Why Substack Is So Difficult (and Strange)

“There are many Substacks about Substack. This one is the OG.”—Gregg EasterbrookToday we talk about the reality of Substack, a reframed I want you to make, and a revelation I want you to consider. This is about figuring out why your Substack might be stalled, maybe a little jammed, maybe not getting started. It's not you. It's Substack. And if you're not a paid subscriber or free subscriber to Substack Writers at Work, please come join us: https://www.substackwritersatwork.com/ This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.comHere I discuss how five of my favorite Substacks (though I go into more than five) created amazing platforms without losing their souls. That means a range of subscribers from 2,000 to 50,000.For all Substack Live Podcasts, join Substack Writers at Work: https://www.substackwritersatwork.com/

This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.comNormally, I would do a written summary, but this is one you need to watch or listen to on your favorite podcast platform: * Remind yourself why you’re on Substack in the first place. (Spoiler: it begins with an f.)* Find out how this might actually be the golden age of writing.* Discover the magic of putting your right hand in your left armpit.You can get Substack “information” anywhere. Paid subscribers get guidance from founding Substack writers who’ve mastered the platform and made it their own in Lives like this one with Liz Gilbert. Become a paid subscriber today!You can get Substack “information” anywhere. As a paid subscriber you get access to founding Substack writers who’ve mastered the platform and made it their own in Lives like this one with Liz Gilbert. This is exclusively for you.My Substack Live series features writers, creators, teachers, and visionaries who’ve created something entirely new and/or transformed their Substack into community gathering spaces, educational institutions, cultural touchstones, and/or works of art. Previous guests include Elizabeth Gilbert, Susan Cain, Austin Kleon, Mason Curry, Jessica DeFino, and Emily Kirkpatrick.

Nearly 400 people joined us live to talk about Susan Cain’s amazing Substack The Quiet Life.If you don’t know Susan Cain, she’s the author of the mega bestsellers “Quiet: The Power of Introverts in a World That Can’t Stop Talking” and “Bitter Sweet: How Sorrow and Longing Make Us Whole.” She was a lawyer before becoming one of the most compelling writers of our time.We talk about envy and jealousy, how to write your posts/articles as kindred letters, how loving what you do makes a successful Substack and a more enjoyable life, the magic of her candlelight chats (the community feature she offers as an introvert and for introverts), and why "vibe" might just be the word for 2026. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

“There are many Substacks about Substack. This one is the OG.”—Gregg EasterbrookThis week:Substacks making news, newsletter dating, Substack in Japan, why you don’t have to go viral on Notes anymore, it’s okay to ask for what you want, the new way to restack your posts, and who’s here.SW@W homepage | Premier homepage | Substack Starter Pack | 24/7 Community Chat | Manage your subscription | Book a 3-Month Substack Growth Package 1:1 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

Today’s live was phenomenal! Please listen to the podcast version while you’re cooking this weekend or walking or running or whatever.In my live with the amazing Austin Kleon reminded me that on Substack, we’re writing news-letters.I wanted an expert in letter writing to share how exactly the principles of letter writing could help us be better writers on Substack and write more engaging Substack articles.Lindsay Hurty offered a wealth of advice on how we can use letters and the act of letter writing in many different ways to nurture our subscribers and write better Substack articles. (You can subscribe to her Substack here.)Be sure to listen, too, because the story she tells in the beginning will (if I have anything to do with it) someday be a viral TED Talk.SW@W homepage | Premier homepage | Substack Starter Pack | 24/7 Community Chat | Manage your subscription | Book a 3-Month Substack Growth Package 1:1 with me This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

This is a free preview of a paid episode. To hear more, visit www.substackwritersatwork.comBrand sponsorships on Substack aren't just about some sort of weird brand placement that's awkward. It's about rethinking Substack and how you make money on here, and how we support each other in making money. In this episode, I give you everything you need to know about Substack's new brand sponsorships program — how it works, what brands actually want, and how to fill out your Creator Kit strategically, not generically.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

The highest earners on Substack aren't debating whether to use AI. They're asking a better question: how to stay valuable in a world that's full of it.I spent a day in New York in a room with some of the biggest names on the platform, and the words that kept surfacing weren't the ones the growth-advice economy sells. No one said hacks. No one said viral. What they talked about was fun, taste, and the person behind the words.This episode covers:*Why the era of giving your best work away for free may be over.*Which skills are about to gain value on Substack, and which are about to lose it.*Why slow, steady growth is the only kind with substance. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe

Welcome to our new series for paid subscribers: “The Minimalist’s Guide to Substack.” Declutter your Substack brain and life, so you can actually grow in what is an increasingly crowded Substack landscape.The biggest mistake I see on Substack is people making it way too complicated.Principle #1: Post when you have something worth sending.Each post should pass two tests: Is this something people need right now? Is this something they could get from ChatGPT?Enter the Golden Nugget post.It's an easy, short post you can create when you don't have time for a full, high-quality post. A gift—a book, a song—something that doesn't ask readers to do anything. A full post, not a Note, that comes from a genuine desire to share one thing that means something to you right now. No call to action, no questions for comments. Don't make readers do any work.But a Nugget post isn't about you. It's a gift to your readers—something they can absorb without much effort. The Nugget gives you and your readers breathing room while maintaining connection.Join SW@WBook a Substack Strategy 1:1 with me This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.substackwritersatwork.com/subscribe