From Pivot Magazine

Lessons from the Gig Economy

Going freelance is liberating, and new technologies make it possible for more and more professionals to jump in. Some even think they will make more money. But fortune doesn’t always favour the bold.
Neal Pollock seemed to be on his way. In 2005, he was a twenty something engineering graduate with a job at a software company that serviced the Canadian mutual fund industry. “I liked my colleagues, and the work was interesting enough,” he says.

But something was missing. In his off hours, he taught himself coding in order to build an app for skateboarders to create and share videos of their best moves—he’d skateboarded a bunch growing up in St. Catharines and Oakville, Ont. “The skateboarders’ app didn’t become what I’d hoped, but I enjoyed creating something,” he says. “I realized I could get paid for doing something I liked.” He thought about going out on his own, but met resistance from his parents, immigrants to Canada from Ireland. “The move was actively discouraged.”

Nevertheless, he persisted. Pollock eventually quit his job and offered his services as a freelance Web developer. He didn’t have much of a network when he started, so he built one, founding his own Meetup group. “That’s been good for keeping up with new developments and, well, for meeting people.”

It’s gone well. He’s built Web presences for the likes of furniture retailer Klaus by Nienkämper (suitably modernist), and the pro-exercise non-profit ParticipACTION (suitably peppy). Pollock got his big break, when, in 2015, the Super Bowl asked him to do its app. “It fell into my lap,” he says. “There was a sports marketing firm working in the same building as I was, and that gig came through them.”

A few years in, his brother joined him, and now he has two others working with him in a small office in west-end Toronto. When he’s had overflow, he’s found other freelancers to help him, often members of the software developers Meetup group. That group has grown to 1,400 strong. Many are just like him: young professionals leaving behind what their parents’ generation would have called a career, for this eat-what-you-kill, gig-to-gig existence.

Pollock was a relatively early adopter of what is now a major trend—a mass migration toward freelancing.

One study found Uber and Lyft drivers make only US$8.55 an hour. Is the gig economy sustainable?

One recent study, commissioned by the Ontario government, found jobs outside the traditional mould, such as freelance jobs, to be growing at nearly twice the rate of more conventional ones. The term “gig,” of course, was first popularized to describe the session-to-session, club-to-club work done by musicians. Writers and actors have long worked this way, hopping from one assignment to the next. But this way of working is rapidly moving out of bohemia and into the mainstream. Increasing numbers of eminently employable individuals in professional lines of work—IT, human resources, marketing, finance, accounting—are moving from gig to gig, untethered to a traditional employer.

In 2016, the human resources consulting firm Randstad surveyed Canadian workers, finding that just over one in four of them worked independently, with IT professionals and engineers like Pollock identified as those most likely to work this way. Based on a recent survey conducted in the U.S., Randstad said most employers and workers anticipated that, by 2025, more than half of us would be working in what it called an “agile” capacity—as contractors, consultants, temps or freelancers. The professional networking site LinkedIn estimated that some 43 per cent of the American workforce now does at least some freelancing.

Many have this relatively precarious gig-to-gig existence thrust on them, as, over the last three decades, employers have continually outsourced work that used to be done exclusively by employees. Last year, Statistics Canada reported that there are 11 per cent fewer Canadian men, and nearly six per cent fewer women, in full-time jobs—or “job jobs,” as freelancers call them—than a decade before.

Not only that, the way young people break into their chosen industries has profoundly changed. According to a recent StatsCan study, in 2016 employers structured nearly half of their entry-level positions as part-time work (less than 30 hours a week) while one in three entry-level jobs were temporary contracts, with set end dates. And in a climate of flatlining salaries, potential freelancers are actually expecting to be better off on their own. In a survey by the cloud-based accounting software company FreshBooks, 67 percent of individuals from a cross-section of professions who plan to leave salaried work for self-employment expect to earn more by freelancing.

woman talking on a phone headset, in front of a laptop in a cafe 

FreshBooks, like its competitors Xero, Sage and others, has skin in the game. They’re part of an entire category of tech products that allows self-employed individuals to do their own accounting, while also giving freelance accountants inexpensive tools to manage clients. Technological advances have enabled this type of work in other ways. With greater connectivity, it’s possible to work with clients from all over, to substitute virtual FaceTime sessions for actual face-to-face time. A proliferation of apps like TaskRabbit, Uber and Lyft speedily match workers possessing certain skills and assets with consumers in need of them. Have a few extra hours in your week? Have an apartment that often sits vacant? Want to start a weekend bookkeeping business? You can register on one of these sites, or buy an off-the-shelf piece of software, and develop a side-hustle—another suddenly ubiquitous term.

