When Your Boss Is an App

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Brenda Handy started doing temp work nearly 40 years ago. Back then, landing jobs took time and effort, even for a licensed practical nurse. In the 1990s she lived in Tampa, Fla., with her three children, but got her work through a man named Tony Braswell, who had his offices a half-hour away, in St. Petersburg. Braswell would call nurses with the details of their next jobs. Handy would learn her assignment and drive the family van an hour south to Sarasota, or maybe 40 minutes east to Lakeland, to reach one of the care facilities that contracted with Braswell’s company. She was one of his most reliable nurses, and she liked working with him. He knew her schedule and the jobs she preferred; he was the kind of hands-on guy who would, in a pinch, drive out in his own car to give a nurse a ride. Still, the whole process could be time-consuming. After a week’s worth of jobs was complete, Handy would drive to Braswell’s office in St. Petersburg — usually getting there before he’d even shown up and unlocked the door — and wait in the parking lot with a handful of other nurses for him to arrive and cut her a check.

“That is how you know I’ve been in this a long time,” she told me recently from her kitchen in St. Petersburg. “Nobody uses paper anymore. Nobody gives you checks.” Everything, she said, is now on her phone. “I’m on the app every day,” she said, as dinner sizzled audibly in the background. “I’m on the app when we’re talking right now.”

Handy still works for Braswell, but the days of phone calls and lingering outside the office are gone. In 2016, Braswell realized that he could not scale his business up without some degree of automation. So he created a software platform he called Gale Health, in honor of Florence Nightingale. Handy can now log in and book work within seconds of a shift becoming available. “It’s like — you’re at the grocery store, you see something you like, you pick that shift,” she said. “They come up 24/7. You have to be quick on the draw.”

Handy has a full-time nursing job and works these additional shifts on the side. When we first spoke, she was also spending her mornings studying to become a registered nurse. She has an overarching philosophy of working both smart and hard — a philosophy about life stages, efficiency and making the best use of the tools available. She is not an entrepreneur, exactly, but she speaks a language that unifies personal and career growth. “So, I’m going to tell you how I do this,” she said. “On the days that I have to be in school, we go from 8 to 2. Then you get out of school. Then you can pick and choose if you want to work 3 to 11 or 11 to 7. Then I do a full-time on the weekend. I do 12 hours on Saturday and Sunday.” At 59, she spends most of her days caring for elderly and infirm patients, watching the details of their expressions, how they hold themselves, the little signifiers of how they are feeling. Then, in her off hours, she keeps an eye on her phone.

For most Americans, the concept of “gig work” has been synonymous with a handful of Silicon Valley giants — companies like Uber and DoorDash, Instacart and TaskRabbit. There was a moment in the 2010s when pundits told us to expect the “Uberization of everything”: a future in which the typical worker would move from job to job or task to task, finding either independence and flexibility in freelancing or, more realistically, the precarity of working for platforms that may be light on benefits and aggressively exploitative of labor. But there were also those who came to wonder whether the entire phenomenon had been overblown. “The gig economy,” Annie Lowrey wrote in The Atlantic in 2019, “was then and is now a more marginal phenomenon than it might have seemed.”

We do remain dependent on traditional gig labor, a fact that blazed into our collective consciousness with the pandemic and our sudden reliance on workers like delivery drivers. What is less often appreciated, though, is just how much, and how steadily, the structure and technology of gig work have expanded beyond our most obviously “Uberized” jobs. The gig economy, at this point, encompasses not just drivers or repairmen, not just designers or proofreaders, but also retail workers, the armies of itinerant nurses who crossed the country to shifting Covid hot spots and even white-collar professionals like lawyers and consultants. Whether they seem like “gigs” or not, countless varieties of jobs are sliding into the ecosystem of the gig — the world, broadly defined, of technology-enabled temporary employment — and steadily loosening the ties between workers and employers.

The battle lines that have been drawn around gig work and labor protections usually center on the issue of classification. Workers considered “independent” are paid by 1099, a tax category that exempts them from labor protections like a minimum wage, unemployment insurance and overtime — and requires them to cover their own payroll taxes. Others are paid by W-2 and covered under the Fair Labor Standards Act of 1939. Businesses often push to categorize flexible workers as independent; labor advocates push for W-2s. The standards and tests that determine classifications vary from state to state and can be open to interpretation — workers are easily misclassified.

