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


  1. Carmel Murugen

    Great post, Kaitlin with lots of new takeaways. I particularly liked your point about prospects with active websites. I always passed those over assuming they didn’t need help but now you’ve got me thinking. Thanks again!

    • Kaitlin Morrison

      Thanks, Carmel! I did too – I actually have a funny story about that. One of my many experiments included sending LOIs to “unusual” prospects. I.e., prospects that weren’t using writers that I could “convince” to hire me. It worked about as well as you could imagine.

      At one point, I got into a back-and-forth argument via email with a magazine editor: “I don’t need freelancers and don’t use them.” “Well, could I follow up with you in six months?” “Ugh, sure, but I won’t use them then either.” “May I send you some writing samples just in case?” “Why? I don’t need help.” I heard stories of companies hiring freelancers who contacted them and said, “you need a blog and here’s why…” so I was persistent with prospects who told me “no,” figuring I could eventually convince them they needed a freelancer. I don’t think it ever worked for me. And I was added to a lot of mailing lists in retaliation. 🙂

      • Evan Jensen

        LOL. Lesson learned, right? There’s plenty of businesses out there that don’t understand the power of content marketing or or have intentionally chosen not to produce certain types of content marketing. And there is no convincing those types.

        Good thing, is there’s many, many businesses that do need and value great writers. Note to self…don’t waste energy on bad prospects. Better clients are just a pitch away.

        • Kaitlin Morrison

          This is SO true. I am learning that ongoing marketing just needs to be a permanent part of freelancing.

          We have to be prepared for anything. That “perfect” prospect could end up not being a fit or not having enough work to assign. In the last six months, I’ve had at least two clients who didn’t really work out. In 2020, I’ve had to replace ALL but two clients. With ongoing marketing, we can replace accounts without breaking a sweat, if we have to. This is the year of changed plans. Everything is constantly evolving and whatever we can do to prepare will put us in a better position to manage change.

      • Carmel Murugen

        You’re nothing if not tenacious, Kaitlin, lol. But it worked out great for you, anyway. 🙂

  2. Mary Stephenson

    Awesome post. I have been looking at different ads and when I see 500 already applied and then all the skills they request, it leaves me with doubts if this is even possible. So now instead of dumping those possible prospects, I will just wait until all the frenzy has died down. Thank you for the great insight.

    • Kaitlin Morrison

      Thank you, Mary. Absolutely – I think a lot of companies sort of “tune out” when they get flooded with applications.

      An agency guy was talking about offering me a job a couple years ago. I asked him about the job ads they have – perpetually – running online. He told me, “Oh, those are just to collect resumes in case we ever need them, but we don’t LOOK at those.” I’d seen the old ad, sent a LOI, then started freelancing with them – seems they respond to LOIs but not the actual job ads they post!

  3. Jan

    Unique perspective – thank you!

    • Kaitlin L Morrison

      Thanks Jan! This has certainly been an interesting journey. I still have so much to learn!

  4. Willi Morris

    This is a really cool idea! Going to try it. Thanks!

    • Kaitlin Morrison

      Honored I could share something useful, Willi! I’d love to know how it works out.

  5. Evan Jensen

    Hi Kaitlin,

    Question about your process.

    When you find an old job ad to pitch, many probably don’t have a contact person/email listed.

    So you’d probably search LinkedIn and the company’s website for the right person and contact info.

    Do you pitch a contact about an old job via email, LinkedIn, or both?

    In your experience, which seems to have a better response rate?

    • Kaitlin Morrison

      Hi Evan,

      Ooh…good questions! Now I wish I’d talked about this in the article. Oops.

      Usually, I’d go find the marketing manager, as I would if I were to pitch most companies. LinkedIn is really valuable for this. I prefer email since I don’t have a ton of InMail credits. I move on if it takes too long to locate email addresses – unfortunately, that’s what happens sometimes.

      Personally, I think LinkedIn has a better response rate, but if you need to send A LOT of pitches/LOIs, then it’s harder to do when you only have 15 – 45 InMail messages to send in a month. That really limits you. But if you’re looking to do a small, “drip” marketing on the side of a busy freelance schedule, then I’d start with LinkedIn messages.


  6. Vibor Cilic

    Thinking outside of the content mill constraints.
    I like your thinking and I will give it a try.
    Thank you for showing a new, smart way to see job boards.

    • Kaitlin Morrison

      Thanks, Vibor! Go for it! What do you have to lose? 🙂

  7. Diane Worley

    Kaitlyn, this is a great piece. I would never have thought to do this. Unfortunately, I don’t even have the content mill background you had. So I only have samples, nothing published to include with a LOI. Any suggestions on how to work with that?

