How To Take A (Real) Vacation As A Freelancer

In the spirit of summer, here’s a sad fact: Even though I’ve been on five vacations in the last four years, including trips to San Diego (twice), New York, Vancouver, and Portland, I’ve always had to pull out my laptop to write a blog post, monitor scheduled tweets, or constantly check email. As a freelancer, I was never able to truly unplug on a “real” vacation.

Schedule in advance

Without paid vacation days, going away as a freelancer can seem more daunting than enjoyable. To actually appreciate a break, freelancers need to do two things more diligently than most people: plan and budget. Andy Meek, a freelance writer from Memphis, takes several vacations a year, and to make it work, he plans his schedule three months in advance.

“If anything conflicts with the vacations that I have to take, such as an anniversary trip with my wife, which has to be at a specific time, I make the freelancing work around it,” he said.

For Meek, part of the planning includes letting clients know he’s taking a break, so they aren’t blindsided when he’s gone. He lets his top clients know one month in advance that he won’t be writing during his vacation. “On the other hand,” he said, “sometimes articles for certain publications come with a deadline that might be one to two weeks away from the end my vacation, so I’m able to just fold my vacation into that article, come back, and knock it out without a problem. For these clients, I don’t need to tell them I’ll be away.”

Hire extra hands

For Seattle freelancer Briana Saunders, whose work includes social media monitoring and content development, finding people to help run her business while she is away has allowed her to sit back and relax during vacations. She looks for temporary help, since, as she explained, her business won’t stop just because she wants to go to a beach.

“By hiring temporary help, I’m able to unplug from work,” she said. “I can find professionals who I trust to handle my clients, so I can actually turn off email on my phone. Not having email constantly pinging me allows me to unwind and focus on what’s right in front of me.” She typically meets her temporary support staff through personal connections to help ensure they’re reliable.

Finish off the details

Of course, it’s also critical to plan your budget around any vacation, so you aren’t stressed about the lack of production while you’re gone for a week. Any communication lag can ultimately carry over and negatively affect your workload even after you return. Meek, for example, compensates for time off by “doing lots of extra work beforehand and getting some savings in the can.”

And for any doubters still out there, think of it this way: Your clients take vacations, so maybe all you have to do is overlap with their schedules and set up an out-of-office reply. While I have yet to accomplish this myself, the tools available for freelancers to schedule social media posts and email ahead of time have made it significantly easier to get away.

Meek and Saunders attest to having enjoyed several relaxing vacations in the past few years, and yes, they still run their businesses today. It may take extra effort and communication when it comes to planning ahead, but—as your own boss—taking a real vacation as a freelancer should never be impossible.