Podcast #840: When to Quit

“Don’t be a quitter!” “Quitters never win, and winners never quit!”

These maxims encapsulate our usual attitude towards quitting, which is to see it as a bad thing, a weakness, a character defect. We celebrate those who stick with things, who have grit.

But my guest would say that quit and grit are just two sides of the same coin, and that quitting is a valuable skill to learn and get good at. Her name is Annie Duke, and she’s a former professional poker player, a speaker, a consultant, and an author. In her latest book, Quit: The Power of Knowing When to Walk Away, she seeks to rehabilitate quitting by showing how — whether it’s in the context of ending a relationship, leaving a job, or climbing a mountain — it has essential benefits. We discuss those benefits in today’s show, as well as how to know when to quit. We unpack how whether you should stick with something comes down to an equation of its positive “expected value,” how setting goals too rigidly can get in the way of our being able to assess that value, and the cognitive biases that keep you from quitting when you should. We end our conversation with two strategies for overcoming these biases, including establishing “kill criteria” to give yourself a timetable for how long to go after an aim.