Freelance Writers Need Vacations, Too. Here’s How to Take One

by | Mar 2, 2015

If you’re following my Tracking Freelance Earnings column, you probably noticed that my January Income Report mentioned I was going on vacation.

From January 31 through February 8, I was on the JoCo Cruise, a geek-themed cruise featuring performers such as Jonathan Coulton, David Rees, Jean Grae and Hari Kondabolu. I go on this cruise every year as both a vacation and an opportunity for professional development — this year, for example, the cruise included a writing track led by John Scalzi — and consider it one of the best parts of my year.

Because freelancers don’t get paid vacation days, I put in a lot of late nights completing extra work so I would still meet my monthly income goals.

In addition to working ahead, how else should freelancers prepare for extended trips? It all comes down to two words: communication and planning.

Prepare your clients

As I wrote in a recent Ask A Freelancer column, communicating your vacation schedule and availability to your clients is one of the most important parts of vacation preparation. Although I am technically “my own boss” and don’t have to ask for permission to take time off, freelancers lose clients pretty quickly if we get in the habit of disappearing without any warning!

I started preparing my clients for my upcoming vacation in mid-January. I gave each of my clients three key details:

  1. The dates I would be gone
  2. My availability while I was away (for this trip, I let them know that I had limited access to the Internet and was not planning to check email; in other situations, I might say “I will be checking email once daily”)
  3. The assignments I would complete before I left

That third point is particularly important, because it helps manage expectations and provide assurance. Clients want to know that their magazine, blog, website or project is going to run smoothly regardless of whether their freelancer is behind a desk or on a cruise ship watching David Rees sing “Shake It Off.”

Here’s how I addressed this issue with The Write Life:

On January 14, I let them know that I planned to draft my January Income Report on January 29 and complete any revisions on January 30. Giving my clients specific dates and action items helps assure them that I have a plan for completing all of my necessary work.

I turned in my Write Life draft a day early, on January 28, which had been my plan all along. It’s an easy way to exceed expectations and give my editors a buffer in case we needed a longer revision process. (Editor’s note: I love this strategy.)

On the night before my trip, I set up an out-of-office email stating that I would be on vacation and away from email until Monday, February 9. Don’t forget this step! At least one of your clients is bound to forget that you are on vacation, and the out-of-office email acts as a reminder. Likewise, if anyone contacts you about any new work while you are away, the out-of-office message reassures them that you are not ignoring their email.

Plan ahead to prevent surprises

The biggest worry I have, when I go on vacation, is that one of my clients will have an expectation about my availability that I won’t be able to meet.

When I went on the same cruise a year ago, for example, I was working for a copywriting firm that connected me with various third-party clients. One of those third-party clients, not knowing that I was on vacation, sent me a revision request on a project. The copywriting firm was able to manage that expectation and assure the client that I would complete the revision after I returned.

This worry about managing expectations is one of the reasons why so many of us check email while we’re on vacation — 44 percent of workers, according to a 2013 American Psychological Association study.

It’s not necessarily the fear of missing work; it’s the fear that someone is going to be disappointed or frustrated that we aren’t immediately able to help them. Good planning helps mitigate that frustration, and advance communication reassures clients that all of their needs will be taken care of either before or after we get back.

I have to admit that when our ship docked in San Juan, Puerto Rico — where I had domestic cell service — I turned on my phone and scrolled through my messages. I had prepared well; none of my clients had any immediate requests, and there were no surprises in my inbox.

Get back to work

The “back to work” phase of vacation is just as important as the planning phase.

Before you leave on vacation, figure out what your work schedule is going to look like for the week you get back. Are you going to be starting any new freelance assignments? Do you have deadlines to meet? Pitches to send?

Making a plan before you leave helps you jump straight back into your workflow without wasting time — or, more importantly, losing track of something important that might have slipped your mind while you were relaxing by the ocean!

I also put in some extra time on the Monday and Tuesday after I got back to catch up on the emails that needed answering. (Just because there weren’t any immediate requests in my inbox didn’t mean that there weren’t about 30 emails that needed a response.) By Wednesday, I was back to my usual freelance schedule.

So that’s how I handle a freelancer’s vacation. I’ve already put down a deposit for next year’s JoCo Cruise, which means that next January I’ll be ready to start this process all over again.

How do you prepare your clients before you go on vacation, and how do you handle the transition back to work? Do you check your email while you’re away?