Dog with sunglasses on vacation.
Storytelling Communications

Planning a Vacation: A Guide from the Tactical Typist

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At the beginning of August, I took a trip with my family. It was nothing too extravagant, but I had a lot of moving pieces to deal with, starting with a four-day camping excursion in the mountains, then five days at the in-laws’ so they could spend time with their granddaughter, and finally a two-day “guys weekend” where I met up with some friends I’ve known for 20 years. All in all it was a fantastic experience—but it wasn’t as simple as planning a vacation and booking days off. Here’s how I balanced freelancing and my (much-needed) free time.

Scheduling Prep

First step for planning a vacation? I took stock of my schedule. It started with sending out emails to my regular clients, letting them know when I’d be away and how they could reach me. Next, I took a look at all the jobs I had on the horizon. For a week before we left, I put my head down and got through everything I possibly could so that not only the actual 12 days of vacation were covered, but also several days after my expected return in case something unexpected (like a car breakdown or illness) kept me from getting back to work when I intended. I also sent in all invoices and payment requests, both so that I had a little more cash and so there was one less thing to do when I got back.

Mental Prep

The other half of the equation was mental preparation. Writing is my day job, so I’m used to a schedule that involves a pot of coffee, my computer, and a (relatively) quiet house. And while I was looking forward to my time away, I had to periodically review all the steps I’d taken and make sure there wasn’t anything I was missing. My goal was to become so confident in my prep that I wouldn’t worry about work over vacation. I also tossed a laptop into my suitcase so I could deal with any revisions or last-minute problems.

Did it work? Mostly.

What Really Happened

Everything went more or less as planned. Partway through the first week, however, some articles I’d pitched for a client the month before got approved, and guess what? I needed to work on them right away. I set up a new schedule: During the day I spent time with my family, and at night I spent an hour or two working. I was able to finish everything, and I didn’t feel like work overshadowed vacation. I also checked my work email regularly. This was worthwhile—I got messages from another client asking if I was interested in work due just after I returned, along with inquiries from a new client, all of which I was able to handle on the spot.

The Freelancer’s Checklist

If you’re planning a vacation, be prepared for the fact that it won’t ever feel quite the same as taking a paid break from a full-time job. The nature and scope of our work means some part of you will always be worrying about the article you just submitted or the piece you have coming up. To make your life easier:

  • Organize your schedule. it helps if you’re writing for a platform that lets you easily track and manage your upcoming jobs, but regardless of your client list, make sure you’re either prepared to take a working vacation or have everything done in advance.
  • Get your finances in order. Submit invoices and collect payments.
  • Contact clients. Let them know when you’ll be gone and for how long. Expect some of them to contact you anyway.
  • Have a backup plan. Bring a laptop or tablet—something you can work on for necessary revisions or sudden “need-it-now” jobs.
  • Make sure you have something on tap when you get back. The odds are good that you’ll be slightly off your game when you get home, so it’s wise to get “normalized” again as fast as you can—and the best way to do that is to start writing.

Planning a vacation as a freelancer? It’s possible, and it’s even possible to enjoy yourself while you’re away. If you forget everything else I’ve said, remember this: As freelancers, we are the work, so it comes with us wherever we go. Preparation eases the burden and ups the enjoyment.

Ready to jump-start your freelance career and write for top brands? Join Skyword’s community of contributing writers.

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