The Ultimate Guide to Workations

Workations have opened new possibilities for all those people who want to work on the road.
The concept of workcationing is exciting because you’re still putting in a day’s work — only this time, from a scenic, gram-worthy location!

What is the meaning of a workation?

A workation is what it says on the tin, really: work and vacation, combined.

A workation is a step up from Work from Home. Instead of working from the office (which is so 2019), or from home, you work from a vacation spot of your choice. The idea is to include both work and leisure elements into your day — something even the best of us might not achieve while working from home!

Hol’ up, you might say, who can take a workation? The answer is anyone whose job is already well-suited to being remote and does not require staying in an office, plant, studio, factory, or any such hands-on workplace. People involved in manual or skilled labour might not be able to take off on a workation like their counterpart in tech or administration might.

What is the difference between remote work and a workation?

They do seem similar — they both involve working from somewhere that’s not the office.

However, remote work often means the employee is permanently remote and does not have a designated place in the organisation headquarters. In the case of a workation, an employee might just be working away from their desk for a temporary period, but they intend to come back.

Why are workations trending?

Now that we’re on the other side of the pandemic hill, so to speak, you’d expect offices to open up and things to go back to “normal”. However, a Gartner study shows a pretty interesting trend: that 47% of respondents intend to allow their team members to work remotely on a full-time basis.

There are many influencing factors there: the number of software and apps that ease the transition, the reprioritisation of work and life, and a glorious change of attitudes about 9-5s in stuffy cubicles. There’s also the clear understanding that flexibility in work has magical effects on productivity and employee retention, which is an obvious win for organisations and teams alike. And we’re here for that!

The bottom line is this: many organisations don’t care where you work from, as long as you work. This is quite like taking the fetters off your ankles — you’re now free to create presentations and bring in clients from the Himalayas, if you wish.

The benefits of taking a workation

Combining the sweet fun of travel with remote work can unlock new possibilities. The freedom to work from anywhere has enhanced productivity levels for many, and that might be the case for you, too. You might also learn a thing or two about your work style. Eventually, you’ll find more inspiration and unique ways to boost your creativity, so that’s a big win.

Get more time away from desks

When you’re working from home or the office, you might find yourself sitting at a desk for hours on end, only nipping out for coffee or to head home. But with a workation, you might be more motivated to spend more time away from your desk. The new environment might inspire you to explore, go sightseeing, dip in the sea, whatever your calling.

Earn money while seeing the world

This is probably one of the most popular benefits of a workation: earning while you travel. Many people might not be able to afford a full-blown vacation, or might like the extra income rolling in for emergency funds. In such scenarios, workations offer you the best of both worlds. At the very least, you end up balancing your income and expenses — and you get a break out of it all!

Prevent job burnout

A side effect of being chained to your desk is job burnout, which can sap you of motivation and productivity. Taking a workation is a great way to ease back into a life of balance. You have a handle on work and plenty outside of work to entice you into taking a break. In the long run, you might find that taking regular workations does wonders for your mental health and emotional wellbeing.

The cons of taking a workation

Not everyone’s sold on the concept of workations. says the travel trend is yet another example of making “work-life balance a relic of the past”. Ouch. But there are some great points to consider here.

Workations might give off mixed signals

Are you on vacation, or are you working? Can you take off to that much-awaited beach party, or do you have to stay for your stand-up call? Workations can give off mixed signals, especially if they’re considered a compromise between work and vacations. A workation is not a replacement for a vacation — you still need time to completely shut off from work and indulge your whims and fancies.

The costs can pile up

If you can afford to work remotely and from nicer digs than your cabin or work corner, then go for it. However, it is worth noting that workations can be expensive. You’ll have to pay for accommodation, food, network connectivity, travel, and so on. It’s always ideal to work out your finances before you set off on a workation.

Boundaries between work and life might become blurred

We know, we said that workations could ease you into a more balanced lifestyle. But if you swap all vacations for a workation, the pendulum might swing in the other direction — a direction you don’t like. You might find it difficult to enjoy the sunshine when Slack is going off on your laptop. On the other hand, you might feel like shirking off work to go off on a serendipitous hike, leaving your team and projects in the lurch.

