In the early 1990s, I called around to a bunch of newspapers and asked if they were hiring. My last work in the newspaper business was in high school, a good 10 years earlier. I had no new writing to show them. I got one managing editor to invite me in for an interview, so I went and talked myself into a job.
Could you do that? If you can write, possibly.
I agree with Simon Aldra to call your local paper and ask if they have any stringer or freelance opportunities for you. They might give you something easy to test your writing, something like an obituary or a short feature article. You won’t make much, but it will give you some experience.
Also, you could start a blog. You don’t have to write to it every day, but if you have an idea for a story you want to write, do a little research and call someone for an interview, then write up the story on your blog. Pretend you are writing for a newspaper and write in the same style (inverted pyramid, AP style, etc.). If you don’t know how to do that, learn. There is all kinds of free information about it online.
These days, newspapers are in decline. New news agencies are popping up as Web-only because it’s cheaper to run a website. But there are still a lot of print newspapers and magazines out there that will hire you.
Still, I’d suggest finding some of these new online news services that are looking for freelancers and pitch a few story ideas to them. You’ll make a little bit of money as you build your portfolio and learn how to write news and feature stories.
I’d also recommend building a website. If you are going to make it as a freelancer, you need a website. This is how people find you nowadays. Some writers put their blog on their website and some have both a website and a blog on a separate domain. Either way, both are an asset.
You should also get a LinkedIn profile and put all of your clips on your profile. Add the Publications module to your profile and every time you get a new publishing credit, list it there. It’s the best online portfolio you’ll ever have.
You’ll also need to learn how to write a query letter. This is a letter you write to an editor to pitch a story. It should include the name of your story and an outline, showing the editor that you know how to structure a story and that you have an idea about how you’ll go about researching it and writing it. Include your contact information. Also, be sure you get the name of the editor. You don’t want to send an impersonal query letter to an unknown person.
Join a forum or a writer’s community for encouragement. The one I recommend is Freelance Writers Den. For $25/month, Carol Tice will teach you everything you need to know about writing query letters, conducting research, writing stories, and so on. She has a 4-week journalism e-course that is included in your membership and you have access to her forum and a job board. It’s an incredible resource if you’re just starting out.