How I Became a Freelance Writer — and 7 Tips on How You Can Do It, Too

From Songwriter to Freelance WriterWhen I asked new writers for their biggest questions back in May, one of the responses I got was that readers would like to hear “what it was like for successful writers early in their career.”

So here’s the story of how I became a freelance writer. It happened in L.A.

In the beginning — like when I was 14 — I was a singer-songwriter. Banging away on my parents’ black baby grand, scribbling lyrics in notebooks and taking them to school to throw out so my mom wouldn’t read my rejects out of my trash. I dropped out of college halfway through to hang around Hollywood Boulevard and go to songwriting workshops, where I eagerly awaited a chance to have my work shredded by my peers.

Songwriting involved starving. It cost money to pay band members, to rent halls, to promote my group.  I needed a day job, so I worked as a secretary at movie studios and talent agencies. There, I learned to stay calm and poised while movie stars asked me questions, or big agents barked orders. I learned to have a snappy comeback. Eventually, I started my own script-typing business, feeding off my show-biz connections, and worked for myself.

Around the time I was nearing 30 — the age at which songwriters have to ask themselves whether they’re up for a lifetime of this starvation or they want to move on — the alternative paper L.A. Weekly was celebrating its 10th anniversary. So they had an essay contest.

It was like they created it just for me. I had moved back to L.A. to pursue songwriting ten years earlier.

So I wrote an essay about what coming to L.A. to be a songwriter was like for me and my friends — namely, like slowly being crushed between two large rock walls. They printed it and paid me $200.

I pretty much never looked back. I had discovered a kind of writing where you got paid. And didn’t have to worry about whether the drummer was going to decide to take psychedelic mushrooms and the overnight party bus to Vegas to put in 12 hours at the blackjack tables instead of showing up for the gig. I literally called friends over and handed them my four-track recorder and my microphones and said, “Here — take this stuff away. I don’t need it anymore.”

Writing prose was empowering. I didn’t need anyone else to do it! I could execute this all by myself. I had all the intruments I needed inside my head. I thought it up, I talked to people, found facts, worked on it, went down to the mini-mart on Thursdays, and boom, there’s my name. Wow! I was a byline junkie from day one.

From there, I got another assignment from the Weekly right away. But then I took a third assignment I got in over my head on, and bombed.

I then pitched their rival, the L.A. Reader (now dead) about some protest I was going to. I ended up writing for the Reader for years, reviewing books, writing cover features for $300, community news for $50.

All the time learning, learning, learning. I’d haunt my editor’s office, latest issue of the paper in hand, saying, “I noticed you changed my first sentence from this to that. Why?” I got better. I wrote faster. I started to earn more from articles, and type scripts less.

Soon, the Los Angeles Times had a contest in the real-estate section. They wanted do-it-yourself fix-up stories. Again, tailor-made for me — my husband and I had just spent several years camped on our living-room floor fixing up our charming hovel in Culver City. I wrote a humorous, “our hearts were young and dumb” tale of our remodeling mistakes.

I won, they printed, I got paid. The editor there said, “You’re funny! I want you to write for me all the time!”

I’d been writing prose for about nine months, and I was writing for one of the largest daily papers in the country.

I was massively intimidated, felt hugely inadequate, and as a result it often took me six weeks to write a feature for them. But my editor put up with it and took the time to mentor me, because my writing was fresh, and honed, and really brightened up their section covers. And I was willing to work hard, beat the street, and find great stories.

Around this time, it started to dawn on me: I am a freelance writer.

Maybe I should take this freelance writing thing seriously! I love this, and it could be a career. So I took some classes through UCLA Extension in journalism, magazine writing. I learned more. I got better gigs.

One day, my husband said, “Why don’t you stop typing scripts and just write articles?” And I did. Not long after that, he was losing his job, and I applied for this weird full-time writing job I saw advertised, for a trade publication based in New York. They looked at my Reader covers, my L.A. Times covers, they gave me a writing test, and told me of 24 writers they auditioned, I was the only one who wrote something they could publish. The job paid $45,000 to start. And so began my 12 years as a staff writer, in which I learned many new skills, filed three or four stories every week, and laid the ground work for my second stint as a freelancer, which I’ll write about later this week.

Looking back over this, I see some defining points to why I was able to build a successful writing career, basically from scratch. I think these traits would be helpful to anyone looking to get into freelance writing.

1. I  didn’t develop a lot of writer insecurities, because it didn’t dawn on me that I was a freelance writer. I was just having fun!

2. When I hit roadblocks, I immedately looked for a workaround. It never occurred to me to stop because of one “no.” I liked being published too much!

3. I was willing to study my craft, both with my editors and by going back to school.

4. I got a lot of positive early feedback that encouraged me. I entered two contests, and won them both. This made me feel, “I must be good at this!”

5. I looked for opportunities that were a great fit for my background.

6. I developed a thick skin early on and was open to criticism of my writing.

7. I had run a home-based business before, so I had some knowledge of the hustle and administrative skills required to make that work.

That’s the story of how I wrote my way into a career as a writer. How did you get started? How did you keep going? What skills did you bring to it that made you successful?

Leave a comment and tell us your story. Later this week, I’ll tell you how I broke into freelance writing all over again, 12 years later, in 2005.

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Photo of singer-songwriter Kathleen Edwards via Flickr user ibm4381

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