How do you know when it’s time to stop? Most high achievers would say never. We keep going because quitting feels like failure. But Lindsay Crouse argues that sometimes the bigger failure is continuing past the point you should have. The four-time Emmy Award winner, four-time Oscar nominee and author of the new book The Case for Quitting spent 15 years at the New York Times covering endurance sports before walking away. This week she joins Jessi in the studio to make the case that sometimes stopping is the most courageous thing you can do, and that knowing when to quit is an essential skill. In this episode, Jessi and Lindsay discuss: Why quitting on time almost always feels too early The moment when perseverance flips into self-sabotage, and how to catch it before you crash Why the decision to continue always has costs, we just can't see them as clearly as the costs of quitting What Lindsay's own running career taught her about the difference between stopping and giving up Why women in particular are conditioned to override their instincts and keep going, and what it costs us The spotlight illusion: why we overestimate how much anyone notices when we leave Jessi on quitting Wired too late, and what it took from her before she finally walked away The five-to-ten year question: a simple way to know whether it's time to start building an off-ramp What Lindsay's 15 years at the New York Times taught her about identity, and why leaving felt like both nothing and everything How writing a book about quitting transformed her What’s next for Lindsay Crouse Follow Lindsay Crouse and Jessi Hempel on LinkedIn.