7 Questions Medium Writers Should Ask Themselves

Even If They Don’t Want to Hear The Answers

What if the job you once did for a living…

…morphed into something else — like a lamplighter after cities installed electric lights, a blacksmith after cars caught on, a milkman?

I face such a reality every day. When I first got into publishing, I composed on paper or on a typewriter — and my words were put into printed age using linotype and ink.

Thankfully, I can still practice my craft. I am not obsolete. Writing (I pray!) will always be essential to human existence — an art as much as a tool.

Writing is still writing, but the job has changed. At risk of sounding like an old curmudgeon, I miss the brick-and-mortar magazine and book publishers — their offices, their libraries and staffs, their editors. Now, I’m pretty much on my own.

In truth, writing in the good old days wasn’t easy either. As my Aunt Ruth often reminded me, “Honey, you’ve chosen the hardest profession.” Her words still ring true.

Margaret Atwood put it this way in 2010:

Writing is work. It’s also gambling. You don’t get a pension plan. Other people can help you a bit, but ­essentially you’re on your own. ­Nobody is making you do this: you chose it, so don’t whine.

Now there’s more to whine about — and more to question..

As an Old School journalist writing online, I often wonder the best way to approach the perils of online publishing. Here are just six of the questions I ask myself, over and over…

1. Should I write for a platform other than Medium?

While I don’t spend a lot of time obsessing about this, a Medium article like “Don’t Be Stupid — Post Your Words on More Than One Platform,” sends me down the rabbit hole. The author, David B. Clear, claims that that “platform promiscuity” is the way to go — just “repurpose” my old stuff. Gain greater exposure and maybe make more than the $6.29 I earned on Medium so far in November.

The article nudges me — for the umpteenth time — to check out Quora, Substack, and NewsBreak, big platforms, each with different angles and reputations. Googling further, I discover more possibilities in articles like “54 Writing Platforms That Pay.“

I want to go back to bed. But I write this piece instead, testing out the ideas first on my blog — despite all those articles that warn me not to “waste time” on my own website. Then, as per Mr. Clear’s advice, I adapt it to Medium.

2. Should I have been more diligent these many years about collecting my readers’ emails?

Too late for me, I conclude. I’ve been remiss. But thank YOU, dear reader, if you’ve “subscribed” to me!

So why am I still asking the question? Because I’ve just received another offer promising to teach me how to do it. The “expert” is a writer with a huge following who already has my email address. He wants me to follow the bread crumbs he left on the way to his fortune.

The new paradigm for writers is all about creating a community. I love that, and I want in. I love people, love to exchange ideas. It makes sense to collect emails.

In the old days, I could only meet readers on book tours and through the occasional letter (remember those?). I cherished fan mail.

Now everyone in the world is a potential reader — clearly, way beyond Dunbar’s number of 150, which, supposedly, is how many people we can “know.”

Ugh. I didn’t sign up for this. Apparently, it takes a database to raise a village.

3. Should I ask readers to pay?

On one hand, I wonder, how different am I than the clochard on my street in Paris, who sits on the ground outside the bakery with a tin cup?

On the other hand, I’m not just sitting here. Even a piece like this takes a day. Some take several, others more than a week. I’m already asking readers to become a member of Medium, so that I might earn 50% of that whopping $5/a month fee (see below). Should I be doing more?

Some writers charge subscription fees to augment their income. They cut out the middleman. Others go the crowd-sourcing route.

If you like what I wrote, you can tip me directly, instead of my having to wait for this platform’s algorithm to reward me…

Okay, I’m exaggerating; they don’t spell it out quite that way. And who am I to poke fun? This is our livelihood. I do not judge struggling wordsmiths who add, “buy me a cup of coffee” at the end of each piece they write, linking the request to KoFi, BuyMeACoffee, or Patreon.

But….a cup of coffee? Really? I finally found an article in which one writer says that through one or more of those sites, he made “a few dollars every now and then.” Is it worth the time it takes to read the fine print on the crowd-sourcing sites and give out my bank information? I don’t think so.

4. Should I be writing MORE?

OMG! If I read another article urging me to be more “productive,” to make writing a part of every day, to rise to the 30-day challenge…I’m going to scream.

Perhaps this is my inner old coot, kicking and screaming because all those young whippersnappers out there keep churning out article after article.

