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The image of a freelance writer seems so easy and glamorous: Write important articles on your laptop at coffeeshops by day, rub elbows with thought leaders at cocktail parties by night, all without ever punching a clock or having a boss like a square. Unfortunately, it's just not that simple.

The latest depiction of the easy, choose-your-own-adventure lifestyle comes from Mary H.K. Choi who draws a flattering parallel between the much-romanticized lives of pirates and the (much less romanticized) lives of freelancers in the March issue of Wired. "Real pirates are sellswords on missions of their own making," says Choi. "They have near-total autonomy (and way less health insurance). The model for them is a particular Bahamas-based crew, circa 1720, known as the Flying Gang, the coolest real-life pirates ever." Notice, how Choi points towards the swashbuckling lives of pirates you read about in fiction, not the real lives of the hungry, violent Somali pirates.

But what the heck does that have to do with freelancing? "It's every cubicle-jockey’s dream," Choi explains. "The romanticism of off-loading the day job to rock the bejesus out of the boat is intoxicating. Sure, it feels crazy to quit during a recession, but it’s even crazier to ride the sinking cruise ship of a corporate career."

We hate to be Danny Downer about this issue, but it really is not that easy. Sure, it would be nice to "off-load" one's day job -- and Choi admits that America's economic woes are a problem -- however, the notion of going it alone professionally remains a complicated, exhausting, and potentially dangerous choice. Consider the small scale tales of woe included in this New York Times article about people who quit their day jobs to live out their dreams selling crafts on Etsy. Writer Alex Williams introduces readers to Yokoo Gibran, a scarf maker who puts in 13 hours a day working on her products: "Her hobby is her job," Williams writes. "But consider this before you quit your day job: at the pace she’s working, she might as well be a law associate." When you're a freelancer, you are running a business that produces a product, and that product is you. Business is always open and an off day means you will not get paid. At all.

When you're not hustling, you're not earning a regular paycheck. It may not quite as bad as the careers of actual pirates (not the Robert Louis Stevenson kind Choi imagines), but it's not all that different since the lives of Somali pirates -- many of them are in their 20s, just like the kids typing away in those coffee shops -- is, in the words of The Guardian, pretty grim. They do what they have to do to survive in a world of limited opportunities. The scale is quite different (no one is foolish enough to think a college-educated knowledge worker and an impoverished Somalian pirate are in the, um, same boat), but Choi's analogy is closer to truth than we suspect she knows.

Then there's that point about the health insurance, which Choi glances at. That's a real concern for the generation of young professionals whose age will catch up with them before they know it. There are, of course, resources like The Freelancers Union that can help make the pirate life a little safer. The government is even investing in it; just last week, Uncle Sam gave the Freelancers Union $340 million in order to expand its membership. But even though things are looking up for the freelance infrastructure, some basic facts remain: This is a tough career path, one that involves constant hustle and rejection, and it's probably not for everyone.

In conclusion: Don't quit your day job just yet. The open seas are rough and not everyone survives the crossing. And the rewards for those who do are often hardly worth the risks.

This article is from the archive of our partner The Wire.

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