Girlboss or Bust

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Girlboss culture is now, as they say, cringe, but during the 2010s, SO MANY of us thought we were on the precipice of busting through that glass ceiling. We thought we could rise and grind, hustle our way to the life of our dreams, and as long as we loved what we did we wouldn’t work a day in our lives. Leigh Stein is also a recovering girlboss, who went into debt building an organization that supported women but left her burned all the way out.

About Terrible, Thanks for Asking

Terrible, Thanks for Asking is more than just a podcast (but yeah, it’s a podcast).

It’s a show that makes space for how it really feels to go through the hard things in life, and a community of people who get it.

TTFA on social: TTFA on Instagram | TTFA on Facebook

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Transcripts may not appear in their final version and are subject to change.


Girlboss culture is now, as they say, cringe, but during the 2010s, SO MANY of us thought we were on the precipice of busting through that glass ceiling. We thought we could rise and grind, hustle our way to the life of our dreams, and as long as we loved what we did we wouldn’t work a day in our lives. Leigh Stein is also a recovering girlboss, who went into debt building an organization that supported women but left her burned all the way out.

About Terrible, Thanks for Asking

Terrible, Thanks for Asking is more than just a podcast (but yeah, it’s a podcast).

It’s a show that makes space for how it really feels to go through the hard things in life, and a community of people who get it.

TTFA on social: TTFA on Instagram | TTFA on Facebook

Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcripts may not appear in their final version and are subject to change.


leigh stein holding a microphone

About Our Guest

Leigh Stein

Leigh Stein makes fun of what the internet is doing to us. She is the author of five books, including the critically acclaimed satirical novel Self Care and the poetry collection What to Miss When. She has written culture pieces and personal essays for the New York Times, the Washington Post, the New Yorker online, Airmail, Allure, ELLE, BuzzFeed, The Cut, Salon, and Slate.

Find her on TikTok, Substack, and Instagram.

View Leigh Stein's Profile

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