Ever since the pandemic hit, the media has been awash with trendwatching pieces about how society might change. Some of these virus-induced trends will surely fade over time, but one I believe will stick is the remote work revolution.

Companies around the world have been forced to adopt flexible work-from-home rules — and now it seems many will make them permanent.

If so, this will have a huge impact on travel. 

Millions of office workers will not just be able to work from home but they may do so without, well, actually being at home. The opportunities to combine travel and work have never been so widespread.

If you want to experiment with being a digital nomad of sorts — even for just a week or a few days — now could be a perfect time. 

How to start working remotely

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Working remotely from anywhere

As the world was thrown into crisis in 2020, remote working became almost universally accepted overnight. It’s been fascinating to watch this unfold and seeing people adapt to this different way of working.

To the surprise of managers around the globe, their companies did not spontaneously implode the moment they sent employees to work from home. In fact, the opposite may have happened: productivity went up while company costs went down.

Managers’ next shock will be when they realize many of their employees have been working from all over the place… without them even knowing it.

I’ve been remote working for many years now, so I’m accustomed to the idea of working from anywhere. For the first time, I’m now seeing this trend take off all around me. As soon as lockdowns ended (but remote work practices were kept in place), I heard of people with 9-to-5 jobs who eloped to a beach house or country cottage. One person who works in a corporate job even told me he’d been working from the tropical island for weeks… without anyone noticing.

Booking sites have certainly seen this trend. The CEO of Airbnb has said they’d seen a surge in demand in 2020 from people booking holiday homes in rural areas for longer periods, taking advantage of work-from-home policies.

Evidently, what digital nomads have known all along is now going mainstream: that when all you need to work is a laptop and internet, you can potentially work from anywhere. 

But what seems different now is that we’re no longer just talking about digital nomads — the kind of remote workers who typically spend their entire year on the road. To be honest, I always thought the digital nomad phenomenon as quite a niche one. After all, few people want to travel all the time or live their life without a fixed address.

But just doing some flexible remote working here and there?

And having a different place from which to work from time to time?

That’s a whole other story. It’s not nearly as dramatic as going nomadic, but still lets you travel more and break from your usual routine.

Benefits of a remote work trip

I love working while traveling — I do it all the time! I manage my site from pretty much anywhere, which can be my home, a cafe in my local neighborhood, or from some far-flung location.

I’ve also been on dedicated remote work trips where the whole point is to work somewhere in an inspiring location, either by myself or with other freelancers or remote workers.

But you might wonder why you’d ever want to travel somewhere while still having to work there. I mean, doesn’t that defeat the whole point of traveling?

Yes, kind of… but only if you just think of it as a normal holiday. A remote work trip is clearly something different.

While not exactly a holiday, a remote work trip will give you an amazing chance to break from routine, to enjoy a change of scenery, and have some fun experiences during the evenings and weekend — but without having to burn up valuable holiday allowance.

Just imagine: you can spend the day working from wherever there is WiFi, then spend your lunchtime and evenings in nature, surfing, or chilling in a hammock.

Or you can live a mini-life in a different city for a while, experiencing the place in a deeper way than someone who’s just there for a weekend city break.

Remote work trips clearly are not the same as a vacation, but they are a great way to hack around your normal holiday limitations and to enjoy a bit more freedom.

Many people get very little annual holiday allowance, which I think is pretty messed up. Even when companies give workers a decent amount of annual leave, there are often all sorts of limitations around how long or when employees can take them. It forces many to only travel during high season or to take only shorter trips.

With remote working trips, you gain some new possibilities. For example, you can more easily travel in the off-season, or extend a holiday with some remote working in the destination.

As a full-time travel blogger for 7 years, I’m used to having total flexibility over when or where I work or travel, which has been amazing. But the current remote work revolution is having an impact even for me, as suddenly I’m able to take some mini nomad trips with people who were previously completely office-bound.

It’s great to have even a tiny bit more flexibility. It’s so much easier to take a weekend trip if you can spend the Monday working in the location, so you don’t have to rush back home on Sunday night.

Of course, there are also some cons to working remotely.

For starters, you may find it more difficult to work when there are a lot more distractions around. A remote work trip can also cost you money in terms of accommodation and transport, which may not always weigh up against the benefits. It’s also easiest to work remotely if you’re self-employed, as you’re the one who’s making the rules, and more difficult if you are an employee working within certain regulations (but more on that later).

That said, there are some ways to make a remote work trip… work.

How to plan a remote work trip

Want to travel while working? Then there are two key things to remember.

