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Getting Your Foot in the Door: Simple Tips to Break into Freelance Writing

freelance writing

The most essential gift for a good writer is a built-in, shockproof bullshit detector. —Ernest Hemingway

A guest post by Charles Lawrence for Simple Writing.

Regardless of the industry you’re trying to break into, you face two problems:

How do you get a job without experience?

How do you get experience if you can’t find a job?

It’s even harder when you’re trying to break into the fiercely competitive world of freelance writing. And now that the Internet has created a global marketplace, freelance writers compete with people all over the world with varying skills and wildly disparate pay rates.

I started freelancing when I was balding, wearing glasses, and suffering from middle-age spread.

I had no real writing experience.

I never kept a journal.

I never wrote for fun.

I never worked on my high school newspaper or yearbook.

When I was a teenager, I thought about being a writer, but I also thought about being a guitarist for Bruce Springsteen’s E-Street Band.

Neither seemed very likely.

I did spend most of my teenage years and adult life reading anything I could get my hands on—books, newspapers, magazine articles, billboards, cereal boxes, album covers, and Raid® Flying Insect Killer bottles.

I read anything and everything just because I love to read.

How I got from there to here

I’m originally from the Midwest US, but in my late 20s and early 30s I lived and worked in New York City.

To get to work, I took the F train from Brooklyn to Midtown Manhattan. The commute was an hour, door to door—one way. But the time wasn’t wasted. I read two newspapers every day without fail: The New York Times and the Daily News.

I later moved to Staten Island and my commute became even longer—an hour and a half one way. Now I could read three newspapers: The New York Times, The Daily News, and Newsday.

I didn’t know it at the time, but the years I spent reading newspapers during my long NYC commute was my training in writing and journalism.

Becoming the big fish in a little pond

As time passed, I changed careers a couple of times. I moved a couple of times. And somehow (it was because of a woman), I ended up living and working in a rural Florida county.

Talk about culture shock.

At one point, too much time had passed to audition for the E-Street Band, but writing—well, why not?

Citrus County, Florida has a small daily newspaper: The Citrus County Chronicle. It has a very small staff and relies mostly on freelancers to report on the daily happenings in this mostly retiree area.

I thought if there was an opportunity to get published, this small newspaper was probably it. So I contacted the Chronicle’s editor by phone and pitched an article.

Cold calling an editor on the phone is so 20th century, I know. But it’s a pitching technique that can, in fact, be successful, especially in small cities, towns, and rural communities.

The editor bought the idea and told me to write the article and submit it. She said she could run it as a guest column, but there would be no pay.

I wrote the article that night, submitted it the next day, and followed up with her a day after that.

As it turned out, the editor liked the article and made no changes to it.

The editor ran my article, as is.


I was published!

I got the Chronicle when it came out, cut out my guest column, and ran off copies for my parents.

I was 40 years old and wanted to say, “Look what I did, Mom!”

How embarrassing.

I went back to work and had all kinds of thoughts swimming in my head.

Maybe this was just beginner’s luck.
Maybe it was just a hole in one.
Maybe I should just leave the newspaper writing to the professionals.
Maybe I was pissed off I hadn’t pursued writing sooner.
Maybe I waited too long to do it.
Maybe I was afraid of success.
Maybe I was afraid of rejection and failure.

As you can probably tell, I was full of doubt, worry, and fear.

I started thinking my guest column was like going to baseball fantasy camp, where you get to wear a uniform and hit baseballs off Roger Clemens for a day.

Maybe that’s what I really needed after all, I thought. To know I was good enough to be published, even if it was just this little rural newspaper.

And maybe, if I’d made other decisions in my life, maybe I would’ve been a great professional writer by this time.

Maybe if I’d taken a risk when I was younger, instead of doing what everyone else does . . .

Go to school. Get a job. Take home a steady paycheck. Take advantage of the benefits.

It’s safe. It’s secure.

But it’s not much fun.

Finally I thought . . .

Seriously, what do I have to lose by just trying to get published again?

It took me almost a year to contact the Citrus County Chronicle again to pitch another article.

By this time, the previous editor I’d worked with had left.

I told the new editor I’d written a guest column for the newspaper a year earlier, and I wanted to know if he’d be interested in having me write another article.

I sent him my one and only guest column for review.

He said he’d get back to me.

When we reconnected, the editor asked me to pitch some articles, and he’d consider having me write them.

I pitched an article. He said he was interested. I wrote it. He published it.

And I got PAID!

I pitched another couple of articles. He accepted them.

And I got PAID again!

I must have done a good job because the editor started giving me assignments to cover human interest stories for the Citrus County Chronicle. Eventually, I had a byline and wrote a few articles a month for the newspaper.

I saved my clips and, after a year with the Chronicle, I approached the next biggest newspaper in the area, the Ocala Star Banner.

This time I emailed the editor and provided links to my clips. I pitched a couple of articles. He accepted them.

And I got PAID.

The same thing happened!

And then, this editor started giving me assignments, too. And I was given the title Correspondent.

I felt like Walter Cronkite, but I didn’t let it go to my head.

