Women are told to lean in, hustle harder, and be the girlboss, and then penalized for doing exactly that, which is the contradiction Stefanie O'Connell takes apart in her book The Ambition Penalty. In this episode of Charlie's Toolbox, Stefanie talks about what she personally wanted from girlboss feminism, the moment the spell broke for her, and why the word "ambitious" so often lands as a critique when it is applied to a woman.
The conversation moves through the research on how institutions rather than women's behavior create the penalty, what it takes to name that out loud without apologizing for it, and what choosing yourself looks like inside a system that charges you for it. Stefanie also shares what writing the book cost her and what it gave back to her. If you have ever been told you were too driven, too much, or too ambitious by the same rooms that asked you to perform ambition, this conversation gives you the language for it.
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