What does it really take to ask for what you want—and actually get it? Jenny Wood, former Google executive and author of Wild Courage, breaks down why fear of judgment, failure, and uncertainty keep so many people stuck. This episode dives into the surprising science of ambition, why women are still penalized for being "bossy," how guilt and comparison steal more from us than failure ever could, and why being a little shameless might be the smartest move you make. Plus: what chasing a stranger off a subway platform can teach you about betting on yourself.

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