Posted with permission from National Post

"Freelance is kind of a dirty word now; it sounds like what you do in between jobs," says Ryan Emberley, a 30-year-old society and celebrity photographer who travels the world shooting A-listers like Kate Moss and Victoria Beckham. "Like, I'm not freelance. I'm successful. I'm self-employed. Freelance has this aura of unsuccessfulness and failure to it."

Whatever one thinks of the term 'freelance,' there's no denying the freelance economy is booming. More and more and more workers are choosing self-employment and short-term jobs over traditional 9-to-5 office environments. Many freelancers are creatives – graphic designers, photographers, writers – but they can also be marketing pros, SEO consultants, accountants and even limo drivers. There are 53 million freelancers in the U.S. today and 50 per cent of the U.S. workforce will be freelance by 2020. While comparable stats aren't readily available in Canada, John Ruffolo, Chief Executive Officer of OMERS Ventures, predicts the percentage could be even higher here.

Emberley is right about the perception, however. Although Stats Canada reports that self-employed workers consistently earn more than "standard" workers, freelancing is widely dismissed as being one step away from unemployment and destitution. Often referred to patronizingly by media and politicians as the "gig economy," there's a perception that workers only remain outside the traditional job market if they're unskilled, unlucky or unmotivated. Hillary Clinton once said the freelance economy raises "hard questions," and business magazines treat the trend more like a plague than an evolution.

But if innovation and independent spirit are qualities we supposedly value, what's so wrong with taking your career into your own hands? Corporate employers' fearful reaction to the freelance economy gives us a clue. If workers are lucky enough to snag a job that doesn't involve serving coffee or waiting tables, they're often employed on a contract basis with no benefits, no job security and little hope of career advancement. As companies become less loyal to workers – creating work conditions most favourable to the Patrick Batemans of the world – people are pushing back and setting their own wages, hours and terms of employment.

Erin Richards, a 29-year-old publicist, worked at the CBC for five years before deciding to take the leap into freelancing. "The CBC has basically stopped doing pensions. My dad worked for the CBC for 25 years and was awarded with an amazing pension, but that's non-existent now," she says. "Basically, they just hire people on one-year contracts that they may or may not renew."

Today, the goal isn't a promotion. It's not getting laid off.

RyanWhile adapting to new, mostly unfavourable labour conditions with entrepreneurial spirit would usually be prized by society, it missed the memo when it comes to freelancers. They're more likely to be described as lazy, immature and unprofessional than inventive, self-motivated and accountable. This may have something to do with the fact that many freelancers are millennials.

If you believe most things you read about millennials, you probably think they're a generation of entitled, spoiled jerks. A cohort of undesirables who can barely survive, let alone thrive in a traditional office environment. Perhaps that's why millennials are the age group most likely to freelance. According to a survey conducted by Freelancers Union and Elance-oDesk (now known as Upwork), 38 per cent of Generation Y has shunned typical lifeless cubicles and morning commutes in favour of freelance work.

On the other hand, maybe Gen Y's penchant for freelancing isn't the result of entitlement – but a reaction to an unstable and increasingly oppressive corporate world created by their parents' generation: a corporate world that widely sees young workers as disposable. Despite being the most educated generation to date, adults between the ages of 18–34 make the lowest average earnings since 1980 according to data from the Federal Reserve Survey of Consumer Finances. The CBC took the liberty of dubbing millennials "Generation Jobless" in a 2015 documentary that explored why the unemployment rate for young adults in Canada is close to 15 per cent – double that of the general population.

Freelancing certainly isn't anybody's idea of the easy way out of a tough situation. "It was really stressful when I first started freelancing. I had no idea how I was going to make it work," says Claudia McNeilly, a 24-year-old freelance writer. "I got a couple jobs that paid, like, $25 an article and worked part-time at a juice place."

McNeilly's writing gigs have picked up steam with a few big placements in outlets like Broadly and Teen Vogue, but she's only able to continue freelancing because of regular copywriting work that supplements her income. "It's by no means cushy," she says. "There's no way I could do this if I had anyone else to support ... if I had kids or anything like that. The only way I'm able to do this is that it's just me."

