How I managed to get a month overseas despite having a nine-to-five job - plus some tips on how you can do the same

What differentiates travelling from simply going on holiday? Everybody will have their own opinions on this, but for me, it’s time. With time you forget about home. With time you can immerse yourself in foreign lands. Time lets you let mentally let go of those things that clamour for attention in your head every waking hour.

But time is a scarce resource if you’re bound to the commitments of a full-time job. Across the world, the amount of annual leave you get varies wildly; here in the UK, we get 28 days of statutory annual leave; in the US, you get none.

And even with annual leave, there’s no guarantee you can use it all at once - that’s totally up to your employer. You may very well find you can take no more than a week at a time. With all these limitations, the thought of long-term or even medium-term travel might seem as far-off as all the places you want to visit.

I have a full-time job, and I’m travelling for a month. I’m going to explain how I made my situation work, before going on to give you some other tips and rules of thumb. And along the way I may very well employ some handily illustrative stock photography 👌.

Travelling with a full-time job – My story

Plan A: An unpaid career break

I work as a commercial journalist for a publishing company in London.

I started working there in June 2018, and it wasn’t long before I realised I’d made the right decision taking the job. It was a hugely positive change in my life. At the same time, I was well aware that something was missing for me. After a long, slightly fitful summer of thinking things through, I decided I needed to go travelling.

One very cool perk that the company offers is a six-week paid sabbatical after five years of service. (This used to be fairly common in journalism. In a previous job, it was written into the house agreement of all union-eligible staff. Unfortunately, that’s since changed.) I was impressed to know this policy was there, after five years. I also knew I couldn’t wait for five years.

After some thought, I arranged a sit-down with manager, and propose that I take a three-month unpaid career break in 2020. My manager arranged a meeting with HR, and came back to me soon after with a regretful no. There simply wasn’t a strong enough business for them to have to provide freelance cover for a quarter of a year.

I was disappointed, but not surprised. I knew from the off this was a bold ask, especially since I’d only started there a few months earlier. But I approached it with the phrase ‘Don’t ask, don’t get’ in my head. I did ask; I didn’t get. So it was time to reconsider.

Plan B: Working remotely

One thing to note about my job as a commercial writer is that everything takes place online. I really do mean everything. My entire daily workload takes place within the confines of the Chrome browser. I write my content in Google Docs. It gets shared, signed off by my editors, and published online via CMS systems. Conversations with colleagues take place on Slack, the messaging service. (Often with people sat within speaking distance, which is weird but all Slack users end up doing it.)

The office has a hotdesking policy, and we all work out of laptops on different floors of the office each day. For capacity reasons, employees are asked to work from home one day a week. If there’s a meeting on that day, that’s no issue: we simply connect to the meeting room via Google Hangouts webcam. While trying to keep your dirty dishes out of shot.

This ‘location-independent’ nature of my work, I realised, threw up all sorts of possibilities. If I can do my job 10 miles from the office in my house in Leytonstone, then why not 2,000 miles away in Tbilisi? (By this point, travel plans had started to coalesce in my head.) Providing I had a desk to work at and steady wi-fi, it would be exactly the same. There might be a time of difference - Turkey and the Caucasus are only 3 to 4 hours ahead of the UK - but I couldn’t see it being much of an issue.

Not that I wanted to go overseas to spend my days inside, tapping away at my laptop. Then, my annual leave came to mind. I could use that too. When I was in towns and cities - places where I could sit in Airbnb apartments, cafes, anywhere with wi-fi - I would work remotely. But for more off-grid activities - trekking in Georgia’s Svaneti region, hiking in Dilijan in Armenia - I could use my leave, and forget about work.

I broached this second idea with my manager. This time, I had to wait a little longer for her to take the proposal to HR. The answer was a yes.

READ NEXT: Caucasus Travel – An Introduction

That’s how I’ve made travelling with a full-time job work: with mixture of working remotely and using annual leave. Is it perfect? No. It’s a compromise. And I know that to many travellers and nomadic types, a month is little more than a heartbeat.

But if it weren’t for this, outside of quitting my job, I would be waiting until 2023 for the opportunity to travel. And I plan to make those thirty days count.

This is my situation, and yours could well be very different. Below, I’ve put together a list of options for how you might commit to long-term travel with a full-time job, each with their pros and cons.

How to travel with a full-time job

Ask for an unpaid career break/sabbatical

Maybe this sounds like an outrageous request to make it your employer - but think about it. You’re essentially asking to go off for a spot of self-development… and you’re not asking for a single penny. It will probably be harder for those in senior and managerial positions - but if you’ve worked your way to that point on your workplace’s career ladder, you’ve hopefully earned the respect of your seniors.

More and more workplaces are growing to appreciate that extended breaks help foster happy, fulfilled employees. It’s pretty obvious why my own company offers a six-week sabbatical after five years: it’s an incentive to keep you there. If you’re feeling particularly Machiavellian, you could always subtly suggest that a career break is what will keep you from looking for a new job elsewhere.

