Freelance Writing: The Early Years

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Shared with permission:

Dear Deborah,

I have a confession to make. I Googled you to learn more about you and your “early years.” I can’t find much about you save for online articles and your blog.  I’m interested in learning more about the beginning of your writing career, how you juggled a full time job while you were starting out and when you knew it was time to quit your day job.

Thank you for your blog. You and your colleagues provide a valuable resource.


Loretta M.

I asked Loretta if I could respond to her email publicly because so many of you ask me about how I knew I wanted to be a freelance writer, my publishing career and when it was time to leave my full time job. It’s not a very interesting story, probably it’s typical and normal.

An early start

Like most of you, I always enjoyed writing. When I was in school, I didn’t join my fellow students in their moaning and groaning over term papers and essays. I looked forward to these assignments and did well. My favorite classes were those having to do with writing such as Journalism or English composition. I fed my addiction by keeping notebooks and diaries, even as far back as high school.

A career in publishing

I didn’t go to college upon graduation like most students my age. Instead, I took some night courses when I was a little older. My real writing experience began in 1985 at the age of 20, when I was hired as the receptionist for a boutique publishing company. They published over 100 titles including knitting magazines, tattoo magazines and even some adult oriented magazines. As I  moved up the ranks, some editors took me under their wings to encourage me to write more.

After 8 years I left my job in publishing to work for the graphic design and editorial firm that designed and handled the editorial and writing for many of the magazines published by my original employer. Though the gig was to be administrative, my duties were that of an Editorial Assistant and I loved my job. For a while.

My first byline

My first print byline appeared  in the early 90’s for a now-defunct music and tattoo magazine.  My boss sent me to attend a concert at Bryant Park put on by a top New York City hard rock station. The band wasn’t very well known but I felt special as I hung out backstage to ask questions about their tattoos. I got the gig because the original writer became ill at the very last minute. There was no one to fill in but me.

I loved seeing my name in print and wanted more.

Another of my duties was to give a final proofread to magazines before they went to press. Though I enjoyed this as well, it was also the reason I left the job. Many of the magazines were adult in nature and I didn’t enjoy proofreading them or looking at the accompanying images.  I left after several years to work for the accounting department of an upscale retail chain.

But I was bored. I didn’t want to add, I wanted to write.

The beginning of a freelance writing career

Throughout the 90’s, I attended night courses, mostly related to small business, at Baruch College in NYC. While there I also learned basic HTML and created a website so I could write whatever I wanted. I didn’t know it then, but it was my first blog. My dad was my biggest fan and one of my two daily visitors.

I began fantasizing more about writing for a living and researched the ways to begin. In 1999 I landed a humor column with Suite 101. In those days they paid a monthly fee which wasn’t much but I felt very important. The column was very popular and I enjoyed responding to the lively community in the comments. Through the Suite 101 gig, I landed a few other humor writing gigs here and there.

At that point in my career I had just gotten married and my husband and I were saving for a house. It didn’t occur to me to consider leaving my job to freelance, but I began looking for freelance writing jobs simply because I enjoyed writing.

Movin’ on up

In 2001, my husband and learned we were pregnant and bought a house in another state. Here was my chance to start over as a freelance writer. I was going to leave my job anyway to move and raise my child, now was as good a time as any.

I will say first and foremost, I probably wouldn’t have left my full time job if my husband didn’t already have a very good job. If we didn’t have two salaries, it would have been a lot more difficult for me to support myself in the beginning.

Goals are good

We set a goal. I would take a year to get my career off the ground and if it worked out well I could continue to write until our son was enrolled in school full time. Though I didn’t want it to be a temporary thing, I really didn’t expect to still be doing this now.

During the first two years I worked as hard as I could with a baby by my side. I didn’t keep all my eggs in the same basket. I worked for content sites, web clients such as iParenting Media and Legal Zoom, newsletters like the Dollar Stretcher, a couple of private clients and even landed a newspaper column using, believe or not, content site clips.

I believe the diversity was the key to my success.

I guess the rest is easy enough to figure out. I don’t find my story particularly interesting or inspiring. The truth is, I enjoyed writing and when I had to leave my job to relocate and have a baby, I saw my opportunity. It turned out to be the best thing that ever happened to me.

Now tell us your story. What is your background and how did you get to where you are today?






8 responses
  1. Thursday Bram Avatar

    I always find the paths that people take to freelance writing to be fascinating.

    Personally, I got my first clip in high school, writing for a magazine my mom published. In college, I figured out people would actually pay me for writing articles (rather than just letting me out of doing the dishes). After graduation, I started freelancing full time while I looked for a job — when I figured out I was making more money freelancing than I would as an entry level journalist and had more job security, I stopped looking.

  2. Jeanne Avatar

    I won my first writing contest – a nation one, in which I competed against grownups – at age 13. I published two short stories by age 19. I got a part time job in college writing ad copy and then they hired me full time when I graduated. I pounded out radio commercials, quick little scripts, and short profiles on local landmarks. I remember one long stretch of writing nothing but ads for podiatrists. I think I can describe foot care about sixty different ways thanks to that stretch.

