How To! How To Know When to Quit Your Job (Encore)
Jan 13, 2026
Annie Duke, a cognitive scientist and decision-making guru, shares her expertise on quitting and its emotional toll. She reflects on her own experience quitting poker to improve her well-being. Together with Victor, who feels stuck in his humanitarian job, they dissect common biases that keep people from leaving positions that no longer serve them. Annie emphasizes assessing happiness probabilities and setting a clear deadline for decision-making. The conversation is a refreshing take on knowing when it's time to walk away.
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Victor's Career Dilemma
- Victor has worked over a decade in humanitarian roles and feels plateaued inside a slow, political bureaucracy.
- He values purpose and stability but worries switching could cost him seniority and time to return if it fails.
Remember Most Doors Revolve
- Recognize that many choices are reversible and you rarely permanently shut doors by switching.
- Factor in how easy it would be to return when assessing the cost of quitting.
Why Staying Feels Easier Than Leaving
- People overweight the risks of starting something new and underweight the harms of staying due to loss aversion and omission bias.
- Status quo bias makes staying feel passive even though not quitting is an active decision.
