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

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 hellomonday@linkedin.com and let us know!

You can listen to How to Live With Uncertainty: Asking Better Questions About Work and Life online on Radio and Podcast. Open the player on this page to stream the available audio.

How to Live With Uncertainty: Asking Better Questions About Work and Life is an episode from Hello Monday with Jessi Hempel by LinkedIn.

This episode is 28:08 long.

This episode was published on Dec 22, 2025.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Hello Monday with Jessi Hempel when more episodes are available from the podcast feed.