How to take a proper holiday as a freelancer

Leave the laptop at home and don't freak out



It’s taken me over two years, but I finally took a proper holiday this year. I took two weeks off, went to Sicily and did zero work. I’ve taken time off before, but I’ve always ended up working a bit or only taking a long weekend off. This time, the laptop stayed at home, I didn’t check my emails and I took an actual, proper break. This is how I did it.

Book your holidays like annual leave

When I first went freelance, I thought I’d take holidays whenever I felt like it. A slow Tuesday would mean a last-minute dash to Paris on the Eurostar. Two years in and I’m barely able to clock off early on a Friday, forget international train rides.

Freelancer holidays are a bit like unlimited vacation days that lots of trendy startups offer – sounds amazing but in reality, you end up taking less time off than if you had traditional annual leave. When it comes to holidays, it’s a good idea to plan them out in advance and block out weeks for them way before you actually book a holiday because otherwise, you’ll still be waiting for that magic day to go Paris.

Budget for the freelancer holiday tax

When you work for yourself and go on holiday, you pay a freelancer tax. On top of the cost of the holiday, you forfeit the money you could have made had you stayed at home. It’s not a good idea to dwell too much on this idea because it will prevent you from ever taking time off. Instead, budget for your freelancer tax the rest of the year. Put a little a bit of cash aside so that when you do take a couple of weeks off, it won’t hurt your overall finances. I’ve gone into detail about how to think differently about your money in my Ultimate Guide to Freelancer Finances, which FJ&Co members have been receiving over the past few weeks. Sign up for membership to access the guide and the rest of the members-only content.

Make a pre-holiday work countdown

About a month before I went away, I made a double-page spread in my notebook detailing everything that needed to happen in advance of my holiday. It included the following lists: What needs finishing before I go; What needs scheduling; Who needs to be told that I’m away; What I need to be followed up on when I come back. When you’re about to go away, you have to prioritise ruthlessly in order to finish what actually needs to be done and park the stuff that can wait til you get home.

Tell your clients

It’s not a great idea to hand in an assignment the day before you go on holiday and then disappear for two weeks. Clients also shouldn’t be finding out about your vacation time from your out of office. Give them plenty of advance notice that you’re going away. Just as you would tell your boss in good time that you’re booking time off, you need to the people you’re freelancing for that you’ll be out of action. Don’t be worried that they’ll be mad at you – they will be a lot madder if you don’t tell them and they try to reach you and get hold of you.

Set a clear out-of-office

Sometimes I get people’s out-of-offices and wonder why they even bothered to put one on. After you decipher the message it essentially says, I’m away but feel too guilty to completely stop working so I’m still in my inbox. If your intention is not to look at your emails at all (which it should be if you’re on holiday!) then say that in your auto-reply. I wrote that I was away and not checking emails at all until the date of my return. I said that if someone had a true emergency, they could WhatsApp me but I didn’t provide the number because guess what – if someone has an actual emergency and doesn’t have my number, I’m not the person they should be contacting.

Book in work for when you get back

This is the golden goose. Coming back from holiday with nothing but a credit card bill and no work lined up is daunting. In the months leading up to my holiday, I took on a big commercial project. Ordinally, I might not have taken on that kind of project but it offered a fixed income and meant I could come back knowing that my first month was taken care of.

Try to book in some shift work, or think about finding a short-term contract for when you return from holiday. Sian Meades’ Freelance Writing Jobs newsletter is a great place to look for contract and part-time work.

Leave your laptop at home

The only way to take a proper holiday is to leave the laptop at home. I will repeat this again: the only way to take a proper holiday is to leave the laptop at home. Don’t kid yourself that “you’ll on bring it to watch Netflix in the evenings” – that’s a slippery slope to thinking that you can “just do this one thing” because you have your computer with you. If you get all your ducks in a row before you leave, there really will be no reason to bring it with you. I left mine behind and the sky didn’t fall down, quite the opposite in fact.