Updated: Oct 31
I’d started selling articles to magazines in 1996, and I’ve recently made the leap to freelancing. I’ve given myself six months to make it work. If I can’t earn my goal amount, I’ll look for a 9-5 job.
A few months later, I’m earning more as a writer than I had been at my previous office job.
Fast forward two years, and I’m writing for newsstand women’s magazines like Family Circle and Woman’s Day. In 2003, I co-author The Renegade Writer: A Totally Unconventional Guide to Freelance Writing Success and start teaching and coaching other writers.
Later, I start landing content gigs from household-brand names like Best Buy, Intel, CVS, and GE—and begin training content teams for brands like Qualtrics and Meredith College.
How did I do it? The answer may surprise you.
In 1997, there were no online job boards. Emailed pitches weren’t a thing. You couldn’t build a website in a day with cheap software. There were no places to quickly find or contact writing prospects.
Read on to see what a typical week looked like for me in 1997. If you want to get right to the tips on how you can make a good living writing today, scroll on down to the bottom.
My Freelance Writer Monday
Stop by the local hairdresser; I have an agreement with her to pick up the stack of aging magazines in her waiting area.
Run to the library to get more magazines. The librarian told me that my husband and I accounted for 25% of the library’s magazine circulation!
While I’m at the library, copy down business info from a huge set of business directories. You aren’t allowed to check these out, so I have to either photocopy the entries (at 10 cents per page) or sit there and copy them out by hand!
Also at the library, do some research for an assigned article.
My Freelance Writer Tuesday
Go door-to-door in our apartment complex. A handful of neighbors have agreed to leave their old magazines on their doorsteps for me.
Skim through my pile of magazines for ideas. Jot down the contact info for any magazines I’m interested in pitching.
Go to the bookstore, skim through more magazines, and copy down interesting entries from Writer’s Market. (I’m too cheap at that point to actually buy myself a copy.)
Work on a query letter (pitch) for women’s magazines, using advice from the book Queries and Submissions by Thomas Clark. (Yes, I do the unimaginable—I send the same pitch to multiple markets at once, tweaking as needed.)
My Freelance Writer Wednesday
Add the names I copied from the business directories into Filemaker Pro. Merge them into my copywriting sales letter, which is heavily inspired by the sales letter template in Bob Bly’s Secrets of a Freelance Writer. (Sorry, Bob!)
Read through each letter to make edits as needed; for example, the merge may not have gone smoothly, or I might want to change a few words in a letter to be more relevant for that particular business.
Print out return postcards. These have my address on one side, and the other side has boxes the prospect can check off such as, "I’d like your Information Kit," "Please call me," and "Never write to me again" I rack up an 11% positive response rate!
Set up an assembly line for sales letters: Envelopes, letters, and postcards. Sign, address, and stuff.
Set up an assembly line for requested Information Kits.
My Freelance Writer Thursday
Print out clips (samples of previously published work), put them in order, and staple. File these away for when I need them.
Schedule phone interviews for an assigned trade magazine article.
Write a radio script for a local liquor store. (I won’t break into the women’s magazines until 1999; most of my work right now is for trade magazines and businesses.)
Print out the draft of a trade pub article I wrote yesterday. Go over it with a red pen. Enter the edits into my Word doc.
Print out the new draft and ask my husband to edit it. Enter those edits into the Word doc.
Email the finished article to my editor along with a list of the sources I interviewed, their contact information, and attachments of any backup materials for the fact checker.
My Freelance Writer Friday
Conduct phone interviews with sources with a complicated set-up involving a landline phone, a headset, an analog recorder, a tape cassette, and lots of wires.
Do a database merge for my magazine query. Go over each letter to adjust wording; for example, to change the name of the department I’m pitching or to highlight a more relevant bit of my experience.
Set up an assembly line for the query: lay out the letters, clips, envelopes, and SASEs. (These are Self-Addressed Stamped Envelopes for the editor’s reply; I use them until it becomes commonplace to receive replies by email.) Sign the letters, address and stamp the envelopes, and stuff the right packets into the right envelopes.
Walk down to the post office with an armload of query letters, copywriting sales letters, and Information Kits.
Update my website, which I built using HTML from an instructional manual I found in a phone booth.
The point of all this isn’t "You kids have it so easy today!" In fact, in some ways freelance writing is much harder today than it was then.
Freelance Writing Is Easier Today…But Also Harder
Twenty-five years ago, freelance writing involved much more manual work—like copying, printing, and mailing. I mean, if you’re one of the readers who skipped down to this part of the article because you didn’t want to read about all those tasks—imagine doing all those tasks!
The rules were a lot more stringent, too. Content today often gives a superficial nod to the idea of journalism best practices, but 25 years ago you had to actually practice journalism best practices.
You would never get away with writing an article without doing at least two or three phone interviews.
There were no platforms like HARO or Qwoted where you could put out a request for sources and take your pick from the people who responded. You needed to figure out who were the best people to talk to—not who were the most available people to talk to—and then reach out to them for interviews.
You were expected to send the editor all your research materials.
A fact checker would likely be calling you to ask for more backup.
Editors would come back to you multiple times for additional rounds of revision.
But thanks to all these steps, the manual work, the equipment required, and the rules involved in making a living as a writer—fewer people were trying to do it. Not many people had the stomach to call strangers to ask for interviews, find and read print copies of magazines, or print and mail pitches. Not everyone wanted to (or could) buy a printer, fax machine, or computer. So the pool of competitors was a lot smaller.
