Write Substack Subscriber-Worthy Personal Essays

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One writer I was helping grow her Substack asked me if she had to write personal essays on here—as if it’s a requirement. One might think so given the number of writers who come on here to write about themselves. 

But are Substacks that feature personal essays worth subscribing to and paying for? 

The hard truth

As

Anjali Prasertong

writes in “Intuitive Eating Is Not for Everyone,”

Personal essays are a tough sell on Substack. Although shelling out $6 (or more) a month for journalism that brings them fresh reporting or for finance articles that analyze the market for them makes sense, paying that much to read our thoughts, bursts of creative expression, and Facebook-esque stories of our daily lives doesn’t.

So how do we write (often confessional) personal essays in such a way that they

• attract paid subscribers and

• lead to subscriber engagement and subscriber retention?

And all without losing the artistry and intimacy that can make the personal essay one of the most exquisite genres in literature and us feel free and fulfilled as writers? 

The answer isn’t to sit down at the computer and just write. That won’t entice subscribers or help you grow as a writer.

Yes, people are topping the Substack leaderboard who do just that, but most of them attract subscribers because they have one or more of these:

• a five- or six-figure social media following,

• a bestselling book(s),

• literary awards galore, 

• the benefit of being a media darling.

What they’re doing is more of a Hey, my best stuff is in my books and here you can get whatever I’m thinking about and even a few typos.

That isn’t to dismiss these writers. You can get a gazillion subscribers and if you aren’t producing what subscribers want, you won’t keep them. 

But many Substack writers don’t have those advantages. In marketing parlance, most writers are enticing “cold leads,” i.e., people who’ve never heard of them. More privileged writers are dealing primarily with “hot” and “warm” leads. They’re already interested before they subscribe.

The good news

Substack is the land of opportunity, where organic growth is aplenty. Plus, the personal essay is a beautiful form and not self-indulgent when done well. 

Personal essays aren’t “dead,” i.e., people still love them. Yes, they’ve been pronounced dead many times during the past two decades. In 2017 in The New Yorker, Jia Tolentino wrote “the personal-essay boom is over.” But it isn’t. Even the worst versions of the form—i.e., “internet confessionals” that make up what Slate writer Laura Bennett calls “the first-person industrial complex” are very much alive.

(True, personal essays are primarily alive in the blogosphere, where you’ll get little organic traffic, or in literary journals read by ten people. And essay collections rarely lead to book deals or sell. Yes, you can go to an independent press and possibly have a breakout success but only if you write as well as Leslie Jamison,

Esmé Weijun Wang

, and Eula Biss do, which very few people do, and are as brilliant as they are, which very few people are. So put your energy into Substack.)

On Substack, we can create a space for a new kind of personal essay—the Substack personal essay that people want to read and pay for, even from someone without a following or a coterie of devoted readers. 

But how? 

How to write personal essays subscribers want

We have to know the personal essay as a form before we can make it our own and adapt it to Substack. 

The personal essay has been with us for seven centuries and, despite the name, it’s not personal, i.e., not about the writer. It’s always, always about the reader.

The personal essay has its own subgenres. Here are the four most common:

• The classic personal essay considers a topic.

• Argumentative sets out to prove a point.

• Narrative tells a story.

• Lyric stacks images and plays with language and isn’t beholden to meditation, argument, or narrative.

Are these always distinct? No. Can they be blended? Yes. Is it helpful to study them as distinct genres? Absolutely.

Step 1: Know your genre

The classic personal essay

The classic personal essay comes to us via Michel de Montaigne, the sixteenth-century French bureaucrat who retired at thirty-eight to devote himself to writing essays.

Montaigne was interested in the essay of ideas and in tracing the natural pattern of human thought on paper. He called himself an “accidental philosopher.”

Although others dabbled in the form before Montaigne, he is the granddaddy of the personal essay 

Montaigne’s essays circle an idea or topic (idleness, friendship, disability), attempting but never succeeding to define or understand it fully. Essai can be translated into English as to try.

Phillip Lopate defines the Montaigne-style essay here: “The essayist attempts to surround a something—a subject, a mood, a problematic irritation—by coming at it from all angles, wheeling and diving like a hawk, each seemingly digressive spiral actually taking us closer to the heart of the matter.”

Personal essays on Substack fail when they only go this far. They end up indulging in me! my thoughts! my beliefs! and/or “musing.”

The focus should be on the topic, not the writer.

How do we do this on Substack? Read on.

Below is step-by-step guidance on how to write a personal essay, plus examples of personal essays on Substack.

Personal essay prompt & examples

Writing/creating the new Substack personal essay is a process. I want you to start by getting to know the traditional form and how it’s playing out on Substack to get ideas for how to make it your own.

This is really important. Writers read and learn from each other.

The examples below aren’t necessarily “the best” (though some are) but the most illustrative.

During the Write Personal Essays Substack Subscribers Will Pay to Read workshop (replay available!), you’ll get the 6 steps to writing a personal essay with knowledge of the traditional form and how it works best on Substack.

Prompt and examples

Part 1: Understand the traditional form

1. Read at least one of these traditional examples:

• Michele de Montaigne’s “Of Smells”

• Virginia Woolf’s “On Being Ill.”

• Leslie Jamison’s “The Empathy Exams”—it has elements of a narrative essay but read it as a meditative/classic personal essay

2. Notice what the essay does:

• How does it meditate on a topic? This topic might be

  • an abstract concept (empathy) or

  • a human experience (smelling, being ill).

  You can also write on

  • a custom (wearing clothes) or

  • a cultural phenom (celebrity).

• Notice the philosophical approach to the topic: What is illness/empathy/smelling? Why does it exist? What does it do for us? This can be humorous too: What would an alien think if it saw this?

• How does the essay circle around the topic? The point is to try—try to get at it but never quite arrive.

• How does it “conclude”—or does it?

3. Go on to part 2.

Part 2: Get a sense of how that might need to change for Substack readers

1. Read

   rayne fisher-quann
   ’s “suffering mix” (warning: like a handful of writers on Substack, she doesn’t use capital letters, which pains me to no end and though I realize it’s a thing, my love of punctuation runs deep)

• What differences do you notice between what she’s doing and the more traditional forms?

• What similarities?

I love reading your comments. Don’t feel you need to comment on the prompt.

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For more, paid subscribers get access to my Write Subscriber-Worthy Personal Essays Workshop:

Write Subscriber-Worthy Personal Essays

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Other people just tell you how Substack works; I guide you to make Substack work for you. Become a paid subscriber to get access to my full Substack Accelerator Framework. All strategy. No hype.

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