How Freelancers Get Holidays

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.

Free book: Jump Start HTML5 Basics

Grab a free copy of one our latest ebooks! Packed with hints and tips on HTML5's most powerful new features.

  • BlaineSch

    I hope none of your clients read this and realize you’ll be back Friday! :P

  • Textfriend

    So really, you have a lot less flexibility and a lot more hassle than most employees, why bother freelancing?

  • robert

    hi,
    i understand your concern, i have been there too. sometimes is better to pass your task to a friend/partner/associate or somebody who does the same thing as you, and has time to cover your holiday. the most important thing is the work to be done for the client / you to be on holiday for recharge. good luck! :)

  • Maya

    How about a Virtual Office service for while you are away? They can handle all your calls, take messages, and let people who forgot that you were going away know when you’ll be back!

  • http://www.brothercake.com/ James Edwards

    What’s a holiday? :)

  • Ivan

    Great post!

    Yeah, its like that, clients don’t realize when you give them a notice, and they double the workload, like thinking well like “youll be out for a week, then do the double this week” and its pretty hard to take or say no.

    On my last vacation I even had to work til 3am! the last day before my trip, so I totally agree with this.

    I guess this is one of the bad sides of freelancing compared to a full time work…..

    Any advices are welcome, as I plan to go out in a few weeks!

  • Tanvir

    I am a new freelancer. Reading your article I can easily understand that its a long way to go, far away to planing and wide sense of organization. Good Staff. Best wish to you.