How Millennials Became A Generation Of Freelancers

After the recession, newly vulnerable workers were forced to take crappy jobs and a decade later, they’re still screwed. Read this excerpt from Can’t Even: How Millennials Became the Burnout Generation.

Over the course of the Great Recession, over 8.8 million jobs were eliminated in the United States alone. Americans lost jobs in construction, at colleges, at nonprofits, at law firms, and at big-box stores going out of business. They lost jobs in recreation, at newspapers, at public radio stations, at car factories and startups, in finance, in advertising, and in publishing. In the past, recessions have busted the job market, but then recovery has rebuilt it: The jobs disappeared as companies tightened their belts, then reappeared as they felt confident expanding.

That’s not what happened this time — which is one of the main reasons why millennials, many of whom were struggling to find their first job, any job, during this era, have had such a negative experience of work. To be clear, it’s not that jobs weren’t created. In fact, strong job creation numbers were flouted every day — first by Obama, then by Trump. It’s just that they weren’t the same sort of jobs as before. A “job” can be a temp position given to a freelancer, a seasonal gig, even a part-time job. According to one study, nearly all of the jobs “added” to the economy between 2005 and 2015 were “contingent” or “alternative” in some way.

But for those desperate for work, especially millennials graduating into the post-recession market, these jobs nonetheless provided a much-needed paycheck, however meager — and the freelance and gig economy exploded. The willingness of workers to settle for these job conditions helped foster an even deeper fissuring of the workplace: first, by normalizing the low standards of the freelance economy; second, by “redefining” what it meant to be “employed.”

The general logic behind freelancing goes something like this: You have a marketable skill, maybe in graphic design, photography, writing, digital editing, or web design. Various companies are in need of that skill. In the past, medium- and large-size companies would’ve hired full-time employees with that skill. But in the fissured workplace, those same companies are reticent to hire any more full-time employees than absolutely necessary. So they hire multiple freelancers to do the work of a full-time staffer, which gives the company high-quality work, without the added responsibility to shoulder freelancers’ health benefits or ensure fair working conditions.

From the outside, freelancing seems like a dream: You work when you want to work; you’re ostensibly in control of your own destiny. But if you’re a freelancer, you’re familiar with the dark side of these “benefits.” The “freedom to set your own hours” also means the “freedom to pay for your own healthcare.” The passage of the Affordable Care Act has made it easier to purchase an individual plan off the marketplace. But before that — and given the concerted attempt to undercut the ACA — obtaining affordable healthcare as a freelancer has become increasingly untenable.

In California, one person told me that the cheapest insurance they could find — for one person, with very little coverage and a high deductible — goes for $330 a month. I talked to a dog walker in Seattle who pays $675 — without dental coverage. Another person reported that their bargain basement plan in Minnesota costs $250 a month. In Dallas, $378 a month for a catastrophic plan with a $10,000 deductible. And that’s if there’s just one of you: A freelance writer told me she’d had breast cancer, and her husband, a freelance photographer and photo editor, is an insulin- dependent Type 2 diabetic. They live in suburban New York, and currently pay $1,484 a month for coverage. Many freelancers told me their deductibles were so high that they avoided going to the doctor if at all possible, which frequently ended with even higher bills when they were finally forced to seek care — and, because they were freelancers, there was no such thing as paid time off to recover.

Many freelancers told me their deductibles were so high that they avoided going to the doctor if at all possible.

Freelancing also means no employer-facilitated 401k, no employee match, and no subsidized or concerted means, other than the portion of your freelance checks that go to Social Security every month, to save for retirement. It often means hiring an accountant to deal with labyrinthian tax structures, and getting paid a flat fee for the end product or service, regardless of how many hours you put into it. It means complete independence, which in the current capitalist marketplace is another way of saying it means complete insecurity.

“I get no general or consistent feedback on my skills,” Alex, who works as a freelance designer and illustrator, told me. “I accept pay less than my worth just to get a job. There’s consistent price undercutting. And there’s the anxiety over the lack of control over my own life.” “Clients,” after all, owe you nothing. When the supply of freelancers with a given skill or service is greater than the demand, wages cannot be negotiated. You adjust your rate to whatever a client is willing to pay.