    But my career really took off when I began writing for magazines. I began publishing articles in equestrian magazines because that was what I knew; I’d ridden and trained horses since age 16, and I had a lot of experts I could interview on horse care. I also began to write some articles for business publications. I won a few more contests for personal essays. One was even picked up from a magazine for a book anthology, which was very exciting to see my name in a book.

    I put my writing on hold around 1997, however, when I had the opportunity to move up in the ranks and become a marketing manager. I wrote very little for the next decade, but in 2007 I quit my executive job, we sold our Long Island house and moved onto a 17 acre farm in Virginia. Now I write full time and provide online marketing services to my clients. Re-entering the freelance writing world was tough after such a long break. A little thing called the Internet had happened. I was amazed by the opportunity and fast response now. I can write copy for Demand Studios, I can write for revenue sharing sites, I can write for private websites and oh yeah – I can still write magazine articles, books and such. It’s amazing how much the world has expanded thanks to the web.

    I now write for several sites and private clients, edit and write for LovetoKnow, have a few non fiction book projects going, and continue writing for magazines.

    Thank you Deb, for providing this website. You were one of the most important ‘voices’ easing me back into freelance writing. If I haven’t said it enough, I really appreciate what you have done for me and my writing career.

  3. Jeanne Avatar

    I actually paid part of my way through college by writing advertising copy and radio scripts. I pounded out ads for podiatrists and all sorts of businesses. I broke into magazine writing a few years after college by writing for equestrian magazines. I found that niche markets were easier to break into than mass markets. For many years, I worked full time, then came home and wrote well into the evenings. These were the days before the internet. I found the markets through Writers Digest and learned all I could about writing through magazines and books.

    I stopped writing from 1997 to 2007 to focus on my marketing career, but after moving from New York City to our 17 acre farm in Virginia, I began freelancing again. What a difference the internet makes. Daily I can apply for many jobs and writing opportunities, try my hand at writing for revenue sharing sites, or write a few articles for a fee. I write for private clients, offer my expertise in online marketing, and write for many wonderful websites as well as edit. I am also a blogger for many private clients. Oh, and I still write for magazines, and have written several non fiction books now.

    Thank you Deb for all the information and opportunities you give through your site.

  4. Dawn Avatar

    I don’t have a story to tell – yet. But I wanted to comment because I disagree with your thought of your story NOT being inspiring. I found it completely inspiring! I love that your success is through opportunity and passion, not a fancy degree hanging on your wall… I love that every move you made career-wise wasn’t a strategic climb to the top but a well-thought out map of what YOU wanted and needed at the time outside of a paycheck. I especially love that so much of your personal story sounds JUST LIKE MINE (age, night classes, baby on the hip, criteria for work pursuits…). I am new to this site – very new, this is my first post alert, actually – and I have hope that perhaps an opportunity in freelance writing need no longer be a lofty dream out on the horizon but an actual possibility right here at my doorstep (or countertop since that’s where I’m currently typing from!). THANKS MUCH!!!

  5. Chris Anderson Avatar

    I agree with Dawn, your story is just as interesting as any other story. I’ve always been interested in people and how their life goes. I would love to get into doing biographies. Have any tips on that :D.

    Your story was very inspiring though. It’s nice to be able to relate to someone as I’m currently writing part time and working in a factory full time as well as taking care of two kiddos. Trying to balance things with a family and work is hard, but possible as your own story shows.


  6. Lee Avatar

    I found your story completely inspiring as well!
    I have written poetry here and there that has blown people away, and, been published, yet actual articles, I just got a position writing for for the Charlotte, NC Teen Relationships section. It’s flexible, yet now during the holiday season I’m not going to have much time travelling and all so i’ve got two articles published and that’s it so far.

  7. Jill Preston Avatar

    I am needing to change careers. Nursing at my age is too hard physically. Your story is helpful. It points to a path for me. I started writing on Like you I love seeing my name in print and I love writing about my hometown. I am not making a whole lot but I can see opportunity’s which is what is important to me. I thank you for posting your story.

  8. Emily Watson-Rice Avatar

    The thing that really struck me about your story is that you did something that I advise artists to do all the time: Show up. Do the work. It’s something that I myself have only recently come to fully understand. There is rarely a moment of divine inspiration or the one in a million chance of being “discovered”. I’ve found with visual artists it takes showing up every day and putting in the work, especially when you don’t feel like it or lack inspiration. One of my favorite saying sums it up perfectly “some days are diamonds, but some days they’re just rocks”. It’s slow going and takes years of hard work, celebrating triumphs, and dusting yourself off after failures. But eventually, one day you’ll wake up and realize that you’re making it as an artist. It’s reassuring to know that the literary world works the same as the visual art world. Thank you for sharing your story and wisdom.

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