Team communication might be hampered

Team communication is integral to making workations a success. However, communication might be jeopardised if the workation is happening in a different time zone or lacks access to solid internet and connectivity. This becomes even more of a problem if at-home teams aren’t kept in the loop when a teammate takes a workation. No matter how small the disruption, teams have a right to know what to expect so projects can move along smoothly!

To workation or not to workation?

Ultimately, the answer to this Shakespearean question depends on you, your organisation, and your team. It might help to ask yourself the following questions:

  • Can my bank account handle a workation?
  • Am I actually in need of a proper, no-electronic-devices-allowed vacation?
  • Can I continue to work seamlessly when I’m on a workation?
  • Am I putting projects or teams in jeopardy with this choice?
  • Are there lower-budget options that can satiate my need for travel, a change of scenery, or a break from work?
  • Will I be able to connect and disconnect at will, and not be chained to one or the other?

If you decide that a workation makes sense, great! We’re here to make that transition easier for you and your team.

Prerequisites for a successful workation

To balance both words in this portmanteau successfully, there are some must-haves and nice-to-haves. Here’s a checklist to get you started:

  • Strong and steady internet connection
  • 24/7 electricity
  • Working means of communication and payment modes
  • Suitable work infrastructure including a desk, ergonomic chair, lighting
  • Health and/ or travel insurance
  • Access to hardware you might need, including laptops, tablets, printers, bigger screens

The bottom line is that you shouldn’t have to compromise on efficiency during a workation. This might mean looking for accommodation that has most of what you need, or carrying everything you might need with you.

Tips to make your workation work for you and your team

Clear communication is the key to enjoying your workation without throwing your colleagues under the bus.

Speak to your manager and teams ahead of time

While WFH culture has become normalised, we’d recommend you explicitly tell your manager and team when you’re about to head off on a workation.

Making everyone aware of your plans will give you the wriggle room you need to get set up (get good WiFi, find the perfect desk, set your Slack status… you get the drift). You might need to negotiate your working hours or tweak a few communication processes — and your manager or team lead is well placed to do that. Your team also knows what to expect and will be more understanding of any hiccups!

Watch out for time zones if you're going overseas

If you’re heading into a different time zone, we’d highly recommend evaluating how that might impact your work and team communication. First, we’d recommend you explore a location from the time zone you live in or find a place with overlapping zones. This way, you’re not changing your work schedule overnight, and you won’t feel overwhelmed with your workation.

Choose your workcation buddies wisely

Maybe you decided to take your family with you on your workation, or you’ve asked a few of your friends to tag along. What might be a workation for you could be a vacation for them. Unless you speak with them in advance and plan how you’ll spend your time, you run the risk of getting minimum work (or play) done.

Let your travel companions know your schedule ahead of time. This way, they can engage in other activities or explore the city a bit in the gap they’re waiting for you to finish your work.

Pack all the work tech items you need

Make a list of all the things you use when you work in a flow state. This can range from notepads, post-its, pencils, earphones, specific documents, external hard drives and more. Look around your office or WFH workspace: if any of them look important to you, pack them! You’ll be ready to jump into work without the fleeting feeling of forgetting something important.

Scope out shared workspaces for better productivity

It’s not difficult to find a WeWork or Regus in 2021, especially if your workation spot will be in popular cities across the world. When you use shared workspaces, you’ll find yourself in the company of others who are also there to get work done. This could inspire you and give you an incentive to complete your daily goals as well.

Shared workspaces are also a great backup to your vacation home’s workspace if something goes wrong. They’ll provide you with the perfect environment and backdrop to conduct your meetings. So, don’t hesitate to work from offline workspaces!

Ready, set, go!

A final word before you go, pinky promise.

Workations require coordination and understanding between you and your team. That’s why we’d recommend you set boundaries at work so that your work doesn’t spill into your vacationing time or vice versa.

Being a digital nomad can be messy and tiresome if you don’t know where to start. A successful workation is one where you’re able to feel productive while also enjoying your time away!