How To Work-From-Home While (Shhh…) Also Traveling • Indie Traveller

How To Work-From-Home While (Shhh…) Also Traveling • Indie Traveller

Ever since the pandemic hit, the media has been awash with trendwatching pieces about how society might change. I’m guessing some of the pandemic-induced trends will fade over time, but one that I think might actually 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. This will open up different forms of travel.

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. 

Working remotely from anywhere

It’s fascinating how remote working became almost universally accepted overnight. 

To the surprise of managers around the world, 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.

Just from my friend circle I can sense this trend is happening. I’ve heard of several people with 9-to-5 jobs who eloped to a beach house or country cottage since the lockdowns ended. A colleague of a friend, who works in a corporate job, let slip he’d been working from the tropical island of Madeira all along… without anyone noticing. 

Booking sites have seen the trend too. Last week, the CEO of Airbnb said they’d seen a surge in demand from people booking holiday homes in rural areas for longer periods, taking advantage of work-from-home policies. 


I think this is 100% amazing. 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. 

To be honest, I’ve always thought of becoming a digital nomad as a niche phenomenon. After all, few people want to travel all the time.

But just doing some flexible remote working here and there? Or having a different base from which to work? That’s a whole other story. 

Benefits of a remote work trip

I love working while traveling — I do it all the time. But you might wonder why you’d ever want to travel somewhere while still having to work there. Doesn’t that undermine the whole point of traveling? 

Sure, if you just think of it as a regular holiday. But a remote work trip is something different.

It actually gives you an amazing chance to break from routine, 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.

Clearly, remote work trips are not the same as a vacation, but they are a great way to hack around your normal holiday limitations.

It’s really messed up how little annual holiday allowance most people get. 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 people to only travel during high season or to take only shorter trips.

With remote working trips, you gain some extra possibilities. 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. But the current remote work revolution is having an impact even for me, as I’m suddenly able to take mini nomad trips together with people who were previously completely office-bound. 

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

Of course, there are also some cons to working remotely. You may also find it more difficult to work when there are 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.

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

How to plan a remote work trip

There are two things you probably want to think about if you want to travel while working. One is keeping your travel costs down so that it’s really a net positive. The second is to ensure you can work easily in your destination.

Firstly, the costs.

It would really suck if you’d spend loads of money on a remote work trip. I think a trip is one where you don’t feel like you’re working just to pay for the trip. Digital nomads 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 it cheap.

To keep costs down, you can:

  1. Stay in one place instead of traveling around (this is easiest for working remotely anyway)
  2. Look for cheap places to travel not on the typical tourist radar
  3. Travel out of season (you can go flexibly any time of year, not just in the usual in-super-high-demand periods, which sometimes lets you find amazing deals)
  4. Search for a week-long or month-long stays on sites like Airbnb, which often give you discounts for longer stays. (Example: I just booked an Airbnb for a week for 30% off.)
  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 quite in flux this year with the pandemic, so it could be that only a domestic trip is a realistic possibility at the moment — part of this article is aimed at the future.

Besides cost, it’s clearly important that you can work well from your remote location.

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

Of course, you might want to book a place that has a good desk, or some cafes or other working spots nearby.

Make sure you don’t give your clients or employer any excuses against you working remotely. For a successful remote work trip, it’s best to keep these things in mind:

  • 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 back-up, which takes away a lot of potential stress.
  • Be online on time. Punch in on your slack, email, or whatever, 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 could use a personal VPN. This is a type of security software that will mask where you’re actually logging in from.

So, uhh, should you tell your boss?

The one question everyone always wonders about is whether to ask permission to work remotely. There’s often some debate around this among digital nomads.

It really depends on the company. Some are already remote-friendly, or they’re smaller companies with flexible policies. 

If you work for yourself, then there is really nothing stopping you. 

It’s trickier if you work for a larger corporation or one that has many rules. There might be policies against working from places that are not the office or your own home. Things like employee insurance or health & safety policies might just not be designed to cover some Airbnb somewhere. There could also be tax implications if you work from abroad.

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… maybe no one needs to know.

It’s surely still preferable to work remotely in an above-board way. If your employer is open to having that discussion, now is the best time to have it, as the pandemic may have changed many companies’ thinking on this.

Is remote work here to stay?

Remote working is surely still in its honeymoon period. Eventually, the focus will turn to some of the drawbacks. It will always be easier to talk in a room than a Zoom, and some companies will always prefer seeing butts in chairs than names in a Slack list. There will inevitably be a backlash to the current trend.

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

It would be amazing if workers can have more control over where they can work, live, or travel. It can inspire more sustainable forms of traveling, such as staying somewhere for a month or spending winters away (a lot better than flying somewhere just for a 2-day weekend city break). In the long run, remote work can even relieve pressure on city centers and repopulate the countryside.

For now, I’m just glad to see this great experiment with remote working underway, even though it took this godawful 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.

Have you been able to work remotely from outside the home? What do you think about traveling and working at the same time? I’m curious to hear your thoughts in the comments.

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