Initially, many observers and commentators tended to speak of these apps as contributing to the sharing economy, but since the bulk of these tech-facilitated exchanges involve payment, some other terms—the “platform economy,” the “on-demand economy”—have also become common.

These new terms all aim to describe aspects of this explosion in freelancing. Surveys typically show that more than half of all respondents prefer to work this way, even if the jobs and monetary rewards are less predictable. (The British academic Guy Standing coined a term to describe these workers: the precariat.)

Maybe they’re making a virtue of necessity but, certainly, a significant chunk of those working this way say it’s been their call. They’re going solo, they say, for the freedom to plan their own days, their own course, for the chance to do a combination of work that is tailored to them, something that speaks to who they are—even more than their Twitter profiles do.

An English graduate based in Oakland, Calif., Sarah Gerber works from the Bay Area offices of an office-space company oriented toward freelancers and start-ups, WeWork. She shoots long-form ads using documentary film techniques. “I didn’t train in filmmaking,” she says, “But I was a photographer, and when I tried my first digital SLR that could take video, I had an aha moment. The dynamic image is for me. And so I work with startups, some larger organizations, to tell their stories.”

She also co-founded a non-profit that brings men and women together to discuss gender issues. “There is a value shift happening,” she says. “I don’t have the perks of a traditional job, but those would be decided on by someone else. My perk is that I’ve got balance, some sense of purpose, in my work life. I’m not just waiting to find happiness when I’m not working.”

Her words echo those of one of the big books to come out of 1960s America, Charles A. Reich’s The Greening of America. He wrote: “For most Americans, work is mindless, exhausting, boring, servile, and hateful, something to be endured while ‘life’ is confined to ‘time off.’ ” And so some see this as the belated realization of one of the dreams of the 1960s—not working for the Man.

This out-of-nowhere multinational WeWork—it started in New York in 2010 and now has offices all around the globe—certainly wraps itself up in that free-to-be-you-and-me spirit. WeWork’s two founders, Adam Neumann and Miguel McKelvey, both lived in communal situations, one on a kibbutz in Israel, the other on a commune in the Pacific Northwest. In one of its San Francisco spaces, high up a skyscraper, there is a big glass urn of water full of citrus on a bar, self-serve coffee from the trendy La Colombe roastery, hip wallpaper in the conference rooms, and a big mural anatomizing an iconic Mexican restaurant’s special burrito. The glamour of the offices, the prettiness of the space and it’s mainly young occupants, certainly valorize this mode of work—but these occupants are, of course, paying for the privilege of being here.

FreshBooks found that 67 percent of professionals planning a move to freelance expect to earn more

In Canada, WeWork has similarly high-design, open-concept offices in Montreal, Vancouver and Toronto, right in the thick of each city’s action. I speak to several who use one of the two Toronto offices as a base. Among them is Brian Sekandi, who left a major executive-placement firm to go out on his own, and has since moved from one retainer to the next, often working with companies helping to figure out their personnel needs after a merger or other major change. He says he’s been surprised at how many big corporations—his clients have included Kraft Heinz Canada and McDonald’s Canada—are willing to work with an independent operative. “The thing is you can have as good a Web presence as a bigger firm, often better, and the best software is now often available at less cost, without these long-term contracts. It didn’t used to be the case that big firms would work with small outfits, but now they will. They know they’re going to get to work with you, not have the work farmed out to someone else in-house.”

Sekandi says he simply couldn’t work with clients across North America without the connectivity and other tools his software and devices afford him. Like many people in their 30s, when he needs something in his personal or professional life, he also makes copious use of the apps that have set up online marketplaces for goods and services. “I was using Uber when it just came to Toronto, when all they had were black town cars.”

A recent Pew Research Center study found that 72 percent of Americans had used on-demand services via such platforms as these, and that one-third of those under 45 had used four or more. In the Bay Area, where I live, and from which many of these apps emanate, you can use Handy for home repairs, Postmates for deliveries and Fiverr for, really, almost any odd jobs, seemingly the odder the better. In a recent ad, Fiverr pictured one of their workers so keen to get onto her next gig that she keeps checking her phone while she’s canoodling with someone.

I decided I didn’t want anyone quite that keen to help me give my kitchen a good, deep scrub before a particularly fastidious friend visited from Toronto—who’d said she wanted to cook with me. And so I ordered someone up through TaskRabbit, an app that sends out “taskers” to assist people in whittling down their to-do lists. It was recently purchased by Ikea for an undisclosed sum, and some U.S. and U.K. stores offer taskers’ help in assembling the furniture customers take home. (The nearest Canadian equivalent to TaskRabbit is AskforTask.)

The cleaner I hired, Kristen Carranza, had a nearly 100 percent satisfaction rating from past clients. Her rate was average among the others listed: $42 per hour, of which roughly 30 per cent goes to the company, and 70 percent into her pocket. She arrived on the appointed day, bucket in hand, and went at my fridge and freezer with a vengeance.

