As someone just getting his journalism career off the ground, this Medium post was a bit of a punch to the gut:
You almost certainly can’t make it as a freelance writer. I’m not trying to be a jerk. I’m saying: you almost certainly can’t make it as a freelance writer. I think the essential thing to understand is that the next level, the really lucrative stuff that you get after you “get your name out there,” doesn’t exist. The little publications can’t pay and the medium publications want to con you into thinking that publishing for them for next to nothing will get you a piece in one of the big ones and the big ones figure just giving you the platform is payment enough. You can’t live on publishing in the New York Times and The Atlantic three times a year. Look: a lot of the supposed freelance writers you know of either come from money or work as shills on the side. Everybody’s gotta eat, I’m not judging. But many or most freelance writers aren’t. Ask other writers, preferably after a couple drinks. They’ll tell you.