How to Take Your Best Ever Working Vacation

August 25, 2016
Archived, Productivity

I agree – working vacations are not ideal. But if the alternative is no vacation at all, then it can be a great option. Flexible working is more feasible than ever, but how can we ensure that workations are successful, for both ourselves and our work?

While those lucky enough to take a long vacation busy themselves with preparations, the rest of us look on enviously.

Grudgingly, we accept that often there simply isn’t the possibility to take a chunk of time to go off to a far-flung destination.

Projects need work. Deadlines need to be hit. Customers must be looked after.

Perhaps this is one reason why working vacations, or workations, are increasing in popularity, as they are fueled by tech innovations that remove the requirement to be at our desks to complete our work.

While no match for the benefits of taking a full vacation away from work, working vacations are a viable way to see more of the world, recharge batteries, or soak up some sun.

Disrupting the long-established work-life pattern

Make sure to enjoy your working vacation

Tech is playing its part in disrupting the long-established work-life pattern.

More of the office exists virtually than ever before. And access to remote devices can be easy and secure.

Combined with societal change and the rise of flexible working hours, remote working and hot-desking are challenging the traditional office culture.

Quite apart from enabling working vacations, it is driving a fundamental shift away from many of the work patterns we take for granted.

This includes the five day working week, working from nine to five, and even the necessity to commute.

We are more able than ever to work from wherever we want, at whatever time we want. This is precisely why more bosses are leaning towards allowing working vacations.

So, what’s needed to make for a fantastic workation?

Decide if it’s right for you

Decide if a working vacation is right for you

Great! So, the technology is there to make a workation feasible. Ready to book flights, pick up your laptop, and head out the door? Hold on a second.

Are you sure a working vacation is right for you?

Workations are not for everyone. Before taking any further steps, think hard about whether or not a workation is even something you would benefit from or enjoy.

If you work most effectively as part of an open office space, and need your working environment to be set out in a very particular way, a working vacation might not be a great idea for you.

It’s very unlikely that you will be able to replicate such an environment from a vacation destination. You will be left stuck having a difficult, unpleasant, demotivating time for two weeks.

No amount of Sangria on a Spanish coast can make up for that.

Working remotely can require a big shift in your rituals. Take a moment to examine the learnings made by regular teleworkers to get an idea if it is something you would enjoy doing.

Still interested? Great! Next step is to think about the type of location you’d get the most out of.

Location for a Workation

Would a workation work best for you if it enabled you to go stay with family? Working during the day and socializing with relatives in the evening?

Or would a Thai beach bar be the type of location you’re looking for? Exchanging lunch for a dip in the ocean?

For inspiration, take a look at this list of workation countries.

Think ahead to how you could envisage splitting your time between work and taking advantage of the vacation location.

Once you’ve got a clear vision in mind, it’s time to get the boss on board.

Pitch it to your boss the right way

Pitch your working vacation to your boss

Although working vacations are a growing trend, they are still on the fringes of mainstream working culture.

This means it’s likely that you’ll need to get approval from your boss to get the idea up and running.

As part of this approval, it will be vitally important to establish how much your workation will count toward your available vacation time. If it does at all.

Will you be devoting 30%, 50%, or 70% of your time to your work? This amount can even vary from one workation to another and must be defined in advance.

Handily, there are lots of things we can do to ensure the best chance of receiving unconditional approval for a proposal.

Step #1 will be to clearly and constructively outline the objective benefits in a way that describes how a working vacation benefits the team or business.

This will be the first question your boss will ask. So it pays to be ready with a succinct answer.

For example, would a workation result in:

  • Greater productivity during and after?
  • Higher levels of motivation?
  • Improved performance results?

Whatever you foresee as the clear benefits, have them ready to hand.

Step #2 will be to find the best way to communicate your idea to your boss. You’ll need to be able to communicate in a way that will allow you to fully propose the idea and handle any objections before the idea gets shut down entirely.

