The Millennial Revolution: We’d Rather Be Our Own Boss

The company man is dead

Nick Vadala, 24

Nick Vadala, 24

The last time Alex Hillman quit a job, it was over a broken promise. At the time, he was a young Web developer for a Philly-based digital strategy company. Hillman wanted to expand his skill set into team leadership—an advancement opportunity that his superiors ultimately didn’t deliver. Road-blocked from the white-collar corporate highway so few seem to be able to merge onto these days, Hillman decided to go the independent route. That road, once less-traveled, is increasingly the primary exit ramp for millennials seeking career fulfillment.

“We’re tired of waiting for permission, so now we’re saying ‘Fuck it, we’re going to do it on our own,’” Hillman, 30, says of the millennial approach to work. His words hint at some sort of libertarian capitalist paradise. Lofty, yes, but this is the rallying cry of my generation’s workers: The jig is up. This year has offered as proof several high-profile class-action suits against Fox Searchlight, Hearst, Condé Nast and NBCUniversal, signifying the beginning of the end for the indentured servitude that is the unpaid internship. With that gatekeeping tradition on its way out (Condé Nast just nixed its internship program completely), millennials are instead turning increasingly to entrepreneurship.

Hillman today runs Indy Hall, the co-working spot in Old City. It has about 250 members, the majority of them freelancers. Generationally, his story isn’t unique. One recent study from the Young Invincibles nonprofit found that 54 percent of 872 millennials either want to start a business or already have. Millennial Branding, a Gen-Y research and consulting firm, conducted a survey of more than 3,000 freelancers—two-thirds were millennials—earlier this year and found that 72 percent of respondents holding “regular” jobs in addition to their freelance gigs want to quit; about two-thirds expect to do just that within two years. Of those willing to quit, 69 percent say “freedom” would be their main reason for leaving their current jobs. Philly Mag’s recent survey of local millennials found that four out of 10 of us consider working for ourselves a dream job—not a majority, but still a sizeable portion.


In that sense, our perception of work is a lot like that of Peter Gibbons in Office Space: It’s not that we’re lazy—it’s just that we don’t care about traditional employment. We weren’t spurred to view the working world this way via hypnosis, like Gibbons, but rather by the confluence of three factors: the maturation of the Web; the recession we’re still reeling from; and the reversal of “white flight” from cities, which has led to more millennials than ever wandering our beloved grid. The result, at least in Philadelphia, has been a trend toward innovative, collaborative start-ups with a technology focus.

“Philadelphia’s tech scene would be much more fringe if not for those factors,” says Technical.ly Philly co-founder Chris Wink, 27. “The recession made us independent workers, while the Web made it easier to find and vet one another.”

Suddenly, says Wink, organizing and promoting small, focused groups became extremely simple. And while that can breed a sense of self-absorption, often such self-absorption helps further a community—especially in terms of social entrepreneurship. As Wink puts it: “We want to have an impact on our communities-at-large because we’re arrogant enough to believe that we can.”

That arrogance has served him well. Since Technical.ly Philly’s inception in 2009, the site has been not just covering the rise of Philly’s tech notoriety but constructing it, with regular conferences and events. They’ve blurred the line between media outlet and economic activism—a hallmark of the millennial view of work, and a function of our changing aspirations. To define those aspirations, Hillman invokes a trinity from Daniel Pink’s Drive: The Surprising Truth About What Motivates Us: “autonomy, mastery and purpose.” That is to say, we millennials want independent control of a craft that contributes to something larger than ourselves.

And this change in our approach to work isn’t limited to the tech start-up scene. Indy Hall is home to freelancers of all stripes, with founder Hillman estimating that just 40 percent of members have any direct technology-business connection. The remaining members work in areas ranging from the fine arts to science to marketing. One has transitioned from Web developer to chef since joining.

If you look at Indy Hall as a microcosm, it seems that jobs never before seen as freelance gigs are now capable of being just that. In a small circle like Philadelphia, all this independence means there’s a lot more room to be a tastemaker in your chosen craft. “We want to own the work, not necessarily the company,” Hillman says. “We want to leave our mark on something.”

The implications of that sentiment for the future of Philly’s workforce go far beyond co-working spaces. Millennials are rewriting the definition of employment, meaning that the libertarian capitalist paradise Hillman invoked might not be so far off. “That proprietary notion of ‘I work for this company out of their office’ is starting to go away,” says Wink.

Several companies have already formed out of partnerships established at Indy Hall; for Hillman, seeing his community spawn these companies signifies that this new professional attitude could have a big impact here at home.

Of course, millennial unemployment nationwide hangs at about 11 percent—more than four points higher than the average for all age groups. In that regard, this work revolution won’t be rushed. Millennials will still have to knock on plenty of doors to find opportunities. Now, though, it seems like many have been open the whole time.

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