Squeezing in freelance work while travelling

On balancing zero paid leave with needing time off

Photo by Alex Perez on Unsplash

As I write this, I’m sitting in a bright, airy Delhi apartment, the verandah lush with tropical plants. My family is out sight-seeing, but I’ve taken today to finish up some bits of work (including writing this substack piece). I can imagine that for many people, this might seem like a depressing intrusion of work into family holiday time, or evidence of my inability to switch off. But in this instance, it’s neither. It’s just a trade that I have willingly made as a freelancer to be able to get a week’s extra holiday in India. Being able to juggle time off with the odd work commitment is more of an art than a science - done wrongly, and you will stay in work mode, unable to immerse yourself in your new surroundings. But as a freelancer, my ability to work from anywhere in the world is one of the things I love most about my job.

If you’re self-employed, you’ll be familiar with the total lack of paid leave, sick leave or any other benefits like a pension. This can mean either that freelancers take very little holiday, or that they take what they want, but earn much less than they would like to.

Enter the work-holiday juggle that some freelancers, including me, embark on.

Some freelancers style themselves as digital nomads, permanently living out of a suitcase, working in cafes until the mood takes them and they hop on a plane to somewhere else. But with a kid and a husband, I’m a bit past the digital nomad lifestyle, and need to be rooted in one place - which happens to be Barcelona, so I’ve got less of a hankering to be working anywhere else in the world.

But I do love to travel, and as I don’t yet earn enough to let me have three months a year off, I almost always take my laptop with me to squeeze in a bit of work that will pay for some of those days away. The reason it doesn’t ruin my holidays is that I have strict rules about how I work when I’m travelling.

1. The work has to be relatively stress-free

This may seem like a no-brainer, but there’s work and then there’s WORK. If I tried to focus on a project that required zoom calls, or back-and-forth emails, or interviewing someone in another time zone, it’s guaranteed to be beyond stressful.

I learnt this to my cost in Bali a couple of years ago, where I spent a week out of four working for one of my main clients. It seemed ideal - one week where I worked afternoons to be on European time, and had my mornings free, in return for a slice of paradise. Except that one of the pieces I was asked to do was interviewing the head of an NGO, that ended up requiring millions of emails with press officers and was an absolute nightmare to pull off, even though the interview itself went well. My body reacted so badly to this stress that I ended up with digestive issues so severe I could barely eat.

2. It has to be work I enjoy doing

As with the last point, this may seem obvious, but there’s work that’s pretty low-stress but also pretty boring. If I’m sitting somewhere beautiful and spending time working, I want it to be doing something I love, because that’s the only way the trade-off feels worth it.

Crucially, work you enjoy energises you, leaving you with enough juice to shut your laptop and head out the door to explore, which is a critical thing when you’re working on holiday - if it’s going to affect your mood, your energy, or your general will to live, don’t take the work with you, it is not going to feel worth it.

3. There needs to be a good reason for working while away

It’s one thing to work on a project that you love and that will bring a decent amount of cash, but it’s another thing to take random work crap with you on holiday. I know too many people who answer work emails on holiday, and do bits of unnecessary work here and there so as not to have too much to come back to. This way of operating is totally counterproductive. Your holiday is there to fuel you, to inspire the way you live your daily life, and to give you time with your loved ones if you’re not travelling solo.

Anything that detracts from a rest for your mind and body will probably make the holiday pointless, and you’ll come home needing another one.

But if you can make it work, there’s nothing more delightful than having a big chunk of time off, and not coming home broke and needing to work overtime to bring in more cash.