Organizing Your Freelance Business Before Going on a Vacation


If I told you that you were to take a two-week break right now, what would your response be? I’m willing to bet that none of you jumped up in the air and screamed ‘Yes!’ much less fall to the ground in thanks.

Your first thought probably was ‘I can’t take a vacation. I have work to do!’

The most annoying thing about freelancing is our inability to take vacations. Sure, theoretically, we can take them. Practically, it’s nearly impossible. After all, who’s going to run the business if we’re on leave?

Running a freelance business means that there is no paid leave. If a freelancer wants to take a vacation, he can’t just pack his suitcase and leave for two weeks. There are clients to answer to after all!

Unfortunately, if you don’t take a break, you’re going to burn out faster than a tire on a race car. And to avoid burnout you need to– you guessed it – take a vacation.

But ‘How?!’ you ask me. How am I supposed to leave my work? There are so many people depending on me. The world as I know it will end if I don’t answer every email I get within a few hours!

Newsflash, my friends. The world will not end if you take a break. The world will realize you’re human and tell you to go have fun.

If you’re still not convinced, here are a few ways you can handle your work obligations when going on a vacation.

Submit work early

I take my vacation seriously. Every year I take one long break to travel and submitting work early is my favourite method of taking care of my workload.

Complete any work due during your vacations beforehand and send it off to your clients before leaving. Let them know you’re going on a vacation (and when you’ll return) and don’t accept any more work during your break.

Keep yourself available via email in case of (work) emergencies.

Yes, it will mean extra work for you. It will get hectic and you’ll probably work nights and weekends to get things done in time for your vacation. But think of the alternative – two or more weeks of complete and utter bliss.

You’ll be able to sleep in late if you want with no tension about work because you’ve already taken care of it!

It’s also an excellent way to impress your clients. After all, which client doesn’t like receiving work in advance? You’ll stick out as a freelancer who is dependable and conscientious and guess what? Clients love working with freelancers like that!


If you’re working on a project with a team, consider delegating your work to them. Team members are usually open to dividing extra work between them, as they know you would do the same when they go on a vacation.

Even if your work isn’t their area of expertise, you can swap deadlines with them and submit your work earlier or later.

Ask for an extension

If you can’t submit work early, ask for an extension for your deadlines. Letting clients know beforehand means they know what to expect and can work around your vacations. Most clients have no problems granting extensions for a vacationing freelancer – as long as you’ve been consistently meeting deadlines.

Just give them enough time to make decisions. Sending them an email asking for an extension two days before your vacation will probably get you fired.

Let them know a month before. Give them enough time to make any changes required. Like you, they’re on a schedule too so they might need to move around projects because of your vacation.

If you’ve planned your vacation a few months in advance, then it’ll be easier for you. You can simply negotiate the deadline at the start of a project when discussing it with your client so that it’s after your vacation and not before or during it.

Hire another freelancer

If you’ve got a big project that absolutely can’t cope with you taking time off, consider hiring another freelancer who can work for you. Get the freelancer to start a week or so before you leave for your vacations. This way the freelancer you’ve hired will be familiar with your work and you’ll be confident that he’s going to do a good job.

One drawback of hiring a freelancer is that you can’t completely plug off on your vacation. You will need to check in regularly to see if your freelancer is on schedule. If he faces any problems, you’ll need to work in order to sort them out.

Chances are, if you hire a freelancer worth his salt, you won’t need to spend more than 30 minutes or less per day with him.

Refer someone else

Referring another freelancer to your clients is a good idea. Talk to a freelancer whose work you admire and trust to deliver results as well as you. Let your client know you’ve assigned the project to someone else in your absence and assure them that they won’t have any problems.

Give them a personal guarantee that you will go through the final version and make sure that it’s in accordance to the client’s wishes.

When choosing another freelancer to take over your work, make sure that it is one you’ve worked with before. To assuage your client’s fears about the project changing freelancers, you need to believe in the freelancer you’re recommending.

That can only happen when you’ve worked with the freelancer before. Remember, this is your reputation on the line so recommend someone you trust.

Take a working vacation

If you still feel that you can’t take a vacation, then as a last resort, consider taking a working vacation.

Work only a few hours a day and leave your smart phone and laptop in the office when you’re done.

Set up an email auto responder letting people know that you’re on a break and include the date you’ll be back. This way you’ll be able to choose what to work on and what to leave till after your break.

Before you go on a working vacation, let your clients know that you’ll be meeting their deadlines but working reduced hours so might not get back to them as promptly as you usually do. For everyone else, there’s no need to let them know that you’re on a working vacation. If you do, you’ll be working all day before you know it!

All set to take a vacation

There is no reason for you not to take a vacation. Choose any of these tips to organize your work before taking a break and you’ll be enjoying a stress free vacation before you know it.

Just remember, planning is the key to a successful break. Make sure you’ve covered all your bases and prepared for all eventualities. But even then your best laid plans go might go awry – so keep allowance for that and take it easy.



  1. An excellent article! it’s nice to know that we have options available to us as freelancers.. I like to take my breaks at the end of the year, when I know companies close, or people also go on holiday. In South Africa, that’s in December, around Christmas and New Year.. You get a 3 week stress-free holiday, with hardly any interruptions.. But like you say, ensure that all deadlines are met, else you won’t have that client back in the new year :)

    • Samar Owais

      Hey Samantha, glad to know you take your break. I like to take mine during the summer. Allows me to spend time with my family. Later in the year during the winter months, I make sure I take weekends off and enjoy myself.