Hello Monday with Jessi Hempel

How to Live With Uncertainty: Asking Better Questions About Work and Life


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Uncertainty has become a defining feature of modern work. From shifting economic signals to rapid technological change, many professionals feel stuck in a constant state of not knowing—and they’re exhausted by it. In today's episode, Jessi Hempel sits down with journalist and behavioral scientist Elizabeth Weingarten to explore how asking better questions --not demanding faster answers--can help us navigate uncertainty. 

Elizabeth is the author of How to Fall In Love With Questions. Her work focuses on uncertainty, decision-making, and how curiosity can help us build more meaningful lives and careers. In this conversation, she challenges the culture of binary thinking, and offers a powerful framework for living well in the unknown.

Elizabeth and Jessi discuss:

  • Why our tolerance for uncertainty is shrinking—and how technology plays a role
  • The danger of binary questions and why “yes or no” often isn’t the right frame
  • How to change the relationship we have to our questions
  • Burnout, work, and what happens when we stop asking meaningful questions
  • How to use questions as an internal GPS for career and life decisions
  • We are no longer hosting weekly Office Hours but are thrilled to launch the Hello Monday Book Club starting in 2026. If you’re interested in joining, send us an email at [email protected] and let us know!

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