How Freelancers Get Holidays

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By the time you read this, I’ll be on holiday.

That statement makes it sound simpler than it is, of course. Taking a holiday as a freelancer requires a fair bit of preparation, plus some savings and determination—and not necessarily in that order.

As you’d expect, I’ve spent weeks preparing to leave my work for just seven days, some of which are public holidays in my country. I always completely disconnect when I’m on holidays, so everything had to be self-sustaining for the duration of my break. As I worked to get everything in order, I wrote this post—a sort of freelancer’s pre-holiday diary.

One month before departure

I feel a vague sense of panic every time my holiday pops into my head. I schedule it into my calendar. Until now, it’s been a nice idea. Suddenly, it’s become a burden: I have a lot to get ready before I go. I try simultaneously to ignore this, and act on it—an unproductive combination.

Three weeks before departure

“Okay,” I tell myself. “It’s time to knuckle down, buck up, and grab this bull by the horns.” I decide to make a list of all the things I need to do before I go. I make a half-baked start on this.

Fear of things going off the rails makes me take the initial steps toward cementing arrangements for my absence. I start writing—including this post—and stockpiling content like a squirrel hoarding nuts against the winter. Because I’m doing this so far in advance, I’m hoping things won’t get too hectic immediately before I go.

I also start telling my clients the dates I’ll be away. I’m actually back in town on Friday, but I give them the following Monday as my first day back on deck, because I’ll need a bit of time to pull myself together once I get home.

Two weeks before departure

Things seem under control at this point, and I lull myself into the belief that it’ll all be fine. I just go about the week like nothing’s awry.

Then, toward the end of my week, my clients start sending me work. Some of them have forgotten I’m going away (I did tell them, right?). I have to turn them down, and instead schedule that work for the week I get back from my break.

Around this time I realize that, given some meetings I have in the week before I go, and the fact that it’s only a four-day week, I’ll only really have about three days in which to do my final week’s work and holiday preparation. Yep — it’s freak-out time!

The week before departure

Controlled mayhem. There are early mornings and late nights as I work in the most unlikely times — and places.

As is often the case when we’re faced with a mountain of work, once I get started, I find it’s not quite as insurmountable as I thought. It’s true that compromises are made — my first week back won’t be quite as cruisey as I’d hoped and planned — but I do succeed in getting everything ready for my absence, and then some.

As it turns out, the panicking I did two weeks ago was really helpful in giving me at least a few days’ grace on my return to work. I won’t be taking it easy — the clients who have booked up my time in the last week or so have seen to that — but at least I have a sort of production bedrock in place, so that the day-to-day tasks, at least, should go smoothly and without too much extra input from me.

That’s it — there are no last-minute dramas or all-nighters. I’m pretty sure that’s because I started preparing for this holiday a good month ago.

I expect you have a different, more sensible approach than my calm-and-panic holiday preparation philosophy. What are your tips for taking time off from freelancing? Share them in the comments (we both know I could use some help here!).

Image by stock.xchng user mn-que.

Georgina LaidlawGeorgina Laidlaw
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Georgina has more than fifteen years' experience writing and editing for web, print and voice. With a background in marketing and a passion for words, the time Georgina spent with companies like Sausage Software and cemented her lasting interest in the media, persuasion, and communications culture.

freelanceproject management
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