Whichever method of communication works best for you, begin by summarizing all the main points you uncovered during step one. Touch on points your boss will be most concerned with, and in a way that will be appreciated.

Step #3 will be to demonstrate how you propose to handle working from a remote location. If your boss is not convinced that it is viable, ask for a trial period where you work from home.

The idea here is to get past any preconceptions of technological barriers standing in the way.

Step #4 is to be patient. If this is the first time anyone has proposed a working vacation it might take a while for approval to come through.

Polite persistence is the name of the game. Don’t let the pressure of a ticking clock on flight deals affect how you proceed with approval from your boss.

Got the go-ahead from your boss? It’s time to ensure it’s as successful as possible.

What to prepare before you go

Prepare for a working vacation by getting your devices ready

Preparation is key to making the most of a working vacation. There’s no fun to be had scrambling around trying to figure out fundamental roadblocks when you’re already half a world away.

Instead, think through exactly what you’ll need to have with yo
u, and what functionality you’ll need from the tools available to you.

Such as:

  • Do you have access to devices you require? Is it a work laptop you’ll take, or your own?
  • Is it in good working order, because you don’t want it overheating on you!
  • Will you need simple, secure access to your computer in the office?
  • Are you all set with communication tools, such as chat, online meetings, and video calls?
  • Do you have a backup of your important data in case your laptop gets damaged or stolen?
  • Is your phone set up to receive important calls if something crops up?
  • Are there any other critical things you need to get your work done while away?

Whilst you’re figuring that all out, the fun part can begin. Booking your trip.

What amenities does the location need?

Some things to keep in mind when choosing a location for your workation:

  • Where will you work from while you’re away?
  • Is there reliable WiFi connection?
  • Is there easy access to power?
  • Will you have suitable privacy for your work?

With all of that in order, the last bit of preparation is in communication with coworkers and customers.

While you are not technically away, you may want to think about whether or not a time zone difference will disrupt your regular communication pattern.

Email autoresponders can be a handy way to help smooth things over if correspondents expect a quicker answer than you can provide.

Last but not least, what can be done once you’re away to ensure your workation is a success?

What to do when you’re there

Make sure you take time off work during a working vacation

Not as simple as you might think.

Workations run the risk of leaving you feeling more drained than before if you spend the whole time working.

Or they can leave you having to play catch upon your return, with coworkers disappointed by your work for the previous weeks.

Neither situation is ideal.

Work on what matters most first

Because a successful workation for your boss and your team means that the work gets done, it’s vital that you prioritize tasks.

To-do lists are great, but they have a habit of getting out of control.

So instead, take an easy approach to quickly organize your tasks neatly in order of priority.

Keep to clear hours of work

It’s too tempting to allow the working day to stretch from daybreak to the depth of night.

Being strict about our working hours will actually allow for the vacation part of the working vacation, and ensure you return feeling like you’ve had some semblance of time away.

Rules for when something crops up

It’s not beyond the realm of reality for something important to crop up outside of your assigned hours of work.

In this case, you can expect your phone to ring and an urgent message to be delivered.

Make a clear decision about when you will and won’t answer that call to find a balance you and your team can work with.

Planned fun

Be strict about using the vacation part of your workation for what it is meant for.

Make concrete plans for activities, outings, and social occasions that you will not be able to put off for an extra hour’s work.

It’s incredible how effective commitments can be when working remotely, in ensuring the working day has a beginning and end.

Key Takeaways

Workations are no replacement for a full-blown vacation. But with the right preparation, technology, and mindset, they can be a darn good alternative.

There has never been a better time to take a working vacation. The technology is there, and bosses are coming round to the idea of it.

To have your most successful workation this summer:

  • Make sure working vacations are suitable for you
  • Pitch it the right way to your boss to get approval
  • Prepare all the tools, tech, and communication you’ll need ahead of time
  • When you’re there, get the important work done first, and stick to a strict work pattern

Got any other tips? Share them below!

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