One is keeping your travel costs down so that it’s truly a net positive. The second is to ensure your destination is suitable for working.

Firstly, the costs. It would really suck if you’d spend loads of money on a remote work trip. I think a great remote trip is one where you don’t feel like you’re working just to pay for the trip. Digital nomads typically keep costs down by not having a home at all (and by traveling to cheap countries), but if you just want to travel and work for a short break, you can still keep the costs under control.

To keep the costs down, you can:

  1. Stay in one location instead of traveling around a lot (this is easiest for working remotely anyway)
  2. Look for cheaper destinations that are not on the typical tourist radar
  3. Travel out of season for better deals (remember that you can go flexibly any time of year, not just in the super-high-demand vacation periods)
  4. Search for week-long or month-long stays on sites like Airbnb, which often give you discounts for longer stays. (I’ll soon be staying in an Airbnb for 30% off because it’s booked for a whole week. Month-long stays sometimes get you 50% discounts.)
  5. Find free house sitting or house-swapping arrangements, so you don’t have to pay for accommodation at all

You can even rent out your home on Airbnb or VRBO while you work from another location for a while, ensuring your expenses aren’t duplicated.

Sites like Nomadlist in turn can help you find cheap locations to work from, or even to move to if you want to work remotely in another country permanently. Needless to say, the situation is rather in flux this year with the pandemic, so it could be that only a domestic trip is a realistic possibility at the moment — but this can also change quickly in the future.

Besides cost, you will also need a good set-up for working.

If you’re staying in a B&B, hostel, or Airbnb, make sure they have good WiFi. Sadly, online listings don’t always give you any assurances about this. I usually check the reviews for any mentions of bad WiFi or ask the hosts what their internet bandwidth is like.

Consider booking a place that has a desk, or at least some cafes or other working spots nearby.

For a successful remote work trip, don’t give your clients or employers any reason to be unhappy. Always make sure of these things in particular:

  • Ensure reliable internet. If you’re not 100% sure your WiFi connection will be reliable, buy a portable hotspot that takes a data SIM card. That way, you always have a backup, taking away a lot of potential stress.
  • Be online on time. Punch in on slack, email, etc., exactly when you’re expected to. Be visible and complete your tasks.
  • Respect security policies. Some companies prohibit using public WiFi or have special rules for handling confidential information outside the office. Make sure you’re aware of any such policies so you won’t needlessly get into trouble.

If you’re feeling paranoid about security (or your company’s IT department knowing what you’re up to), you can use a personal VPN. This is a type of software that will mask where you’re logging in from. It will also add a layer of encryption for extra security.

So, uhh, should you tell your boss?

This is often the number one question on everyone’s mind — at least, among those who are not self-employed. The answer probably depends on what kind of company you work for.

Some companies are already remote-friendly, or they’re smaller companies with flexible policies. And if you work for yourself, then there is also nothing stopping you. 

It’s trickier if you work for a larger corporation that has many rules or restrictions. There might be policies against working from anywhere that is not the office or your own home. Things like employee insurance or health and safety policies might not be designed to cover some random Airbnb somewhere. There could also be tax implications if you work remotely from another country.

But hey… maybe it’s easier to ask forgiveness than to ask permission. Many people work from the road but keep it on the down-low. As long as there is WiFi and the webcam is angled correctly, it won’t be obvious where you are. So… the cheeky answer here is that maybe no one needs to know.

Still, it’s surely preferable to be transparent. If your employer is open to having a discussion about remote work, now might be the best time to have it, as the pandemic has clearly changed many companies’ thinking on this matter.

Is remote work here to stay?

Remote working is still in its honeymoon period. Eventually, the focus will turn to some of the drawbacks.

Let’s face it: it will always be easier to speak in a room than on Zoom. Some companies will always want to see butts in chairs instead of names in a Slack list. It’s inevitable there’ll be some backlash to the current remote work trend.

But… if even just some increased workplace flexibility remains after the pandemic, that would be a huge change.

And wouldn’t it be great for workers to have more control over where they can work, live, or travel?

If everyone can be just a bit nomadic sometimes, it can also inspire more sustainable forms of traveling — like staying somewhere longer, rather than flying somewhere just for a weekend city break. It could also relieve some pressure on overly expensive urban centers and make it more attractive to work from a smaller town or in the countryside.

For now, it’s just great to see this remote work experiment underway — even though it took an awful pandemic to trigger it. With any luck, more of us will get to work from where we truly want to, not just where an office happens to be.

I’ll see you with your laptop at the beach.

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