Heather Havrilesky’s writing career has spanned the life of the internet, starting with the satirical site Suck.com, moving through Salon, The Awl, and New York Magazine, and ending up on Substack, where she publishes two much-loved newsletters: Ask Polly and Ask Molly. 

Heather has mastered the art of reinvention, bending with the winds of the web, as news sites have variously chased SEO, blogging, Facebook traffic, and the rest. She settled on an approach that has worked for her: doubling down on what she likes. That attitude ultimately took her into advice giving, where she has carved out an immense reputation as one of America’s preeminent practitioners of the form, primarily through Ask Polly, for years a mainstay of New York Magazine’s The Cut. Polly got her start, though, at The Awl, the fan-favorite blog co-founded by Choire Sicha that was home to many of the best and most obsessive online writers of the 2010s, before social media had completely corrupted the landscape for essayists and delightful internet weirdos. 

While writing Polly for The Cut, Heather saw social media grow in reach and then start to infect the minds of fellow writers who toiled under its constricting influence. “It’s almost like an issue of when the auditorium becomes too big and filled with voices,” she says, “you start to feel self-conscious about making sounds when everyone is in the room.” 

Those pressures came to bear on Heather with exaggerated force after the New York Times published an excerpt of her latest book, Foreverland, an irreverent marriage memoir that comes out in paperback this Valentine’s Day. The excerpt carried the subheading “Do I hate my husband? Oh for sure, yes, definitely.” It was enough to create a meme, and Heather spent the next few days being knocked around Twitter for being a husband-hating harlot (or worse, depending on the tweets). 

What was that experience like for someone who has been writing online for 27 years? Well, it turns out, not easy at all—even for an advice columnist who always manages to find the right words for those who are brushed by misfortune. However, in the pain, she has managed to find a balm for herself in a book idea that emerged from her essay writing on Substack. 

“One thing that kept me feeling good,” Heather says, “was this idea that life could be deeply romantic even when everything felt terrible.” Her new obsession with finding the romantic in the mundane is proving to be more than just a coping mechanism—it’s a way of looking at life. “Discovering new ways of being happy in spite of a lot of things that are aggravating you is—it’s the most romantic thing of all.” 

https://www.ask-polly.com/ 

Heather’s recommended reads:

https://www.todayintabs.com/

https://therealsarahmiller.substack.com/

https://hunterharris.substack.com/

https://laurenhough.substack.com/

https://www.blackbirdspyplane.com/

https://cintra.substack.com/

https://griefbacon.substack.com/

https://indignity.substack.com/

Show notes

Subscribe to Ask Polly and Ask Molly on Substack

Find Heather on Twitter and Instagram

Suck.com, Salon, The Awl

Heather’s books: Disaster Preparedness (2011), How to Be a Person in the World (2017), What If This Were Enough? (2019), Foreverland (out in paperback on Feb. 14)

Excerpt of Foreverland in the New York Times, and the New York Post response

Writing about voice lessons on Ask Molly

[02:17]: Working at Suck.com

[08:31] Changing San Francisco

[09:13] The “jackassery” of boomer optimism 

[10:58] Smart, weird, fun people everywhere 

[12:57] The shape-shifting nature of being an online writer 

[16:12] Becoming an advice writer 

[18:43] The awe of the Awl 

[24:58] The freedom, and danger, of social media 

[30:00] Ask Molly, Polly’s evil twin

[31:57] Publishing books 

[36:59] Being misinterpreted in mainstream media  

[40:55] Reacting to being attacked online

[46:44] Workshopping her next book 

[50:31] Writing an advice column for 10 years 

[52:53] Recommended writers on Substack

The Active Voice is a podcast hosted by Hamish McKenzie, featuring weekly conversations with writers about how the internet is affecting the way they live and write. It is produced by Hanne Winarsky, with audio engineering by Seven Morris, content production by Hannah Ray, and production support from Bailey Richardson. All artwork is by Joro Chen, and music is by Phelps & Munro.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit read.substack.com