How the Hell Is Anyone Over 40 Supposed to Make a Living As a Freelance Writer?

At one of the first press junkets I attended after quitting my full-time government job to become a freelance writer, one of my editors turned to me and said, “I really have no idea how freelancers who write for our publication make a living.”

Now he tells me.

Actually, he told me that back in 1994. Before Wikipedia. Before Google. Before Wi-Fi. Hell, before broadband cable. Before cheap cell phones. And in the middle of what I guess we might call the Golden Age of Magazines.

What was it like back then? Well, if you got an assignment, chances are it paid a dollar a word. Maybe even more, if you were assigned stories in the feature well of A-list magazines like Esquire, Vanity Fair, or Travel + Leisure.

Nowadays, long after the Golden Age of Magazines lost its luster, all of these publishers have massive digital properties and thinner print versions. And even though both are run by the same company, the work is very different on each medium. Esquire, the print property, and Esquire.com are worlds apart. I talked to a veteran writer who pitched a story to Esquire.com and was offered a $100 for 1400 words. The editor told him, “If it makes you feel any better, Tom Junod could walk through the door and I could still only offer him a hundred bucks.” That didn’t make my friend feel any better, but he took the story anyway.

Another former online editor explained that “most of the contributors to Outside would be horrified at how poorly our online division pays.”

For me, my foray into freelancing online started quite promising, in retrospect. The first digital piece I ever published came thanks to a Canadian editor who had landed a job at Wired during the first tech boom. Looking back, things were much better in 1998 than they are in 2015.

My friend at Wired told me that the magazine was going to roll out a “website version” of the magazine, though at this time, websites really were still in their infancy. The writing had to be short—really short, factually correct, and, of course, clever.

“This is like radio,” he said. “It has to make an immediate impression. A lot of people won’t read beyond the first two or three sentences.”

Even more curious was his choice of topic: folding bicycles. Between 300 and 400 words. The editor told me he couldn’t pay quite as much as the print side, but that I shouldn’t worry, because the piece wouldn’t take long to write.

I was a bit puzzled. Wired was about digital culture; folding bikes are about as analog as audiophile vinyl. Still, the pay was pretty good, somewhere in the range of $300 for 400 words. The structure was obviously new at the time, but the rate was at least somewhere in the same area code as a print byline.

Two (or is it three?) recessions later, and those early days seem to have been a kind of high-water mark. Digital editors were often folks who’d been employed in print and relied on magazine writers to file short pieces. Decades later, these publishers still haven’t figured out how to monetize their websites effectively. J-schools continue to pump out grads, and bloggers, though they may lack journalistic polish, can bring expertise to their specialities that some writers with polish will never have. That’s a confusing food chain, and for someone who has been freelancing for almost 20 years, the current infrastructure makes me feel like I’m just treading water.

Is freelancing now just a young man’s game? The huge swings of acceptance and rejection, the lack of stability, the low(er) pay. Sure, there are exceptions, veteran freelancers who have managed to turn their careers into thriving businesses, but for most, it seems the system is set up as a minor league of sorts—a place where writers can get experience that might lead to editor or strategist positions down the line. For someone who is already a bit farther down the line, those prospects don’t sound so appealing.

I’m pessimistic most days about the ridiculous amount of content that is produced on the web, and since I wasn’t born rich and didn’t marry into money, this online (and now mobile) world stinks pretty badly. Earlier this week, I pitched the digital side of an A-list print mag that immediately accepted my story, and, although the pay is $175 for 600 words, I was actually glad to get the work.

I still advise neophyte writers to “live the dream.” Just make sure you know where you are when you wake up.

The Freelance Strategist is a daily publication for and by freelance creative workers navigating today’s changing employment landscape. Brought to you by Contently.

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