Do You Want to Monetize That?

My Love-Hate Relationship with Writing for Cash

Photo by Sharon McCutcheon on Unsplash

I’m an old writer.

My oldest stories, which I still have in a banker’s box on the top shelf in my basement, are written in striving cursive on blue-lined manilla paper that is more than a half century old. My fifth-grade teacher has written “great story” in red ink next to a gold star at the top.

In the next box over on the basement shelf are 3 x 5 floppy disks that back up the typed manuscripts that back up the tall stack of yellowed newspaper clippings of stories I wrote for a Boston rag when I was 25. I got paid $30 a story.

The box next to that one contains 300 pages of manuscript and file folder after file folder of notes and drafts for a memoir I wrote over six years of self-employment in my 30s, punctuated by grant-funded writing retreats in sort-of prestigious studios and colonies, and then never sent to the agent I never got.

Two decades and one career as a teacher-turned-writer-for-a-nonprofit later, I got POWW’d, which my also-laid off colleague tells me stands for “Purge of the Old White Women.”

At almost 60, I’m self-employed again, which is to say, unemployed—and posing as a freelance writer.

So far it’s an awkward dance around what is both a new gig and an old side hustle. You know how at any diner you can order just sides? That’s what I’m living on these days: coleslaw and baked beans, fried apples and fries. I now have all the time in the world for penning essays and poems for the occasional peanut of publication. Except I have the little problem of no income.

For a little perspective, I call up my 31-year-old friend who got a lucky pitch as a freelancer and landed a softball job writing credit card reviews for a New York digital mag. To me that sounds as futile and boring as drinking water from a shot glass, but, hey, she’s getting paid.

“What are you writing these days?” She asks me, with a dollop of pity in her voice.

Hesitantly — now the tables are turned . . . I’m remembering when I was the wise, ’em, salaried, writer in our conversation — I explain that I have some story pitches in mind. “But mostly I’m just writing personal essays on Medium,” I say. It’s a habit that both gets me through and wrings me out, like the eight cups of coffee I start the day with, exhilarating and exhausting at the same time.

Her mouth, which is to say, her voice, doesn’t move. I can sense that she’s pursing her lips and staring out her New York window into the brick wall six feet away.

Finally, impatiently, she asks the perennial millennial question: “Do you want to monetize that?”

And all the feelings immediately start to gurgle in my gut.

Chagrin: I don’t write for money! I write to express myself. I write to make meaning. I write because I breathe.

Self-loathing: This is why I am poor, because I never ask about the money. I never think about the money. I’m not sure I’m worth the money. The words “Money” and “Writing” are in different volumes of my life encyclopedia.

Disdain: This is what’s wrong with X, Y, and Z. Every story is now a “campaign.” They get their choicest words from Youtube videos and FB ads instead of books. They scoff at the blank page because it has no brand. The prospectus they prepare for the agent they don’t have is bulleted with strategic messaging to leverage sales, convert loyalty, and optimize the customer journey.

Surprise: You mean, you can make money from pain, joy, and insight? Tressie Cottom just got a McArthur, for God’s sake. Ross Gay scored a Guggenheim. Emilie Pine jumped from academia to the grocery store book aisle. Maybe if I become a regular with Tara Mohr and start Playing Big, build a website, scale my community, and amplify my followers, someone will hear me on the other end of this sales funnel we call the Internet.

Skepticism: It’s called Medium for a reason. It’s not called Excellent or Hot or Outstanding. If this fortune teller channel is channeling our fortunes, the best most writers can hope for is average, middling, mediocre. After all, anyone can write on Medium (and does). It’s a forum designed for imposters like me.

And finally, curiosity. I look up the word “monetize.

Despite the tell-tale modern suffix, it’s been kicking around since the 19th century as a banking term and only recently has wriggled its slippery self into the buzzy lexicon of marketing and entertainment. We writers know that words sustain us. We eat them for breakfast. We roll them around on our tongues, savoring the tart metaphor, the sweet image. We share them with our friends — a potluck of poetry, epiphany, and promise. We remember them like grandma’s cinnamon rolls or Aunt Betty’s latkes, a taste we have known all our lives, prepared by the people we’ve loved since we first learned to speak.

The problem is our words don’t pay the mortgage, buy groceries, or fill the tax coffers. They don’t transact. And as tasty as words are, we need to buy actual potatoes too. So we have to invent ways to turn this non-revenue generating item into cold cash.

What does that mean for me, an old writer with no steady pay check? For now I’m going to keep writing on Medium just for the jolt it sends through my veins, for the wake-up call of self-understanding. In the 1970s gameshow The Price Is Right, Bob Barker would call that Door Number One—anonymous, predictable, but satisfying.

Off Medium, I may pick door number 2 or door number 3, the ones with sparkly dollar signs on them, making a bid for the big prize by monetizing my soul. When the price is right . . .

Writer. Taking a leap.