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The Startup Industry’s Toxic “Side Hustle” Fixation

Startup culture’s obsession with “side hustle” gets more unsettling the closer you look

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

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A handsome man gazes at the camera. “These days, everyone needs a side hustle,” he shrugs. We cut to scenes from his well-lit life, and it’s a mix of pleasant chauffeur jaunts, and hangout sessions with his daughter, dog, and pals. “Earning, chilling, earning, chilling,” the man sing-songs, a prosperous avatar for enviable work-life balance. His existence is so delightfully calibrated, I could play the scene for my therapist to best explain what I’m aiming for, except I won’t do that, because the man is an actor and he’s in an ad for Uber. The transit company has embraced the concept of “side hustle” to entice people to become contractor-taxis, spinning the idea of having a second job as a form of freedom, a salvation from drudgery. “Get your side hustle on,” Uber’s website beckons new drivers.

Uber is the most prominent business in startup culture to explicitly use the term as a way to sell piecemeal labor as a savvy lifestyle choice, but the phrase is frequently deployed within the startup industry to hype all sorts of gig-economy work. Websites like Side Hustle Academy and books like Side Hustle to Success and Side Hustle Blueprint promise readers they’ll explain how to build wealth as an extracurricular habit. A marketing consultant who refers to herself as a “digital nomad” published a self-help book called The Side Hustle Gal. It’s like those spambot comments at the bottom of blog posts — make extra money working from home — were interpreted credulously and turned into an economic game plan by a cadre of self-published wannabe Suze Ormans. But the way Uber and startup culture has co-opted and bowdlerized the phrase into an anodyne signifier of entrepreneurialism is gallingly hollow. The side hustle is a survival mechanism, not an aspirational career track.

Two definitions of the “side hustle” are hyped by startup culture. One is the Uber interpretation, and it’s simple: side hustle as second gig. The other, what I’d call the “life coach” definition, is a little more specific: the side hustle as second gig that is also a passion project. While these two definitions are distinct, they are not so distant from one another. Both imagine that the side hustler is on track to a better life through ceaseless piecemeal labor rather than 9-to-5 employment. Even in Uber’s estimation, the “side hustle” is a sanguine endeavor, something that makes life easier, a way to grease one’s most ambitious life track. It’s a captivating tale. The idea that success depends on after-hours striving speaks to an archetypically American combination of values — the national preoccupation with work ethic and individualism. It also misconstrues economic reality to make companies like Uber look like benevolent job creators rather than businesses tailored to maximize profit while shifting as much financial risk onto contractors as possible.

Companies like Uber want to spit-shine the concept of “side hustle” so it looks like a better alternative to steady, gainful employment. If people see gig-economy labor as a flexible stepping stone to a better life, they’re less likely to also see it as a force eroding a work culture with protections and benefits for employees in favor of a low-ball freelance marketplace. (Also, one that will eventually be automated, making their jobs obsolete.) Uber is selling a fantasy of economic advancement through the corrosion of employment benefits and stability, pitching increased subjugation to the corporation as some sort of salvo. That Uber is promoting itself as a solution for the financial flailing is particularly eye-popping when one considers the company’s ultimate goal to eliminate the job of driving in favor of large-scale automation.

People don’t get rich as Uber drivers. They evade poverty as Uber drivers. And while many entrepreneurs toil at night and on weekends until they’re able to quit a day job, that situation illuminates the difficulty of changing careers and starting a business, and it is simply not feasible for many people responsible for childcare or already working several jobs in order to make enough money to live. Performing whatever paid work is available is sometimes a necessary step to literally surviving, and working on a passion project in one’s free time can help launch a new career. Neither situation is aspirational. Both belie an economic system that is not designed to lift masses out of poverty, but rather one that both creates and maintains poverty. “We are proud that Airbnb has become an economic lifeline for the middle class,” an Airbnb report boasts, without acknowledging the dire subtext of the statement, that the middle class is grasping for lifelines.

