Are freelance holidays just a flight of fancy?

Are freelance holidays just a flight of fancy?


I won’t lie: before going self-employed, I was under the impression – perhaps naively – that as my own boss I’d be free to go on holiday whenever I wanted, at the drop of a hat. If I fancied a break, then hey, I’d book a flight and shut my laptop for a few days. Nothing like making the most of that brilliant work-life balance everyone talks about, is there?

But soon enough, work got busy, and keen to build my reputation and a client base that offered some form of security through recurring projects and retainers, getting away for one week – let alone two – felt virtually impossible.

Luckily, it didn’t take me long to realise that I needed to take back control. Why work for yourself if you can’t enjoy the flexibility it offers? With the remote working revolution well and truly upon us, millions of self-employed people like you and me are now in the fortunate position of being able to mix work with play and even holiday.

Sure, these holidays aren’t necessarily holidays in the traditional sense. And for me, work usually plays some part in my trips away. But my point is that you don’t need to lose clients or stop earning money the moment you go on holiday. Far from it, actually.

In my experience, holidays as a freelancer just take a little extra planning, communication with clients before you go and coming to terms with the possibility that you might spend time working – unless you have someone to take care of business in your absence that is. Unfortunately, I – like plenty of small business owners – don’t at this moment in time. So if you find yourself in the same boat, a quick read of my tips for taking a freelance holiday should help.

Plan ahead

Get an idea of your clients’ busiest periods and, if possible, pencil in a break when they’re away themselves or, when you’re less likely to be called into action. Don’t clear your holiday as if you’re an employee asking a boss, simply let your client know out of professional courtesy that you’re taking a break.

If you’re valued, more often than not, your client will understand that you – just like anyone else – need to recharge the batteries. The more time you give them, however, the better, and the less likely you are to take a holiday when you’re in high demand.

Get ahead

Let’s say you produce assets or set deliverables for clients – whether it’s content, apps or design – it’s worth getting ahead of the game and completing the work due when you’re away before you even go.

Granted, this might entail early starts and late nights in the lead-up to your trip, but it does mean your work will effectively be complete before you clock off – barring any emergencies. Do this and theoretically you can switch off for a few days, or as much as you’ll ever be able to when you’re self-employed...

Choose carefully

We small business owners are so-called digital nomads, free to work from wherever we want. If you aren’t making the most of this, maybe it’s time you did. I would, however, suggest checking that your villa, hotel or Airbnb has all the tech you need to be able to work from it – however much that might be.

You really don’t want to be trekking around looking for reliable Wi-Fi and a half-decent mobile signal, trust me.

Pack Wisely

In fairness, the world caters for remote workers much better these days, but make sure you’re armed with everything you need, nonetheless. Free data roaming in Europe has been a lifesaver for me on countless occasions, and so has the nifty portable charger I bought for my iPhone, which I take wherever I go. It goes without saying that my laptop comes on holiday too, and I usually spend the journey there tying up any loose ends.

Recce the area

The moment I arrive, I go scouting for a bar or restaurant where I can work from for a few hours if needs be. I know a holiday is meant to be a break from work – something my girlfriend often reminds me – but I have to say, there’s something quite liberating about firing up your laptop, ordering a glass of rosé and looking out to sea. Come to think of it, I should probably do it more often.

Above all, remember that as a freelancer you no longer live your life in compartments. In my opinion, the boundaries between work and play will always be blurred. But if you ask me, there’s something special about this, and since taking back control, I’ll never take the freedom I have for granted.

By Benedict Simth