Hello Monday with Jessi Hempel

When Perseverance Becomes Self-Sabotage

Hello Monday with Jessi Hempel

Show Notes

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.

More from Hello Monday with Jessi Hempel

Oct 19, 2026

We plan our careers like life is short. Go to school, climb the career ladder, retire. But as we live longer, the model doesn’t hold up.

Oct 12, 2026

After more than two decades exploring courage, vulnerability and leadership, Brené Brown’s work has helped millions of people and changed how we talk about shame and belonging. In her latest book, Strong Ground, Brené introduces the idea of “grounded confidence,” a practice of leading with consistency, clarity and courage instead of bravado.

Sep 28, 2026

Danny Meyer has built some of the most beloved and enduring restaurants in the US. The “secret sauce” behind Union Square Cafe, Gramercy Tavern, The Modern, Shake Shack, and more? How diners feel when they walk in the door.

Sep 21, 2026

Ten years ago, Angela Duckworth wrote the book on grit. Now she's back with the advice you need to keep moving forward. The MacArthur genius fellow, University of Pennsylvania professor and bestselling author joins Jessi in the studio to make the case that individual effort only takes you as far as your situation allows and that changing your situation is one of the most powerful tools you have. Her new book is called Situated: Find the People and Places That Bring Out Your Best.

Sep 14, 2026

Laura Vanderkam tracks her time in 30-minute increments and has been for over a decade. That’s 336 half-hour blocks over the course of a week. After reviewing thousands of people’s schedules, she finds, again and again, that most of us are sitting on more time than we think. We just have to shift our mindset to believe it. The time management expert and author of the new book Big Time: A Simple Path to Time Abundance returns to Hello Monday to talk about what it actually takes to move from time scarcity to abundance.

See all episodes →