How to Survive Vacation as a Freelancer

How To

The survival of your freelance business rests on you and you alone. You don’t have a staff to keep things moving when you go out of town, at least not when you’re first starting out (Sounds nice, though, doesn’t it? Many freelancers get there.). With all the work you’re putting in, you deserve a vacation every now and then, but how do you step away from your home office (or your couch or kitchen table) for a week without things falling apart? Stressing that you’re falling behind on work and that you’ll have nothing waiting for you when you get back doesn’t make for a nice, relaxing vacation. So how do you properly prep yourself to survive a vacation as a freelancer?

In the 2+ years I’ve freelanced, I’ve been lucky enough to go on at least one vacation a year, outside of travelling to family reunions for Thanksgiving and Christmas. I’ve actually been on two already this year: I went to Florida in March and just got back from a long bachelorette weekend in Orange Beach, AL, yesterday. I’ve managed to survive and keep my earnings in roughly the same ballpark for each of those vacation months. Here are a few methods, tips, and reminders I’ve used in the past.

Preemptive Pitching:

Okay, this sounds like a gimme, but I’m not simply going to say, “Send out more pitches before you leave so you have stuff to do when you get back,” and leave it at that. I’m going to give you a few strategies.

Ramping up your pitching and job board application game is essential if you want to make sure your month doesn’t go stagnate for a week or two after you return from vacation. However, timing it correctly can be difficult. There are few ways you can approach this.

One, pitch like the wind in the week leading up to the vacation. I mean send out 20-30 a day at least. Check all your favorite job boards daily and apply to everything that fits your job description. It’s a numbers game, so if you want to up your chances, dedicate a few hours each day to it. Now, when you’re on vacation, you’ll need to check your email daily (after the day’s main festivities) to see if you’ve gotten responses. Then, tell the interested parties that you can start as early as next week.

Two, pitch like crazy the month before and take on some extra jobs. This is preemptive preemptive pitching. I call this the cramming method. You take on a little more in the weeks leading directly up to the vacation so that you can get yourself a nice little nest egg that allows you to (almost) completely forget work while you’re away. I used this method for that bachelorette weekend. I was working more hours than normal for the two weeks leading up to the vacation, but it left me with $850 invoiced when I left. That’s keeping me right in my usual ballpark. To make sure I had some income coming in when I came back, I set a few deadlines for early this week but actually crammed in a lot of the work last week. I didn’t have to do anything over the long weekend, and I’m so glad. This method is pretty stressful on the front end, but I chose it this time because I knew I would have absolutely no time to relax or work on this particular vacation. It was go, go, go the whole time.

The third method is good if you are too busy in the week leading up to the vacation to send a high volume of pitches/applications. Instead, you can send around 10 a day the week before and take an hour or so every day of the vacation to send out 10 more. This method will require some downtime during the vacation to send those pitches, but you won’t have to stress yourself out so much the week before.

Working Poolside:

If your vacation is of the “sit back and relax” variety and you don’t want to deal with a pitching frenzy, you may decide you’d like to just keep your work schedule pretty much the same as always, maybe just cut back by one or two jobs. I have edited manuscripts on a tablet sitting in a beach chair on the sand and lounging by the pool, and I didn’t mind at all. I actually really like this method. I usually try not to have any writing jobs while on vacation, but editing a manuscript (especially if the author is very talented) isn’t far off from what I’d be doing by the pool if I had zero work: reading a book. If your vacation allows, I personally think this is a great option because you don’t have to shift things around, the work seems to go faster in a new setting, and you get the bonus of being able to shut the laptop and go do more than watch TV or go grocery shopping. However, I totally get it if you don’t want to have any assignments while on vacation. Just go with one of the preemptive pitching methods.

Keep Connected:

You run a business. Your work is never 100% done. To keep things running smoothly, make it a point to check back in on things at some point every day: maybe when you first get up or right before you head off to bed so you don’t interrupt any fun activities. For instance, I didn’t do any real work this past Thursday–Sunday, but I did get a request for a quote on a ghostwriting project thanks to my Reedsy profile. I also had an old client reach out about sending me a manuscript. In freelancing, it pays to be prompt, especially when you’re dealing with a request from a new client. For instance, that Reedsy request was sent to 3 other freelancers. I made it a point to take time to ask the client a few questions one morning and then send the quote the same day I got his reply. Reply promptly to get ahead of the crowd, but you don’t have to take on the job right away. For instance, I told that old client that I wouldn’t be available until Monday, but I’d love to take on the project. Stay in the loop, and your network may just bring you new work for the remainder of the month without too much effort on your part.

Realistic Goals:

When you’re planning a vacation and trying to square things with your business beforehand, during, or after, realize that taking some time off is most likely going to make that month a little slower and take a small bite out of your monthly income. And that’s okay. You’re taking the vacation because you need a break. Don’t work your fingers to nubs trying to hit the same deadlines, take on the same number of projects, and make the exact same amount of money. If some of these strategies help you do that, awesome! But don’t set your goals so high that you diminish the whole point of the vacation. For instance, I worked really hard the past few weeks to keep my income in the same boat, but I didn’t post my usual blog post yesterday. I figured I could let that slide. I have a few things lined up for the coming week, but not as much as I probably would have if I hadn’t cleared my schedule for that bachelorette weekend. Honestly, I’m glad; it was the type of vacation that makes you need another vacation afterward, haha. Be easy on yourself.

Relax, Damn It!

Surely I’m not the only one who feels they need to keep on top of things all the time. I want to respond to every email as soon as it pops up on my phone. I set hard deadlines for myself to optimize my monthly income. I try to get things done in big blocks to get them out of the way quickly. When I go on vacation, I have to constantly remind myself to change those habits, just for a few days. Luckily, I have an awesome, super chill husband who is wonderful at (sweetly) reminding me to relax, so I have some help. But you can also help yourself. I didn’t have my husband this weekend, so I turned off my data on my phone so I wouldn’t get email notifications until I got back to the beach house at the end of the day. That cut back on my email reply compulsion. If you’re using the “work by the pool” method, don’t be afraid to shut your laptop whenever you start to get tired. Go hop in the pool, chill out, and come back to it when you’re ready to dry off. It also helps if you make sure you set yourself longer deadlines for the projects that will carry into your vacation.

If you take a few preemptive steps to cut back on your workload and keep your mind off work, you can focus fully on enjoying your time off. If you’re a freelancer, you’re basically the CEO of a company you built from the ground up. Treat yourself like one.




2 thoughts on “How to Survive Vacation as a Freelancer

  1. clairejones323 says:

    Some good tips Hannah, you make it all sound very manageable! I’m off on vacation soon, so your post is just the right time. I’ve got a couple of larger jobs to do that I know I won’t get to until after I return. But at least I know they are there waiting for me. I’ll definitely be doing a little bit of drafting while I’m away. Just rough outlines of things, but if there are odd moments of peace I’ll try and use them. Once it gets to September and the children are back at school I need to hit the ground running and really put some time and energy into things.

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