Writing-Job Ads: A Pro’s Time-Stamp Trick to Earn $1 Per Word


Applying to writing-job ads always felt like I was paper-airplaning my resume into a bottomless void.

Starting my new freelance career without a ton of work lined-up, I’d turned to freelance writing job boards and ads hoping to bring on new clients. 

Now, with the recession, most writers are stepping up their job-application game like I did. 

But here’s what will happen…a lot of hustle without a lot of results. My experience applying to writing-job ads was pretty terrible.

Have you ever heard someone define insanity as “doing the same thing over and over and expecting different results?” I was insane. 

So when Carol Tice recommended against relying on job sites to build my writing career, I started thinking about other ways to use them. 

That’s when I discovered my own weird trick…the secret that helped me launch my writing career and land assignments that pay $1 per word: Old job listings.

Want to learn how to land great clients with writing-job ads? Here’s how:

Meet freelance technology writer Kaitlin Morrison

Writing-Job Ads: Kaitlin Morrison

Kaitlin Morrison

With a small content mill and literary mag portfolio, Kaitlin jumped into freelancing in 2015 without much professional writing experience and with a part-time retail merchandising gig. 

Aside from some volunteering and minimum-wage work at a big-box store, she had a liberal arts degree and zero professional experience. Since she felt underqualified for the top-shelf gigs, she figured waiting around for the perfect client to show up seemed like a bad idea. 

But applying to writing-job ads didn’t seem much better. Yeah, thousands of writers competing to reach the hiring manager’s inbox first, only to never hear back from anyone.

Carol’s advice: “Kaitlin, you need to STOP applying to online-job ads.”

What happened next changed EVERYTHING…

Try a writing-job ads experiment 

Instead of applying to more newly-listed writing jobs, I came up with a different plan. No more:

  • Filling out those soul-sucking forms about education and employment history
  • Applying to writing jobs and competing with thousands of other broke and desperate freelancers
  • Feeling desperate and out of control to find freelance work


The experiment

Step 1. Find the oldest job ads for writers you can track down.

Step 2. Send them LOIs (letter of introduction) introducing your freelance writing business.

Keep in mind…these are going to be writing-job ads that probably had lots of applications months ago, but are now old and stale.

The results

This little experiment pitching old writing-job ads helped me:

  • Snag my first $1 per-word client
  • Enrich my portfolio with new-to-me niches
  • Win recurring work (found a client who paid my utility bills for a whole year) 
  • Get a variety of interesting clients, such as university nursing schools and even a few Fortune 500s 

Say good-bye to competing for newly-listed writing jobs

Compared with send fruitless applications to new listings, you’ll get better results sending LOIs to year-old job posts.

Why? When you  send LOI in response to an old job ad, you don’t have any competition. It’s just YOU.

FYI…When I figured this out, pitching old job ads quickly became one of my reliable go-to marketing strategies. 

Tips to find prospects to pitch from old writing-job ads

Using old job ads to build your list of leads takes care and creativity. You need to know the basics of writing a great LOI (check out this pitch-letter checklist).

A few things to look for:

  • Companies that respect writers (no pennies-per-word gigs)
  • Potential clients that are big enough to need your help
  • Avoid small businesses and solopreneurs, since they usually don’t have writing budgets or experience working with freelancers

This is how job ads are helpful, though. They’re actually a decent filter. If a company is big enough to hire a writer before, they’ll probably still be a good prospect down the road. Add them to your list. 

6 places to find online-writing jobs

So where do you find high-quality job listings for writers? Here’s 6 resources I’ve used:

  1. LinkedIn job listings 
  2. Mediabistro listings 
  3. Cision Jobs 
  4. FlexJobs
  5. Freelance Success Newsletter listings 
  6. Freelance Writer’s Den Job Board

Tip: Google is another helpful tool. Just be careful. A lot of job listings online are low-quality and you don’t want to waste your time in the wrong places. 

How to write the perfect job-ads pitch

With your list together, it’s time to write a pitch letter or LOI that get’s noticed.

Your LOI doesn’t have to be long or complicated, but it does need some customization to prove you’re the real deal. No need to mention the job ad either.

Just follow this format:

  • Introduce yourself
  • Mention something specific the company is doing well (See example below)
  • Include a line or two about your work
  • Close with an offer to send clips or schedule a quick call
  • Add your writer website and portfolio link to your email signature, and you’re ready to go. 

Need to book some freelance work ASAP?

If you want to add a short bulleted list of ideas to your pitch, go ahead. But don’t let the ideation process (or writer’s block) stop you from sending out more LOIs to more companies if you urgently need work. The more you send, the sooner you’ll turn prospects into paying clients.

Tip: Even today, when I use job ads, I hit snooze on anything newer than four months. It’s okay to wait. Reaching out too early means you may compete with 1,584 resumes.

But wait, don’t they already have writers? 

Now that you’ve seen my method, maybe you have a few lingering doubts. 

They already hired someone, so don’t they already have the writing help they need?

Maybe. But in my experience, the companies that use writing the most are actually the ones with the greatest ongoing need. 

Instead of blowing off old writing-job ads as dead leads, it’s possible that:

  • They’re busy and need more writers
  • Haven’t posted another ad because it takes forever to read 1,000 resumes…so they don’t bother
  • They tried out a writer who didn’t work, so now they still need someone
  • In the downturn, they let a full-time staffer go and now the writing workload is still piling up 

Case in point…recently, one of my top clients asked me if it’s okay to double the amount of writing I do for them. They already have a full in-house writing team, several other freelancers, a content marketing manager, and even an assistant content marketing manager. 

When I saw their website the first time, it didn’t look like they needed help, at all. Which was a good sign to me that content marketing is a big priority to them. 

THAT’s the type of company you’re looking for, not a business that doesn’t have a blog yet, or an organization that hasn’t posted new content since 2015. 

What you do is valuable and not everyone can write. 

Use stale job ads to win more writing work 

If you take anything away from my experience, let it be this:

“Getting creative with your freelance writing business pays off. “

Times like these are your moment to stand out as a writer and separate yourself from the masses. Most writers won’t market right now, in a recession. Most will assume there isn’t writing work to be had. 

Be different. Putting yourself out there with a creative and consistent approach to marketing gives you a big advantage in today’s freelance marketplace. 

What’s your experience with writing-job ads to get freelance work? Let’s discuss in the comments.

Kaitlin Morrison is based in the Pacific Northwest and writes for B2B software, cloud, and technology clients.

Grow Your Writing Income. FreelanceWritersDen.com

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