    • Angie Mansfield

      Hi, Diane –

      The best way to get clips if you’re starting from zero is to approach a small business or two in your niche, offering a pro bono piece (something small, like a blog post) in exchange for the clip and a testimonial. You only need one or two to start marketing to paying clients.

      • Diane Worley

        Hi Angie,

        I’m trying that as well but haven’t had any success. Will keep at it.

        Thanks for reaching out!

        • Kaitlin Morrison

          Hi Diane, this is a tough one! It’s the chicken or egg problem.

          Are you in the Den? There’s a bootcamp where the instructor suggests doing an exercise that creates a sample, then presenting the sample as work you did in a professional development program.

          I suppose you COULD even create a blog. The problem with your own blog is it’s not FOR a client. But if it’s really good, it might help you get your foot in the door.

          The other thing I’d look to is nonprofits. Tiny nonprofits – lots of profiles on LinkedIn and Volunteer Match and such.


          • Diane Worley

            Thanks for the suggestions Kaitlin. I’ll look for that bootcamp. I do have some samples and a blog I did for a friend’s website but still no hits.

  8. Paul Jones

    Great post Kaitlin, you’ve just talked something that I’ve been wondering about for quite some time. I’ve noticed jobs ads that are 6 even 12 months old and they just seem to stay in the system. I now know what to do about so thank you 🙂

    • Kaitlin Morrison

      Haha, thanks Paul! Isn’t that interesting? Who knows. But it’s great for us!


  9. Ben

    Forgive me for pointing this out…but this post is one of many I’ve read, which blames a “recession” as being the reason for our present woes. I suppose it makes no difference, but I would point out that it’s a “Covid-induced recession”… since we seemed to be doing quite well as a country before the pandemic too hold.
    I’m just curious why it keeps getting brought up so frequently.

    • Kaitlin Morrison

      Hi Ben, thanks for your comment. Hmm…interesting. Covid-19 definitely had a lot to do with it – I know some experts argued we were on the cusp of a recession anyway and this put it over the edge, but I digress.

      I know Carol (and I agree with her) just wants to offer freelancers strategies that work and can be used – recession or not – to grow our businesses. Many people see the economic challenges/Covid-induced recession and assume there’s NO work to be hard – and give up. We want to prevent that!

      On a personal note, I’m shaping up to earn more in 2020 than in 2019. It definitely didn’t start out that way – it’s been really hard-won. It gives me hope we can all survive somehow.


      • Ben

        Thanks for clarifying Kaitlin!
        Your article DOES provide good information, and since I go through the writing jobs on LinkedIn now and again, it wouldn’t have occurred to me to go back in history.

        I’m wondering though, if we’re soliciting them (in general) why is it specifically necessary to do so from a “stale” ad? Many companies have probably had multiple ads over the course of a year. So when they receive our inquiry, they might assume we’ve just seen their latest job post. Any thoughts?

        • Kaitlin Morrison

          Ah, this is a great question, Ben, and I’m glad you bring it up. You are right – we definitely can reach out to companies posting ads right now if the position looks highly relevant. It’s certainly possible to find clients that way.

          The problem is, some of these companies are receiving hundreds or thousands of applications. That can make it harder to stand out even if someone is perfect for the role. So in the Freelance Writers Den community, we generally encourage people to pitch companies instead of applying to job ads, just because the competition can make it difficult to be noticed.

          It’s certainly true that some companies regularly put out job ads. The “Holy Grail” of freelance work, if you will, is often with the companies that don’t have time to look through a ton of applications and have ads going constantly. By going direct to them, you are providing them with a service – “here’s this writer I DON’T have to sift through 100 resumes to find because they showed up and introduced themselves, so I can save money and time on recruiting them and just put that into my content budget instead.” Is what a lot of companies are honestly thinking. Responding to companies that aren’t regularly putting up ads is one way to find these people before they go through the expense of putting up an ad. It’s also another way to find more company names you could pitch – essentially that’s what this strategy does, is create a list to target. There are other ways to create lists. Tradeshow attendee lists, sponsors for trade magazines, and sometimes just Googling “biotech companies Tulsa, Ok” or whatnot.

          I’m not sure if that helped, but hopefully some of that was useful!

  10. David Hicks

    Great article, Kaitlin. I was laid off back in 2018 and have purposely not deleted all the employment ad emails I had gotten since then thinking I should create a database of who is looking and what skills they are looking for (relevant to my skills and interests). I haven’t opened any of those old emails yet to see if they still provide the old information or if they have gone away or auto-updated with current ads. I’m almost scared to go look!! 🙂

  11. Patricia Sutton

    Kaitlin, thanks for sharing your great idea!


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