Stefanie O’Connell joins The Pain Gap for a fiery, deeply validating conversation at the intersection of women’s health, financial health, and power. A leading voice on money, ambition, and gender equity, Stefanie breaks down what she calls “the ambition penalty”: the reality that ambition is praised and rewarded in men, but often penalized in women, at work, at home, and in public life.

Together, Anushay and Stefanie connect the dots between the pay gap and the pain gap, how patriarchy relies on undervaluing women’s labor, time, and bodies, and how gaslighting (culturally and politically) keeps women questioning what they know they’re experiencing. They unpack why financial advice for women so often tells us to “shrink” (save, sacrifice, coupon) while men are encouraged to “build” (earn, invest, accumulate), and why women aren’t “risk averse”; they’re risk-aware.

They also dive into the real-life consequences of inequity: how women face backlash for negotiating, why burnout isn’t caused by women “wanting too much,” and how community and collective care, not individual self-optimization, are the path forward. Stefanie shares the mission behind her work, the importance of data in cutting through gaslighting, and why women are entitled not just to income, but to wealth and long-term power.

Plus: Stefanie’s new book, The Ambition Penalty: How Corporate Culture Tells Women to Step Up and Then Pushes Them Down, is available for preorder now and ships May 19.

Episode Resources:

The Ambition Penalty: How Corporate Culture Tells Women to Step Up and Then Pushes Them Down: amazon, barnes & noble, bookshop, books-a-million

@stefanieoconnell on Instagram

Stefanie's Substack

The Pain Gap

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To learn more about Anushay Hossain's work, check out Anushay's website or sign up for her substack. To continue the conversation, feel free to DM @anushayhossain or email me at thepaingap@gmail.com

Becca Rea-Tucker (aka The Sweet Feminist) joins The Pain Gap for a disarming, deeply human conversation about abortion, stigma, and the radical power of emotional support—served, of course, with cake.

Becca shares how it took years after her own abortion to say the word out loud, and why reclaiming language (“abortion isn’t a bad word” and “pro-abortion”) became central to her activism. Together, we unpack how shame gets baked into the “scripts” society hands us—and what changes when we stop debating our right to care and start focusing on the people who actually need it: the ones having abortions.

We also talk about her new book, The Abortion Companion, created to fill a gap she felt firsthand: stigma-free emotional companionship, practical abortion information, affirmations, prompts, and even comfort movies for the moments when you just need to breathe. Becca explains why adults deserve emotional education just as much as kids do and why “support” should never require remorse as the entry fee.

The episode closes with an honest look at doing this work in Texas as abortion bans intensify (including “bounty” laws meant to isolate communities), the resources Becca trusts most, and the message she’d write on a cake for this moment: We’ll never stop. We’ll always support you.

Episode Resources:

The Abortion Companion

Follow Becca on Instagram

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To learn more about Anushay Hossain's work, check out Anushay's website or sign up for her substack. To continue the conversation, feel free to DM @anushayhossain or email me at thepaingap@gmail.com

Renee Bracey Sherman is an abortion storyteller, researcher, and movement builder, for a clear-eyed conversation about what gets erased in mainstream abortion narratives, and why reclaiming truth is part of the fight for bodily autonomy. Renee explains why “people of color have always had abortions,” how history has been intentionally distorted to serve white supremacy and population control, and what we lose when we let criminalization, not care, shape the conversation.

Together, they unpack the long arc of stigma: how abortion moved from community-based healthcare to something framed as shameful and secret, and how policing and surveillance have always been the through line, then and now. Renee also shares why storytelling is more than personal, it’s political: a way to refuse shame, share “abortion wisdom,” and expose the patterns that gaslighting depends on.

The episode closes with a powerful reflection on what Renee would tell her younger self, and why her abortion wasn’t the end of her story; it was the beginning of the life she chose.

Episode Resources:

Liberating Abortion Website

Renee Bracey Sherman

Instagram/Facebook/Bluesky/Threads/LinkedIn: @ReneeBraceySherman

Twitter: @RBraceySherman

The Pain Gap

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To learn more about Anushay Hossain's work, check out Anushay's website or sign up for her substack. To continue the conversation, feel free to DM @anushayhossain or email me at thepaingap@gmail.com