How to Live With Uncertainty: Asking Better Questions About Work and Life
Hello Monday with Jessi HempelShow Notes
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!
More from Hello Monday with Jessi Hempel
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.
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.
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.
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.
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.