Difficulties
As Ned explained to me later, one of the biggest difficulties of being a freelancer is payment. Freelancing, especially in the beginning, is a rough and uncertain path to take, and poverty is probably the foremost obstacle.
Because you're not working a steady job, you don't have a salary coming in at the same time of the month. Furthermore, you're entirely at the will of the publication to pay you. They pay you when they want to pay you and you have to put up with it because that's how the game works.
Now, editors are a bit like college professors: they're incredibly busy and terrible at responding to emails. (Although I have to say that professors have been great at responding to my interview requests...) The more urgent the email, the better the chance that you'll get a response. Emails that freelancers send in about when exactly their pay will be deposited are not high on the priority list.
Ned told me stories about writing articles that he was not paid for until weeks or months after they were published. This can be quite a difficulty if you're living hand to mouth, so it's usually necessary for people starting in freelance to take another job.
If you're in Asia like Ned and me, private English teaching positions are great, since they're well-paying and flexible, allowing for time off for travel. I'm still having to support myself with teaching, although it's entirely possible that I will be able to support myself entirely on writing soon enough.
With freelancing, it's the beginning that's the hardest. It's hard to establish yourself, but when you start accumulating clips and editors start to get to know you, pay can become more regular and opportunities start to open up. That doesn't mean that you won't have to bug editors for payment anymore.
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