We've been told to lean in, speak up, ask for the raise, and take up space. But what happens when doing everything right still isn't enough? Journalist and financial expert Stefanie O'Connell joins Jean to talk about her deeply researched new book, The Ambition Penalty: How Corporate Culture Tells Women to Step Up — and Then Pushes Them Down. In this conversation, Jean and Stefanie dig into why the girlboss era failed us, why women are penalized not for a lack of ambition but because of it, and what we can actually do about it. They cover: Why being fluent in the language of empowerment is not the same as actually being empowered How the ambition penalty follows women outside the workplace  Why you can't outwork inequality, but you can outorganize it What it really takes to build a life where your ambition is championed, not penalized And if you loved today's conversation, don't miss Jean's new book, The Forever Paycheck — your guide to building a secure, steady income stream that lets you actually enjoy the retirement you've worked so hard for. Learn more about your ad choices. Visit megaphone.fm/adchoices