By Stella Orange

When I started a writing business ten years ago, I wrote stuff for my clients five days a week. It made me a much more skilled writer.

So years later, when I started teaching self-employed people how to improve their writing, I thought it made sense to teach writing skills.

“Tell us how you write a headline,” my students would ask. “Show us how to write a catchy subject line for an email.” So at first, that’s what I did.

But what I quickly came to realize was that learning skills weren’t actually helping my students connect with, move, and inspire other people in their writing.

For several years, I thought about this. If the act of writing is made up of a bunch of different skills, why wasn’t learning the skills enough? What was I missing?

I thought about how I learned to become a better, more skilled writer. And the truth was, I showed up and wrote.

Sure, I read eight books about writing the specialized persuasive and sales style of writing that I do (called ‘direct response copy’). But after that, my method to get better was to practice everyday.

I realize that does not sound sexy, or particularly novel. But it’s the truth.

Practice is what makes us better at things. It’s what made me a better cook. It’s what made me a better friend. It’s what made me a better athlete.

And practice is what makes us more powerful and fluent communicators, too.

That’s when it occurred to me that my students didn’t need to learn more skills. Instead, what they needed was guidance for how to find that spot within themselves where the words flow from.

Because when we find that spot, we finally relax the white-knuckle death grip on finding the perfect words or having perfect grammar or crafting a textbook perfect headline. Or really, being perfect people. We shift our attention from the spectacle outside us to the universe within. And that, my dear reader, is where the power and magic comes from.

Suspecting I was onto something, I stopped teaching skill-based classes, and started doing something called ‘Shut up and write.’ These were 90-minute group writing sessions, where people around the world showed up on videoconference to silently write together.

At one point, we had people from Israel, Italy, New Zealand, and across Canada and the U.S. writing together, every Monday.

We were all testing my idea that parking your butt in your chair and writing for 90 minutes, then hitting send, post, or publish, could teach a person almost everything they needed to know about improving their writing (and, I’ve been told, a whole lot about grit, showing up, and sticking with it when the gremlin voices inside your head are screaming nasty things). I’ve been sitting and writing with people ever since.

Fast forward to last week. At our group writing session, a luminous and suspiciously wise member told me I needed to start writing again in my journal.

“You need to do what you tell us all to do: show up and write.”

Dammit. It was as if I heard the voice of God herself. So I did what any of us would do if we heard that voice.

I’m now writing again in the mornings. And the cosmic joke is: I’m going through the same stage I talk about with people who write with me.  

“Stage One: Judging what you write as frivolous.”

I remember when another woman started writing regularly with me last year. She reported she felt like a teenage girl writing in her diary. We love you, teenage girls, but this was not meant as a compliment.

An accomplished former high-powered lawyer who saved enough money to retire early, she wanted to recover the color and personality in her writing. It had been drained out of her as a practicing attorney, and she now wanted it back.

When she told me this, my response was: “Get curious about that judge-y voice.” Turn it into a character. And then write a dialogue with it. It’s got a name and a message for you. And if you are curious and ask kindly, it’ll give it to you.

So she started writing to that voice. And lo and behold, the scene shifted. It opened up. She found herself writing about different things, richer things, juicier things.

Right now, I’ve got a hankering for a breakthrough like that.

As I show up each morning and write about seemingly superficial stuff — decorating our house, how I’m feeling, what happened yesterday — I find myself wrinkling my nose.

Geez, *this* is what my conversation with myself is about? Small talk??

But here’s the thing: this is totally normal. And as Emily Dickinson has said, the best way out is through.

We need to keep going. Keep writing. Even get interested in the stuff that strikes us as dumb as a bag of bricks.

Give it our full attention. Get curious about what’s at its core. Heck, write out the nasty, judgmental crud so we can see, witness, and make sense of it.

I know all this. Heck, I teach all of this.

But that doesn’t mean I get a magical shortcut door with a high-speed escalator so I don’t have to go through the experience of it. That’s not how it works.

However, I do know how this story goes:

I show up.

I write banal, uninteresting things.

I relax my knee-jerk reaction to writing banal, uninteresting things.

Something magical happens — the direct result of my showing up, willingness to suck, and trust in the process.

The world cracks open on the page.

The words come through me — and they are wild and generative.

This is the song I sing. This is the song I discovered when I was thirteen, and needed a witness.

And this is the song I forget, then remember, then forget again, in the dance of memory and forgetting.

This is my gift to give to others. (And be with them as they stay the course.)

So: here we go again!


A teacher and advertising writer based in Buffalo, New York, Stella Orange spent a decade having adventures across Japan, the Pacific Northwest, and Montana, and another decade building a popular writing business. She is the creator of Writing Your Way Home, a workshop where people write their stories. Find out more about her work at