Today, you have every tech tool imaginable to help you make a living writing. But because of this, you’re now competing with thousands and thousands of people from all over the globe. Anyone with a computer and an ability to type thinks they can write, and hundreds of "writing gurus" make money telling them that this is true. Even if you’re a great writer, your voice can easily get lost in the crowd.
The tech advances that have done away with so much of the manual work of pitching and writing have also spawned new challenges and expectations:
You need to have at least a basic understanding of SEO.
You’re expected to understand at least one social media platform, including how to write for the platform, what hashtags to use, the best times to post, the best frequency to post, and so on.
Every client has a different tech tool they require you to use—from Slack to complicated Content Management Systems.
Some clients prefer writers who have video editing or graphic design skills.
Since COVID, it seems like every writing client wants to conduct calls over Zoom—meaning you need to get dressed up, organize your background, and make sure the lighting is good.
Instead of spending hours researching, printing, mailing, and so on, you spend hours on the phone with tech support people.
So what does all this mean for you as a freelance writer?
Of all these issues, there are two that stand out as the biggest culprits keeping you from making a living writing. Let’s talk about these challenges, and how looking back to the freelance writing world of the 1990s can help you overcome them.
PROBLEM #1: Writers are trained to believe writing jobs are “out there somewhere.”
Here’s the biggest problem: Writers have been trained to believe that the best freelance writing jobs are out there somewhere, lying around in a forum or on a job board or on social media. And all they have to do is find out where those jobs are hiding and pick them up.
So instead of finding, qualifying, and pitching to great clients, writers get sucked into spending all their time scouring:
Free freelance job boards
Sadly, the clients that pay really well aren’t out there posting job ads on free sites. You’ll rarely see, for example, a Fortune 500 company or a newsstand magazine on Craigslist or a free job board.
Clients on these job sites are usually bottom-feeders looking for the lowest price. Markets that pay well (and are a pleasure to work with) don’t need to place an ad and then wade through 500 poorly written responses from writers looking for a quick gig. Businesses that do this tend to be not only cheap, but dysfunctional as well.
Sites like Upwork and Fiverr are havens for clients looking for cheap writers. Enough has already been written about content mills that I won’t spend a lot of time on them here.
To be fair, there are now similar platforms like Contently that have more of an "agency lite" sort of model. These pay better, but you aren’t likely to consistently earn well because the rates can vary widely—and they still aren’t even close to the top rates a good writer can earn.
The businesses advertising for freelance writers on social media sites are a step up from those that rely on random free job sites…but when you see the poorly written, weirdly aggressive, and clueless comments on these posts you’ll quickly realize you’re in the wrong place.
(That’s not to say good clients don’t search social media looking for writers! Having a professional, updated LinkedIn profile is important. Before I retired, the vast majority of my clients came through LinkedIn because I made that my one social platform…and I worked the heck out of it.)
PROBLEM #2: The “inbound” phenomenon makes writers feel like they don’t need to pitch.
"Inbound" is the strategy of attracting clients to you, meaning you don’t need to find and pitch to them. That’s what all the fuss over SEO is all about: It gets people to come to your website.
There’s nothing at all wrong with inbound marketing, except that it gives shy, scared, rejection-phobe writers an excuse to not put themselves out there.
After all, why reach out to prospects via email, LinkedIn, postal mail, or phone when you can obsessively tweak your website all day? Why risk a rejection when you can spend hours creating a lead magnet instead?
The problem is, inbound marketing is a long game; it can take many, many months to build up your online presence, authority, and reputation enough to start attracting clients to you.
How to Make a Living Writing in 2023 and Beyond…the 1990s Way
The big secret that’s been hidden from you is this: You’ll earn the most, and get the best clients, by doing all the legwork the content mills and job boards say they’re doing for you. And by getting out there instead of waiting for work to come to you.
You know…the way we did it in the 90s!
I’m not going to go in depth on the steps because there is so, so much information you can already find online, in classes, and in books. But in general, you want to:
Define your niche
Instead of picking up whatever dreck is lying around online, you decide who you want to write for. (And yes, you can build up multiple niches over time.)
Pre-qualify businesses or publications in that niche.
Make yourself a list and then do your best to figure out which of these companies can afford to hire you at your (high) rates. How many employees do they have? Do they have funding? What are their profits? This way, you avoid wasting time on businesses that aren’t in a position to hire you.
Develop personalized pitches.
Again, there are whole books and websites devoted to the art of the freelance writing pitch. To learn about magazine pitches, check out my co-authored classic, From Pitch to Published: How to Sell Your Article Ideas to Magazines.
And if I may plug another one of my products: The Brainstorm Buddy App is a fast and inexpensive way to validate your ideas before you pitch them, upping your chances.
Follow up on the pitches.
I’d give it at least a week for businesses, two weeks for magazines. And keep the follow-up short and sweet.
Maintain a professional website and LinkedIn profile.
These are where you’ll send prospects for more information about you in your pitches—and who knows, you may get some inbound clients that way, too.
Do outreach via LinkedIn if you enjoy the platform.
I didn’t just wait around for prospects to come to me on LinkedIn…I signed up for LinkedIn Premium so I could do more searches, connect to more prospects, and send InMails even to people I wasn’t connected with.
Do amazing work.
Once you have a good stable of clients, you want much of your work to come from referrals, referrals, referrals!
Get an Edge Over the Writing Competition with Old-School Tactics
While all the other freelance writers are out there scouring job boards for gigs and writing free ebooks to attract clients, you’ll be making a name for yourself by doing the work these writers won’t do: researching, pitching, following up, and getting the job done right.