#155 Breaking the Rules of Publishing with Jane Pratt: From Sassy to Substack

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Magazine Editor, Jane Pratt

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When I think about how confessional writing came into its own, I always think of Jane Pratt. Jane is a traditional editor like me, but she broke the mold—creating the first “confessional” style publication that made teenage girls everywhere thrilled.

I first met Jane at Open Secrets Live, thanks to Rachel Kramer Bussel (a former guest on the podcast #128, Crafting Cathartic Personal Essays with Rachel Kramer Bussel of Open Secrets Magazine).

At the event, Jane was the keynote speaker, and I was on a panel about sex and relationships. Years earlier, I had written for her publication XOJane—a piece called “I Shamed My Niece for Dyeing Her Hair Pink.” (yes, I found it in the archives, and yes, that’s me with bright red, super short hair, courtesy of a London hairdresser).  I worked with Emily McCombs on that story, and later again at HuffPost Personal. Watching how editors like Jane and Emily champion writers across multiple platforms has always inspired me in my own editorial journey.

So it was a true thrill to sit down with Jane for my podcast.

Jane Pratt is nothing short of a publishing pioneer—the founder of Sassy, Jane, and XOJane, and now the voice behind the hit Substack Another Jane Pratt Thing. She’s built a career on breaking rules, centering women’s voices, and creating space for personal, confessional storytelling long before it was mainstream. From her groundbreaking “It Happened to Me” column to her current Substack community, Jane has always put authenticity (being real) and conversation (just check out the comments section on her pub) at the heart of her work.

In This Episode

  • How Jane started Sassy and why it resonated with an entire generation

  • How she builds community by jumping into the comments and encouraging readers to turn feedback into full stories

  • The challenges she faced publishing taboo topics like abortion, birth control, and sexuality in teen magazines

  • The evolution from print to online media to Substack—and why Substack feels like the most authentic home for her writing yet

  • Her new Controversial Books Only Book Club and what makes it so different

Jane paved the way for a generation of writers to reveal their inner lives on the page. And as someone who has built a career editing and teaching personal essays and memoir, I feel a deep connection to the spaces she’s created—and continues to create—for authentic storytelling.

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Connect with Jane 

Another Jane Pratt Thing

Instagram

Substack

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  • NEW: Sign up for my free online Editor-on-call NYU event on October 29th Inside Slate: An Unfiltered Conversation with Senior Editor, Rebecca Onion. Register here
  • Sign up for my webinar on October 9th in collaboration with Writer’s Digest Mapping Your Memoir: How to Find the Heart and Shape of Your Story. Sign up here.

 TEDx Talk: How to Get Noticed in Your Writing and Beyond
Estelle blends personal storytelling with actionable strategies for standing out—starting with a chaotic moment involving Thomas the Tank Engine.
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