How To Really Take A Holiday When You’re A Freelancer

How To Really Take A Holiday When You’re A Freelancer

Good morning from sunny Sri Lanka!

I’m here for a couple of brief weeks with my kids enjoying lots of tropical sun, curries and shopping. And a bit of beach. It’s bliss.

One of the main reasons it’s bliss I have to say is that I haven’t even opened my laptop in about 4 days. (Though, okay, I have checked my email several times a day on my phone but I haven’t written anything more taxing than an updated out of office message).

I worked around the clock for about 2 weeks in the lead up to this trip, and I have at least 3 deadlines awaiting me the week I get home. But it’s been sweet to have the luxury of ignoring my computer for several days in a row. And I realised how much I needed the break; a thought I rarely focus on.  


So, if you’re planning a holiday or a break, today I want to brainstorm about how you can prepare for it. Because the last thing you want is to be hurriedly finishing a project in the dead of the night, or slipping off to schedule some content just when someone’s popped open a bottle of wine. Oh, terriblé!

More than that, you don’t want to rely on dodgy internet connections and misplaced time zones while you’re on holiday. Cue stress. So, it makes sense to do as much as possible beforehand.

In the 2 weeks before I came [on a horrible midnight flight with 2 small children] to Sri Lanka, I wrote and scheduled 6 blog posts, 1 Eat Drink Laos post, and 2 newsletter posts (except this one!); scheduled dozens of social media posts via Buffer; did the initial research and outline of 2 travel articles due after my return; and put together a scope and contract for a new content client.

By the time I left, I felt like a powerhouse (albeit a tired one!) and was even wishing I had just a few more days to keep churning my tasks. It’s funny how motivated you can be with a holiday dangling in front of you!

So, here’s my top tips for switching off the electronic devices and putting your feet up with a mojito in hand, if only for a few days.

1. Clear time for your holiday

It’s hard for a freelancer to switch off completely but it’s also important to set boundaries so others value your time, as well as yourself. Mark it on your calendar, tell everyone about it, set up an out of office on your email. Just because you’re running a solo show doesn’t mean you can’t have holiday like everyone else.

2. Write your blog and/or newsletter content in advance

I love Squarespace’s blog post scheduling feature and your blog will have something similar. As I said above, I knocked out 6 blog posts in a few days but I’d also planned them on paper before that. So list out a few easy topics and try to get a bunch done in consecutive sessions, then schedule them for the dates you’re away.

3. Schedule your social media

I’ve talked before about how I manage my social media scheduling on Buffer but it really is a time saver. I like to spend an hour every month or so filling up my Buffer feed for my LinkedIn, Google+ and Twitter accounts. I can usually slot about 2 months worth of content in which is great because then I can just forget all about it!

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4. Outsource if you need to

If you’ve got a load of deadlines looming and time is running short, outsource parts of your work to someone else. Sometimes it’s just not possible to do everything yourself. So, if it saves your sanity, it’s worth the money to hire some help.

5. Keep your last day free for calamities

Or just unexpected events. When I’m really under the pump is usually when one of the kids gets a fever or some other calamity befalls us. So, it’s sensible to factor in a bit of leeway time for the unexpected. On the morning of our flight, our kitten fell off the staircase and hurt his little paw so I was at the vet getting x-rays!

6. Purge your email inbox

My email inbox is never at zero. It’s a nice thought but some stuff just needs to stay in my inbox otherwise I’ll forget all about it. But I definitely try to delete as much stuff as possible, or squirrel it away in folders. Out of sight, out of mind.  

7. Line up some work for your return

The last I’ll feel like doing is diving into my deadlines as soon as I get off the plane (because no one ever said travel with kids is “relaxing”) but as a freelancer, I’m also mindful of the bottom line. So, I’ve lined up a few projects for July to get stuck into when I’m back. It’s also a nice reminder that I can shop just a little bit more…

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8. Finally, give yourself one extra day before you get stuck into work

We arrive home on a Friday morning; I’m not planning on getting back into work until the Monday. That way, I’ll be well rested and probably chomping at the bit to get stuck into work!

Tell me, what’s your top tip for a smooth, work-free holiday?

About the author: Lilani Goonesena is an Australian freelance writer, SEO copywriter and Squarespace web designer based in Vientiane, Laos. She loves boosting freelancers and small businesses with web design, SEO content and digital marketing strategy. She writes an awesome weekly newsletter on digital marketing, social media, blogging, web design and "all that online stuff". Lilani also blogs at the delectable Eat Drink Laos, just for fun.