guess how many times I got asked about my income when I was a lawyer? Zero. Zilch. Never. For a while I experimented with the telling the truth. When people asked how much I’d made, I simply told then and they commonly looked at me like I’d just shot their kitten. And in a way, I had. The truth is I don’t break even every month and I still have savings I’m relying on. For many people, travelling the world on a one-way ticket is a dream lifestyle and to be that person is living proof of the possibility that maybe, just maybe one day it’s a dream they may get to fulfil. Tell people their dream has its downsides and that many of those are financial and you may as well tell a five year old that Father Christmas is just his fat, old dad. Reality bites and being the one to tell people that can be sucky.

Many people just won’t ‘get’ you

I’ve had many people (from strangers to family to friends) tell me point-blank that they couldn’t do what I do and it’s often delivered with a look in their eyes as though I’ve just crapped on their apple turnover. Fine, maybe you can’t/don’t want to/would rather die than “do what I do” (i.e. live like a gypsy wanderer without the comforts of home and security of a 9-to-5), but guess what: a) you don’t have to – that’s the beauty of autonomy and b) what you’re saying is actually kind of offensive because you’re looking at your life, you’re looking at mine and you seem to be saying that yours is better. Maybe it is…for you. Maybe I couldn’t do what you do (anymore). But maybe we should both keep our thoughts to ourselves (in person – of course I’m allowed to rant about it on my blog!)

You may end up travelling less, not more

But let’s get to the real rub. If there is one piece of knowledge I wish I could go back and share with myself at the point that I decided I wanted to transition from a gap-year to long-term travel, it’s this: what I fell in love with during my year of travel was a lifestyle, and that lifestyle is not sustainable long-term.

I was on extended annual leave, I had 365 days of carefree play, no responsibilities, a nice budget that I was underspending on and life really was all rainbows and butterflies. I didn’t have a bad thought in the world. When I decided I didn’t want my travels to end, what I really meant was that I didn’t want that stress-free, hedonistic way of life to end. Yet, reality (at least in my world) is different. I couldn’t financially, nor mentally spend the rest of my life lounging at the beach. Despite myself, I’m a driven, goal-oriented person. I’m the kind of person who is easily bored and as much as the beach thrills me, after a spate of time, that tires me to. I like to work, but we all know what work means, regardless of how much you enjoy it: deadlines, responsibilities, commitments. In short: Long-term travel equalled work and, in-turn, work (aka The Anti-Christ of Bohemia) spelled the end of my hedonistic ways.

Finding work-life balance can be harder than at home

Which neatly brings me onto my next topic – finding work-life balance. I’ve already mentioned above the struggles both internally (should I work/should I play and the associated guilt I felt with each) and externally (can I get wi-fi, what if my night-bus breaks down and I’m not online for 24 hours to hit my next deadline). If people think finding work-life balance is difficult in “mainstream” life, try adding in the challenges of full-time travel.

You can become travel spoilt

Somewhere along the way, without really realising it, I found myself uttering sentences like “I’ve seen Mummies is the Egyptian museum in Cairo, why would I want to see them in Mexico City?” and, “We’ll it’s nice, but you can’t really beat the beaches of the Caribbean.”

Two words for myself: Spoilt. Bitch.

Realising I’d developed this attitude was one of the hardest things to hit me last year. My saving grace was that I was around another long-term traveller and when I confessed my badness, he offered up some excellent advice:

When you travel long-term, you need to travel differently. You’re no longer exploring museums, beaches, street food – none of that is as new and exciting as it once was. Instead you have to dig deeper, search wider and stay longer. Somewhere along the way you shift from focusing on the big hitting sights (because you’ve probably seen something better or at least as good elsewhere), to paying attention to the details and finding the magic in the smaller aspects.

A couple of days after my pep-talk and after a somewhat disappointing boat trip in El Nido (not as nice as Halong Bay, thought the spoilt travel bitch), I found myself stuck under a shop awning as the monsoon boomed on down. I watched as a young girl stood out in the downpour, her clothes sodden, washing her hair under a gutter pipe. She was filled with genuine delight and suddenly I knew exactly what my friend meant.

