🎧 Write Substack Subscriber-Worthy Personal Essays
The accompanying workshop is Workshop: Write Personal Essays Substack Subscribers Will Pay to Read. It could be the best yet.
Should Substack subscribers pay for your personal essays?
🎧 Listen to the podcast version:
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
Aswrites 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 other hard truth
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,, 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.
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.
I’ll go over all four in this series and accompanying workshops, but today we focus on the classic personal essay (meditative) and go deep into how it works best on Substack in the Write Personal Essays Substack Subscribers Will Pay to Read workshop (replay available!).
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.”
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.
Step-by-step guidance on how to write a personal essay and examples are below.
As a paid subscriber, you get the full Substack Writing Series to deepen your writing, monthly Substack workshops, access to the incredible Headline Help chat, and the full archive of must-read posts to help you succeed on Substack.