How to Take Vacations as a Freelancer

Luke Ottenhof contemplates whether freelancers can ever fully unplug.

Illustration by Brandan Ray Leathead / IG: @brandamsel

Halfway through a trip to Colombia in January, my partner and I visited an organic coffee farm just north of Filandia, a small town in Colombia’s coffee region. The farmer, Julián, picked us up from the town square, and on the way to the finca, he told us some of the history of his farm, which straddles the green, mountainous terrain of the Cordillera Central. It had been in his family for four generations, and he truly loved his work and his land. At one point, stationed on a slope looking down over the coffee trees, he told us that his children didn’t want to take over the farm after him. They said the work was too hard for such meager pay, and besides, the climate crisis was going to make it even more difficult.

It was wrenching and intense, and as I heard it, I just listened, and thought about it quietly. I asked Julián if he was sad. He grinned and shrugged that it was just the way it was. His children would find their own way, and hopefully secure jobs that allowed them some comfort and happiness. There was no point worrying about the future. One day at a time.

It didn’t occur to me until a few weeks later that what Julián shared with me would make a good story. A month before going on vacation, I’d promised myself that I wouldn’t do any work, and I wouldn’t interpret my lived experiences through the filter of freelance writing. I’m still proud that on that afternoon, I was just there with Julián, listening and walking, as a human and not a content salesman.

I’d been freelancing full-time for just over six years when my partner and I planned our trip to Colombia together in late 2022. In that time, I had never taken what I’d call a true vacation. I didn’t have enough money for extended trips, anyway, but had squeezed in a number of one- to two- week excursions away from home over the years. I’d camped across the United States, visited family in Alberta, tagged along with a friend to the Canadian east coast, and road tripped around Costa Rica with a few pals.

On each outing—and on many others shorter than these—I stayed Mostly Online. I responded to emails in the car, conducted interviews from crowded hostel dorms, wrote drafts hunched over campsite picnic tables, and edited and filed pieces while my friends explored and played pool and drank beers and met strangers.

But this trip to Colombia would be different, I told myself. My partner’s workplace was closed for 10 days in January, and December to January were always the months when I felt the worst about work. Like a lot of freelance media workers, I could never manage to sell much substantial, well-paying work in that window. A mid-January adventure to the Andes felt like a good, low-stakes opportunity to try something I’d never really given a proper shake in my adult life: do not a lick of work for 12 days.

The first week was incredible. We explored Medellín and learned about its complicated political and cultural histories; we read about the brutality of colonialism and La Violencia, and gaped at the glorious weirdo power of Fernando Botero’s paintings. We hiked in the Andes Mountains, peering for colorful birds in the dense tangles of branches. We sipped aguardiente and hid from a ferocious rainstorm under the eaves in Salento’s Plaza de Botero. I only experienced the odd fleeting moment of guilt over not doing work. Once or twice, the familiar freelancer pop-up intruded: would this make a good story? Could I pitch something on this? This tendency to turn all of my experiences into writing assignments always struck me as a deeply uncomfortable instinct, and one of my least favorite habits of freelancing. I meet my material needs by producing content, and so my brain has defaulted to constantly scanning my surroundings for an angle to extract. This time, I managed to shut down the urge fairly quickly, and reminded myself to just be a normal human in the world, not a story miner prospecting for a paycheck.

But the tail end of the trip was characterized by needling anxiety. I didn’t really have any new assignments on the go until the next month, so I wouldn’t have payments coming in any time soon. I had turned off Is That A Story? brain in service of enjoying the moment. I get a lot of my news and story ideas from Twitter, so I wasn’t really aware of what was happening or what I could be pitching, and I had three reported stories’ worth of edits to tend to when I got home, which would take up time that could be spent chasing new work.

Since 2017, when I first tuned into social media discourses regarding media workers’ labor issues, the theoretical contradictions and complexities of doing freelance journalism have probably eaten up as much of my life as writing has. What does it mean to report on labor issues while being poorly compensated myself? I had always figured that taking a true, unplugged vacation was the remedy to at least one of those issues, but it turned out that for me, it wasn’t.

***

Vacation time and how to take it is a healthy, well-debated point of contention for freelance media workers who all, in our precarity and nosy spitefulness, crave healthy vacation time and also secretly resent other freelancers who appear to have healthy amounts of it. Unlike our colleagues who are employed full-time, freelancers don’t get benefits or paid time off, so time off is a bit more delicate. 

“My most effective tool has been literally going into the backcountry and telling everyone (truthfully) that I’ll have no phone or Wi-Fi access,” Eva Holland, a freelance writer and author based in Canada’s Yukon Territory, told me in our freelancer’s Slack channel. But burying yourself in the great outdoors isn’t everyone’s bag: “Sometimes you want to have a vacation that doesn’t involve carrying all your own food on your back!” she added.