You have to make a lot of sacrifices

Returning back to that well-worn statement “I couldn’t do what you do,” well, guess what, sometimes I can’t do it either… or at least I find it more difficult than people might imagine. Is my big dream to spend my forties (not quite there yet, but fast approaching) as a single woman, sharing 20-bed dorm room with Spring Breakers, sleeping on night buses every fourth day and trying to consume new cities in 72 hours? It probably won’t surprise you to hear me say no!

I love travel, but it would be nice to have a place to call home (even if I’m not there very often) and it would be nice to swap out a few more of those dorm rooms for hotel rooms and apartments. I don’t need all the fancy-schmancy I had as a lawyer, but until I can pass the tipping point on my freelance writing career, where people are knocking on my door for work more than I’m knocking on theirs, I have to make some sacrifices, the biggest of which is living and travelling in cheaper countries.

There’s a very good reason a lot of digital nomads live in Southeast Asia and Latin America – it’s more affordable. And as good travel maths dictates – spend less, travel longer, work fewer hours. That’s the balance many of us are searching for but it’s rarely delivered on a (street-food paper) plate. Being away from friends and family is often lonely and so is moving around so frequently. However, the reality for most people who are starting their own online business is that it simply makes more financial sense. The upside to spending time overseas is that I can build my business slowly and in the right way for me without the financial pressure I’d having if I was looking to find rent in London each month.

You get tired of explaining what you do

“What do you do?” “I’m a lawyer” “Oh.” <conversation over> My old job wasn’t exciting for other people but as soon as you tell people that you travel long-term and write stuff about travel to try and squeeze out a living, they get all…interested. I know that should be nice, but when your lifestyle is on your mind 110% of the time, the last thing you want to do when you’re chilling out or just engaging in an everyday transaction (at the bank or the hairdressers – my most recent encounters), is talk about your lifestyle, especially when the most common questions are a) how much do you earn (see above); and b) how can I do that? (Seriously? Even if I were qualified to answer, it’s been a mammoth learning curve over more than three years so not something I can distill it into a 5-minute how-to). From now on, I’ve decided I’m going to tell people I launder money. I suspect that will close the conversation down quickly. Anyone who expresses too much interest in the details is getting passed onto the authorities.

You’ll fail a lot – and it can hurt financially and emotionally

Doing a job I’d been formally trained to do in an environment where I had more experienced lawyers and mentors to turn to, it was actually pretty difficult to fail, and absent a Royal-Screw-Up, I would probably still have a job and, vitally, a pay cheque at the end of the month even if I did muck up. That’s not the case with freelancing. But the double-whammy is that even when you don’t screw up, you can still fail (in my world that most commonly means not getting the work I’ve pitched for). In a big company, bringing in clients was someone else’s worry and I got paid regardless. In a company of one, failing can seriously diminish your taco fund. Take enough of those failures on the chin and your emotions can start to bruise too, leading you down the dark path of “What the F$ck am I doing with my life?” to the town of “Serious Self Doubt”.

Following your passion isn’t always the dream it may seem

Remember that article I mentioned? The one that completely articulated how I was feeling about pursuing my passion? I’d highly recommend giving it a read: 5 things no-one ever tells you about following your passion. I can relate to every one of the points it makes.

• You may feel worse before you feel better (because aiming for your dream and achieving it are different things and the path between the two can be challenging):
• Your fears will be bigger
• Your comfort zone is a thing of the past.
• You loose the ability to make decisions.

But most of all…

It’s totally worth it

Travel has changed me. It has changed me in so many ways, and overwhelmingly for the better. Life in my new world is heaps more scary than anything I faced before and sometimes I toy with the familiarity and comfort of returning to a job where someone else can tell me what to do and shoulder the burden. But ultimately, I doubt I could go back. I’ve had a taste of life down this new road and I like it. I just need to keep working out how to make it work. In the meantime, every day I grow – and for a 5ft girl, that’s important.

Have you transitioned from a gap-year to long-term travel? Is it a life-long dream? I’d love to hear your story and experience in the comments below.

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