Similarly annoying are writers who recommend their “system.” Write only in the morning when your mind is fresh. Write only in the evening when everyone else has gone to bed. Outline five articles on Monday, write three on Tuesday, two on Wednesday, go dancing on Thursday, and then devote the rest of the week to editing. No, wait! Take Sunday off to be with your loved ones. You’re spending waaay too much time on editing. It’s never going to be perfect.

Actually, that’s the only valid point: There’s always a point when you have to stop.

I know the old days are gone. But I come from a tradition of journalism. Many of my articles were inspired by real-life moments — like the time I spotted a personal ad in the back of New York magazine, placed by a dominatrix — but I had to work to turn it into a cover story.

I immediately called my editor. Turns out, the magazine had just received an invitation to the Black and Blue Ball.

“I think there’s something here I should investigate,” I said, and she agreed.

Some of my best articles, including “Mean Sex: S & M Culture Goes Mainstream, took months, not days. I interviewed the now-retired Mistress Ava, who placed the ad, as well as dominatrix wannabes and the “submissives” who loved them. I attended a meeting of the Eulenspiegel Society and visited the Vault, a club in Manhattan. It takes time to write a piece like that — to research, reflect, synthesize.

Sure, I can dash something off. Recently, a fellow journalist complimented me on my thank-you email after I was featured on his podcast: “That was one of the best emails I’ve ever received. You are the queen of connection.”

Here’s my opinion: Writers are like snowflakes. Each of us is different. Some are sprinters, rushing to a close finish line; others pace ourselves, like marathon runners. Some writers go in with a clear vision — an outline suggests itself. Others are like sculptors, working with stone, gradually chipping away, until the masterpiece becomes clear.

Each of us develops our own path to the finish line. Even when it’s a painful run, it’s familiar; it feels right. If I try to be someone else, I am no one.

5. Should I stick to ONE niche?

“They” say I should. It’s how readers get to know you and trust you. You become their go-to person when they need information or advice. Even better, write several articles a day on that subject, so they can’t live without you. Once you have gaggles of followers and fans Googling your work, you become an “influencer” — the Go-To-in-Chief.

My problem — although it feels more like a gift — is that I’m interested in many things. The vast majority of my work is about relationships, family, and social phenomena, but as Peggy Lee famously sang in 1969, “Is That All There Is?“

I once wrote an article about home schooling, even though I had no interest in the subject. Going in, I knew next to nothing and assumed home-schooling parents would be weird and radical. But it was an assignment; I did my job. To my surprise, I genuinely liked some of the interviewees, and the piece was different from what I’d imagined. Discovery never disappoints.

Why deprive myself of such surprises now? Today, with no assignments, few editors, and scant guidelines, I’m free to explore and, thankfully, I’m still curious. I love finding new ideas, mining new worlds. I’ve paid my dues and have nothing to prove. Damn it! I can write about anything I want.

6. Should I do more to support other writers?

This is part of that “community” issue. In the old days, I had real-life friends who happened to be writers. I read their work, sometimes offered comments and editorial help, but this was never part of a necessary exchange, as is often implied in Medium articles: In addition to writing well, formatting so it’s readable, picking the right title and the right tags, finding a great image, you ALSO need to acknowledge other writers. One publication builds this into its submission guidelines.

At the other extreme are writers who say enough!

I fall somewhere in between. I sometimes mention pieces I like. I once included a list of writers I respect at the end of a piece. But I do it when it’s relevant. I enjoy the back-and-forth in the comments when that happens. And if we become email pals, so much the better.

I’ve encountered a handful of writers on Medium whose “voice” I adore. For a while I tried to keep track, but then I decided to play it like real life: when exchanges between us accumulate I trust that I’ll naturally recognize certain names and will more likely read and reach out to those writers.

There’s just so much to remember, so much to do! Which brings me to the question that plagues me most:

7. Should I be doing more to “market” myself?

A writer today can’t just write. Sure we always needed connections — my first introduction to a major magazine was through a woman who worked for me in education publishing and then segued into journalism.

So yes, we always needed a foot in the door — and, of course, skill. But most of all, we needed luck.

I was fortunate to have as my first editor, a man who was willing to nurse me through four painful drafts of my first piece. If I had had another less patient and less generous editor (I would later encounter many!), my trajectory as a journalist might have been different.

In the print era, editors edited, and fact-checkers made sure you got it right. Others wrote the headlines and chose the best images. No wonder I now struggle to write a “catchy” title and, even more so, to learn the tools that sometime bedevil me, like search engine optimization.

