Thank you Tarra, Renee - Itsbooktalk & More, Kirsten K. Shockey, Mary Roblyn, Magdalena Ponurska, Marie-Elizabeth Mali, and 200 others for tuning into our latest Substack Live.
Here’s an overview of what we discussed—with examples, thanks to Substack giving us the ability to screenshare on lives (!).
The main takeaway: writing on Substack is its own genre, and we don’t talk about it enough. I teach the Craft of Writing on Substack because it fascinates me—how we’re writing in a whole new way on here. Kind of journalism but also essays and blogposts and newsletters and…
Substack has changed the media, publishing, and creative landscape and brought us this new form we use to reach readers in three places at once: on the web, in email, and on the app. That makes it very challenging.
On the live, I show you how to check where you’re actually being read:
Go to any post (ideally one that’s more than two weeks old), click on Reach, and scroll to How readers found your post. You might be surprised. My posts are read 97% in email — and I teach people who are on Substack. Some clients are 50-50 email to app. The point is: know where your readers are so you can write for how they’re encountering your posts and know that it might change as more of us are read in the app.
Experience how your subscribers encounter your post:
Send yourself a test email. You can preview your posts on mobile, desktop, and email. You get to experience your post the way your subscribers do. Sometimes a headline sounds different in email than it does on the page.
Create a familiar, consistent post structure.
Four years ago, we wanted variety. Now, with so many Substacks and so much email marketing, we want to be familiar. When I get a post, I want to know what I’m getting.
Ashley Neese (The Deeper Call) always opens the same way: a welcome message, a photo, “dear friends,” and then clear language about what’s below the paywall. Her posts look the same every time, and that’s what makes me excited to get them.
Austin Kleon has done this forever: image, “hey y’all,” 10 things worth sharing, a surprise link, XOXO, a P.S. Always the same structure. Learn from people who’ve been doing these things forever.
Leslie Stevens (Morning Person) always has her banner, three recommendations, a photo, her essay, and something below the paywall. She’s been doing this for 10 years. That familiarity is part of why it works.
Always tell readers what’s below the paywall
We don’t know unless you tell us. If you just have a paywall with nothing after it, a reader on the app might think the post is over. Use italics, a quote, or a block quote — something that signals there’s more.
Your first sentence matters —make it about them
When you open with “me me me,” it can backfire — unless it’s an experience your reader can relate to. You can get away with all the “me me me” in the world if you’re opening on a moment others recognize.
Should you open with an image?
Two years ago I was telling people no images, it’s email. But email marketing has become what people are used to seeing, so I’m moving back toward images — with a caveat.
Great images are amazing. Generic stock photos are the surest way to devalue your writing. If you’re going to use an image, make it relate to the post. Use images as stepping stones to move readers through.
Use your own photos when you can. Subscribers want you, not your Substack. A photo you took is always better than one someone else created.
For sourcing images: the Noun Project ($3.99 subscription, images done by artists), WikiArt, the Getty Museum, and the Metropolitan Museum’s open-source collection all have actual artwork you can use.
If your post is hitting “too long for email,” compress your images. Google “image compressor,” drag and drop, and the file size shrinks significantly.
For free image sites: many say non-commercial use, so if you have a paid Substack, check the license.
The big takeaway.
Ask yourself: what’s the Substack post I would open? How would it open? That’s what you should create.
We’re entering crowded inboxes. We’re not competing — we just want to meet our subscribers where they are.
Join me for my next live video in the app.