Ask to work remotely

This is the one that worked for me. If you’re happy taking some professional commitments overseas with you, and you can make the logistics work, then this could be ideal. Time difference might be a challenge. You may find yourself in places where there’s no reliable wi-fi; you want to go trekking in remote locations where you can’t pop your Macbook’s charger into a plug socket. But if you plan to stick to civilisation, it’s far from impossible. Best of all: you’re still getting paid! That’s no small thing, as the costs of travelling can quickly accumulate. You could also do something like sublet, or get a lodger while you’re away from your home. With that extra money coming in, you could very well break even.

Move into freelancing

Did you know the word ‘freelance’ comes from Walter Scott’s novel Ivanhoe, describing a group of mercenary soldiers who offered their ‘free lances’ to a medieval lord? These days, instead of soldiers for hire, it usually refers to perpetually neurotic people who whine about 1) being hopelessly overworked or 2) desperate for work. But hey, if you’re salaried (like yours truly), being your own boss still has all that romanticism.

Which leads me to the digital nomads: a global class of freelancers/wanders/citizens of the world who I have to be honest and say of this, I know little. But I hope to delve a little more into the world of digital nomadery (?) in a future post.

Get a new job

Okay, this probably sounds a bit drastic. But I imagine there are plenty of people out there who want to travel, and wouldn’t mind a change of workplace either.

Here’s a way to play it. You find a new job. You get ‘creative’ with details of your notice period, and you use the breathing space between jobs for travel. Something similar happened with a friend of mine, who works in occupational psychology. He was headhunted for a new job, and his (slightly fucked off) employers put him on gardening leave instead of getting him to work his notice. Discovering he suddenly had six weeks of free time at his disposal, he promptly booked a return flight to Sydney to spend time with a mutual friend of ours.

READ NEXT: Caucasus Travel – An Introduction

As with any change of job, you might find you preferred your old place. But experience has taught me that this is the exception rather than the rule. Most people are attached to their current jobs because they’re stuck in the quicksand of their comfort zone, or feel irrationally guilt-stricken at the thought of abandoning their co-workers. I know I’ve felt as much - which is why I’m so grateful for one of the best pieces of advice I’ve ever been given: ‘Never let great colleagues keep you in a crap job.’

Quit working altogether

A bit more drastic, admittedly - but not impossible. I don’t mind admitting that I’ve given this thought. It certainly sounds cathartic, right? The idea that you’ve abandoned all those tedious commitments, and all you’ve got is your luggage and the proverbial open road lying before you? Ultimately, nerve failed me. i had savings, but I knew they wouldn’t last for much more than half a year.

This is one, I think, those nearer to retirement age, who are more likely to have a well-stocked savings account. Go out and spend it! Your kids don’t want that money anyway.

Get fired

I’m not making light of being made redundant. I’ve worked at places which have gone through mass redundancies and although I was lucky on each occasion, it’s still a godawful experience. But losing your job might be exactly the kick up the arse you need to go off on an adventure. Personally, I couldn’t think of anything better do with a redundancy payout than spend it on travel.

Actually, let me regale you with an anecdote from one of those redundancy periods. When it was announced out of the blue by the CEO, everyone looked devastated - except for one colleague of mine, who looked delighted. Later in the pub, I asked him why. He explained he’d been seeing the redundancies coming for some time - and he knew he had a hefty, NUJ-negotiated redundancy package to collect. He used the cash to buy land in Cambodia, and now runs a reggae bar there.

A disclaimer

At this point, I want to stop and say: Yes, I know that many of the options I’ve laid out simply aren’t possible for many professions. I know I’m a dickhead who lives in a metropolitan media bubble. I know that for teachers, doctors, cleaners, members of the emergency services, those in precarious zero-hours jobs and many, many others just can’t desert their jobs for months at a time, or work out of a laptop thrown in their backpack.

So I’m wrapping up not with options, so much as general attitudes that I hope will help you in find a way to secure long- or medium-term travel.

• Don’t ask, don’t get. The worst you’ll hear when making requests from your employer is ‘No’. On the assumption they’re decent people, they’ll respect your assertiveness. Seriously, don’t end up in a situation where you end up looking back and regretting that you never even asked.

• Embrace the modern age. We live in a time where work is growing increasingly flexible. Less and less do people follow the old, rigid workplace models. We millennials all know that our careers won’t look like our parents. Conversely, our parents (very few of them, anyway) ever considered long-term travel overseas as a valid options.

• Earn it. You’re obviously a model employee already, but if you want your workplace to get on board with your travel plans. My workplace rejected my initial application for a career break - but I’d only been there for a matter of months. If you’ve been toiling away for decades and proved yourself a good employee, you stand a far better chance.

• There’s always a Plan B. Think laterally. Don’t get stuck in binary thinking of can or can’t, success or failure. If you have a leave proposal turned down, think of another option to pursue. Take heart. There’s no shame in finding compromises. It also helps not being too rigid in your travel dreams. If you’ve decided you want to walk from one end of the Great Wall of China to the other, that’s great. But circumstances might force you to reconsider.

Finally: good luck! MB