Freelancing Basics: Organizing a Vacation When You’re Freelancing

The sun is shining for more than 10 minutes a day, finally, and the heat is on. Summer is upon us, and we freelancers are surrounded by clients and colleagues with regular jobs who are busy planning their vacation time while we try to figure out how and if we can do the same.

It often seems impossible for a freelancer to take a vacation—it can seem too hard to juggle deadlines as needed, and we worry that being out of pocket might cost us either current or potential new clients—but it’s important to at least try to organize one. Everybody needs a break from the daily routine and at least a little time away from work. It’s vital for your mental and physical health to get away from the demands of making a living and enjoy the fruits of doing so.

The good news is that nowadays, it’s possible to get away for a couple of days, a week, or maybe even longer, either without losing out on much of a freelancer’s work time or even without clients knowing you’re away. Thanks to laptops or smart phones, email, and other modern resources, we can keep up with work from almost anywhere. Unless you’re on a project that involves working onsite at the client’s office, you should be able to get away for a break, whether brief or substantial.

I don't think of myself as a workaholic, by the way; it’s just that the life of a freelancer is often hard to plan, because assignments don’t always show up as scheduled and new opportunities tend to pop up unexpectedly. A successful freelancer can build downtime into day-to-day activities, but it can be hard to plan real vacation time and stick to the plan, thanks to last-minute schedule changes or attractive new projects with interfering deadlines.

It helps to stay ahead of deadlines whenever possible so you can build up a few days or more of open time.

There are two sides to whether to tell clients that you’re going on vacation. One is to say nothing and figure out a way to keep up with assignments and client communication while gone, which, as I’ve said, is pretty easy to do these days. The other is to let clients know you’ll be not only out of the office, but unavailable for assignments. That feels kind of scary—we always worry that being unavailable means even our best clients might look for someone else—but some of my colleagues say that just telling clients you’re about to go on vacation is enough to result in offers of new projects!

Early in my freelance career, going on vacation was more of a challenge than it is now. Those years didn’t coincide with access to laptops, wifi and cellphones. I remember doing phone interviews for an article on payphones at places like a Dunkin’ Donuts en route to Ocean City, MD, and both borrowing a hotel typewriter and using its fax machine to send an article to a client one time.

When I was single, I didn’t take real vacations. For several years, I had clients that would take me along on their annual conferences to write onsite coverage, and I thought of those trips as a sort of vacation—I got out of town, I interacted with new people, and I often was able to spend an extra day before or after the conference with old friends in whatever city the conference was in. That was enough at the time.

It wasn’t until I was married to someone who believed in (and genuinely needed—he was a steelworker) vacations that I even formally scheduled them and took them as planned. We'd have a week at a time, three to five times a year, usually “down the ocean.” I'd take along my laptop and do some phone, email, and writing or editing work first thing in the morning and last thing in the evening, but we’d be out exploring, beachcombing, and restauranting all day. I would warn those who sent me on-demand editing and proofreading work that it might take until the late afternoon or early evening to get that day’s projects back to them, but I rarely had to tell my clients that I was out of the office.

Now that my husband has retired, he feels as if he’s on vacation permanently and doesn’t need the physical or mental breaks that used to be so important when he was working; in addition, he had heart surgery a few years ago and hadn’t felt up to traveling until recently. I enjoy my work enough and am able to schedule myself comfortably enough that I don’t feel a real need for formal breaks. For some reason, though, we both felt the need to get away and decided to just try it and see what might happen. We just got back from a few days in Cape May, NJ, and it was great!

I kept up with my writing, editing, and proofreading work while gone, letting clients know that I might not send items back until later in the day than usual. No one seemed to mind, and several said items didn’t have to be done until after I returned. My freelance business survived and I feel rested, relaxed, and ready to face new challenges. I highly recommend that all colleagues try to fit vacations into their freelance lives.

Ruth E. Thaler-Carter (www.writerruth.com) is a long-time freelance writer/editor and owner of Communication Central, which holds an annual conference for freelancers, this year September 26–27 in Rochester, NY (www.communicaton-central.com). She has gained unexpected new clients and projects through referrals and online or association visibility, including her STC membership.

2 Replies to “Freelancing Basics: Organizing a Vacation When You’re Freelancing”

  1. Good article! I manage to take holidays by having a trusted colleague who will look after those of my customers who are happy having a back-up. I tell the main ones when I’m going to be away 3 months, 1 month, 1 week and the day before, and let them know when I get back. I put out of office on but do access email on my phone about once a day and will answer anything urgent. I then cover my cover lady when she’s away. But it’s taken me a while to get to this stage!

  2. In response to a comment elsewhere about this column, I said: It isn’t impossible to vacation without doing any work. Since I enjoy my work, I don’t consider doing a little work here and there while out of town as a problem, but that’s just me. For those who find it ruins the vacation: Start putting some vacation money aside now. Once you decide when you want to go on vacation, tell your clients you won’t be available for a certain time period. Get all your current done ahead of deadline and before the vacation. Put your e-mail on autoresponse (but not for discussion lists; go no-mail for lists or you’ll drive your colleagues crazy and make them hate you). Don’t take a computer/laptop/tablet with you. Don’t check for phone messages. Ta-da!

Leave a Reply