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Hello Monday with Jessi Hempel

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

Hello Monday with Jessi Hempel

LinkedIn

Careers, Business

4.81.1K Ratings

🗓️ 22 December 2025

⏱️ 28 minutes

🧾️ Download transcript

Summary

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!

Transcript

Click on a timestamp to play from that location

0:00.0

Just tell me what to do. I hate this feeling of not knowing. The advice that I think is often out there is this form of toxic positivity. It's like embrace uncertainty, right?

0:09.2

Yeah.

0:09.6

Oftentimes we don't want to do that. Uncertainty is really hard. It's really painful. It's really scary. How do we really make sure that the questions that we're asking ourselves in these moments of uncertainty are ones that are helping us to imagine

0:22.4

greater possibilities for our future rather than keeping us stuck.

0:28.9

From the news team at LinkedIn, I'm Jesse Hempel and this is Hello Monday.

0:34.1

Friends, for our final episode of the year, I want to go deep on uncertainty today.

0:40.3

Because if this past year has had a theme, well, it would pretty much have to be that.

0:46.3

We have devoted so many of our episodes this year to how we manage the discomfort that comes along with it.

0:52.3

I mean, there is the state of the world. There's the

0:56.9

question of whether the economy is good or bad, whether jobs are going or coming, whether it's all

1:02.7

AI's fault or not. I mean, it's all questions. There are no clear answers. You know, this uncertainty

1:09.5

can paralyze us, or it can propel us forward on the momentum of our curiosity.

1:15.6

And a lot of this will come down to our own inquisitiveness.

1:19.6

Now, today's guest will help us reframe that approach to inquiry.

1:24.6

She's Elizabeth Weingarten.

1:26.6

She's an accomplished journalist and a behavioral scientist.

1:29.3

Her book is How to Fall in Love with Questions. Today we're going to talk about how to do just that.

1:35.3

You know, I'm bringing you this conversation because Elizabeth challenges us to think about uncertainty in a brand new way.

1:42.3

She believes that rewriting the questions we ask ourselves,

1:46.2

well, it can be transformative. Now here's my conversation with Elizabeth Weingarten.

1:52.4

Your book is the tool for how to invite uncertainty into our lives in a meaningful way,

1:59.5

in a way that actually it has a role

...

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