Part of the Substack Writer at Work Series.

In 2026, I’ll be giving paid subscribers and Premier members a taste of the writing guidance I use with my students at Northwestern and my Craft of Writing on Substack course.

Today, we dive into Substack writer's block, a unique but common ailment.

Substack writer’s block looks like not posting—or posting lifelessly. Or giving up entirely. There are a lot of dead Substacks:

Many as a result of “writer’s block.”

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SW@W homepage | Premier Membership homepage | 2026 Notes Boost Challenge | Paid/Premier Chat | 2026 Substack Pathway | Upcoming courses & Intensives | Substack Essentials Workshop library | Archive | Index | Guidance on Notes, Growth, Revenue, Writing on Substack, Serialization

Maya C. Popa and I talk about self-promotion for the self-promotion averse.

Find out why self-promotion is all about bravely falling backward into a ball pit and why we can blame our dislike of it on the Modernists, Roland Barthes, and the Iowa Writers Workshop.

Welcome to the Substack Live Podcast!

Conversations with the best Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so. Plus, get updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life.

Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay.

Over 300 people showed up to this live recording of the Substack Live Podcast to hear Emily Farra and Jessica DeFino talk about how they built newsletters that became something bigger than the platform itself, including:

* Why having tens and hundreds of thousands of subscribers doesn’t mean the Substack writer has it easy—far from it

* How to create your own platform and not to be platform-dependent

* Why it’s ill-advised to try to write a “genius essay” every week on demand and it’s better to create a framework you can apply consistently

* Why consistency is everything—unless it’s not

* And so much more…

Jessica DeFino is an award-winning beauty reporter and critic (the New York Times, the Sunday Times, Vice). She’s also written for Vogue, Allure, and more. She now writes the Guardian’s beauty advice column, Ask Ugly, a position that arose out of her Substack. Adweek named her one of their Creative 100 for 2023. She’s smart and sharp and funny and wry. FLESH WORLD by Jessica DeFino is “the newsletter the beauty industry fears.” She’s a Substack icon who showed what’s possible beyond the platform. And her CTAs are the best, e.g., “Subscribe now. (Because retinol won’t work in the face of your mortality.)”

Emily Kirkpatrick is the Roland Barthes of fashion writing—with a little bit of Stephen Wright and Tig Notaro mixed in. She’s written for People, i-D, The New York Times, and Vanity Fair, among many others. Her newsletter I <3 Mess is essential reading, whether you care about fashion or not.

Thank you, Helen Roy, Amy Gabrielle, Lynn Jericho, Brad Wetzler, Morgan Strehlow, and many others for tuning into my live video with Emily Kirkpatrick and Jessica DeFino!

It was so fun to talk about the importance of mindset when you're a writer and a Substack writer.

It’s everything.

Substack Writers at Work is the only expert guide to Substack.

* We’re one of the Top 10 Substacks, globally—a bestselling Substack featured by Substack and trusted by writers and creators since 2022.

In case you don’t know me, I’m the leading Substack Strategist. I’ve been on this platform for over five years and over a thousand writers and creators 1:1 and tens of thousands on Substack Writers at Work.

Everything you get on Substack Writers at Work is based on real results: clients who’ve doubled, tripled, and 10x’d their subscribers; grown their revenue; produced their best work; and built deep engagement.

Join us.

www.substackwritersatwork.com

Welcome to the Substack Live Podcast!

Conversations with the best Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so. Plus, get updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life.

Brought to you by Substack Writers at Work Founder and Director and former Paris Review interviewer, Sarah Fay.

You can also listen on your favorite podcast platform →

Over 700 people showed up to this live recording of the Substack Live Podcast to hear Austin Kleon give some of the best advice on how to have a newsletter/Substack that means something to you and your readers, including:

* making what you want to see in the world,

* taking time to process in a world that wants us to just move on and scroll,

* writing the newspaper column you’ve always wanted to write,

* the So what? test,

and so much more…

The Atlantic called Austin Kleon “positively one of the most interesting people on the Internet,” which is why his Substack is so damn good.

To have a Substack newsletter that people are interested in, it helps to be interesting, which typically comes when the writer of said Substack is interested in the world and specifically, the part of the world he writes about in a way no one else can.

Austin was Substack before there was Substack, having started his newsletter in 2013, before Substack existed. He came to Substack in 2021 because, he said, he liked the simple interface.

He’s the New York Times bestselling author of a trilogy of illustrated books about creativity in the digital age—Steal Like An Artist, Show Your Work!, and Keep Going—and of Newspaper Blackout, a collection of poems made by redacting the newspaper with a permanent marker.

I love how he describes his trilogy, which is a masterclass in creativity and living a creative life:

* Steal Like an Artist is the book you give to somebody who’s just starting out and needs a kickstart or a boost.

* Show Your Work is for the person that has found their thing but they haven’t been found themselves yet — people who need to self promote or need to get their work out there.

* Keep Going is really the book for people who are trying to make a career out of creative work — people who are trying to be in it for the long haul

***

About the Substack Live Podcast

Join me for conversations with Substack early adopters who created amazing newsletters and continue to bring their good work to the world and make the world a better place in doing so.

I also bring you updates and expert guidance on the platform as it changes and changes again and again, so you can use it to fuel your creative, professional, and financial life.

Subscribe to receive every episode»

Thank you Tom Sykes, Beth Spencer, Jason Chatfield, Petya K. Grady, Emilie Friedlander, and many others for joining us.

Nearly 400 people showed up to listen to Maya C. Popa and I talk about:

- The realities of pitching, publishing, and rejection

- Mindset, motivation, and the myth of “having it all together”

- Substack strategies, authenticity, and audience growth

- The dopamine loop, validation, and the writing process

and more…

Maya is a poet, prose writer, exceptional human, and someone I’m so lucky to call a dear friend. She’s the author of three books of poetry: Wound is the Origin of Wonder (W.W. Norton 2022; Picador 2023), named one of the Guardian’s Best Books of Poetry; American Faith (Sarabande 2019); and her third collection coming in 2026, which we’re all going to make sure it gets on the bestseller list. She’s also the Poetry Reviews Editor at Publishers Weekly. She’s been teaching for thirteen years at NYU and is just such an exceptional human. Her poems have been published in The New Yorker, The Paris Review, Poetry, Granta, the Nation, and elsewhere.

What I love most is Maya’s Conscious Writers Collective (CWC), her online school and writing community that offers a rigorous, MFA-level education for writers without forcing them to take on the debt an MFA program would. Having taught at NYU and elsewhere at the graduate and post-grad level, she’s created a not-to-be-missed-out-on mentorship and training for writers at all levels, those who already have an MFA, those who might go on to receive one with the training they need to make the most of it, and those who may get enough to produce a body of work ready for publication without it.

Thank you Jonas Ellison, Lulu Pearl Trevena, Andō, Sarah Brennan, Eric K. Carr, and many others for tuning into my live video with Maya C. Popa! Join me for my next live video in the app.