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Freelancing on holiday – should you do it?

Ah, the blissful life of a freelance writer. You get to work from wherever, whenever. All you need is a solid battery and even the slowest of internet connections.

That also means, and many of you will agree (especially those who aren’t freelance writers), that you can work while on holiday. Summer, winter, skiing, site-seeing, doesn’t matter – wherever you go, you can take your lappie with you and get some words sent one way, and get some greens sent the other way.

But should you really do it, or should you stick to the more traditional yearly leave principle? You know, the one where you work your ass off all throughout the year, and then turn off everything for two weeks, and eat all the possible food in colors you’ve never seen before, made by people whose name you can’t pronounce.

Oh yeah, and you’re doing it between prolonged sleeping sessions that look more like you passing out?

Traditional vs Modern

The dilemma here is in the word ‘traditional’. There’s nothing traditional about freelance writing, or freelancing in general, for that matter. It’s a completely new approach to doing work, and it’s turning the entire work industry upside down. But when it comes to taking time off, I’d say – stick to the traditional – never work during vacation.

I’ve tried it – two years in a row and failed – miserably. First, I never managed to completely shut off. Wherever I was, whatever I was doing, I was always checking my phone for emails. I looked for client’s comments, and was thinking about what I need to have done by tomorrow. I had to plan my work schedule around my holiday, around outings, dinners, dates and whatnot. Even though I reduced my workload for the time, significantly.

On the other hand – the work I did during my ‘time off’ was below my standards. I simply couldn’t get myself into the creative workflow I usually have, and couldn’t keep my focus as I usually do.

So I did very little freelance work, did it poorly, and ended up as tired and drained as I was before leaving for vacation in the first place.

The issue here is that freelance writers get paid after submitting work. That means if you’re not working – you’re not earning. And many freelancers (myself included) fear losing two weeks’ work of pay, especially if they know they’ll be spending extra on vacation.

The solution is in careful planning – and this relates not just to vacationing, but to everything freelance.

Just as you have to plan your day, and stick to a pre-defined schedule in order to make the most of your day and make sure you submit quality work, you also need to plan your vacation. And that starts a little earlier than usual.

Start saving early

Don’t rely on your June paycheck to hit the beach in July – start saving in September, a year before. Think about how much you’re willing (and capable) to spend, split it into eight months, and then plan your savings. Also plan on saving a little extra to cover any unexpected expenses, and to cover that month you’ll be working less.

Prepare your clients

If you’re planning your vacation, let your clients know as early as possible. I’d say at least two weeks up front, but some prefer even earlier. Some will ask you to do a little extra work before you go, and if you can – you should definitely do it.

By planning your vacation, you will:

  • Have enough money to travel worry-free
  • Be able to to cover current expenses
  • Return to satisfied clients
  • Get plenty of rest

It’s a win-win situation, and it all boils down to one thing – plan ahead. After all this time in the business, if someone were to ask me to describe freelancing in two words, I’d say ‘planning ahead’.

Image Credit: Journalancer


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