After getting her bachelor’s degree from San Francisco State University, Carranza worked for six years in San Diego with a record label, whose artists included Eric Clapton and Glen Campbell. “You meet them and you’re just in awe,” she says. She decided to strike out on her own, setting up a music promotion and artist management business nearer to where she grew up, in the Bay Area. Although she works with some of Northern California’s top young bands—she reps not one, but two popular sister acts—it’s not enough to make ends meet, and she sets aside a few hours per week to do these tasks.

She does a great job, and the pay seems fair, but something bothers me about our interaction. In a conversation with a TaskRabbit spokeswoman, I ask her what happens if someone gets injured when they’re doing jobs they’ve booked under the app.

The spokeswoman sends me an email with a link to the company’s Happiness Pledge, which denies liability in such cases. It states that, in order to keep its customers happy, it has put in place a procedure for claims to be submitted in the event that homeowner’s insurance and other legal options don’t cover the loss—to a maximum of $10,000.

TaskRabbit’s Happiness Pledge denies liability if a worker using their service is injured on the job

There’s something else that bothers me. With just a slender digital connection between us, Carranza came into my house, bearing only her bucket and her good attitude for protection. Slightly more than half of TaskRabbit’s workers are women—so are most of those who participate in the gig economy according to surveys.

For women especially, risk is endemic to this relatively unregulated, unscripted mode of work. A former English professor based in Indianapolis, Tyra Seldon left academia to set up her own writing and editing business, going from one project to the next. Early on, she agreed to meet at a restaurant with a writer about editing his manuscript. He kept asking her personal questions, while she tried to turn the conversation to business matters, like the contract and the deposit. He suggested another dinner, one where he’d cook, while they discussed his writing but added, “It’s going to be hard to focus on work.” She says he then reached across the table to toy with her scarf. She left and turned down the work, then received a nasty text in return. “You weren’t that good anyway. I planned to hire someone else,” she recalled it said.

“I was concerned that if I said anything, it would prevent me from getting other freelance contracts, especially since I was just starting,” she says. “I decided to leave it. There was no HR department I could talk to.”

A recent study published by the MIT Center for Energy and Environmental Policy found that Uber and Lyft drivers were earning an average of US$8.55 an hour, taking into account the depreciation in value of the cars they used to do their work. A spokesperson for Lyft’s relatively new Canadian operation disputes this figure and the methodology behind the study. Another recent survey found drivers reporting earnings of just over US$17 an hour.

Either way, a big question regarding the gig economy at this point is whether it’s a sustainable proposition for those who do the work, or just a stopgap. This is a question that Andrew Cash has spent a lot of time pondering, both personally and professionally. He has worn many hats in his 56 years: he’s been a rock musician, a freelance journalist and a federal MP. “There were so many things I wanted to do,” he says, “and it didn’t seem possible to do them all in a nine-to-five set-up.”

woman performing some plumbing work under a kitchen sink 

He currently runs a Toronto-based national non-profit called the Urban Worker Project, which aims to help, in various ways, the growing numbers of us who work outside the traditional employer-employee relationship. “It’s a sea-change in the employment market that we’re witnessing,” he says. “Forty years ago, independent workers occupied such a small portion of the labour market that policy-makers, government, labour, academia—they could all ignore it really as being an anomaly. No more.”

His fledgling organization connects these workers with one another, while also advocating with law- and policymakers to put in place new protections for freelancers. “There are a lot of freelance workers who embrace working this way and they love it. But they still don’t think their work should be so precarious.”

In one way or another, I ask all of those I’ve interviewed about this. How do they manage the insecurity that currently comes with this territory?

The executive search consultant Sekandi says, “You know you’re only as good as your last placement.” The website developer Pollock agrees: “Even when the work is coming in, you worry, will it dry up?”

And so, after ten years of going gig to gig with a fair amount of success, Pollock and his small shop have come up with an app, Audiogram, that pairs video to podcast sound bites. “They can feature clips on social media easily. With software as a service, you can count on a solid monthly payment.”

When he was freelancing, Cash’s then five-year-old son, Charlie, developed a bone condition that required him to wear a body cast for some time. Cash had to stop work. At present, he doesn’t like what he sees in this sphere. “These freelancers generally have no sick leave, no pension, no backup. They’re one bike accident away from the abyss.”

In an interview after she’s made my kitchen gleam, I ask Carranza what she has for backup. “I feel like I’ll always be able to make it happen,” she says. “I’m blessed to have a good family and support system, if things go south. But I’m optimistic, and doing this enables me to pursue my passion—in an almost reckless, but still, I hope, mindful manner.”