How do freelancers take vacations?

by Rachel Sanders

I’m writing this from a patio beside a cabin on one of British Columbia’s beautiful Gulf Islands. Hummingbirds are hovering around a feeder close by. There’s a cold beer by my elbow. And I’m working. On my vacation.

I’m not complaining. I like my work. And I really like to be able to combine a little work with a lot of holiday — to keep projects moving but still be able to laze on a patio during the hot summer months. To me, that’s one of the great joys of being a freelancer.

But working holidays aren’t for everyone. So I’ve been wondering: how do other freelancers take vacations? I checked in with some friends and colleagues this week to gather some intel and advice on how to organize vacation time as a freelancer.

First of all, there’s the issue of simply being able to schedule time away without leaving regular clients in the lurch. Toronto writer and editor Jaclyn Law says the key is giving plenty of notice:

“I don’t have an annual holiday ritual, but when I do take time off, I try to give clients as much as two months’ notice, especially the ones that rely on me every month or every other month for a recurring project. That’s probably my best tip – no surprises for the client. If they need suggestions for someone to fill in, I provide a few names with contact info for other freelancers.”

Other freelancers, such as Vancouver comedy reviewer and podcaster Guy MacPherson, are more relaxed about scheduling holidays:

“I literally never check to see if I have stories due when we book our vacations. Obviously if I’m away, I can’t review anything, but if it’s a feature, I can easily do that. In fact, I have. They have phones and electricity where we vacation.”

“I don’t feel bad about having to work while on vacation because I do lots of whatever the opposite of work is when I’m supposed to be working. As for my corporate work, if they ask me to do a job while I’m away, I tell them I’m on vacation unless it’s a super quickie.”

For travel writers such as Keph Senett, working while on vacation is the norm:

“I actually don’t really take true vacations because I am also a travel writer, so a lot of my ‘getaway’ time doubles as research or whatever. This can be draining, but all other things considered it works out quite well for me.”

Working while traveling has its advantages. Trips can turn up a wealth of story ideas and if you write about your vacations, some of your travel expenses end up as allowable expenses come tax time.

Freelance food and travel writer Don Genova says he’s only been able to take vacations that don’t involve work for the past few years… although on a recent vacation in Italy he still spent some time writing down story ideas. In the past, he used to work extra hard before he left, and then keep working through his holidays:

“I would try to get stories recorded before I left, arrange to do live or recorded calls into my [CBC] show on a specific day, and simply give up a couple of columns worth of income just to be able to not worry about them while I was away…but I also tried to have subjects lined up for my return so I wasn’t scrambling when I got back.”

“Oh, and having to plan your touring day around the phone call is fun as well, especially when I was relying on calling cards and phone booths. One time I was in Tuscany with a group of friends and we all had to stop in this little village just so I could call into [CBC’s] Early Edition.”

When you freelance, it’s difficult to take long stretches away from work without jeopardizing your income. So Toronto writer and illustrator Alison Garwood-Jones just schedules lots of 4-day weekends during the summer. But she makes sure those long weekends are proper breaks from work:

“I’ve never taken a full two weeks in one go — not even a week, just a string of long weekends. Then I work around it. In the two or three weeks before I leave, I push hard for work and file before I leave (I’ll even file early to get it off my plate). I don’t take assignment files with me (except if something is in fact checking). I’m no fun to be with if I’ve got one foot in an assignment and one in the sand. Clearing the decks is important to me.”

Ontario writer and small business owner Angie Gallop also says that non-working holidays are important to her. To make it work, she schedules vacations around the natural rhythms of her business. There are obvious times during the year when it makes sense to take time off, and she and her husband have learned to take advantage of them:

“Over the years, we’ve learned that our slow times are pretty consistent. For us it’s January and July. There is really no point in being at our desks. So we close shop for a couple weeks in January to close the year and plan. And we use July to kick back (if cash is low) or go away if we can afford it. Our girls are still young — 1 and 4 — but I’m dreaming of starting an annual bike trip with them in a year or two.

“With no paid days, I think it is tempting to never have vacations. But I think it’s critical to try — even if you just cover up the computer & have stay-cations. Even an indulgent weekend can help you get perspective on work & life.”

Ontario writer Miranda Miller, on the other hand, takes working vacations several times a year and enjoys it. She says it helps that her partner also has to stay connected to work while on holiday.

“We take working vacations all the time. My partner is a chef who oversees commercial kitchen operations at two properties, so he also needs to be available to his team while we’re away. It’s great, because he understands why I usually can’t just go off the grid.”

“The key is making sure we have access to good wi-fi and planning ahead, so I can get necessary tasks done quickly. There’s nothing worse than spending a few hours trying to get your Internet to work well enough to get 20 minutes of work done when you could be out exploring somewhere new.”

“I used to prepare clients a few weeks ahead by requesting that anything time-sensitive be submitted to me with time to get it done before we were leaving. Honestly though, I often don’t even tell clients now when I’m working on the road. Ensuring we have good Internet access means they don’t know anything is different. I lighten the work load as much as I can in advance, then get up early and get to work. If I do have a heavy day, we just accept that without this career, we wouldn’t be able to have this lifestyle!”

“And hey, I’ll take working by a pool in stride any day of the week.”

Now if you’ll excuse me, it’s time for me to hit “publish” and go for a swim myself.

Happy summer, freelancers! I hope you have some relaxing downtime over the next couple of months… however you manage to make it happen.