☕️The Caffeinated Writer

☕️The Caffeinated Writer

Publishing

Some Thoughts After Four Years on Substack

The post that keeps my newsletter afloat, and the writers who had me at hello

Michelle Richmond's avatar
Michelle Richmond
Jul 31, 2026
∙ Paid
kayaking at the Russian River, Monte Rio, California

I first started writing on Substack in 2022. I maintain four newsletters here, including a flash fiction magazine, an author newsletter, a travel newsletter, and this educational Substack about writing and publishing. Over the years, I’ve made new Substack friends and found books by writers who weren’t on my radar before. Substack has changed the way I write and the way I read.

In the morning, after pouring my first cup of coffee, instead of turning to the news, I browse my Substack feed to find new long form posts by individual writers. It’s a calmer way to begin the morning—not a way of tuning out, but of tuning in to personal stories that take me to different cities, into bookshops and parks and people’s homes.

Most of the time I spend on Substack is spent reading. But it has become my home for writing too, a kind of working notebook, where I keep drafts of stories and essays, notes on future novels, fragments of lectures for my writing classes.

After writing hundreds of posts, I’ve been surprised by which posts resonate with readers, which posts lead to new subscribers, and how subscribers find their way to my newsletters. I’ve also discovered best practices for the paywall. So in this post, I’ll share what I’ve learned.

Personal stories bring readers into your world

Getting personal works incredibly well on Substack. I’ve subscribed to many Substacks because of a single, personal post. One of my first subscriptions was to Eleanor Anstruther, whose voice is so compelling, particularly in the series A Memoir in 65 Postcards, I wanted to hear more of what she had to say. The same is true for Emily Monaco of Emily in France. I was missing Paris, where I used to live, when I stumbled upon Emily’s post How Did I Get Here? I appreciated the honesty of this line:

And then, somewhere along the way, life got in the way of my imagination. I put it in a corner for safekeeping and forgot it there; I let it gather dust.

Sometimes, one post—even one sentence—is all it takes to make readers want to know you better and come along for the ride. When you share something meaningful about your life and your experience, you are building a relationship with your readers. They begin to hear your voice—your unique way of putting a sentence together, your way of observing and understanding the world.

One post on my author newsletter that seemed to resonate with readers is Notes on a Marriage by Way of Joan Didion. It’s an odd little essay I wrote about looking for a book in my house. Touching on marriage, my personal penchant for losing things, and, of course, Joan Didion, the post offers nothing in the way of information—it is just a postcard from my life. But for some reason, the post found its people—which is to say it helped me find my readers.

One of the most surprising things about this post is how people found it: not through Substack, but by googling “Joan Didion Marriage.” And even though they were looking for Joan Didion, and instead found a writer they’d never heard of, rambling on about losing a book one morning, many of them decided to subscribe anyway.

It can be difficult to let down your guard in such a public space. It certainly is for me. But opening up—in a way that feels comfortable to you—doesn’t just bring “subscribers.” It brings readers. People who truly want to hear what you have to say.

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