Is it possible for freelancers to ever disconnect from work?

For full-time freelancers, which roughly 40% of Canadian millennials have been at some stage of their career, boundaries between work and life barely exist. Is it possible to disconnect?

Dylan Doyle was in Mexico with his partner for a friend’s wedding last November when the emails started to come through: a marketing graphic scheduled to be posted on Twitter contained errors. And, while he thought the issue was under control, the freelancer covering for him had unfortunately taken him up on his offer of being “available over email.” Doyle had planned to go on a 45-minute hike and spend the rest of the day at the beach with friends. But, the emails were coming in so fast and furious that the Toronto-based social media strategist decided to stick close to wifi. He remained at his AirBnB to do damage control instead.

Doyle, 29, spends approximately 20 hours a week on freelance work on top of his demanding full-time job; partly to pay off the egregious amount of student debt he accumulated in school. “There hasn’t been a vacation since 2016 when I haven’t brought my laptop,” he says.

If Doyle’s story sounds unique, it shouldn’t. According to a study done by the business and financial management platform HoneyBook, 92% of freelancers regularly work through vacation. 60% do so because they feel like they don’t have a choice. Celebs like Ed Sheeran, Selena Gomez and Kendall Jenner may tout the benefits of a digital detox, but those with the ability to actually unplug are the lucky ones. The forty-hour workweek, where evenings and weekends represented sacred personal time, is a thing of the past. And for full-time freelancers, which roughly 40% of Canadian millennials have been at some stage of their career, those boundaries between work and life barely existed in the first place.

“The financial uncertainty of freelancing can make it feel impossible to stop hustling even for a day or two,” says Eva Holland, a freelance journalist based in Whitehorse, Yukon. One of the only ways Holland says she’s able to stop working is by physically leaving the house to avoid the gravitational pull of her laptop. “It’s an extreme rarity where I’m not working on a weekend.” Truc Nguyen, a Toronto-based freelance writer and stylist went on a ten day vacation to Japan in 2019 with family and ended up filing 10-15 stories during the trip. Days were spent sightseeing with her daughter, but evenings she stayed up past midnight scrambling to meet deadlines.

Freelancers have difficulties creating firm boundaries between work and life for a number of reasons. According to Dr. Nancy Worth, a geographer at the University of Waterloo, the labour market is becoming more insecure and freelancers feel the need to be consistently available in case a last minute request or gig comes through. Freelancers live in a state of constant flux and often have no idea where their next cheque is coming from, so those with fewer boundaries may be more likely to get work. “There’s a danger of being rewarded for something that might ultimately cause you to burn out,” she says.

Freelancers also take on an increased mental load of responsibilities compared to salaried employees. Worth uses the metaphor of an iceberg to explain the inventory of tasks freelancers must perform: above the water is the paid labour that gets invoiced for; below is an even larger chunk of mass that involves looking for work, chasing down invoices, networking and skills training. The sheer magnitude of tasks that can be considered work-adjacent helps contribute to the sense that freelancers are working all the time.

In a joint paper from the University of British Columbia and Harvard Business School, researchers Alice Lee-Yoon and Ashley Whillans determined that people who prioritize time over money experience greater levels of “subjective well-being” and are more likely to spend leisure time on activities that promote happiness. On the flip side, people who view time as money – aka most freelancers -- are liable to spend significantly less time with family and friends. “Specifically, when people are asked to think about the economic value of time, they adopt a mindset focused on maximizing productivity, which increases impatience and even diminishes the meaning people derive from their work – increasing psychological stress.”

As the number of freelancers in the labour market continues to grow steadily, Worth is optimistic that governments and institutions will begin to increase protections for freelance workers, such as California’s newly-introduced AB5 legislation. But until then, it will continue to fall on freelancers themselves to create boundaries that protect them from exploitation.

Holland says taking time off work is more feasible now that her career has stabilized, “but it's still easy to fall into a bad cycle of working after dinner every night, working all weekend.” Renee Sylvestre-Williams, another established journalist, takes breaks from work, letting her clients know in advance that she will be unavailable.

For Sylvestre-Williams, this kind of break isn’t a luxury, it's a necessity. “I can see the quality of work [dip] when I’m stretched too thin,” she says. “I’ve had work come back from a couple of my editors and it’s marked up, really heavily edited.” According to the law of diminishing returns, investing more energy and resources into a process cannot infinitely improve its output. In other words, working constantly isn’t necessarily going to make the work better or more plentiful so we might as well take a break.

This spring, Doyle has planned an upcoming vacation to Iceland with his partner, and has vowed to leave his laptop at home. “I want to go enjoy myself and untether,” he says. He plans to delete Slack from his phone and only check his email once every 48 hours. “I think back to the times I’ve gone on vacation and been super wired about work and nothing actually happens.” In other words, it’s time to let go.

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