• Advice

How – and why – to plan a workation as a freelancer

As a teenager, I had it all planned out – I’d be a freelancer. I’d make a lot of money. And I’d be a digital nomad for life.

I have been freelancing since I was 19. At times I made a lot of money. But I’ve never become a digital nomad. 

I made different choices, and I don’t regret that. Yet, I still have the travel bug, and as a freelancer I have great freedom. That’s why, from time to time, I like to play the digital nomad game for a couple of weeks. How? With a workation, of course!

What’s a workation, exactly?

A workation is a mix of work and vacation. Since you can work anywhere, why wouldn’t you do it on a cruise ship, or in that foreign capital you’ve been wanting to explore for years?

With a workation you can do all of that while still working part-time. 

Don’t get me wrong – I am not advocating for workations instead of vacations. I love to take a proper vacation, and you should totally do that at least once or twice per year. 

But if you are like me, you can’t take five 2-week vacations per year. That’s where workations come in handy.

How a workation helped me restart my freelance business

My first ever workation was in spring 2022. I took off to Lisbon and stayed there for 2 weeks. It ticked all my boxes – Portugal has a low cost of living, Lisbon is a fantastic city, and it wasn’t far from Italy, where I live.

Most importantly, though, I took it while I was struggling with burnout and had no motivation to keep working on my freelance business.

It turned out to be a reinvigorating experience that reminded me of all the great things about freelancing that I had come to take for granted over the years. 

I can safely say it was instrumental for me to finally manage to get back on track – two months later, I started to slowly phase back to work.

Define your priorities…

Are you looking to primarily relax, with work taking a backseat? Or is your goal to maintain a regular work schedule while enjoying a change of scenery?

If your priority is relaxation, be prepared to allocate a larger budget for activities and accommodations where you can truly unwind, if that’s something that you value. 

If your aim is to keep up with work while enjoying a new environment, instead, your planning should lean towards a balance. You might explore local sights and experiences, but the primary focus remains on work.

In either scenario, being clear about what you want from your workation helps in making the right choices, ensuring that your time is both productive and enjoyable, whether it’s tilted towards more work or more play.

… and set your budget accordingly

Setting a budget is a crucial step in planning a workation. Begin by outlining your major expenses: accommodation, travel fares, food and leisure activities. (factor in occasional splurges like a fancy dinner or a local tour – it’s still part vacation, after all!)

This exercise will help you make informed choices, ensuring you enjoy your workation without financial stress. By planning your budget in advance, you can find the perfect balance between work, exploration, and relaxation.

Choose a destination

The world is your playground… but keep in mind you’ll still be working, at least a few hours per day. If you are travelling to another country, you have to plan your working hours based on the time difference.

An example? 9 AM in Boston is 11PM in Seul. If you mainly work with clients in the Boston area and you want to spend 2 weeks in Korea, you would have to wake up at 6AM to be able to answer emails at 4PM, client time. That’s a time difference nightmare for you to handle. 

If you spend those 2 weeks in Paris instead, you’ll be free to explore the city in the mornings and still be there for your clients’ start of business time – 9AM in Boston is 3PM in Paris.

You will also need a reliable Internet connection. In big cities and popular tourism destinations, that’s not hard to come by. However, if you plan to explore more remote areas, you will need some preparation.

Where to stay

While I love hotels, and they are usually my first choice when I travel, I don’t usually recommend them for a workation. Opting for a short term rental can be a much better choice, mainly for two reasons: you can cook your own meals, which helps to keep costs down and to stay in shape; and they often have something better than a chair and a small desk to create a basic workstation.

If you want to take your workation to a brand new level, though, my top tip is to work from a coworking space. There is simply no better way to meet locals and work in a comfortable setting, and you can choose one that’s close enough to wherever you are staying. 

With digital nomadism getting more and more popular, there are plenty of guides to find coworking spaces in most touristic destinations in the world.

Plan each day beforehand

Remember that you're juggling work and leisure, so striking the right balance is crucial. Start by setting realistic goals for each day. Are there specific hours you need to be online, or tasks that require deep focus? Work around those to plan when you need to be at your desk.

Next, integrate your leisure activities. If you're an early riser, perhaps a morning walk or exploring local cafes can kickstart your day. If you prefer evenings, save local attractions or dining experiences for then. By allocating time for both work and fun, you're less likely to feel overwhelmed or guilty for not meeting work obligations.

Remember, flexibility is key. Sometimes, work demands may shift or you might discover a must-see spot. Being adaptable while keeping a basic structure will help you enjoy your workation to the fullest, without compromising on your professional responsibilities.

My advice for first timers

Is this your first time planning a workation? Keep things simple.

  • Choose a local destination – Choose a destination that’s just a few hours away, possibly in the same country. National parks, skiing destinations in the winter and beach areas in the summer come to mind
  • Make the most of your slow season – If you have been freelancing for a few years, you know what times of the year you are busiest and what months are usually slower. For me, the first two weeks of December are usually the slowest time of the year. That is the best time for me to go
  • Stay for a week – As you become a workation expert, you’ll be able to take much longer workations. For your first one, though, a week should be enough
  • Tell your clients you will only be working part time – No need to hide this from your clients! Tell them well in advance that you’ll be working part-time from X to Y. Just don’t go MIA on them

Domenico Trimboli Born and bred in Rome, Italy, Domenico became a six figure translator in 2017. Today, he blogs about translation and freelancing. Self-employed since 19, he has never worked for a boss in his life.

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