How to go on holiday when you freelance, without damaging your business

Photo by Matthew Henry from Burst

When you first went freelance, you probably had two ideas that you were a little bit thrilled about.

One was that, with the right clients and a strong work ethic, you could potentially earn more money than you’d done in your previous, salaried job.

Another was that, by freeing yourself from the bureaucratic demands of working for a company, you’d be able to live life to your own beat, and especially, take time off whenever you wanted it.

Exciting times.

But then, a few weeks later, the slightly harsher realities of actual freelance life began to hit.

Work from clients came in, but on their timescale, not yours. You’d have a few anxious days of waiting for the next commission to come in. Only to find, like London buses, three arriving at once, all with super-tight deadlines.

As freelancers we’ve all found ourselves, at some point, feeling like our clients’ demands are never ending. And while it’s nice to have a lot of work, the idea of planning a holiday seems like an unreasonable dream. Maybe next month. Or maybe next year.

But I’d urge you not to fall into this trap.

Holidays are an essential part of avoiding burnout and keeping your creative energies fresh. So it’s really important you take them.

At the same time, though, you don’t want to damage your business. So I’ll offer some simple but achievable tips to help you strike the right balance between taking time off and keeping clients happy.

1. Learn to turn down work

When you start freelancing, it’s tempting to take on as much work as you can get, and this often leads to a work overload that you just never seem to catch up with.

You’re constantly behind on your deadlines, you don’t have time to sleep, and yet you keep accepting more and more work, for fear it will all dry up if you don’t.

Here’s a secret: it won’t.

In the same way that playing hard to get with an admirer just makes them more infatuated with you, patiently explaining to a potential client that you don’t have space in your schedule for them right now will probably make them think more highly of you.

After all, if you’re in demand, you must be good, right? Which means when they come back to you with another project further down the line, they’ll be sure to give you more notice, and may even offer more money.

First, you’ve got to bite that bullet, though. So start to get into the virtuous habit of saying no, slow your workload down to a manageable pace, and you’ll begin to be in a position where you can start thinking about taking a holiday.

Before you can do that, though, you still have to…

2. Get organised

Some freelancers are super-organised, with easy-to-access spreadsheets and to-do lists setting out exactly what needs to be done, when, and in what order.

Others operate in a state of constant panic, unsure of what they’ve promised certain clients, and constantly on the backfoot, reacting to demands of “Why haven’t you delivered what you promised yet?” with feverish apologies, a flurry of excuses and a desperate search for that two-month old email that had all the details.

If you’re more the latter than the former, you’d be too daft to go away on holiday right now. No one wants to be sipping a cocktail on a sunny beach, only to be interrupted by a call from an angry client. Once you’re properly organised, though, the chances of that happening will be slim to none.

So yes, we know it’s a pain, and you’d rather be creating beautiful things than doing boring admin. But actually, it never takes as long to organise yourself as you think it will.

Remember, as a freelancer, you don’t have to work inside someone else’s antiquated systems but can create ones that will work for you. And you’ll feel so much better once you have, whether you’re at your desk or on a beach.

3. Give clients fair warning

It sounds obvious, but so few freelancers do it: give your clients as much notice as possible that you’re going away.

They’ll thank you for it, because it shows you’re considering their needs (which, after all, is half the battle to transitioning an occasional client into a regular one).

And when it comes to your freelance workload, they’ll be much less likely to dump extra demands on you in the last week, while you’re desperately trying to get all your other work done.

4. Set an email bounceback (and stick to it)

It’s standard practice when you’re on holiday to set up an email bounceback to all enquiries explaining that you’re on holiday and will reply to messages on your return. But sticking to it is another thing entirely.

You may be sat by a pool, but whenever you glance at your smartphone, you can see exactly how many emails are piling up. And it’s tempting to think: “Why don’t I just have a quick glance through them, just in case there’s something really urgent? It won’t take a minute.”

In one sense, you're right. It certainly won't take a minute. It'll probably take hours. And even if you realise your error and stop, you’ve now been dragged back into the world of work worries and all the sun and sangria in the world can’t help you relax.

So just don’t do it. Uninstall the Gmail shortcut from your homescreen. Or just put the phone away and forget about it. Whatever it takes.

5. Designate an email catch-up day

One of the reasons it’s so easy to get sucked into work emails while you’re on holiday is the fear of being overwhelmed by a flowing inbox on your return. So it’s sensible to allay that fear by devoting the first day back entirely to replying to emails.

That may feel like a 'wasted day' in which you’re 'not earning any money', but that’s the wrong way to look at it. Communicating with clients is an important part of what you’re paid for, and is vital to staying in their good books.

So spend day one answering all enquiries carefully and patiently, get to that magical ‘inbox zero’, and you’ll be massively more refreshed and efficient when you return to your creative work on day two.