Why Not Try A Remote Work Vacation?

If you’ve been thinking about becoming a digital nomad then you might want to consider dipping your toes in the water to find out whether the lifestyle suits you before you quit your job and pack your bags.

The remote work vacation sometimes called a “work-cation” is the halfway house between the real world and digital nomadism. You can try on the lifestyle for size and if it’s not for you; you can go home without feeling bad and if it is for you – you can start planning your escape as soon as you return.

What Is A Remote Work Vacation?


A remote work vacation is where you go on vacation, but you continue to work remotely. It’s definitely not the ideal way to take a break for most people who aren’t intending to become digital nomads because if you get paid leave, why would you want to work on it?

However, it’s worth noting that many Americans may still want to consider a remote work vacation given that many employers there don’t give out huge amounts of vacation time and worse, many employees don’t use that time because they’re worried that the job won’t get done or their boss will decide they’re replaceable while they are away.

It’s better to take some form of vacation rather than waste your vacation days and a remote work vacation can help the worried employee feel better about going away.

What Are The Benefits Of A Remote Work Vacation?


If you feel like trying this out, then there are some distinct advantages to a remote work vacation over a regular vacation too:

  • You can earn while you travel. Some forms of leave from work are unpaid. Getting paid always beats not getting paid. It can also allow you to take a longer break than you might have been able to if you weren’t getting paid.
  • You may be able to deduct travel expenses on your tax returns. You’d need to discuss this with your accountant or employer – this area of tax law can get complicated very quickly.
  • You may find that your productivity goes up. They say that “a change is as good as a rest” and it is, to some extent, true. A view of the beach from your hotel room balcony can be good motivation to get the work done and then go for a swim.
  • You may be able to reassure your boss or clients about how dedicated you are. I’ll be honest, I’ve never known a client or employer to begrudge you a break but if you think they’re going to get resentful – a remote work vacation is probably the answer.
  • You can continue to accumulate paid leave – if you’re working and getting paid, you’re not burning your annual leave paid allowance. That may mean you can cash it in at the end of the year or take another break (a proper vacation) later in the year.
  • You can avoid a huge pile of work waiting for you on your desk when you get back. It’s the worst thing about coming back from a vacation and there’s something nice about not having to deal with the accumulation of a fortnight’s absence.
  • You can better understand what digital nomad life may be like. It’s not exactly the same as living like a digital nomad but it’s not far off either. It can help you decide whether you really want to work and travel or whether you want to work and then travel.
  • You can stay in the loop. When you’re working, you’re still in the loop with colleagues and the office environment. You’re not losing visibility.

What Are The Drawbacks Of A Remote Work Vacation?


It’s fair to say that a remote work vacation is not all good news. There are risks that you face from choosing to take a remote work vacation rather than a real vacation and they include:

  • Physical and mental burnout. You need time away from work. The most productive people in the world are the French and they have a regulatory environment that minimizes their weekly workload and gives them plenty of vacation. You need to be honest about how you’re feeling before you opt for a remote work vacation.
  • Failure to appreciate the places you have visited. Work is work and it comes first. This is an accurate reflection of what it takes to be a digital nomad. If you book 2 weeks somewhere but work 6 days a week, you only have 2 days to enjoy it, if 1 of those days is booked for travel, you only get a day.
  • It can work out more expensive than you planned. There’s nothing worse than booking yourself into a nice hotel to discover their internet sucks worse than a broken Hoover and you now have to jump in a taxi to get into town to use a co-working space that you also have to pay for. Yet, it happens to us all at some point or another.
  • It’s easy to get distracted. The flip side of not appreciating where you’ve visited is appreciating it too much and not getting any work done. This is a serious risk, you are on vacation after all.
  • You may lack motivation. It’s hot sunny and beautiful outside and here you are, pouring over a spreadsheet in your hotel room. It can be hard to want to work when you know there are nicer options out there.
  • You might get lonely. If you do your remote work vacation on your own, you may find that it’s lonelier than you expected. Working by yourself leaves you less time to socialize in a new place and that can make it harder to form relationships than on a regular vacation.

How To Approach Your Remote Work Vacation


Firstly, let’s be clear about this – you don’t need one of those remote work vacation companies to do this for you. They represent poor value for money and unless you really must have a group of people identical to you on hand at all times; they offer no advantages over arranging your own remote work vacation.

You can then take the money you saved on using the service and spend it on having fun, instead.

  • Plan ahead. The ideal time to plan is when you’re not busy and you’re thinking about what you’re going to do for your next vacation. Work out what you want from your trip and nail down the destination. Check that Internet is OK in the place you want to stay too.
  • Book flights online. There are dozens of flight aggregation services like Expedia, Opodo, etc. that you can use to find deals on flights and there’s Google Flights too now. Do shop around a little but there’s not as much variation in pricing as there once was.
  • Book hotels or apartments online. I prefer booking.com for this but Agoda works too and Airbnb is always worth checking as a comparison to see if you can save a lot of money by living in an apartment instead of a hotel.
  • Provide your manager and colleagues with notice that you will work remotely. Then provide them with a communication plan and boundaries for your time away.

Then when you’re on that remote work vacation you want to think about:

  • Working somewhere other than your bedroom. Separating work and real life is hard as a digital nomad and it becomes impossible, quickly, when you work from the place you sleep in. Balconies, coffee shops, and even co-working spaces are all a better idea.
  • Keep an eye on the time zone. Don’t forget you need to communicate with your colleagues when they’re at work.
  • Computer security. Talk to the IT department before you leave and get their recommendation for logging in, etc. You may choose to use a portable mobile connection for the most secure access.
  • Work in the cloud. This reduces the risks of losing work if your device malfunctions or is stolen or damaged.
  • Use remote working technology to support your efforts. Slack, Trello, Skype, etc. can all help bridge the gap between where you are and where the rest of your team is.



A remote work vacation can be the ideal way to find out whether you’re going to enjoy the digital nomad life. There are also some clear benefits from taking a remote work vacation, however, you have to balance these against the clear drawbacks too.

Always book your own remote work vacation, the services out there that arrange these things are pretty much all a rip-off. Then take positive action to make sure that your remote work vacation serves both your work needs and your need to relax and enjoy a new place.


Nicholas Barang

Nicholas Barang is a veteran digital nomad. In fact, he was probably "digital nomading" before it was called that. He believes that anyone can make a free and independent life if they want to. He wants to help those who commit to finding their own path. And to cut through the nonsense told about this "lifestyle" by those in search of a quick buck. If you want to reach him you can send him an e-mail to nick at nomadtalk.net. You can learn more about him here - About Us

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