But even this division does not encompass the full scope of gig work and its influence. Handy, for instance, operates both within the gig ecosystem and outside it. Gale Health insists that all its nurses be paid by W-2, maintaining a floor of labor protections, but still falling short of providing Handy with the level of benefits she can get from a regular, inflexible, full-time job. Hers isn’t the only industry in which some of the benefits once associated with W-2 work have grown complicated. Both inside and outside the gig world, the century-old compact that has determined who is entitled to key protections is eroding. There aren’t many labor questions more consequential than how we redefine or replace it.

Credit…Illustration by Derek Abella

No one is entirely sure how many Americans are working gigs, in part because the definition of gig work grows muddier by the year. Labor economists are certain the practice is growing, but it remains incredibly hard to measure. Annual surveys conducted by the Bureau of Labor Statistics are not designed to capture gig work as a category, and studies elsewhere use different parameters to define it. In an annual study commissioned by the “work marketplace” Upwork, 39 percent of the U.S. labor force was found to be doing some variety of freelance work last year — a share representing around 60 million people and $1.35 trillion in U.S. earnings, an increase of $50 billion over 2021. A study by Pew Research Center, focusing more narrowly on platform-based gig work, found 16 percent of U.S. adults had found work via an online platform at some point. Depending on how you define them, gig workers include people taking all sorts of temporary jobs. The person taking tickets at a basketball game or your order at McDonald’s may be picking up shifts using an app. Copywriters and marketing professionals offer their services on Upwork or Fiverr or via LinkedIn. There are bartenders, carpenters and even doctors looking down at their phones right now, searching for their next shift.

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.)

Daniel Olayiwola is one such Amazon associate, working a “flex schedule” in San Antonio; he also creates content about the experience on a YouTube channel called “Surviving Scamazon.” After five years of experience, he earns $18.40 an hour. On his flex schedule, he told me, he has to work 30 hours. “If you don’t, you get a point, and once you get to 8 points, you’re fired.” (That’s 8 points within a 60-day period, according to an Amazon spokesman.) Show up late, or miss a shift, and you get points. Shifts become available at specific times, and flex workers have to sign up quickly — some set alarms to remind them the moment shifts are released — “or else you’re going to end up working nights.” In this job, Olayiwola told me, you have to diversify to earn a living wage. Some drive for delivery platforms during their time off. Olayiwola takes gigs as a roofer, and tries to schedule some hours every few days. “You have to get creative,” he says, “in how you structure your life.”

Olayiwola’s job at Amazon comes with a W-2; he is covered by employment insurance, liability insurance, workers’ compensation. Still, he stakes out his schedule via a platform, taking shifts on demand. He must meet productivity quotas and keep careful track of break and bathroom times. Falling short on any metric could prompt a review process. “They put you in a situation where they have very ample opportunity to fire you,” he says, describing a cycle of penalties and rehirings. “They’ve fired everybody I know a couple of times. I operate as if I’ve already been fired.”

It’s hard not to be apprehensive of the ways in which the least pleasant innovations of the gig economy, and the technology that enables them, could seep into ever more industries and jobs — a future in which the “Uberization of everything” doesn’t mean eliminating regular employment, just forcing it to operate in increasingly giglike ways. David Weil — who served in the Labor Department under President Obama and later as dean of the Heller School for Social Policy and Management at Brandeis University — sees the expansion of gig working as part of a larger story, one he calls “fissuring.” When corporations started offshoring manufacturing in the mid-20th century, he says, they did so in part to access cheaper labor in other countries. Soon they found ways to do something similar at home, contracting out for roles that would, in the past, have belonged to their own pool of workers. The janitors at a tech company like Apple, for example, might once have been direct employees, entitled to benefits similar to those of their peers. Now they can be employed by a cleaning service with its own labor policies — severing, or at least loosening, the legal ties between them and the company whose offices they will clean.

