Millennials are obsessed with side hustles because they’re all we’ve got


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On weekends, Colleen teaches fitness classes. Mary builds websites. Luke sells vintage video games. Tony designs and 3D-prints custom Star Wars miniatures. I write for the internet.

Among my friends, and 20- and 30-somethings as a whole, the side hustle–the gig you work in addition to your day job–is so ubiquitous that, in April, Glamour Magazine posed the rueful question: “You don’t freelance on the side… What kind of urban-dwelling Millennial are you?” Failing to participate in the trend might even lead one to a “Millennial identity crisis.”

Advertisers, including those you might not think of as in the vanguard, have glommed on, too. This Chevy ad suggests owning a Cruze is a way to “#FuelYourHustle.” It’s a two minute long rallying cry to being your own boss. Sure, there’s no explicit mention of using your shiny new car as an Uber. But if you’re under 35, you can probably hear that dog whistle.

I’m not objecting. It’s a relief to see facts leading marketing, rather than the other way around. We are Generation 1099. By our side hustles, ye shall know us. What surprises me is that no one, at least to my knowledge, has tried to explain why.

 Millennials didn’t invent the second job, they just branded it. Maybe that’s because many people assume the side hustle is just financially oriented, simply another adaptive response to recession-era economics. Google “side hustle” and you will find thousands of stories, but they are all focused on the how. As in, Dear internet, how can I make another $200 a month to cover my Verizon bill?

Extra cash is far from the whole story. It’s true, the 2008 crisis forced plenty of people to look for additional sources of income, not least of all the recent graduates who, with little experience and limited networks, were confronting the job market for the first time. But the desire to earn more money on the side predates the crisis (as does the Urban Dictionary definition of “side hustle”). Millennials didn’t invent the second job, they just branded it.

Here’s an example. Those friends of mine whose jobs are the most squarely aimed at the public good–teachers, local-government workers, a college buddy who works for a beloved and worthy nonprofit–they all tell me their side hustles are about survival, about being able to afford to live. Or just to eat at a restaurant once in a while. None would claim these jobs paid well before the recession.

And that’s to say nothing of those who don’t have access to college education, those who can’t find day jobs at all, and those for whom, by choice or not, a 1099 is all there is.

The sheer range of side hustles suggests there’s more in play than money. There are the well known app-based gigs, like Uber and TaskRabbit. You’ve got the day job with a freelance extension–the full-time graphic designer who also has her own clients. Then there’s what you might ungenerously call the side hustle as self-promotion, which covers some yoga teachers and life coaches, though by no means all. Next along the line is the side hustle as self-delusion, i.e. spending years on some (doomed) artistic effort that will make the world care and understand, at last!

If that sounds harsh, well, I should know. Last year, writing for the internet earned me a grand total of $415 before taxes, or about the price of two hotel nights on the outskirts of Manhattan or San Francisco. To say I’m not in it for the money would be understatement. Not because I’m above such earthly considerations. There’s just very little money in it to be for.

 The side hustle offers something worth much more than money: A hedge against feeling stuck and dull and cheated by life. In fact, given all the hours I’ve devoted to it, there’s no question in my mind that I’ve lost more than I’ve made, if only in terms of my Starbucks spend. But I’m not complaining.

The side hustle offers something worth much more than money: A hedge against feeling stuck and dull and cheated by life. This psychological benefit is the real reason for the Millennial obsession, I’d argue, and why you might want to consider finding your own side hustle, no matter how old you are.

Now, you might wonder, what would a bunch of twenty-five year olds know about feeling stuck and dull? Put another way, what happens when a generation raised with a “you can be whatever you want to be” ethos meets the worst job market in years? In which many of the traditional dream careers–from working in the arts to becoming a lawyer–go from being long shots to being totally untenable, or more or less cease to exist altogether?

For me, the biggest laugh in Amy Schumer’s Trainwreck was the notion that, in an ostensible 2014-2015, her character has a “great job” as a staff writer at a (print!) men’s magazine–a job so lucrative she can afford a “sick apartment” and also help to underwrite her father’s nursing-home costs. Romcoms, even when written by a progressive, typically on-point comic like Schumer, aren’t intended to be realistic portrayals. Still, the detail struck me as less fanciful than simply uncanny, more appropriate to a Buñuel film with explicit surrealist intentions.

Much closer to the mark was how, in Lena Dunham’s Girls, Marnie aspires to be an art curator until she is told, by a curator, that “curator as a job doesn’t really exist anymore.” I can relate. The person who encouraged me not to pursue a full-time journalism career was himself a career journalist. We even attended the same journalism school 35 years apart. I’m speaking of my Dad.

Okay, so them’s the breaks. Previous generations have also coped with such semi-tragedy; probably every human ever has been a sort of actor-waiter at some point. In any case, those of us who are employed generally understand ourselves to be lucky. Working as a benefits administrator, an ad-sales rep or even a Facebook engineer might not be the dream job. But your side hustle can keep you from feeling pigeonholed. It’s the distraction from your disappointment, a bridge between crass realities and your compelling inner life.

In the best-case scenario, your side hustle can be like a lottery ticket, offering the possibility–however remote–that you just might hit the jackpot and discover that holy grail of gigs. The one that perfectly blends money and love. The one that’s coming along any day now.

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