Perhaps it has been a mistake to skip those free tutorials. I’ve been on Hoot Suite for years and still know only the basics. A twentysomething taught me hashtags, but I’m not sure I learned.

I worry, but I am still winging it when it comes to social media and SEO. Maybe I need to come up with a more ambitious and consistent plan and actually execute said plan?

I’m tempted, sometimes, to sign up with one of those writer/marketing experts who promises to reveal the “secrets” that elude me. I probably won’t. I’ve watched several of their YouTube videos. I take notes. But I’m reluctant to actually do what they recommend.

Instead, I harbor a recurrent rescue fantasy:

A friend calls to say, “I have a wonderful, knowledgeable person who’s willing to market your work for you. All you have to do is write.”

The only question I don’t ask myself…

The only question I don’t ask is, “Why am I still writing?” I don’t need to write. I’ve written or co-written 15 books and stopped counting articles at “over 200” — a number that now sounds low compared to online writers who churn out twice that many in a year. Still, I can’t stop myself from trying to reach people with my words.

I write because it is who I am and what I do. As I say in this recent Medium story…

Sometimes, I falter; I hit the net and lose time. I start over. But the court is where I am my most comfortable and happiest me. It’s a good struggle, because I know that eventually I’ll get it.

Writing Is Not Publishing

And there’s the rub. Do-it-yourself publishing is the proverbial foot in the door for everyone: retirees who always wanted to write, taxicab drivers who swear they have a great story, and bloggers of all sorts. Among them are a handful of gifted writers who might not have otherwise had a chance.

But hasn’t that always been true? Some great writers only write for themselves, maybe their friends. My friend Margaret is one such writer, and I’ve been urging her to join Medium.

But the so-called democratization of writing doesn’t mean that Margaret or other gifted writers will necessarily be read. For all the changes of the last two decades, “publishing” is still as difficult as another Margaret (Atwood) describes:

Publishing a book is like stuffing a note into a bottle and hurling it into the sea. Some bottles drown, some come safe to land, where the notes are read and then possibly cherished, or else misinterpreted, or else understood all too well by those who hate the message. You never know who your readers might be.

Atwood’s quote routinely appears on sites offering advice and coaching to new writers. I tried to find the source. Since Atwood writes mostly fiction, my best guess is that it’s from Writing with Intent: Essays, Reviews, Personal Prose 1983–2005 — in other words, before publishing migrated online.

What Atwood described 16 years ago is even truer today. The number of writers has grown exponentially, although it gets tricky when you actually try to count them. According to the website Statista,

In 2020, there were over 44.2 thousand writers and authors working in the United States, down very slightly from the previous year but still markedly higher than the figure recorded back in 2011. Many changes have occurred for employees in this sector over the last few years, and it is a truth universally acknowledged that writing for a living is no mean feat.

That’s book writers. Those numbers double or triple when you factor in everyone who sends words out to the universe through blogs, tweets, and posts. On Medium alone, J. J. Pryor estimated in 2020 that approximately 175,000 writers contribute stories.

In short, an unprecedented — and, most likely, incalculable — number of writers are publishing online! Making matters worse, in the last two decades, our attention spans have shrunk.

So Why Write If You’re Not Going to Be Read?

For that answer, I leave you with this quote from Anne Lamott, a deep thinker, a humorist, and a fabulous writer:

I still encourage anyone who feels at all compelled to write to do so. I just try to warn people who hope to get published that publication is not all it is cracked up to be. But writing is. Writing has so much to give, so much to teach, so many surprises. That thing you had to force yourself to do — the actual act of writing — turns out to be the best part. It’s like discovering that while you thought you needed the tea ceremony for the caffeine, what you really needed was the tea ceremony. The act of writing turns out to be its own reward.

In the comments section, please…

Writers: I would love to hear your questions and your answers. Both as a writer and as a reader. What frustrates you? thrills you?

Readers: What does this new world look like from your perspective? Do you “follow” certain writers? Or, do you read a piece because of the title catches your eye? Do you think writers should ask you to pay to read them? Better yet, what makes you willing to pay?

Also a shout out to Tessa Schlesinger, a fellow veteran and a prolific writer, for her brutal honesty — and good advice — regarding our craft. (Tessa, I’m not posting this so that you’ll mention me!):

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