For a lot of freelancers, long- to medium-term planning of your work schedule around time off is critical. John Loeppky, a freelance writer based in Saskatoon, said that he’ll check in with clients two weeks to a month in advance of time off to see if he can bang out any work before going away, which could lower the chances of missing assignments that would otherwise come in on vacation. He said he tries not to work on stories through vacation, but the reality is that his brain is usually working on something. If a pitch idea pops up on a day off, he won’t ignore it on principle. 

“The same goes for when I take a sick day,” he told me in an email. “And there are plenty, I’m a disabled journalist.”

Loeppky said that too many freelancers think of themselves as employees rather than business owners. Conceptualizing oneself as the latter necessitates planning and pragmatism.

“If I haven’t set up a system where I can weather a week or two without work, then I’ve failed as a business owner,” added Loeppky. “Being disabled means that I know time off is an eventuality.”

Good business planning can allow you to take more time off, too. Kelsey Rolfe took six weeks of vacation last year, almost all of which she spent away from her work. She said that two to four weeks before going out of office, she makes sure to communicate to her editors that she’ll be away and not responding as quickly, with some lead time built in in case there are urgent tasks that need doing. Rolfe, like Loeppky, said it’s important to trust that there will be more work after your time off, even if it may take a while for things to pick up again. “There are slow moments in your business, and that’s totally fine,” she said.

Though she’s been tempted to pitch stories about experiences while traveling, Rolfe said she prefers sticking to what she knows best. “Doing a story that’s set in another country or region where I don’t have local context doesn’t seem like the best use of my time,” she said. This was a boundary I tried to keep, too. 

But the precarity and power dynamics of freelancing, where it can feel like earning money is dependent on being deferential to an editor you’ve never met before, make boundaries difficult to manage. Shoring up good relationships with editors, or getting another check on the way before rent is due, can feel like good reasons to set aside your convictions. Freelance journalist Joel Balsam shared that during a two-week jaunt in Italy (one week for work on a story, one for visiting a friend), he had to spend half the time rushing edits on a story at his editor’s request. He wasn’t explicitly Out Of Office, so he didn’t resent the ask. But then he didn’t hear back from the publication for six months. “I planned to work from there, but evidently didn’t need to bust my ass as I was ghosted for months after,” he said. (He later found out that the months-long silence was because of staff changeover.)

Steve Mann, who does freelance marketing in Vancouver, British Columbia, opined that “any day you can’t turn your [work] brain totally off isn’t really a vacation day,” but that it takes particular circumstances (read: financial security) to do that.

Last summer, Mann spent six weeks in Nova Scotia, during which he worked the first five hours of the day. But if work was busy, sometimes the window would stretch and intrude on what was meant to be vacation time. “It was better than not going,” he said, “but not as good as shutting off would have been.” That single sentence perfectly summarized the past six years of time off — or lack thereof — for me.

I sometimes wonder if I’m the problem. Maybe I’m a bad freelancer who just isn’t that great at running a business. But any individual’s business practices can’t totally insulate them from the state of the media industry, where there are fewer and fewer jobs at outlets with constantly-shrinking budgets. After I tweeted asking to hear from other freelance journalists about the vacation quandary, Neal Rockwell, a freelancer based in Ottawa, wrote back, “You can’t log off, you just reduce the flow while sort of working in order to make sure that you never fully relax but also don’t really earn any money.”

***

It’s a bit woe-is-me and cranky, but I’ve come to sincerely feel there’s no best way to vacation as a freelancer. Unless you’ve got a lot of money, every approach sucks equally, in its own special way. And I don’t think that’s only true for freelancers. I’ve tended to look at my vacation struggles as distinct from other types of work, and while the particulars of precariousness are unique to independent employment, we have more in common than not with other working people. Young workers seem to struggle to distinguish their personal and their work lives. Maybe, under the conditions of a system that handcuffs our housing, food, health, and days off to our ability to work, it’s not really even possible or desirable to separate ourselves from our work. Everything is work, because everything revolves around and depends on work.

In the absence of a cash windfall that renders these questions obsolete, what I’ve come to appreciate and what I would advocate is the importance of honesty and clarity with yourself. Think about how you work, your material needs, how much money you make on average per assignment, your relationships with editors and clients, if you’ll have downtime and equipment to work on a particular trip. Can you unplug from work on vacation and still make rent? Can you enjoy a trip while still doing work part of the time? Every freelancer’s situation is unique. Like our work, the answer will probably shift over time.

A few days after I pitched this essay, in a fit of nerves and frustration over having no work, I reneged on my earlier decision not to write about my time in Colombia. I pitched a story about Julián and his coffee farm, and his struggle to adapt to the end of an era. It’s a good story, and I think it’s worth telling. Julián’s experience illustrates timely tensions between small-holder farmers, imbalanced and colonial market structures, and the climate crisis. Still, sending that pitch email to my editor felt disappointing: I drew a hard line between my work and the rest of my life, and later, when I needed money, I crossed it.

I guess I was working on vacation, after all.

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