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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.

On 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.