Take the example of journalism: Every writer used to dream about the freedom of the freelance lifestyle. Pitch only the stories you want to write; write only for the publications you want to write for. And back when magazine publishing was healthy, you could make bank: two dollars a word (on the moderate side of things) for a 5,000-word feature meant $10,000 for a few months’ work.

But when the journalism market bottomed out with the Great Recession, everything reset. Laid-off journalists flooded the market, desperate for freelance gigs. The amount of competition drove down rates, which was about what most outlets could afford to pay. And then there were people like me: non-journalists who’d honed their voice online, on LiveJournal and WordPress, for free. In 2010, I started reading the Hairpin, a website that had sprung from the ashes of the recession.

The business model, like a lot of business models at that time, was contingent on publishing anything good by anyone who was willing to write for free. I began writing pieces, rooted in my academic research, on the history of celebrity gossip and classic Hollywood scandal. Like a typical millennial, I was chuffed that they’d even publish them. I wanted an audience for my passion far more than I wanted to be paid. This model made it possible for hundreds of people to break into writing. You can trace the careers of many prominent contemporary writers back to the Hairpin, its sister site, the Awl, its cousin site, the Toast. Same for dozens of sports writers, blogging for free on sites like the Bleacher Report. We “made it” because writing wasn’t our main gig, which allowed us to write for nothing or, as the sites gained traction and the recession faded, we wrote for what my grandmother would’ve called “pin money”: extra, surplus, gravy.

But because we were all writing as a side gig — which is why we could afford to do it for free — we also helped to drive rates way, way down. Why pay a freelance writer their established rate, the rate that would help keep them paying rent, when you could pay a graduate student in art history zero dollars for their insight?

That’s the sort of desperation that actual companies — far more than esoteric little websites — took advantage of. And no one took more advantage of it than the newly ascendant gig employers: Uber, Handy, DoorDash, and dozens of others. When we look back on the period following the Great Recession, it will be remembered not as a time of great innovation, but of great exploitation, when tech companies reached “unicorn” status (valued over $1 billion) on the backs of employees they refused to even deign to label, let alone respect, as such.

The dynamics and overarching philosophy of Silicon Valley create the perfect conditions for fissured workplaces. Silicon Valley thinks the “old” way of work is broken. It loves overwork. Its ideology of “disruption” — to “move fast and break things,” as Mark Zuckerberg famously put it — is contingent on a willingness to destroy any semblance of a stable workplace. In the startup world, the ultimate goal is “going public”: creating a high enough stock valuation, and, afterward, unmitigated growth, no matter the human cost. That’s how these companies pay back the venture capital firms that invested in them — and that’s how they make their founders, boards, and early employees very rich.

Talking about how Silicon Valley and shifting concepts of work means talking about Uber. You might be as sick of talking about Uber as I am, but its impact is widespread and undeniable. “Under our noses, the company has ushered in a wave of changes touching most aspects of society, be it family life or childcare arrangements, worker conditions or management practices, commuting patterns or urban planning, or racial equality campaigns and labor rights initiatives,” Alex Rosenblat argues in Uberland. It “confuses categories such as innovation and lawlessness, work and consumption, algorithms and managers, neutrality and control, sharing and employment.” The number of Americans who’ve actually driven for Uber is proportionally small. But the changes it set in motion are slowly infiltrating the rest of the economy and our everyday lives — especially those who, in any capacity, rely on the gig economy.

Like so many other startup companies of the post-recession era, Uber was founded on the premise of disruption: taking an old industry, oftentimes one that was a bit clunky, and analog, but that paid its workers a living wage, and using digital technologies to change it into something sleeker, easier, and cheaper that would funnel money to the disrupting company. Uber, along with Lyft, Juno, and a handful of other ride-hailing companies, disrupted what has traditionally been known as the “livery” business: picking people up and taking them places. Their popularity launched an entire cottage industry of services reconceptualizing quotidian tasks: Rover disrupted pet care. Airbnb disrupted lodging. Handy disrupted handymen. Postmates and Seamless and DoorDash disrupted takeout. And while these apps have made vacationing and ordering in and getting from one place to another easier for consumers, they also created a massive swath of bad jobs — bad jobs that workers, still desperate from the fallout of the recession, were (at least temporarily) thrilled to take.

