My first freelance work

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A few weeks back during tax time, I was cleaning up some old files and came across the check stub from my first opportunity to do paid freelance work.

I was just a lowly assistant editor at a golf magazine when I received a call from someone at Boardroom Reports, publisher of the Bottom Line Personal newsletter, which I’m pleasantly surprised to see still exists 23 years later. The assignment was to put together a quick article about golf gadgets, and I remember being stunned that someone was willing to pay $0.50 a word for writing. (Yes, even way back in 1990, there was no need to take pennies a word — yet at the time, I was pumping out thousands of words a month for just over $18,000 a year. It was a revelation.)

With so little experience, however, it would have arguably been foolhardy to attempt it full time. So, I did occasional freelance work on the side for “fun money” while working at a series of magazines through the ’90s. If I had to define my first “real” freelance job, it was the first project I received after starting my freelance business in 1999. That one was important, because I’d quit my corporate job cold turkey. It was the first check that helped pay the mortgage and keep my family fed, and immensely satisfying because of that.

I’d say the third most important check was the one from a project I’d secured through cold calling, sometime in the summer of 2001, thanks to coming across Peter Bowerman’s The Well-Fed Writer. Psychologically, that one was meaningful because it was the first freelance work I’d done that wasn’t from a person I’d known through my previous contacts or their referrals. It was a job I’d gotten on my own, selling my skills and experience to a prospect who had no clue who I was. At that point, I knew I was in business for real.

Update: As promised in the comments, Lori posted her “Bad Writing Contest” winning entry on her blog: “Your Start in Freelancing.” It’s a beauty, definitely worth the read!

Do you remember your first piece of freelance work — how you acquired it, what you did, and how much you got paid? Share your story in the comments!

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  1. Paula Hubbs Cohen says

    My first freelance writing gig was for Parenting Times, a New Hampshire parenting magazine similar to Arizona Parenting here in Phoenix. The article was about how to save money by shopping at warehouse stores and paid a grand total of $25 — this was in 1993. I did several more for the magazine (children’s birthday parties; children’s consignment shopping; etc.), also for $25 each, but then I found out about selling the articles to other parenting pubs across the country. Again, $25 or $35 each, definitely only fun money, but I was on my way to my current full-time-plus freelance career.

  2. Stephanie Thurrot says

    You got me curious, so I dug through my archives. Invoice #1 was possibly something I wrote for you–an article for Future. Remember that one?!

  3. Paula Hubbs Cohen says

    Thanks Jake, you too :O)

    I remember the first article I wrote for the AZ Republic was about the Sun City Poms, a group of fabulous senior ladies who dance in shows, parades, etc. Laurie Merrill was my editor and I was paid, drum roll please – $100. This was about 2004.

  4. says

    I freelanced through college writing “true confession” stories but my first paid freelance copywriting gig was when I was 21. I was writing marketing content for a company and the president’s wife asked me to write a bunch of fundraising materials for her pet charity. I asked for – wait for it – $20 an hour. Which I thought was just the best pay ever.

    Previously I’d written a grant for some nuns in college and got paid in gift cards. But nothing beats the thrill of a check with your name on it.

  5. says

    When I first started getting sick of working in the newspaper business, I thought a lot about going freelance, but didn’t take the leap because it was too scary. Then I was having lunch one day with a friend who owned a marketing firm and bounced the idea off of him, just to see if it was totally crazy. He said, “That is a great idea. I have a job I can give you right now.” The job was copyediting text for a website. It was only about a $60 job, but it was like a proof of concept. Yeah, I can do this thing. I freelanced on the side for two years before going full-time.

  6. says

    Now *that’s* diversification, Valerie! Thanks for sharing your tale. And your final sentence reminds me of something I used to hear a lot in the first two or three years of freelancing: “How can you stand not getting a check every other week?” To which, of course, the answer is: “Sometimes I get a couple of checks in a single day.”

  7. says

    This is a weird story. My first “paycheck” was actually a $50 prize and an ugly trophy. I won the Pittsburgh Press Sunday Magazine’s Bad Writing Contest. A bit of an ironic start to the career. 🙂

    My first sought after and paid gig was a piece in Child Life on a guy who built this massive train display for the Carnegie Science Center in Pittsburgh. Great little story that was fun to write. I think I was paid $200 for it, and at the time, I thought I’d struck gold. 🙂

  8. says

    My 1st check was actually from my last corporate employer that I quit in an incidence that was not one of my finer moments. Fortunately, I had a very understanding boss and they are still a client today. 🙂

    My next one was for health care articles that I thought were at a decent rate of $50 apiece until I was given the subject matter, dealing with DNA and gatekeeper genes. Uh, not something you knock out off the top of your head. 1st freelancing lesson learned. 😉

  9. says

    Lori, that’s hilarious. Any chance you can post that, or a snippet of it, on your blog? Inquiring minds want to know…

    Cathy, there are two lessons there — never burning bridges and always being alert to the difficulty/pay ratio!

    Thanks for sharing, y’all!

  10. says

    Reading your post made me regret on not keeping my first pay check from

    Back then I was selling dish TV deals part-time online and the check was the commission for my 4 sales in 6 months time. The amount, if not mistaken, was $320 (and that’s a lot to me – $320= MYR1,250, half of my monthly salary as a junior engineer). It was a huge motivation for me and it pushed me to grow and expand my Internet venture.

    Nice reading on the post as well as all the stories in comment section. 🙂

  11. says


    My first freelance job was for my previous employer. Don’t remember the pay—this was at least 20 years ago—but it was in the (low) thousands.

    An extremely positive experience that I took as a “sign from the universe.” Getting assignments from strangers proved to be much more challenging.


  12. says

    Jerry, thanks for sharing and the kind words. I actually just saved my teenage son’s first pay stub — washing dishes at a local restaurant. Someday, he’ll look back and laugh, I’m sure.

    Assignments from strangers is definitely tougher, Diana, but ultimately more rewarding! Thanks for commenting.