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How to ACTUALLY Take a Holiday as a Freelancer

Answer me this question: Do you need to take time off work? Now, I know, I know you’re living that sweet, sweet freelance life. I know you’re doing what you love. I know you’ve got the freedom to close up “shop” for two hours so that you can go to your son’s midday soccer game… but the question still stands, regardless of what kind of work you do.

Maybe I should rephrase the question. How about, “Would you appreciate a real, honest-to-goodness holiday break from your freelance work?”

Of course you would appreciate it… and that fact alone means that you deserve one. Why? Because you make the rules, and even people who do what they love need a break every once in awhile.

In a world where clients have “content emergencies” at 11pm and “paid vacation” is an alien phrase, how do you actually take a holiday as a freelancer?

Remind Yourself of the Perks

Here’s the deal with freelancer vacations: you’re the one who has to cover them. You’re going to lose your work time (and be responsible for making it up), you’re going to have to pay for any travel expenses, and you’re also going to have to make sure your business doesn’t fall apart while you’re away.

That’s a little intimidating, right?

When it comes to justifying a freelancer vacation, it’s helpful to do some reflection on your career and lifestyle. As a freelancer, you don’t have to answer to a boss. If you spill coffee down the front of your shirt in the morning, it’s not going to be in the caras you speed down the freeway trying to make it to work on time. You can pack up your computer and get work done at the veterinary office while your cat has surgery. You can correspond with potential clients on your phone without disturbing the sleep-deprived baby who just dozed off in your lap.

Break Before the Burnout

Freelancers are no strangers to burnouts. Working late at night, responding to emails throughout the day, and dealing with the administrative duties are simply hazards of the trade. If not handled properly, this can lead to total collapse. Can you imagine trying to plan a vacation for yourself when all you want to do is eat ice cream on your couch while crying to your cat about 80s movies? I sure can’t.

That’s why it’s important to schedule some time for yourself before you really need it. You’ll end up with a much more enjoyable break.

Get Strategic about Saving

When scheduling time off work, you want to do whatever you can to ensure yourself a freelance holiday that is as stress-free as possible. One of the best ways to do this is to make sure that your finances are sitting pretty and that your vacation expenses are covered. The only way to do that is to be strategic about the money you make and save.

If you’re planning on taking a vacation that lasts longer than a weekend, you’re going to be losing valuable work time. While, of course, you want to have enough money saved up to enjoy your break, you should also consider making up the work time you’ll be losing before you actually go. Get assignments done early. Work an extra hour every day. Work on the weekends if you don’t already. Basically, get as much work off your plate as you can before your trip so that you don’t have it hanging over your head the whole time.

If you can plan your vacation a few months ahead of time, you can also use the same tactics mentioned above to save up for both your travel expenses (think brewery tours and zipline adventures and brewery tour/zipline combo adventures), as well as making up for any income you’ll be losing for that week.

Communicate, Communicate, Communicate

Remember, you’re not taking time off work simply to be able to work in a fancy new location. You’re planning a vacation. An honest-to-goodness break. The idea is to work as little as possible… but if you want to do that without returning to the smoking ruins of your business, you’ll need to communicate with your clients about your break well in advance.

Depending on the type of freelance work you do, this communication might include measures taken to keep your clients’ need consistently met. This may mean working extra before your break, or temporarily sending the work to someone else in order to maintain seamless service.

Send an email, send an owl, give them a call… whatever you need to do to let your clients know that from date X to date Y, you will be unavailable for any new work and conditionally reachable.

Go Into “Emergency Mode”

Alright, so I know I threw out the phrase “conditionally reachable” right at the end of that last paragraph. Let’s unpack that.
We all know, that as owners of our own businesses, it’s very hard to give up control… and sometimes that’s a good thing. Simply throwing up your hands and leaving your business to the wolves while you go on vacation is just a really bad idea. So, you know, don’t do that.

Instead, try employing the 80/20 method. This means that 80% of your time will be spent relaxing, water skiing, dressed up as a superhero at ComiCon… basically, doing whatever you want. The other 20% can be spent checking email, looking over the business to make sure that things are running smoothly, and posting on your business’ social media profiles. You can even do actual work if you want; just make sure at least 80% of your time is staying true to your goal of taking time off. If you do plan to do a little work during your break, make sure you’ve got all your tech needs packed. You don’t want to get stuck waiting in line for the single computer next to your hotel’s front desk.

Embrace a Little Outsourcing

One way to take time off without missing a beat is to delegate your responsibilities to someone else. I mentioned the freelancer’s difficulty with giving up control earlier, but if you know of some freelancers you trust and admire, outsourcing that week’s work might be the perfect way to take a break and strengthen your business network. Who knows, they might ask you to repay the favor when they take their next holiday break.

A Break Should Always Be in the Cards

So, maybe your situation won’t allow a week’s vacation in a far away place. Maybe the best you can pull off is a day. A day away from the kids… a day where you don’t even think about your email. If that’s the case… take that day. Pick up a book and take it to your favorite coffee shop. Buy yourself lunch at the fanciest place in town. Get a much-needed massage. Sit for four hours on your roof snacking on almonds and thinking about space stuff like black holes and Mars.

You’re a freelancer because you want control of your time. You’re a freelancer because you enjoy the freedom this life grants you. You’re a freelancer, and you deserve a break, just like anyone else.

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