If you want to write for a living, you should write for free. Hell, if you already do write for a living, you should write for free. And that free writing should be some of your best work.
Unless you’re already famous for something else, you’ll write for free before you write for money. And if you try to make it your living, you might spend the rest of your life trying to make your paid writing look more like your free writing. Here’s the writing you probably should do for free, and the writing you probably shouldn’t:
Write about stuff that interests you. One typical method is to start a blog; I got my first job (writing for the former Gawker Media site Valleywag) by writing about Gawker in college, at a site called Blogebrity that some guys had set up as a joke. (I was not the first or last person to get hired at Gawker by writing about Gawker.) A more recent example is Kate Wagner, who turned her blog McMansion Hell into a promising career as an architectural critic, writing at sites like Curbed and 99 Percent Invisible.
You can write anything you want for yourself—that’s often why it’s such good stuff. No one’s helping you tighten stuff up, but neither are they watering down your vision. Put in some swear words, go stream-of-consciousness, make jokes that no one will get. This work will probably be a mess, but you might achieve something great. Very few publications would have accepted a pitch for Kate Wagner’s conspiracy-theory-chic critiques of ugly McMansions. But once she’d built herself a platform with McMansion Hell, everyone wanted in on it.
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