Should I publish for free?

I hope that you can give me some advice on getting articles published. My pitches seem to end up in black holes - along with my self confidence :( However, I still want to get my stories out there, because these are stories I want to tell. On the road to hopefully becoming a paid writer, do you think it is worthwhile to, in the meantime, publish for free online, for example on a site like Medium?

Early in my career I wrote for free quite a bit, but mostly for outlets that I helped run or create, such as a blog called Feministing. If you're writing for a professional outlet that's making money off of your words (either in the form of ads or grants), think it's important to insist on being paid, even if it's just a little bit. Medium is a bit of a gray area, but if you have absolutely no published clips and want to get some work samples out there, it's not the worst place to be publishing. Many outlets now republish work from Medium.

My best advice to you is to keep pitching, and to pitch specific articles, not broad topics.