Writing Every Day: You Think It’s Easy? Try it

It will break you or make you, and I’m not talking about money.

It’s up there with completing a marathon or raising a teenager. I’ve done both, so I know the challenge of producing a piece of readable prose for daily publication.

Cliches about careful what you ask for apply when you commit to writing every day. And that’s true whether you embark on a novel or a blog post on Medium. When you monetize your writing, and people are waiting for your work, you enter a special corner of hell. The late Herb Caen, San Francisco’s daily columnist, used to say this about writing: It’s easy. I just slit my wrist each morning and bleed all over the page.

I’ve been writing for almost fifty years. More than twenty-five years ago, I corralled my reckless stop and start habits into a daily writing practice. When I decided to write for Medium, I buffed my nails on my lapel and said stand back. I got this.

But as I learned years ago at Trial and Error U, life is nothing if not a lesson in humility.

It’s one thing to sit down and type out 2k words of useless scenes every day to keep up an unbroken streak of writing no one may ever see. It’s quite another feat to publish half-way readable prose on demand as though your life depends on it. Because it does.

Why is writing so hard?

Tom Jenks, one of my teachers who also edited the best writers in twentieth-century letters: think Jennifer Egan, said the truest thing I’ve heard about writing. He sits down every day to face his shortcomings. Who wouldn’t welcome a boatload of that kind of humiliation on a daily basis?

When I heard him say that in class one night, I could see myself sobbing over a paragraph or a page that I believed revealed my flaws not just as a writer but as a human being. How worthless must I be to produce sentences so wanting in meaning and power, I’d think.

My work often feels like an extension of my body. Any criticism of it can flay my skin from the bone. My harshest critic lives inside my head (it’s true for all of us; I’m not a special princess). So I always subjected myself to relentless beatings of my spirit and confidence over craft, subject matter, or the issue of where I got the audacity even to consider myself a writer in the first place. As though the right to put words on paper was issued by an authority too august to consider someone as lowly as me.

Oh, you want melodrama? I got melodrama.

I have a handwoven shawl given to me around the time I took my first writing class when I lived in Mendocino, California. One evening a week I would produce two pages of fiction for a class held at the adult extension of the local junior college. I wore that shawl to keep me warm for sure. Because of the nature of the gift, it was my most beloved possession. But it also served another purpose when it was my turn to read my story.

I pulled it tight around me as I read my two pages to hide my shaking hands, hoping nobody would notice how nervous I was, how inferior I felt to the task.

And even though I had published a cookbook and been interviewed on TV, radio, and newspapers at that point, I beat myself with any available club before I had the confidence to call myself a writer.

I worked on the craft, learned how to write in spite of the howls of derision from my inner critic. In time, I became a writer, a teacher of writers and an editor.

Forty years later, with more published books under my belt, the only thing that flummoxed me about publishing on Medium was setting up my Stripe account. What did I know?

The first few weeks I wrote when inspiration hit me. I had other gigs. Writing my books and editing for clients. But when my first article got curated, and I started to make money, at least enough to squeak into the 7% club, I had to take this platform seriously.

In due time, that meant publishing every day. I can do that, dancing backward in my orthopedic shoes, I thought. Look how long I’ve been writing.

Enthusiasm and dollar signs can carry you a long way down the road. But eventually, you have to catch a breath. After I made a commitment to myself to take Medium seriously and publish an article every day, writing took on another aspect. Fears I thought I had conquered raised their ugly heads again.

I came to Medium as a literary writer, meaning I aspired to a style of writing that, on a good day, I achieved with relentless editing and polishing until my pages had a high sheen, or at least until they were as good as I could make them. I didn’t have a publisher waiting for my jewels, so time wasn’t a factor in finishing a chapter or a book.

But if you want to publish every day, especially if you are me, you have to write a level of prose that has clarity and cohesion by 9 am. You need to get it published early in hopes of getting it in a decent publication, maybe curated, marketed while most of the world is still awake to read it. None of that will happen if you’re still worrying over whether to use red or crimson to describe a dress at 4 pm, the cutoff for the daily earnings in your time zone.

Even after you’ve manhandled your perfectionist tendencies to the ground, the pride and joy of your writing for half your life, and learned to say “it’s good enough” most days, what do you do about coming up with content every day?

You’ve learned to churn out 1500 words in 45 minutes. But these aren’t practice words to see if they’ll fit in your book. These words have to make sense. They have to be about something. They have to fit what your readers are looking for if you can even figure out what that is, while not losing your soul to your stats.

You have to make something about nothing every single day. And some days, god love you, you find yourself writing nothing about nothing.

But you do it. I do it. We do it, those of us who have targeted a number here on Medium at least. We’ll write one article a day, or 45 posts a month, or we’ll publish 10 times a week or whatever punishment we level at ourselves.

For those of us who are writers in our bones, it seems like paradise at first. The chance to actually write for readers every single day. Until it seems like a job, like every other thing we have to do that’s drudgery, that soul-searing.

Those are the days when our imagination fails us. Well, I can’t speak for you. It’s when my imagination fails me. There isn’t a day I don’t love writing — when I have something to write about.

Coming up with a thousand well-chosen words when my brain has shut down is brutal, though. As Tom Jenks used to say, it makes me face my shortcomings.

What am I, if I’m not a writer. And if I have nothing to say, how can I say I’m a writer? That’s the gaslighting in my head.

I’ve been at this long enough now so that at least I don’t go into full-on torture mode for very long. My entire self-worth no longer depends on producing a good article every day, though it will get bruised.

I’m smart enough to recognize when the well has run dry, and the pump needs priming. A nap can help, going for a walk, or cleaning my apartment, or just stabbing the keys until I have a breakthrough with a few words that spark an idea. Something, anything.

But I do these things knowing that I’m toying with my muse, pretending I don’t have writing on my mind at all so she’ll do her thing and slip an idea into my brain when she thinks I’m not looking. And then, yay me. It worked, and I’m back at it. I’m milking the idea and writing my article, or two, or even, though rarely, three articles in a day.

The really bad days are when I sit down with my coffee at 6 or 7 am and look at my computer and just want to knit. Or read a book or watch a movie. Anything but write. That happens so rarely, it shocks me when it occurs, but then I realize it’s a hill I have to climb that morning to get back to where I love to be: banging out an article, seeing ideas take shape on the page, coming up with snarky dialogue in my head, lost in my world of words.

I always come back from that edge, but there is a moment of terror when I think, is this it? Is it over for me? Have I lost the ability to create a sentence, a thought, an image with words?

I forget that this fear has haunted me since I first began writing. That this thing that I love, that I’ve worked so hard to learn and master will dissolve. That I only have so many stories, so many words, and I’ve used them up.

It goes away this time, and I sink back into my identity again. My comfort place in the land of stories and ideas and language. But suppose the day comes and I don’t. I can’t. Who will I be if I can’t write?

I’m an editor and writer on Medium with Top Writer status. I’m also an editor for the publication, Rogues Gallery. I’ve published 55 titles on Amazon and edit for private clients. If you’d like to hire me as your editor for fiction, non-fiction, or business writing, please contact me here. If you’d like to read more of my work on Medium, click here to sign up for my newsletter. I’ll make sure you don’t miss a word. Thank you for reading.