Photo: Breslavtsev Oleg/Shutterstock

Hey Millennials, Here's Why You Should Go Into Freelancing Vs. a Shitty Desk Job

by Bryce Emley Nov 8, 2013

If you grew up in a middle-class home like I did, a college degree was more like an expectation than an achievement, and thereafter some kind of stable career was thought to ensue like a magical byproduct.

As a Millennial / Gen-Yer / ’80s child, I grew up with well-educated parents who worked whole careers in one industry and position until retirement and probably expected their kids to go the same route. But then the internet happened. And the economy. And now things are a bit different.

Now there’s a whole market for creative types, homebodies, tech people, entrepreneurs, working moms, and otherwise career-defiant workers to make a life and income for themselves outside of traditional brick-and-mortar workplaces — and it’s booming. Hence my being able to make a living writing while watching college football. Lynn Dixon, co-founder and COO of (a sort of job-matcher for people seeking and offering non-traditional employment), backed my assumption that I’m not the only one doing this, saying “Flexible work is the fastest growing segment of the employment market” during a recent conversation.

Though freelance work is increasingly popular for people aged 50+, Dixon pointed out Millennials are taking up a huge portion of that market: “For Millennials and Gen-Yers, freelance work offers the ability to explore multiple interests, balance work and life, and evaluate whether or not they are interested in a long-term career in a particular industry.”

For Lena Dunham fans, this seems like the classic plight of the modern 20-something: I don’t know what I want to do with my life, but I know what I DON’T want to do — I think? We may not know what the hell we’re going to do with the liberal arts degree we sort of sleepwalked into, but we know what interests us and we’re going to figure out how we can get away with getting through life without “working for one company and retiring with a gold watch,” as Dixon put it.

And now more than ever, that’s a possibility. People like me have come to realize the new cubicle is the Goodwill desk with chipped corners in a spare bedroom, that now sites like oDesk and Fiverr are materializing the dream of sustaining yourself on your own interests, that a career can simply be a composite of various jobs. Lynn and her Hourly co-founder Brooke Dixon established their site as a way to fill a need not being met for the “95 million non-salaried workers” out there and guide them to employers “within the top-five segments for flexible work” (hospitality, healthcare, retail, media, technology).

However, not all the prevalence of the non-traditional worker mentality comes from dissatisfied Baby Boomers and wishy-washy Millennials — businesses have actually set the scene for this workplace overhaul to even have a chance to exist. For freelancers, this starts with small businesses.

I’d feel like a failure to myself if I gave up on sustaining myself through my own efforts for a 9-5.

Starting a business is easier than ever. Can’t afford an office? No problem! Rent’s as cheap as hosting when you’ve got a digital office. Don’t have an actual service to sell? Who cares! If you’ve got an excess of personality, you can start a blog and be the next Perez Hilton. Don’t have payroll for customer service? Just outsource to broken-English speakers for $2/hour! As more and more entrepreneurs and wannabe-preneurs use the internet to try to start their own businesses, the need for outsourcing and contract workers comes into increasingly fuller bloom.

The same is becoming true from a temp-worker standpoint in the US thanks to healthcare reform. “From what we are hearing from businesses,” Dixon recalled, “Obamacare will result in hours being reduced for a number of workers as a way to avoid increased healthcare costs.” The result? “These same companies will need more people to fill the vacancies they just created.”

And speaking of Obamacare, now people like me can feel okay eschewing corporate careers and their “benefits.” There’s a scene in the movie Our Idiot Brother in which Adam Scott’s aspiring sci-fi novelist character gets patronized by his over-achieving crush for not having health insurance. I never understood that until I didn’t have a real job, or health insurance. In a line of work like mine, there’s a kind of status that’s missed by not having middle-class benefits, not to mention the security of knowing if you get your lung punctured by a rusty railroad stake, you can afford to get that looked at.

When my mom dropped me from her insurance, I was left in that limbo (I’m still there), like millions of others. It’s tempting to quit the work I love just because it doesn’t afford me health insurance or the kind of money necessary to buy it myself. But choosing a line of work based solely on the availability of health insurance is potentially going away for some of us. I’ll personally most likely qualify for Medicaid, which means I won’t have to worry about things like lying to myself about that weird growth I’ve been calling a mole anymore — or, worse, getting a real job just for that reason.

For people of my generation, this only further propels us away from the traditional work world of our parents. “I wish you would find a steady job with benefits and a regular paycheck,” many of us have probably heard at some point (possibly our own words). Now “steady” becomes a subjective term dependent on our ability to line up gigs. Now benefits can be bought or enrolled in without an employer’s say. Now paychecks are as regular as we want if we’re willing to put in the work every day.

I think all this has changed everything forever; I know I’d feel like a failure to myself if I gave up on sustaining myself through my own efforts for a 9-5 that pays better for more mindless work. And I think it’ll be hard for the rest of us to go back now.

We’re the generation of neo-hippies and trendy DIY-ing, the generation of really abstract Levis commercials that talk about our generation, the generation of getting a Harvard degree and then making a website for people to post pictures of their lunch on, the generation that won’t work in an office without a beer fridge and ping-pong table in it. We might regret not having retirement when we’re 70, but we’re also the generation that plans to die before it gets that far.

And if we regret it, we’ll just continue the cycle as our kids defy everything we believed in.

* MatadorU, Matador’s online education platform, runs courses in travel writing, photography, and film that can help you progress your freelancing career.

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