Weil considers companies like Uber and Lyft to be “hyper-fissured.” They minimize labor costs by categorizing all their drivers as independent — people with, in theory, other jobs and other access to benefits — and casting themselves as mere management systems that allow those workers to operate. Given their power over nearly every aspect of that work, though, many see these brands not as systems of management but of employment. “So much of the platform world, they want to have things two ways at the same time,” Weil says. “They want as much control as they possibly can of the product and the service — whatever the targets are related to product innovation, service and delivery — but they don’t want the messy problems of being an employer.”

The depth of this particular fissure — the obvious way these platforms maximize control over workers while minimizing obligations to them — has sparked multiple battles over how the law should categorize laborers. In courts and in legislatures, workers and labor advocates have butted against tech companies and business interests. The latter have scored plenty of wins. In 34 states, legislation has already been adopted that specifically exempts “Transportation Network Companies” (TNCs) from some state and local labor standards. The gig-working platform Handy, which has since been purchased by Angi Inc., has backed legislation that would ensure those who found jobs on apps or platforms could more easily be considered independent workers; 10 states now have such “marketplace platform” laws on the books. And a growing, well-funded lobby for platform work, the Coalition for Workforce Innovation, has argued for a third labor classification, beyond employees and independent contractors. This category would be created simply by having workers sign a contract called a “Worker Flexibility Agreement,” in which they trade away protections like a minimum wage for the ability to take outside work — thus giving platforms, the argument goes, freedom to offer piecemeal selections of perks and benefits to entice labor.

The strongest alternative to all of this is a standard called the “ABC test,” which gained notoriety during a class-action suit against a California courier and delivery service called Dynamex Operations West. In 2004, Dynamex converted all of its drivers from full-time employees to independent contractors. After much litigation, the California Supreme Court ultimately relied on the ABC test — which sets a high bar for considering workers independent — to uphold a lower-court verdict for the plaintiffs, sparking a flurry of political action. The State Legislature passed a measure codifying the ABC test into law. In reaction, TNCs including Uber, Lyft and Instacart pushed for a state ballot measure, Proposition 22, that would place their drivers in a category of worker entitled to only limited benefits. The proposition passed in 2020, but has been hindered by legal challenges. Versions of this battle have occurred in states across the country, and even nationally. The House of Representatives has twice passed the PRO Act, a law focused on union organizing that also adopts the ABC test at a federal level; both times, in 2019 and 2021, it languished in the Senate. It was introduced a third time this February.

At the same time, the sheer variety of gig-working arrangements has continued to expand, outpacing the speed of most moves to regulate or define it. Many of the newest platforms in the field actually bill themselves as attempts to bridge the gap between flexibility and security — using the tools of gig work to solve the problems of gig work. Yong Kim, the founder of a platform called Wonolo, told me his hope is to build a new model for protecting workers. Kim came to the United States from South Korea as a teenager and has memories of walking into stores with help-wanted signs, only to be turned away — “I couldn’t get a job at a gas station,” he told me, “because of the way I looked and the way I spoke.” His platform connects workers with businesses in need of on-demand staffing. “Most of the gig-economy-based platforms, they are connecting workers with consumers,” he says. “If someone needs food delivered to their house, they use it. In our case, one side is actually businesses. There are companies like Hello Fresh and Coca-Cola that also have to think about the well-being of the workers. Can we design it in a new way and innovate around that?”

One aspect of his company’s design is to require that workers are paid the same hourly rate that a company’s full-time employees get for the same labor. Another is a new offer of portable occupational accident insurance, which is paid for in part by Wonolo, in part by the hiring company and in part by the worker. The platform is also trying, Kim says, to offer an affordable health care program — a difficult task, because of the way insurance is regulated state by state. About two million workers use the platform. Kim estimates that half of the active users do so on a part-time basis. (“They may have another part-time job at Walmart or Target and pick up jobs as needed.”) Another 25 percent of active users work two or three different jobs through Wonolo itself. The final quarter, Kim says, are “people who I call truly flexible” — they might work full time for a few months and then disappear for a while, or use their accounts at seemingly random intervals. Depending on the situation, he said, some of these two million workers could be considered W-2 employees.