Emberley was laid off from a string of TV production jobs in his 20s before deciding to become his own boss. He now makes a salary quickly approaching the mid-six-figures and claims he has more job security than ever.

But Emberley wasn't always living the freelance dream. He barely made any money in his first year as a freelance photographer and had to survive on a cocktail of debt and lines of credit. Not exactly the stuff entitlement is made of. This terrifying abyss between deciding to take your career into your own hands and achieving a vague definition of stability is one most freelancers know all too well.

ErinOn top of the inherent difficulty of kickstarting a freelance career, there are constant reminders that the system wasn't designed for them. None of these freelancers have health benefits or pension plans – but they figure they wouldn't have them at "regular" office jobs anyway. They know the social contract isn't what it once was. "If I get sick, I think that's basically just the end of me. I have to stay healthy forever, that's all," says Emberley.

"It's a bit of a nightmare. I try not to think about it," echoes McNeilly, who recently had a health scare on a trip to New York City without health or travel insurance. "There was one day where it was 45 degrees and I got really dehydrated. I was going to faint, but I literally couldn't afford to. I was holding onto a pole with hundreds of people smashing by me, desperately trying not to pass out because it would've cost me $6,000 for an ambulance ride." Back in Toronto, McNeilly's mother still pays for her dental checkups.

Having to live with a crippling phobia of freak accidents and hospital bills, why would anyone choose this career path?

There's of course the necessity to find paying work, but technology makes freelancing much more viable than in the past. It makes networking and communicating easier, and also makes the world a smaller place. You can still be connected from the comfort of your couch.

As digital-first millennials, these freelancers (or, excuse me, entrepreneurs) believe they have a leg up on older generations trying to make it on their own. "I spend a lot of time on the internet, so I'm literate in that language and all the sub-pockets of Twitter that someone older wouldn't even know about," says McNeilly.

"Social media is big these days, and if you have some sort of presence as an 'influencer,' it helps you in certain industries. As a millennial you have a certain acumen for the internet," says Emberley. "Youth is also obviously very helpful when you have energy and the ability to burn the candle at both ends."

But freelance life isn't all unpaid invoices and endless anxiety; freelancers do enjoy some pretty sweet job perks that could be misconstrued as entitlements. McNeilly often wakes up at 10 a.m. and works in her pyjamas (an office uniform that's only outdone by the bathrobe I'm wearing when I interview her over the phone from my couch), while Richards strategizes for clients from sunny patios.

Claudia"There are very few occupations where you can absolutely choose your co-workers and take them or leave them as you please," says Emberley. "So that's probably my favourite thing."

It also helps to be financially flexible, single and childless when jobs dry up or checks arrive months late – a trend that affects freelancers of all success levels. "Getting paid as a freelancer is really hard," says McNeilly. "Sometimes it feels like you aren't making any money."

More and more companies now set payment terms where they don't have to cut freelancers a check for up to 90 days (and that's assuming an invoice doesn't get lost somewhere in the accounting process). "There are always bad days where money doesn't come when you'd like it to, and you have to chase checks a lot, which can be irritating," says Emberley, who sometimes has clients owing tens of thousands of dollars for months at a time.

The ability to find work that pays both well and on time seems especially challenging in Canada, where companies have smaller budgets and value freelancers less than their American counterparts. "There's not a lot to go around in this country," says Emberley, who wants to try to reach his career goals in Toronto, but is taking on more and more international work.

With freelance pastures looking much greener south of the border, Canada is starting to see a lot of its most promising freelance talent jump ship in what could be called a millennial brain drain. "I definitely don't plan to stay here. Most of the places I freelance for are in America; they pay better and there are just more eyeballs and more media outlets with different voices. Also, you get paid in American dollars," says McNeilly. "There's not nearly enough work in Canada, it's kind of depressing."

Despite Gen Y's reputation for entitlement, freelancers don't actually ask for much more than the opportunity to make money and see a bright future in their fields. Cushy office jobs with benefits are going the way of dinosaurs, and ambitious millennials aren't waiting around for pink slips. To call that entitlement is nothing short of naiveté about where the job economy is headed. Millennials, like generations before them, want the chance to feel like they've "made it."

"I haven't made it yet," says Emberley. "The goal is always to be number one – and if you're not number one, then there's still a ways to go.