When Your Boss Is an App

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The platforms all these workers use vary so widely in their rules and structures that it’s difficult to pin down the boundaries of the modern gig economy. Some platforms are backed by Silicon Valley venture capital and have global ambitions, while others compete in smaller markets or specific industries. Some use workers to fulfill discrete tasks for customers, while others connect labor with traditional employers, taking on the role of a staffing agency. Some allow workers to pick and choose assignments without consequence, while others penalize them for not logging on or for declining tasks. A lawyer on Upwork can set his or her own rates and negotiate directly with clients, but shift-working platforms generally post jobs with a rate already established. For many delivery and driving platforms, rates vary, per service, according to closely protected algorithms that leave income uncertain. Each of these details can have profound impacts on the daily lives of workers. Even in high-income jobs, platforms are in a position to mediate disputes and control access to work; with low-income labor, workers may find themselves entirely dependent on the largess and the algorithms of the platforms they use. About the only thing all these workers have in common is that they are beholden to reviews, with just a few negative responses holding the power to dry up their income or even get them booted from their preferred platforms.

Kristen Anderson, the chief executive of a portable workplace-benefits platform called Catch, compares gig work to the concept of the K-shaped economic recovery, in which some industries bounce back from a recession (the upper leg of the K) while others continue failing (the lower). “I think gig work is K-shaped,” she told me. “The idea of the independent high-earner versus the independent low-earner. Freelance by choice and freelance by force. They have totally different experiences and totally different needs.”

Highly educated white-collar workers are especially well positioned to benefit from flexible work arrangements, using them to create better work-life balances, with time easily carved out for things like family or travel. Samer Bazzi, an online marketing professional, is a longtime freelancer who charges $200 an hour for his services through Upwork. There was a time when he tried to operate outside the platform, but he returned during a bout of kidney disease. “I had a lot of appointments and things that I had to go to,” he told me. “So I hopped back on Upwork.” Freelancing, he said, was not the walk in the park many people imagined. It only makes sense, in his opinion, when you’re making upward of $100 an hour and your reputation is good enough that companies start coming to you. Right now, Bazzi splits his attention between the jobs that come to him and the not-insignificant task of generating new leads. “If I’m down to like two or three clients,” he says, “I’ll go on Upwork, I’ll send out 100 proposals. Out of that 100, you’re going to get like 10 replies and maybe two or three clients.” One of the biggest challenges, he told me, is managing your reputation on the platform: “Not everybody knows that, hey, if you leave me a three-star review and it sounds OK to you, it’s not really OK for me. After a contract’s closed, you’re hand-on-your-heart until the feedback is in.”

Another Upwork user, Jaime Hollander, came to depend on the platform after moving to the suburbs of New York with two children, creating a commute that she found impossible. Full-time gigging let her work from home, stay close to her children and steadily increase her hourly rates. She was lucky, she says, because her husband’s job for a nearby school district offers benefits. Bazzi pays more than $900 a month for his health insurance. (“Health insurance,” he says. “Holy cow.”) Both have set up their own companies, enabling them to write off expenses and avoid the tax pitfalls of a 1099. They are, literally, small businesses. Hollander has even hired a handful of people herself — as full W-2 employees.

For the working class, choice comes at a higher price. In many low-income jobs, flexibility has become entangled with the idea of just-in-time labor and staffing, a practice that cuts costs by slashing back on full-time work and making up any shortfalls with overtime, reduced breaks or last-minute workers brought in from staffing agencies. (This leaves just enough workers to meet demand — or, perhaps, not quite enough, squeezing excess productivity out of whoever is there.) Companies that operate this way need to be able to hire temporary staff quickly. They have found flex-working platforms an efficient solution. According to an advertisement for Snagajob, a platform for on-demand jobs, “Seventy percent of our jobs are filled in 10 minutes or less.”

And it is here, among the working class, that the boundaries of the gig economy have become blurriest, with the technology and the concepts of gig work bleeding into the structure of regular employment. It is on-demand employment that has produced many of the working arrangements Americans have spent the past decade identifying as faintly dystopian. On-demand employment may mean you are subject to strict requirements for how many hours you work, but must compete for unpredictable shifts on online platforms, as if they were hot concert tickets. In retail work, it may mean mandatory overtime during peak shopping seasons and unreliable week-to-week income. In an Amazon warehouse — or even working from home on your laptop — it may mean intense computerized tracking of your minute-by-minute productivity, with grave consequences for even small variances. For railroad workers it may mean being denied, or penalized for taking, sick days during busy periods. These conditions easily cross the borders between gig and nongig work. Amazon, for instance, uses flexible scheduling platforms to enable full-time workers to choose shifts, letting them accrue paid time off as they work or taking it away via an automated penalty system — an arrangement that borrows some of its flexibility, uncertainty and technological control from the world of gigs. It’s also symbiotic with actual gig work: The wages are low enough that many employees do side work for platforms like DoorDash and Uber. (It is to those businesses’ advantage that flex workers accrue benefits from Amazon; the extra income they offer, meanwhile, allows Amazon to keep pay low.)