Much of what Kim has done is simply to take a few steps back toward a model established decades ago by traditional staffing agencies. Such an arrangement might be attractive to gig workers, compared with the competition, but might still strike labor advocates as a net loss. Wonolo, in fact, has in the past been an active member of the Coalition for Workplace Innovation, and Kim has expressed interest in the establishment of a third category of worker. Conventional staffing agencies have not themselves been bulwarks of labor protection. It’s an industry that aims to provide flexibility while trimming labor costs, which means even the most innovative founders may find it challenging to arrive at an equitable deal for workers.

Weil, for his part, does have some optimism that working arrangements can evolve in ways that do not abandon protections for vulnerable workers. “I think certainly people are going to have more different jobs — by choice and by necessity — than they had 20 years ago,” he told me. “Certain things need to be more portable. You need to have portability for pensions. You need to have funds to help yourself to become trained in new areas. Portability of paid leave. Portability of workers’ compensation.” All of this, he said, was possible, in the right environment — “We can do that!”

The gig economy continues to grow. The philosophy of flexibility and just-in-time labor management continues to move from industry to industry. And the technology of gig work — the “flexible” scheduling that leaves workers competing to seize shifts; the elaborate point-and-penalty systems that make work feel like a high-stakes game; the collection of data to monitor every aspect of labor down to the frequency of mouse movements and bathroom breaks — all of this continues to creep into new corners of the American work force. With each of these developments, the future of work is being renegotiated, not just through legal and political arguments but also through businesses’ experimenting, sometimes aggressively, with the shapes work can take. At its best, the gig economy can enable workers to balance child care or illness with a career, expand access to jobs and speed business staffing. At worst, it gives opaque, impersonal and sometimes draconian platforms immense control over not just workers but also over everything else that depends on their labor: our warehouses, our hospitals, our groceries, our supply chains.

The reason that Brenda Handy, the licensed practical nurse, keeps her full-time job — the reason, she says, she will always keep that job — is the package of benefits that comes with it. She gets unemployment insurance, accident insurance, access to a group health plan and a retirement plan. Even Gale Health, which hires by W-2, doesn’t provide the same benefits. Other parts of the industry pay by 1099, which Tony Braswell knows can be a precarious category. He says he meets with nurses who have to pick up shifts around scant child care, nurses who are living in their cars, nurses who struggle to keep their lights on. He has seen horror stories online, like a woman surprised by a $13,000 tax bill she was unable to pay — one of the more costly aspects of being classified as a contractor.

Braswell is currently speaking against the practice of classifying health care workers as independent contractors. Doing so, he argues, will further worsen a nursing shortage and leave the elderly population neglected and underserved. The industry, he says, needs flexibility and stability at the same time. Nurses shouldn’t be required to continually negotiate their jobs or act as independent businesses; they are overworked and vulnerable enough. “We can’t lose nurses,” he says. When Gale did a small survey of its nurses last year, it found that 65 percent were working per diem rather than in full-time jobs — but, according to Braswell, “they want to work full time. They just want to work on their own terms.”

Gale Health is used by more than 60,000 nurses, and Braswell now provides labor to facilities across the country. It was, in the end, the online platform — the structure built by the gig economy — that enabled him to scale up, both expanding his reach and allowing him to offer perks like paying nurses within minutes after they complete a shift. (“I want people to be able to stop for groceries on the way home,” he says.) He wants, he says, to provide benefits. He pays into workers’ compensation for his nurses and is doing his best to offer health insurance. But without a government mandate requiring that such benefits be provided, he says, it may be difficult for Gale Health to stay competitive with other platforms; the usual race to the bottom, in which platforms work to minimize every cost associated with labor, could prevail.

Handy, for her part, recently lost her life savings when, a few months before she was scheduled to graduate, the nursing school she was attending shut down amid an F.B.I. investigation of fraudulent institutions; it had never been properly accredited, and all of Handy’s tuition money was gone. It’s a setback that she, despite her two jobs and a lifetime of work, was not prepared for. “I was on cruise control,” she told me, referencing her packed schedule. “I didn’t want to work nights — I wanted to pull it the way I wanted to pull it. But now I can’t stop. I’ve got to keep pushing. I’ve got to keep working.” She is taking more shifts than ever.

Lauren Hilgers is a writer based in New York. She is the author of “Patriot Number One: A Chinese Rebel Comes to America.” Derek Abella is a Cuban American illustrator based in Brooklyn. He is known for his dreamlike style.

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