Sticking It to ‘the Man’: Why Millennials Are Going Freelance

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HandsSteven Cox, CEO of teaching and learning marketplace TakeLessons, knows a guy.

More specifically, he’s a young guy, 24 years old, which places him squarely in the millennial demographic. What’s interesting about this guy is what he does for a living: he drives for Lyft during the day; he teaches French lessons via TakeLessons at night. He also works as a part-time pet sitter through DogVacay  and rents out a spare room in his condo on Airbnb.

This guy — a son of one of Cox’s friends — is what you might call a “micro-entrepreneur,”  selling his own services via the Internet, rather than working for an employer in a more traditional employment arrangement. And Cox is not alone: plenty of millennials — and workers of other generations — have turned to freelancing and micro-entrepreneurship as their primary means of employment.  According to research sponsored by the Freelancers Union and Elance-oDesk, 53 million Americans now freelance in some capacity, and 38 percent of millennials are freelancers, compared to 32 percent of non-millennials (i.e., people over 35).

“It’s kind of cool now to be labelled an entrepreneur,” Cox says. “It’s almost a status symbol that I’ve seen [more and more] people latch on to.”

In part, the rise of freelancing and micro-entrepreneurship is driven by the flexibility and sense of control that self-employment gives people, Cox says.

“I think that this whole idea of these micro-entrepreneurs being able to do what they want to do, have more free time, and structure [their lives] the way the want to is pretty rewarding,” he explains.

Cox also believes that technology has played a role in this economic shift as well: “I think technology has really … made it very easy to find work. It enables individuals to — instead of just working for ‘the man’ or working at a job they don’t necessarily want to work — monetize their skills and monetize their time in a way they never could before.”

And that fact — the fact that millennials no longer have to depend on large corporate companies (or even small businesses) to find employment — “structurally changes how companies need to approach and look at millennials,” according to Cox.

You Don’t Have to Sell Out to Corporate America — You Can Be a Micro-Entrepreneur Instead

As established above, technology and flexibility/self-determination have both played roles in making micro-entrepreneurship/freelancing a lucrative and attractive employment option for millennials. But, Cox says, there may be an even more powerful force behind the rise of the “freelance economy”: millennial distrust of corporate America.

Consider, Cox says, all of the economic crises and business disasters millennials witnessed in their formative years: the Dotcom Crash, the collapse of the insidious Enron, the subprime mortage crisis, and the ensuing Great Recession. Millennials watched their parents, relatives, and loved ones lose their homes and jobs. Many of them graduated college and entered a world in which their economic prospects were grim, to say the least. All of this left an understandably sour taste in the generation’s collective mouth.

“I think there is this general distrust — more than any generation that I’ve seen — toward corporate America and about corporate America’s [ability] to provide a sense of security or job growth,” Cox says.

The underemployed millennials, unable to find good jobs and suspicious of the economic entities which they witnessed wreaking havoc time and again in their lives, saw an opportunity in the proliferation of cheap technology and the creation of on-demand, Web-based services.

“It basically reshaped how people could start their careers and make money,” Cox says. “I think it bred this form of commerce — which I call ‘service commerce’ or ‘S commerce’ — which allows people basically to buy [and sell] services over the Internet, which just opened a world of opportunity for the young millennials.”

In that new world of opportunity, millennials don’t necessarily need traditional employers. They’re doing just fine for themselves (many of them, anyway).

And what does that mean for corporate America and small business owners? What does it mean for the people who need employees when they’re faced with a generation that doesn’t really need employers?

It means, of course, that employers are going to have to rethink how they interact with millennial talent.

The Changing of the Guard: a New Employee Paradigm

“You have the big Fortune 500 companies that have run business a certain way,” Cox says. “We can bucket some of these companies stereotypically into the old ways of ‘command and control’ and ‘come up through the ranks and maybe you’ll get a corner office one day.’ I just don’t see that as appealing to the younger generation.”

What does appeal to millennials, in Cox’s experience, is culture, communication, and responsibility.

“We find that millennials really want to know not only what the company does, but they also want to know why [it does that],” Cox says. “I think that’s a message for founders and CEOs: culture really matters, and being able to share that vision [of] what the company stands for is extremely important. Millennials want to work for a company that has a conscience and believes in a similar set of values [to what] they believe in.”

(Perhaps as a result of seeing the chaos that unethical businesses — like the aforementioned Enron — can cause for people?)

Cox has experienced the millennial thirst for agreeable company cultures and moral values firsthand. When interviewing millennial candidates, he’s heard them ask everything from “Do you have a recycling program?” to “Do you hire people in other countries for less than minimum wage?” to “What does your company give back to the local community?”

“If you think about the mindset of those sorts of questions, it’s very different from what the books will teach people to ask [in interviews],” Cox says. “But I think it speaks to what’s on their minds. Culture matters.”

Millennials also want communication, which ties in to their desire to know what their employes are doing, both socially and business-wise.

“At TakeLessons, we have ‘all hands’ meetings to expose everyone to how the whole company is operating and how their particular role fits within the larger structure of the organization,” Cox says.

Lastly, Cox says, millennials want responsibility. They want to have a measure of autonomy in the workplace and a sense of ownership and self-control in their roles. This is especially important, given that millennials can attain this responsibility by becoming micro-entrepreneurs. If an employer wont give them autonomy, they’ll look for it elsewhere or give it to themselves.

“They look for responsibility, and they look for it quickly,” Cox says. “I find that when I give my employees the ability to grow, the ability to make mistakes, the ability to try things, and surround that with a nice format and structure of responsibilities and deadlines, it gives them a sense of ownership in the job and makes them feel like they are a part of the bigger picture of something they believe in naturally, [something that has] a conscience directed towards what they believe in.”

Ultimately, Cox says, the companies “that can attract younger, talented people will be the ones that lead in future generations,” simply because those companies will have the best and brightest talent.

“There’s a shifting of the guard because these younger companies that understand millennials and are naturally more nimble have a better advantage,” Cox says. “The millennials don’t want to work for stodgy companies where their ability to make an impact, their ability to learn and grow quickly, is somewhat muted.”

By Matthew Kosinski