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A young man is having a nap in a hammock over the sea.
Reasonable bosses will recognise that it’s in their interest for you to take a break. Photograph: Joakim Leroy/Getty Images
Reasonable bosses will recognise that it’s in their interest for you to take a break. Photograph: Joakim Leroy/Getty Images

How to take a guilt-free holiday as a freelancer

This article is more than 6 years old

Working for yourself means taking time off is not as simple as turning an out-of-office response on

I know the exact moment on my recent holiday where I finally relaxed after months of overdoing it. Towards the end of a trip to the US, my friend and I spent an afternoon of trashy pleasure on the Warner Bros studio tour in Los Angeles.

After winding through film sets, our tour cart stopped outside a building that housed props from the Harry Potter movies. I’m not a Potter addict, but I found myself staring into a glass case filled with magic wands. Without realising, I gasped in a moment of unthinking awe. After months of staring at a computer screen, my brain had finally unclenched.

My holiday coincided with my second anniversary as a freelance journalist – two years where I’ve rarely been short of work, thankfully, but as a result I’ve also not had much free time. Any time I do go away, my laptop comes too, and I’ll often be up at 6am trying to squeeze in bits of work to stay on top of things.

This time I was determined to have a proper rest. It’s well-known that breaks are good for your mental health, but in the age of the gig economy that “celebrates working yourself to death,” as the New Yorker’s Jia Tolentino wrote recently, certain organisations could do with a reminder. While I was away a few unavoidable bits of work slipped through the net. I tried to ignore them, but as deadlines and missed opportunities loomed, I realised I would have to knuckle down. In the end, I worked for two days of my trip, feeling frustrated that I was essentially paying to work in a nicer place than my regular desk.

Taking two weeks off was much harder than I had imagined, but even with the work interruptions, I still came home feeling a million times more clear-headed and capable than the frazzled stress ball that had departed from Heathrow two weeks earlier. Here’s what I learned:

Plan carefully

Preparing to go on holiday as a self-employed person is a chore. With no one to pick up your slack, you end up doing twice as much in half the time – or turning down work, leading to half as much income and twice as much stress. A month before your holiday, write a strict schedule setting out precisely when you’re going to do all your upcoming tasks. If you’re at capacity, turn down new work. If you have regular gigs, let your boss know so you can rearrange deadlines, or they can find a substitute.

Arrange assignments for your return

The more time you take off, the poorer you’ll be when you return. Make sure you have work planned for your first week so that you’re not left facing a blank slate and a pile of bills. This also helped me re-adjust after a fortnight where my only routine activity was eating ice cream. But don’t organise too much work thinking you can compensate for your time off. You can’t. Accept it.

Make peace with missing out

Taking time away inevitably means turning down opportunities. But unless you’re being offered a career-defining gig, try to say no. It’ll be better for you in the long run. Before my recent trip, I felt crushed, and completely burned out. When I got back, working felt like a breeze. I had ideas, words came together easily, and I no longer felt like Michael Douglas in Falling Down.

Don’t fear being forgotten

Unless you’re taking a year-long tech detox in a remote cave, you’re not going to drop off your employers’ radar. Reasonable bosses will recognise that it’s in their interest for you to take a break. On that note, set an out-of-office reply firmly stating the terms of your unavailability and the dates of your return. Realistically, you’ll have to check your emails, so things won’t slip through the net. And if you do spend a year hiding in a cave, someone would probably pay to hear about it in one form or another.

Forgive yourself if you have to work

When you’re self-employed, sometimes it’s impossible to properly down tools for a sustained period. Knuckling down and finishing an outstanding task is a smarter sacrifice of your time than letting the guilt wreck your hard-earned break. Plus, work done on holiday feels extra virtuous, and a legitimate excuse for an extra scoop of ice cream.

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