“Using the language of entrepreneurship, flexibility, autonomy, and choice, the burden of the biggest risks of life: unemployment, illness, and old age have been lifted onto the shoulders of the workers,” New School media professor Trebor Scholz writes in his critique of the gig economy, “Platform Cooperativism.”

The gig economy is not designed to flood its cogs with money. It is an ecosystem that alleviates companies of responsibility for their workers, and while it does offer a flexible, varied assortment of potential piecemeal job opportunities, the overall effect on middle-class prosperity may be negative. As a recent paper from Boston College sociology professor Juliet Schor argues, the “sharing economy” is increasing income inequality among the bottom 80 percent of earners, partly because some people “gigging” for extra cash are highly educated and are replacing people who traditionally perform manual labor as a primary means of employment. The “side hustle” is the provisional pursuit of strivers, yes, but they are striving to succeed in spite of companies like Uber, not due to them.

I recently wrote about how startup multilevel marketing companies, like LuLaRoe and It Works!, are growing in popularity on social media. Many of these businesses push the idea that people can get rich by selling wares as a type of side hustle, but the reality is that the majority of contractors shilling for these companies make little to no money. This does not mean they are indolent or obtuse. Many startup gigs that are breathlessly pitched as ways to transcend the grind are, in fact, often more wearying, riskier, and less financially rewarding than salaried employment.

CNBC recently reported a story about how a college student earned $10,000 using a “side hustle app” called JoyRun. That sounds impressive until the figures are broken down. She worked around 12–20 hours a week for a year. That’s a classic part-time job making around $10–15 an hour. So it’s slightly better than the average wage at McDonald’s. The student’s “success” on this app was apparently rare enough to warrant media attention; what a closer look at the numbers reveals is how easily low-rung employment can get ginned into a success story by slapping a hyperbolic “side hustle” narrative on it.

One particularly perverse aspect of startup culture’s veneration of the “side hustle” is the disconnect between the term’s origins and how it is now being used as a general feel-good term for bootstrapping. The phrase first came into modern usage in traditionally black newspapers, including The Chicago Defender, during the 1950s. A “side hustle” was what one did to survive in a climate hostile to the possibility of prosperity via traditional full-time employment.

“Side-hustle has been in regular use now for almost 70 years, although it is only in the last two decades that considerable attention has been paid to the word. This is attributable in part to the fact that many African-American texts (such as The Chicago Defender) have been under-documented, and also due to the word seeing greatly increased use in the Internet age,” Merriam-Webster’s “Words We’re Watching” column noted. While it has been used to refer to both legitimate gigs and illegal moneymaking schemes, the phrase sprang from the economic conditions of black people in the first half of the 20th century. It’s not a coincidence that it originated in black newspapers while Jim Crow still existed, as the concept was rooted in the idea of looking for other routes to financial stability because the “main” hustle was unavailable in a literal sense. In this way, the “side hustle” was originally an act of economic defiance. Now, the phrase has been bastardized into an advertisement for the gig economy, a way to make discounted, disposable labor seem hip.

The gig economy’s boom was precipitated by the financial crisis of 2008, which caused a surge in unemployment. In desperation, gigs looked better than nothing. “The aftermath of the crisis was a jobless recovery — a phenomenon where economic growth returns, but job growth does not,” Nick Srnicek wrote in his book Platform Capitalism. “As a result, numerous workers were forced to find whatever desperate means they could to survive. In this context, self-employment is not a freely chosen path, but rather a forced imposition.” Srnicek noted that workers on TaskRabbit and Amazon’s Mechanical Turk tend to be highly educated.

“In a healthy economy these people would have no need to be microtasking, as they would have proper jobs,” Srnicek writes.

In this economy, however, Uber is emboldened to sell “side hustle” as a path to a chill life rather than a shuffle away from pauperism. It’s an appropriation so shallow and ill-fitting that the lie is easy to spot when looking at it straight-on. Struggling on the margins of the economy is not a goal for moguls-in-training, it’s a predicament fostered by companies that treat workers like rubes.