How to Prepare for Time Off as a Freelancer

Ahhh vacation. It’s a beautiful word, isn’t it?

For many of us it prompts images of palm trees, colorful drinks, and long siestas.

The North American definition is “an extended period of leisure and recreation, especially one spent away from home or in traveling,” which we all know is parallel to a “holiday” in other locales around the world.

Basically, as an adult, it’s supposed to signify no work—sounds blissful, right?

As humans, we are meant to take time to recharge our batteries and fuel our souls with the people and things that make us happy. And not to say that work doesn’t make some of us happy (because that’s kind of a big goal in life), but it also occupies so much space in both our schedules and our minds that it’s healthy to get away every once in a while.

That’s why vacation time is a main point of discussion in job negotiations, right alongside salary and health coverage.

In fact, taking time off can actually make you more productive at work. As the non-profit TakeBackYourTime.org notes: “Liberal vacation policies create improved quality of life for employees, which translates into increased work quality. Workers also report feeling more creative after taking time off, and more than 70% of them reported feeling more satisfied with their jobs when they took regular vacations.”

However, as a freelancer, taking time off from work is a little bit different than a full-time employee with PTO (paid time off) built into a benefits package.

It’s still just as important—if not more—for freelancers to unplug, but preparing to do so takes a little extra planning.

Things to Consider

As a freelancer, you have the advantage of running your own schedule. This can be amazing and freeing in many ways, but also can cause you to burn the candle from both ends at times. After all, if time directly equates to money, it’s easier to feel motivated to put in long, grueling hours.

(However, don’t forget that you need to step away from work during the day—check out our recent article, The Benefits of Daily Work Breaks.)

So first things first: Don’t underestimate how important it is for you to take a vacation, whether to see friends or family, travel to a new place like any of these top choices for women to live, or just enjoy a relaxing staycation.

But once you train your mind to welcome the idea of a vacation, you need to be methodical about planning for it.

Timing

Planning ahead is absolutely crucial when it comes to taking a vacation as a freelancer, so determine early on when you might want to slip away.

Though a long weekend here or there might be easier to swing, longer trips (we’re talking a week or two, or even more) will require many months of preparation. Get the date on your calendar as soon as possible, even if your exact travel plans end up changing a little.

Cost

Probably even more important than blocking off your schedule is finding the funds to do so.

Being a freelancer, you’ve likely already mastered the art of budgeting—after all, your financial situation is a little trickier than that of a full-time employee. So you should know if you have the cash flow to take that amazing trek up Kilimanjaro or sway in a hammock on a Bahamian shore.

Just keep in mind that the cost of your flights and hotel or Airbnb isn’t the only thing coming out of your pocket—there meals, activities, and maybe even some local shopping to consider.

Where things really get complicated for freelancers is when you have factor in that you aren’t getting paid while climbing or lounging. Unlike a salaried employee, you aren’t getting paid on the days you are offline.

Now, this might not be the case if you work strictly on monthly retainers or something similar. However, it’s still important to note that even on a retainer you are likely held to a certain number of hours each week or month, so you’ll need to pack them in somewhere else.

Client Communication

Communicating clearly with clients regarding your out-of-the-office status is critical on multiple levels.

Communicating clearly with clients regarding your out-of-the-office status is critical on multiple levels. Share on X

First, it’s vital that you alert a client as soon as you know when you will be away. Giving as much notice as possible—hopefully months—will help reduce the risk of issues popping up. This way they are able to accurately predict timelines for projects, plus pull in extra help if and when it’s needed.

It also helps to display how organized you are and how much you respect your client’s time, further demonstrating that you are a partner to be trusted.

On top of that, it’s important to let a client know what your level of communication will be while you’re away.

Listen, you should be taking it upon yourself to completely unplug and forget about work during the duration of your trip. In fact, we encourage it.

But, if you’re anything like this writer (cough, cough), you may find it’s a little too difficult to shut things down completely. And hey, that’s okay, too! Just be sure to set clear expectations and boundaries.

Maybe you let clients know that you will be checking emails during a specific hour of your day (with your morning coffee perhaps?), and can tackle a few small tasks here and there. But just make it known that larger tasks or projects will have to wait until you’re back at it.

Connectivity

Say you go the route of telling clients you’ll be periodically checking emails or to text you if an emergency pops up. That’s all well and good (even though we still think you should say “sayonara” for the duration of your stay), but are you sure you have the ability to even connect?

If your vacation is taking you somewhere remote or to a far, far away land, then it might be safe to assume that your WiFi will be anything but desirable. Or are you traveling out of the country? It’s probably best that you keep your cell phone’s data plan dormant.

The worst-case scenario is over promising your time and accessibility, thus putting everyone (including yourself) in a real pickle.

If you feel you must do some checking in while you’re away, just be sure that you have the means to do so.

Putting in Extra Time

As a freelancer, you know that your income isn’t necessarily going to be consistent every month. However, to help rock the boat as little as possible, you may find it valuable to put in some additional work hours before your trip.

This can be especially true if there is a certain assignment that needs to wrap up before you depart, or if you being gone might delay another stage in an important project.

It can be stressful to feel like you need to pack more work into an already busy schedule, but that’s where Timing can help. By automatically tracking all of the time spent on your Mac, Timing can help you decipher where in your days or weeks you may have some additional time to get stuff done.

Carving out an hour each day that might otherwise be spent surfing the web for entertainment purposes or scrolling through pictures of your cousin’s friend’s baby on social media can really help you log in some productive work time.

Make the more administrative tasks of going away—booking reservations, hitting up Amazon for trip items, or packing—a categorized project. This will help trigger your brain to realize that it’s okay to prepare for vacation—in fact, it’s something you should be doing!

The Bottom Line

The fact that you are even reading this article shows how dedicated you are to being a hardworking freelancer.

It can be exhausting working for yourself and constantly worrying about keeping new work coming in, and sometimes it can even be a little lonely. It’s hard to not have office comrades to lean on—whether to celebrate or commiserate.

You deserve to take a break, and we can assure you that coming back to the grind rested, relaxed, and recharged will only reinvigorate your passion for being your own boss.

So get out there and get your vacation on! Just be sure to let everyone know you’ll be OOO.