Except when my live-in girlfriend asked me to help around the house. Then I pulled the old Don’t you know who I am? routine. But it didn’t work. She’s not a writer, so she’s no Hemingway, but she did have her own built-in bullshit detector.

The moral of the story and lessons learned

It doesn’t matter . . .

  • if you’re young or old.
  • if you have formal training or not.
  • if your friends or family don’t believe in you.
  • if people around you are condescending and critical or if they put you down and don’t take you seriously.
  • if you have moments when you lose faith in yourself.

The fact is you’re writing. You’re pursuing your dream. You’re following the road not taken.

And your friends and family and neighbors?

Chances are they’re doing what’s safe.

But when you get published regularly and especially when you get paid . . .

And when you show your friends and family what you’ve accomplished . . .

Whether they say it or not, they’re going to think it’s awesome that you’re a published writer.

Because frankly, it will always be much cooler to be a paid, published writer than being a life insurance salesperson ever will be.

Your turn! How did you get your start as a freelance writer? Or what do you worry about when you think of getting started? Comments are open. And please share!

Freelance writing tipsAbout the author: Charles Lawrence is a Florida-based freelance writer who has been published locally and nationally in newspapers and magazines. When he’s not reading or writing, he spends time with his friends and family while his dog Toots leads him around by the nose. Learn more at Charles Lawrence Writer.

Photo Credit: Ernest Hemingway Collection. John F. Kennedy Presidential Library and Museum, Boston.

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10 comments… add one
  • Thanks, Charles.
    Very inspiring.
    I like the way you succeeded by doing one step at a time.
    Incremental progress.
    Most of us don’t fail; we give up.
    “Failure is not complete until you stop trying.”
    Rohi recently posted…How James Chartrand Helped Me Publish 6 Kindle Books in 5 MonthsMy Profile

    • Thanks, Rohi.

      It is true that most of us don’t fail. We give up. I’m sure there are scores of very talented people who never made it all because they gave up too soon. Persistence is one of the most important keys to success.

    • Hello! here I am, 57, unemployed, and wondering what am I going to do? I was a licensed respiratory therapist, and because of a very long illness, I gave up my license. I was tired of it anyway! When I was young, I wanted to change the world, by being the most compassionate therapist ever! After 25 years of it, I got tired. I have a nurse friend, who now has several kindle books, and her own blog, with followers. I must say, I am envious. In fact I am plagued with self doubt, at this point, in my life. Writing… is something that I have always been curious about. Thru the years, there has always been a small place, in the corners of my mind, that kept saying, “Joni, you should write!” Help me, please. Give me some advice. How do I start? Where do I go? Should I consider school, again at my age? Thanks for any advice you can give me. Peace.

  • Hi Charles,

    Thanks for your writing this post. It resonated with me at a deep level since I’m an aspiring writer trying to break into freelance writing with no background and experience. Indeed, I’m under the delusion that I’m no good to compete in an immensely competitive marketplace.

    Your sincere story moved me. I got motivated. A lot.

    Chan Huu
    Chan Huu recently posted…The Gratitude Experiment: 3 Steps to be HappierMy Profile

    • Hi Chan,

      Finding writing opportunities where there is less competition is the key. Don’t worry if the pay isn’t great at first. You need to build a clips that you can send to bigger publications that prove to an editor that you have the skills they need.

      It’s also important to bring not only your writing skills, but also your professionalism to a publication.

      The editors want people who are reliable, dependable and are easy to work with. That’s true for any business.

      Good luck!


  • Hi and thanks for this great read! I have a very similar story. I worked for 12 years in a restaurant which wound up burning down. I began a blog to continue the branding of this local iconic restaurant until they could rebuild. It ended up becoming an overnight, huge success with thousands of followers and readers. From this, I realized my passion for writing and started my own content marketing endeavor with a vision of advocating for local businesses through SEO and onine presence. I made a ton of contacts with journalists that covered the fire and began being pursued by some of them. I am now freelancing for my local paper and copywriting for a company. If writing is your passion, do it and fearlessly submit it to anyone who will read it. There is certainly a market for a great writer and if you are skilled, the opportunities will come.

    • That’s great, Loretta! Congratulations on your success! Part of becoming a success in any profession is to become highly skilled in your field and taking advantage of employment opportunities or creating your own opportunities.

      There are plenty of good and even great writers, but few who understand marketing, sales, follow through and long term relationship building.

      If you keep developing both your writing and business skills, there will be no stopping you!

  • Thank you, this is a great article. I am trying to break into freelance journalism. I just had a parenting mag accept my article, for free. Hopefully as I improve, I can land paying gigs. Thank you again

  • This was an inspiring article; the top half portion made me have a chuckle to myself as it reminded me of my own experience from a personal standpoint. No personal experience whatsoever, but always have enjoyed the leisure of reading on everything and anything.

    It’s awesome that you continued your path and have become an published writer. I totally agree with the individuals on this thread; it is definately not failure if an effort is not put forward.

    My friend actually directed me to this site; once i mentioned to her that my passion was writing. Hope to get some tips and directions from you. I know there are many individuals out there that share the same passion but have no idea on where and how to start. I hope you continue to share your personal experiences on a more public platform so individuals like myself will strive to move on with their passion.

    Thanks Charles

    Thusy Vijay


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