The number of Americans who’ve actually driven for Uber is proportionally small. But the changes it set in motion are slowly infiltrating the rest of the economy and our everyday lives — especially those who, in any capacity, rely on the gig economy.

For a short period of time, companies like Uber were viewed as economic saviors. They sold themselves as a means of using and distributing resources — cars, drivers, cleaners, bedrooms — with far more efficiency than the old systems, all while creating the jobs that the clawing middle class were desperate to land. The secret of these jobs, though, were that they weren’t even technically jobs, and certainly not the sort of jobs that could mend the broken class ladder. Instead, these jobs have created what the tech columnist Farhad Manjoo calls “a permanent digital underclass,” both in the United States and around the world, “who will toil permanently without decent protections.”

That’s because, at least at Uber, the tens of thousands of people who drove for the company weren’t even considered employees. In external messaging, Uber’s posture toward these men and women remained steady: The drivers were, in fact, a sort of customer. The app merely connected one set of customers, in need of rides, with another set of customers, willing to provide it. As Sarah Kessler, author of Gigged, points out, “Uber merely took a trend among corporations — employing as few people as possible — and adapted it for the smartphone era.”

After all, actually hiring employees, even if you’re just paying minimum wage, is “expensive” — and requires the company to take on all sorts of responsibilities. When you’re a startup burning through millions in venture capital, the goal is growth, always growth, and responsibility is an impediment to growth. Uber solved the problem by calling their employees “customers” and by officially designating them as “independent contractors.”

“Independence” meant those who drove for Uber could make their own schedule, had no real boss, and worked for themselves. But it also meant these pseudo-employees had no right to unionize, and Uber had no responsibility to train them or provide benefits. Gig economies lured workers with a promise of that independence — with work that could actually bend to fit our lives, our children’s schedules, our other responsibilities. This work was framed as particularly suitable for supposedly self-centered, picky, self-righteous millennials; as the gig economy grew in visibility, Forbes declared, “The 9 to 5 job may soon be a relic of the past, if millennials have their way.”

But that’s not how it worked out. Not for Handy cleaners, or TaskRabbits, or laborers on Amazon’s Mechanical Turk, who bid to complete menial online tasks (clicking on every photo with a picture of a bird, for example, in order to assist with AI recognition) for pennies. Not for Door Dashers, who until a massive online backlash was using tips to cover their independent contractors’ base pay — meaning that if a Dasher was guaranteed $6.85 per delivery and received a $3 tip, they still received just $6.85; users were essentially tipping DoorDash itself. And despite Uber’s past (and thoroughly debunked) claims that an Uber driver could make $90,000 a year, the majority of people driving or cleaning or renting their spare bedroom or clicking relentlessly on a mouse in the gig economy are doing it as a second or third job — a shitty job to supplement a different shitty job. The gig economy isn’t replacing the traditional economy. It’s propping it up in a way that convinces people it’s not broken.

Your ability to work is never as “free” as the word freelance suggests.

Freelance and gigging don’t make drudgery or anxiety disappear. Instead, they exacerbate them. Any time that you do take off is tinged with regret or anxiousness that you could be working. That hour at a birthday party could be thirty dollars from Uber. That hour on a run could be spent pitching to new clients. That hour reading a book could be used to seek out another writing assignment. In today’s economy, going freelance means internalizing the fact that you could and should always be working more. Nick, who does freelance stats analysis through Upwork, described the internalized pressure to be “working eternally and at all times”; Jane, a freelance writer, explains that “there is such a sense in freelancing that you are never doing enough — that you should be doing more, making more, hustling more — and that every failure you have (real or perceived) is entirely your fault. In an office job, you’re still getting paid for those five minutes it takes to make a cup of tea; when you’re freelancing, every minute you’re not working, you’re losing money.”

