Just Because You're Freelance Doesn't Mean You're Free

Brutal truths from the front lines of freelance

businessman with laptop sitting ...
ShutterstockThis is not what life is like if you're a freelancer.

It's almost Independence Day, and here at AOL Jobs we're thinking about what freedom means in the workplace (also, how fireworks are super cool and blow up real pretty). Like most things, freedom is in the eye of the beholder: one person might rage against his employer's restrictive practices, while their co-worker might be happy just to have the option of using Splenda instead of regular sugar in the morning.

But what about when you're only minimally subject to the whims and protocols of your employer? What about when you're your own boss, and you have the whole working world spread out before you, like some unconquered, snack-strewn region of Westeros? What about when you're a freelancer? I was a freelancer in the TV production world for a few years before moving into editorial, and during that period I had the following exchange so many times that I reached a point where I could almost finish the other person's sentences.

OTHER PERSON: So, you freelance. What's that like?
ME: It's okay. It has its pluses and minuses.
OTHER PERSON: Must be nice, not having a boss.
ME: Actually, I have like four bosses-
OTHER PERSON: My boss makes me pick up his laundry every Tuesday and smacks me with his bike shorts when they come back wrinkled. So, can you just stop working and go on fun adventures whenever you feel like it?
ME: Surprisingly, no.

From what I've gathered, there are a number of misconceptions about what the freelancing life entails: 1) that it is fun; 2) that it is easy; 3) that a degree of occupational independence means never having to worry about the same things every employed person on the entire planet worries about. I'm not saying that freelancing is better or worse than holding down a staff position, but...well, actually, yes. It is probably slightly worse. It's certainly harder.

You want to talk about freedom? Okay. How about freedom from benefits? Let's say you want health insurance, because that's just one of those trivial little things that's necessary in order to exist. You can buy a standard plan for top dollar, or you can purchase one through the Freelancer's Union, which advertises plans that are 39 percent cheaper than those sold on the individual market.

With that said, they're still not cheap: they'll run you up to $600 a month (or more than double that, if it's a family plan). The situation has improved moderately thanks to the Affordable Care Act, but you're still banking on the government giving you a decent subsidy, and that's not necessarily a foregone conclusion.

Something else about freelancing: you basically have two full-time jobs. The first job is YOUR JOB, AKA whatever you're doing to make money. The second is scouting around, putting out feelers, and doing everything in your power to make sure that when your current gig ends you're not going to end up on the streets, dressed in nothing but your PA badge from the 2011 Webby Awards, screaming half-intelligible missives about how you once prepared hummus plates for Dr. Oz's green room. You will live life four to six months in the future, one eye perpetually trained on the next job, never knowing what it's going to be. You will burn through and (if you're lucky) replenish your savings so many times your bank account will get motion sickness. You will eat a lot of pasta.

Of course, this chiefly applies to one type of freelancer, the kind whose livelihood is based around a series of finite projects. If you're a freelance writer, let's say, it's a totally different game (although you can still be certain that you'll be eating a lot of pasta). Be prepared to sing for your supper.

It's not my intention to scare anyone out of a freelance career. It can be a rewarding path for self-starters, the ultra-motivated--the human equivalents of those inflatable clown dolls that you punch in the face over and over, only to have them pop up again, unfazed. And the world of staffed positions certainly isn't without its own set of pitfalls (replace scrounging for future gigs with dodging layoffs and navigating office politics).

But it's easy, especially if you're a fresh-out-of-college type, to embark on a freelance career without really knowing what you're getting into. And when you're six months out of work, frantically refreshing your Gmail window and living on a diet of deli ham (you don't buy bread or cheese anymore; those are luxuries now), you might start to ask yourself if all this extra freedom--gobs of freedom, so much freedom you can barely move--if it's really worth the trouble.

Happy 4th of July, everyone!

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