In practice, freelancing often means developing the mindset that “everything bad is good, everything good is bad” — a mantra I threw around with my friends during grad school to describe the perverse alchemy of overwork, in which drudgery feels “great,” and actually pleasurable activities become indelibly lined with guilt. As Kessler reports in Gigged, Uber directly exploits this mindset: When a driver attempts to close the app and refuse future calls, it responds with a variation on “Are you sure you want to go offline? Demand is very high in your area. Make more money. Don’t stop now!”

Your ability to work is never as “free” as the word freelance suggests. If your car has to be repaired, you’re sick for a long period of time, or you simply don’t want to drive, Uber makes it difficult to start working again. You’re repeatedly subjected to the whimsy of drunk passengers who give a single star for fun. And as Guy Standing points out, “The person who works for himself works for a tyrant — you are only as good as your last job and your performance. You are constantly being evaluated and graded. Having to worry so much about where the next bit of bread is coming from means people losing control over their lives.” Or, as one Uber driver told Rosenblat, “you don’t have a boss over your head — you have a phone over your head.”

Freelancing is exhausting and anxiety-building enough. But that’s compounded by the widespread refusal to see what you do as work. Just as the work of teachers or mothers is devalued (or unvalued), jobs within the sharing economy aren’t figured as jobs at all — they’re attempts to monetize your hobby, to have fun conversations while driving around the city, to invite people into your home. Even calling these jobs “gigs,” with all the inherent connotation of brevity and enjoyability, elides their status as labor. It’s not the gig economy after all; it’s the always-frantically-seeking-the-next-gig economy.

“We’ve idealized the idea of portable work, promoting the notion of people roaming about with a portfolio of skills they can sell at a price they set themselves,” Standing argues. “Some are able to do that, of course. But to think that we can build a society on this platform, with no protections, is fanciful.”

Many of Uber’s employees continue to fight for the right to bargain with their employer. Freelancers in media from all over the United States have created their own iteration of union, in which they collectively set rates and, when media employees are laid off from an organization or strike, refuse to “scab” into their former roles. More and more freelancers, gig economy laborers, and temps are realizing that flexibility is meaningless without stability to accompany it.

But the only way to call for these types of action is to have leverage: to have options, but also to be acknowledged as an employee. This means an overhauling of our current system, an action that may need governmental intervention. If lawmakers force companies like Uber to stop misclassifying its employees as independent contractors, it would reinforce the social contract between companies and laborers — the idea that companies are responsible for the livelihoods of those who labor for them, and that the profits gleaned through this labor should trickle down, in some form, to them. That might seem incredibly radical, but if you look back just sixty years, it was also an incredibly American way of conceiving of profits.

It’s a solution that’s especially difficult to implement when the head of the company is saying there’s no problem in the first place: “I think a lot of the question about whether this is employee versus independent contractor misses a little bit of the point,” Tony Xu, CEO of DoorDash, told ReCode Decode. “I mean, if you think about what is the root problem, the root problem is, how do we maximize all this flexibility, which Dashers love, and provide a security blanket for those who need it?”

One very obvious way: Hire them as employees. Masking exploitation in the rhetoric of freelancing and independent contractors’ “flexibility” avoids talking about why that flexibility is coveted: because the supposedly “thriving economy” is built on millions of people being treated as robots. “What worries me most is that this is just the beginning,” Manjoo wrote in the aftermath of the DoorDash tipping backlash. “The software-driven policies of exploitation and servility will metastasize across the economic value chain. Taking DoorDash workers’ tips today will pave the way for taking advantage of everyone else tomorrow.”

Manjoo’s right. But the people it’s most poised to take advantage of in the immediate future are those who have no other options — and those, like millennials and Gen Z, who don’t realize there’s any other way. Which underlines the current conundrum: Shitty work conditions produce burnout, but burnout — and the resultant inability, either through lack of energy or lack of resources, to resist exploitation — helps keep work shitty. Significant legislation to updates labor laws to respond to current workplace realities can and will help. But so will solidarity: an old fashioned word that simply means consensus, amongst a wide variety of people of like mind, that resistance is possible.●

Excerpted from Can’t Even: How Millennials Became the Burnout Generation by Anne Helen Petersen published by Houghton Mifflin Harcourt. Copyright © 2020 by Anne Helen Petersen. Used by permission.

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